Tours and activities in Portland, United States

SimilarTours

Tours and activities in Portland, United States | SimilarTours

Skip-the-line tickets in Portland

Major attractions with reserved entry - skip the queue, walk straight in

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Viator
Two Hour Lighthouse Bicycle Tour from South Portland-Mellow
Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble, before returning to the bike shop.
5.0(54)
2 hours
Portland, United States
Free cancellation
From
$75
No similar experiences found
Musement
Portland Timbers Football Game at Providence Park Stadium
Be there in person to see a Portland Timbers MLS game at Providence Park, picking from a wide selection of dates against Major League Soccer's top teams.
2 hr 30 min
Portland, United States
Instant confirmation
English
From
$59
No similar experiences found
Viator
Half Day Kayak Rental on Sebago Lake
The Must-Do Sebago Lake Experience! Explore the panoramic views of Sebago Lake with our unbeatable rental package! With our EZ Launch system, you'll enjoy easy access to launch right from our private site nestled between Panther Run stream and the north end of Sebago Lake. With your fitted life jacket, paddle and map in hand, you'll have endless opportunities to discover the lake's hidden coves, beaches, islands and wildlife. Paddle along meandering streams before emerging into Sebago's scenic waters. Beach your vessel and savor a picnic lunch. Venture deep into secluded inlets to glimpse native wildlife. Or simply cruise the lake while soaking in Maine's iconic scenery. The varied landscape offers towering pines, rocky outcroppings and sandy beaches. Ample parking, friendly staff, and convenient amenities like bathrooms and changing rooms, our facilities make Sebago Lake an ideal destination for a hassle-free day on the water.
5.0(21)
1 hour - 4 hours
Portland, United States
Free cancellation
From
$44
No similar experiences found
Musement
Morning tour of Portland City
Book your morning tour of Portland City and explore the sights and streets of Portland like a local with your r informative and entertaining guide!
3 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$85
No similar experiences found
Viator
Portland, Maine: Black History Guided Walking Tour
Trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s earliest settlements couldn’t have existed without Black labor, skill, and insight. You'll meet the Black Yankees who founded Maine communities, overturned slavery statewide, drove our maritime industries, gained political influence, crossed color boundaries, and expanded Mainers’ rights in the modern era. Stepping on granite cobblestones crooked with age — that once saw footfalls from national heroes like Frederick Douglass — you’ll pass storefronts once home to Black-owned barbershops where abolitionists whispered intelligence to Underground Railroad conductors. Enjoy 2 hours of entertaining and enlightening historical narration over a 1.5-mile route. Owner and guide, Dugan Murphy, dug through the archives to present an amazing constellation of stories left out of most tours. TripAdvisor named him Portland's #1 guide!
5.0(152)
2 hours
Portland, United States
Free cancellation
Likely to sell out
From
$54
No similar experiences found
Musement
Oregon Coastal tour
Enjoy the Oregon coastal beach with its extraordinary vistas, cliffs, offshore rocks, and sea lions on the Oregon Coastal tour. Buy your tour today on Musement!
8 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$140
No similar experiences found
Viator
Portland, Maine: Hidden Histories Guided Walking Tour
Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising stories largely left out of the history books. Get ready to broaden your sense of what Portland and Maine have been and could be. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, we'll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. We’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk together through the centuries. Enjoy an inclusive, empowering, and surprising constellation of tales that offers a welcome contrast to the more obvious themes you’re likely to experience on other tours. You'll enjoy 2 hours of narration over a 1.5-mile route with owner and guide, Dugan Murphy. He is Portland's top-rated guide on TripAdvisor!
5.0(560)
2 hours
Portland, United States
Free cancellation
Likely to sell out
From
$54
No similar experiences found
Viator
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their rich history. While most lighthouses aren’t open for tours, you’ll still get up-close views and plenty of opportunities to admire their stunning architecture and scenic surroundings. As you navigate through Portland’s picturesque coastline, you’ll be surrounded by breathtaking views that are as storied as they are beautiful. This focused, relaxed tour is the perfect way to connect with maritime past while soaking in the charm of Maine’s coastal landscape.
4.9(970)
2 hours
Portland, United States
Free cancellation
From
$79
No similar experiences found

Viator

Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

5.0(54)

2 hours

Portland, United States

Free cancellation

From

$75

Musement

Portland Timbers Football Game at Providence Park Stadium

2 hr 30 min

Portland, United States

Instant confirmation

From

$59

Viator

Half Day Kayak Rental on Sebago Lake

5.0(21)

1 hour - 4 hours

Portland, United States

Free cancellation

From

$44

Musement

Morning tour of Portland City

3 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$85

Viator

Portland, Maine: Black History Guided Walking Tour

5.0(152)

2 hours

Portland, United States

Free cancellation
Likely to sell out

From

$54

Musement

Oregon Coastal tour

8 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$140

Viator

Portland, Maine: Hidden Histories Guided Walking Tour

5.0(560)

2 hours

Portland, United States

Free cancellation
Likely to sell out

From

$54

Viator

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

4.9(970)

2 hours

Portland, United States

Free cancellation

From

$79

Guided walking tours in Portland

Small-group + private walking tours with a local guide

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Musement
Dinner cruise on Willamette river
Relax on a 2.5-hour sunset dinner cruise on the Willamette River, enhanced by dazzling city sights and lights.
2 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$127
No similar experiences found
Viator
Sunset Tour by Kayak on Sebago Lake Maine
Discover the serene beauty of water-carved bends and meandering streams, where local wildlife thrives against a backdrop of rustic charm. As we embark on our journey, we'll navigate the gentle twists and turns of a meandering stream, revealing the untouched beauty. Let the tranquil waters carry you along as you immerse yourself in the sights and sounds of the natural world. Throughout the tour, our knowledgeable Registered Maine Guide will regal you with captivating stories, bringing the scene to life with native lore and insights. Surrounded by panoramic views we pause and marvel as the sun sets behind the Towering pines. Whether you're a seasoned paddler or a complete beginner, rest assured this outing requires no previous experience - just a sense of adventure and a desire to unwind.
5.0(10)
2 hours
Portland, United States
Free cancellation
From
$59
No similar experiences found
Musement
Morning half-day to Multnomah Falls and River Gorge Waterfalls
Book your morning half-day to Multnomah Falls and River Gorge Waterfalls. Explore the beauty of the canyon walls and learn about the area from your guide.
3 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$85
No similar experiences found
Viator
Portland Explorer: Working Waterfront Walking Tour with Seafood
Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the city’s past. This immersive experience blends local history with maritime culture, offering a deeper look at how Portland grew from a rugged seaport into one of New England’s most vibrant coastal cities. As you stroll the cobblestone streets and working wharfs, your guide will share tales of shipbuilders, merchants, fires, and fishermen who shaped Portland’s story.
5.0(8)
2 hr 30 min
Portland, United States
Free cancellation
Likely to sell out
From
$79
No similar experiences found
Musement
Afternoon half-day to Multnomah Falls and River Gorge Waterfalls
Book your afternoon half-day to Multnomah Falls and River Gorge Waterfalls. Explore the beauty of the canyon walls and learn about the area from your guide.
3 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$85
No similar experiences found
Viator
Intimate Portland Public Sunset Cruise
Witness the stunning sunset over Casco Bay on this two-hour public powerboat cruise aboard the classic Maine-built vessel, Avelinda. As the sun sets, enjoy picturesque views of iconic lighthouses like Portland Head Light and serene islands such as Peaks Island. With a maximum of six guests per boat, relish an intimate experience while keeping an eye out for local wildlife like seals and seabirds. Captains with extensive local knowledge share tales of the region's rich history, making this cruise a perfect way to unwind and soak in the beauty of Maine's coast. Open to all ages, it’s a memorable outing for families and couples alike. - 2-hour scenic sunset cruise through Casco Bay - Maximum of 6 guests for an intimate experience - Spot local wildlife and iconic Portland lighthouses - Knowledgeable captains share local history and ecology
5.0(1)
2 hours
Portland, United States
Free cancellation
New
Likely to sell out
From
$149
No similar experiences found
Musement
Ultimate Acadia and Bar Harbor Self-Guided Tours Bundle
Explore Acadia and Bar Harbor during a self-guided tour. Find out about Bar Harbor's fishing roots and Gilded Age boom. Admire Acadia's beautiful wilderness.
3 hours - 5 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$25
No similar experiences found
Musement
Portland city center walking audio tour
Discover everything Portland's city center has to offer during this walking audio tour. Book now to explore the city at your own pace!
Portland, United States
Instant confirmation
English
From
$11
No similar experiences found

Musement

Dinner cruise on Willamette river

2 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$127

Viator

Sunset Tour by Kayak on Sebago Lake Maine

5.0(10)

2 hours

Portland, United States

Free cancellation

From

$59

Musement

Morning half-day to Multnomah Falls and River Gorge Waterfalls

3 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$85

Viator

Portland Explorer: Working Waterfront Walking Tour with Seafood

5.0(8)

2 hr 30 min

Portland, United States

Free cancellation
Likely to sell out

From

$79

Musement

Afternoon half-day to Multnomah Falls and River Gorge Waterfalls

3 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$85

Viator

Intimate Portland Public Sunset Cruise

5.0(1)

2 hours

Portland, United States

Free cancellation
New
Likely to sell out

From

$149

Musement

Ultimate Acadia and Bar Harbor Self-Guided Tours Bundle

3 hours - 5 hours

Portland, United States

Free cancellation
Instant confirmation

From

$25

Musement

Portland city center walking audio tour

Portland, United States

Instant confirmation

From

$11

Food & drink experiences in Portland

Food tours, market walks, wine tastings, cocktail experiences

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Musement
Portland Urban Wine Tasting Tour in Pearl and Slabtown
Wander through 2 trendy Portland neighbourhoods, while tasting a variety of Oregon wines paired with local bites, in historic wineries.
3 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$129
No similar experiences found
Viator
Portland's Best Craft Beverages Bus Tour
Most recognize Portland, Maine for its vast selection of local craft breweries. And while we retain the title for ‘most breweries per capita,’ we’re experiencing profound growth in our craft beverage scene including a range of spirits and locally produced wine. Neighborhoods like Portland’s East Bayside are brimming with craft beverage options to suit any taste, from Three of Strong’s small batch, organic rum to wines from Blue Lobster Urban Winery which are blended with Maine wild blueberries and apples from local orchards. The third stop of the tour concludes at the Portland Beer Hub, the home of Maine Brews Cruise, and a blend of beer bar and retail space in the bustling heart of Portland’s Old Port. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases at the Portland Beer Hub. Please note that tour stops may change without notice due to events and the availability of staff at each venue.
4.9(39)
2 hr 30 min
Portland, United States
Free cancellation
Likely to sell out
From
$99
No similar experiences found
Musement
Mount Hood Loop Hike With Lunch
Admire waterfalls of the Columbia River Gorge, local farms and orchards at the Hood River Fruit Loop. Enjoy a guided hike around Mount Hood.
10 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$250
No similar experiences found
Viator
Portland Explorer: Boat Cruise with Oysters & Prosecco
Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before being escorted to the waterfront to board your boat. As you glide past the stunning coastline, savor freshly shucked oysters perfectly paired with crisp prosecco. Whether you’re toasting to a special occasion or simply indulging in a moment of pure relaxation, this experience blends Portland’s finest flavors with breathtaking coastal views—an unforgettable way to enjoy the best of land and sea.
4.9(10)
1 hr 30 min
Portland, United States
Free cancellation
Likely to sell out
From
$137
No similar experiences found
Musement
Portland Downtown Donut Tour
Get ready to go on an awesome, deliciously sweet donut tasting tour in downtown Portland!
2 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$54
No similar experiences found
Viator
Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour
Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early 19th century in Portland Harbor are always captivating. They are imposing reminders of days not too far gone when the defense of our coastline required their presence. Despite their prominence, the forts are not easy to access for a variety of reasons, and most locals and visitors have never been to Fort Scammel, the only fort in the Harbor to see active combat. Fortunately, the owners of Fort Scammel have partnered with us to offer private tours of this incredible historic site. This is an experience NOT TO BE MISSED! Along the way, we’ll cruise past some of the other great sights in the bay, including the iconic lighthouses. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible! Our Fort Tour on a Private Island has a 4 PERSON MINIMUM to operate.
4.8(71)
2 hours
Portland, United States
Free cancellation
From
$109
No similar experiences found
Musement
Columbia Gorge tour from Portland
On this tour, you will get intimate with The Gorge through hiking, wine tasting, and a visit to the Columbia Gorge Discovery Center & Museum.
Portland, United States
Free cancellation
Instant confirmation
From
$160
No similar experiences found
Musement
Downtown Portland Coffee and Donut Tour
Learn about Portland's cafe culture and try delicious coffee and donuts on this tasty tour!
Portland, United States
Free cancellation
Instant confirmation
English
From
$59
No similar experiences found

Musement

Portland Urban Wine Tasting Tour in Pearl and Slabtown

3 hours

Portland, United States

Free cancellation
Instant confirmation

From

$129

Viator

Portland's Best Craft Beverages Bus Tour

4.9(39)

2 hr 30 min

Portland, United States

Free cancellation
Likely to sell out

From

$99

Musement

Mount Hood Loop Hike With Lunch

10 hours

Portland, United States

Free cancellation
Instant confirmation

From

$250

Viator

Portland Explorer: Boat Cruise with Oysters & Prosecco

4.9(10)

1 hr 30 min

Portland, United States

Free cancellation
Likely to sell out

From

$137

Musement

Portland Downtown Donut Tour

2 hours

Portland, United States

Free cancellation
Instant confirmation

From

$54

Viator

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

4.8(71)

2 hours

Portland, United States

Free cancellation

From

$109

Musement

Columbia Gorge tour from Portland

Portland, United States

Free cancellation
Instant confirmation

From

$160

Musement

Downtown Portland Coffee and Donut Tour

Portland, United States

Free cancellation
Instant confirmation

From

$59

Boat & water experiences in Portland

River cruises, sailing, sunset boats, harbour tours

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Viator
Guided RIB Boat Adventure of Portland
Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses and our unique 14-passenger RIB boat is suited to tour the region while everyone gets a front-row seat so you can see and experience more of it. Learn about Portland’s nautical history, view wildlife like seals, harbor porpoises, and sea birds, and stop for photos at quintessential sights like all four lighthouses, Fort Gorges, seals, and the working waterfront while also escaping to lesser-known areas of the bay where wildlife viewing is the best. This is a unique tour that is unmatched in the breadth of its experience with a local captain to guide you and answer your questions about the region. Please join us for the Best Of Casco Bay!
5.0(35)
1 hr 30 min
Portland, United States
Free cancellation
Likely to sell out
From
$69
No similar experiences found
Musement
Portland Bigfoot high-speed boat adventure
Discover the legend of Bigfoot around on the Columbia Rivers on the Explorer high-speed boat.
3 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$90
No similar experiences found
Viator
Stand Up Paddleboard Tour with Complimentary Oyster Tasting
Learn the basics of stand-up paddle boarding on land before launching at Mere Point in Brunswick for a leisurely 2.5 hour morning tour of Northwest Casco Bay! We will paddle out to a demonstration oyster farm and then to an island to shuck and enjoy a complimentary tasting of the sweet and briny fresh Maine oysters. Stand-up paddle boarding is a great, fun way to sight see from the water. We are likely to see cormorants, sea gulls, osprey, great blue herons, snowy egrets, ducks, and we might see fish jumping or a seal. Paddlers at least 12 years old will love exploring Casco Bay in this protected, scenic, historic area! There will be a break on land where we will stretch, taste the oysters and have some snacks that you bring.
5.0(2)
2 hr 30 min
Portland, United States
Free cancellation
Likely to sell out
From
$92
No similar experiences found
Musement
Portland Happy Hour Sightseeing Cruise
Admire the sights of Portland from a different perspective, enjoy the city skyline and the narration of the historic waterways of the Willamette River.
1 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$38
No similar experiences found
Viator
Private Yacht Tour in Portland, Maine 2hr, 4hr and 6hr Available
Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups, this exclusive charter offers a personal adventure, allowing you to encounter marine wildlife, view iconic lighthouses, and discover unique islands at your own pace. With flexible scheduling and customizable experiences, this cruise promises an unforgettable day on the water, complete with opportunities for swimming and exploring Maine’s rugged coastline. - Private cruise for up to 6 passengers, ensuring an exclusive experience - Encounter marine wildlife like seals, porpoises, and seabirds - View famous lighthouses including Portland Head Light and Bug Light - Flexible departure times and customizable itineraries available – Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability
5.0(2)
2 hours - 6 hours
Portland, United States
Free cancellation
Private tour
New
From
$648
No similar experiences found
Musement
Champagne brunch cruise on Willamette river
Experience Portland's love of brunch with a 2-hour cruise brunch on the Willamette River.
4.5(2)
2 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$102
No similar experiences found
Viator
Scenic Sebago Lake Historical Tour by Kayak
Kayak through the natural Maine wilderness and vast lake views for an on the water adventure. This two hour guided tour will begin with a safety briefing and lesson covering the fundamentals of recreational kayaking. Using the EZ launching system at Sebago Trails Paddling, the tour will explore the water-carved bends and twists of a meandering stream unveiling local wildlife in a rustic backdrop. Then continue onto Jordan Bay of Sebago Lake as the guides share stories dating back to the settlements of the region.
5.0(1)
2 hours
Portland, United States
Free cancellation
From
$54
No similar experiences found
Musement
Lunch cruise on the Willamette river
Taste delicious Northwest cuisine and beautiful river views on this cruise on the Willamette River.
2 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$87
No similar experiences found

Viator

Guided RIB Boat Adventure of Portland

5.0(35)

1 hr 30 min

Portland, United States

Free cancellation
Likely to sell out

From

$69

Musement

Portland Bigfoot high-speed boat adventure

3 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$90

Viator

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

5.0(2)

2 hr 30 min

Portland, United States

Free cancellation
Likely to sell out

From

$92

Musement

Portland Happy Hour Sightseeing Cruise

1 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$38

Viator

Private Yacht Tour in Portland, Maine 2hr, 4hr and 6hr Available

5.0(2)

2 hours - 6 hours

Portland, United States

Free cancellation
Private tour
New

From

$648

Musement

Champagne brunch cruise on Willamette river

4.5(2)

2 hours

Portland, United States

Free cancellation
Instant confirmation

From

$102

Viator

Scenic Sebago Lake Historical Tour by Kayak

5.0(1)

2 hours

Portland, United States

Free cancellation

From

$54

Musement

Lunch cruise on the Willamette river

2 hours

Portland, United States

Free cancellation
Instant confirmation

From

$87

Cultural & historical in Portland

Museums, ruins, art collections, religious sites with expert guides

See all

Musement
Mount Hood Scenic Loop self-guided driving audio tour
Download the Action Tour Guide app for a self-guided 4x4 tour of Mount Hood Scenic Loop. Discover cascading waterfalls, panoramic viewpoints and historic sites.
2 hours - 3 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$17
No similar experiences found
Viator
Portland Head Light and Fort Williams Walking Tour
Learn about the rich history of Fort Williams park, Portland Headlight and Casco Bay on this guided walk. Designed for both history lovers and casual explorers, this tour offers an immersive journey from the majestic Portland Head Light, along the beautiful cliff walk path to the crumbling relics of the Fort's past. You will learn about Fort Williams and Portland headlight's storied past, from the American Revolution to World War II, with a knowledgeable local tour guide and have opportunities to stop for photos of the iconic lighthouse on this tour. The tour ends with an opportunity to explore the last unburied artillery battery and bunker at the park, a fun adventure that ties in the military history with exploration. What to Expect: Start Point: Portland Headlight Parking Lot End Point: Ship Cove Duration: Approximately 1 hour Distance: About 0.8 miles of walking Audience: Perfect for families, new visitors, history buffs, and anyone curious about Maine’s legendary coast.
5.0(9)
1 hour
Portland, United States
Free cancellation
From
$35
No similar experiences found
Musement
Discover Portland half-day small-group city tour
Explore the "Central City", making stops at Pittock Mansion, the International Rose Test Gardens, and the Portland Aerial Tram.
3 hours
Portland, United States
Free cancellation
Instant confirmation
From
$75
No similar experiences found
Viator
Private Portland to Cape Ann, MA Castles & Coast
Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blends grand seaside estates, medieval-style architecture, colonial history, and authentic harbor towns into one unforgettable journey. Admission is included to the breathtaking Crane Estate at Castle Hill in Ipswich, where sweeping lawns lead to panoramic Atlantic views. A favorite filming location for major Hollywood productions, its dramatic setting feels timeless and cinematic. You’ll also enjoy a guided tour inside Hammond Castle, a stunning 1920s seaside castle overlooking the ocean. Explore historic Ipswich, one of America’s oldest towns, and visit Gloucester’s iconic Fisherman’s Memorial while strolling its working harbor. With private transportation and relaxed pacing, this tour offers an elegant and memorable way to experience the beauty, history, and charm of coastal Massachusetts in a single day.
5.0(3)
8 hours - 10 hours
Portland, United States
Free cancellation
Private tour
From
$350
No similar experiences found
Musement
Portland city and Gorge waterfalls tour
Explore the Gorge Waterfalls on the Portland city and Gorge waterfalls tour. Book now on Musement!
8 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$161
No similar experiences found
Viator
Private Portland to Camden & Midcoast Lighthouse Experience
Join us for an exciting Private Coastal Tour from Portland to Camden, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is Camden Hills State Park, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie. We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!
5.0(1)
7 hours - 9 hours
Portland, United States
Free cancellation
Private tour
From
$350
No similar experiences found
Viator
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows! As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor. This is The Real Portland Tour! Check my website for a complete listing of tour days, times, and availability.
5.0(1581)
1 hr 45 min
Portland, United States
Free cancellation
Likely to sell out
From
$74
No similar experiences found
Viator
Sunset Sea Kayak Tour on Casco Bay
The hours just before sunset offer the best time for paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough along the waterfront or into the islands to enjoy a panoramic view of the sun setting over the city as we paddle back to the East End Beach. This two-hour tour is designed for paddlers of all experience levels -- including first-time kayakers. The exact route you take will depend on the weather conditions and the group's interests and experience, but the Sunset Tour often starts out venturing into the waterfront of Portland harbor, and then into the open waters towards the islands of Casco Bay. We will cancel this tour if there is steady rain, strong winds or other conditions that we believe will prevent guests from having a great paddling experience. However, we will run our tours when there are light showers, overcast skies or cooler than average temperatures.
4.9(113)
2 hours
Portland, United States
Free cancellation
Likely to sell out
From
$60
No similar experiences found

Musement

Mount Hood Scenic Loop self-guided driving audio tour

2 hours - 3 hours

Portland, United States

Free cancellation
Instant confirmation

From

$17

Viator

Portland Head Light and Fort Williams Walking Tour

5.0(9)

1 hour

Portland, United States

Free cancellation

From

$35

Musement

Discover Portland half-day small-group city tour

3 hours

Portland, United States

Free cancellation
Instant confirmation

From

$75

Viator

Private Portland to Cape Ann, MA Castles & Coast

5.0(3)

8 hours - 10 hours

Portland, United States

Free cancellation
Private tour

From

$350

Musement

Portland city and Gorge waterfalls tour

8 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$161

Viator

Private Portland to Camden & Midcoast Lighthouse Experience

5.0(1)

7 hours - 9 hours

Portland, United States

Free cancellation
Private tour

From

$350

Viator

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

5.0(1581)

1 hr 45 min

Portland, United States

Free cancellation
Likely to sell out

From

$74

Viator

Sunset Sea Kayak Tour on Casco Bay

4.9(113)

2 hours

Portland, United States

Free cancellation
Likely to sell out

From

$60

Outdoor & adventure in Portland

Bike tours, e-bikes, kayaking, rafting, anything outside

See all

Musement
Portland parks and bridges 3-hour bike tour
Get your introduction to Portland with a fantastic 9-11 mile ride through neighborhoods, across bridges, stopping at parks and beaches.
3 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$63
No similar experiences found
Viator
Private Half Day Sailing Charter in Portland Maine
A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.
5.0(1)
4 hours
Portland, United States
Free cancellation
Private tour
New
From
$475
No similar experiences found
Musement
Columbia Gorge Waterfalls Botanical Discovery Hike
Hike through lush landscapes to the Columbia River Gorge, learn about medicinal and culinary flora and fauna from an expert naturalist guide.
3 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$125
No similar experiences found
Viator
Casco Bay Half-Day Sea Kayak Tour
Explore the beautiful islands of Casco Bay in this four-hour sea kayak tour. After a brief lesson on the basics of sea kayaking, you'll set out with a licensed Maine Guide. The small group will island-hop through the bay, looking out for seals and seabirds and enjoying the views of lighthouses, 19th-century forts and other fascinating landmarks. We’ll stop at an island for a break and a snack provided by Portland Paddle. This is a great tour for anyone who wants to get a taste of sea kayaking in the rugged islands of the Maine coast. Our most popular trip!
4.9(58)
4 hours
Portland, United States
Free cancellation
From
$85
No similar experiences found
Musement
Rafting at the Columbia Gorge With Brewery and Lunch
Experience the thrill of whitewater rafting on the White Salmon River, admire the waterfalls of the Columbia River Gorge, and taste a delicious lunch.
8 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$295
No similar experiences found
Viator
Lighthouse Bicycle Tour from South Portland with 4 Lighthouses
Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble. Next, the tour will pass by Willard Beach before arriving at the final stop, the famous Portland Head Light located at Fort Williams Park in Cape Elizabeth. It is recommended that patrons bring a lunch or we can assist in purchasing lunch from a local food truck that serves Lobster Rolls.
4.9(122)
3 hours
Portland, United States
Free cancellation
From
$115
No similar experiences found
Musement
Columbia Gorge waterfalls hiking tour
Explore the most iconic waterfalls and overlooks of the Columbia River Gorge's steep rocky sides and hear interesting facts and old stories.
4 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$74
No similar experiences found
Musement
Columbia River Gorge hidden waterfalls bike tour
Ride along the Historic Columbia River Highway and admire some of the most beautiful waterfalls in the state exploring the Columbia River Gorge.
5 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$102
No similar experiences found

Musement

Portland parks and bridges 3-hour bike tour

3 hours

Portland, United States

Free cancellation
Instant confirmation

From

$63

Viator

Private Half Day Sailing Charter in Portland Maine

5.0(1)

4 hours

Portland, United States

Free cancellation
Private tour
New

From

$475

Musement

Columbia Gorge Waterfalls Botanical Discovery Hike

3 hours

Portland, United States

Free cancellation
Instant confirmation

From

$125

Viator

Casco Bay Half-Day Sea Kayak Tour

4.9(58)

4 hours

Portland, United States

Free cancellation

From

$85

Musement

Rafting at the Columbia Gorge With Brewery and Lunch

8 hours

Portland, United States

Free cancellation
Instant confirmation

From

$295

Viator

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

4.9(122)

3 hours

Portland, United States

Free cancellation

From

$115

Musement

Columbia Gorge waterfalls hiking tour

4 hours

Portland, United States

Free cancellation
Instant confirmation

From

$74

Musement

Columbia River Gorge hidden waterfalls bike tour

5 hours

Portland, United States

Free cancellation
Instant confirmation

From

$102

Day trips & excursions in Portland

Half-day to full-day trips out of the city - Pompeii, Tivoli, Tuscany, you name it

See all

Musement
7 Wonders of the Gorge Jetboat Adventure
Experience the majestic Columbia River Gorge on a thrilling jetboat tour from Portland. Enjoy awe-inspiring views and live narration by an expert guide.
3 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$90
No similar experiences found
Viator
New Hampshire White Mountains Day Tour
Our White Mountains Day Tour offers more than just scenic views—it’s a thoughtfully curated journey through New Hampshire’s most charming towns, historic covered bridges, and hidden natural wonders. Unlike larger, rushed tours, we keep our groups small for a more personal experience, allowing time to explore, photograph, and connect with each stop. From the iconic Kancamagus Highway to the massive Madison Boulder, every stop has a story—and our guides bring it to life. Guests also have the option to add a ride on the historic Mount Washington Cog Railway for an unforgettable summit experience.
5.0(2)
6 hours - 8 hours
Portland, United States
Free cancellation
Private tour
From
$325
No similar experiences found
Musement
Portland Culture Tour With Local Guide
Explore Portland hidden gems from a local's perspective, venture off the beaten path, and enjoy luxury transportation throughout the busy streets.
4 hours
Portland, United States
Free cancellation
Instant confirmation
English
From
$95
No similar experiences found
Viator
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.
5.0(2)
2 hours
Portland, United States
Free cancellation
Private tour
From
$675
No similar experiences found
Musement
Portland bike and local food carts tour
Ride your bike and learn the story of Portland's famous food carts and sample some of the best bites the city has to offer.
3 hr 30 min
Portland, United States
Free cancellation
Instant confirmation
English
From
$79
No similar experiences found
Viator
Casco Bay Morning Windjammer Sail
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. See Fort Gorges, Bug Light Park, and the beautiful Portland coastline. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.
4.9(29)
2 hours
Portland, United States
Free cancellation
From
$61
No similar experiences found
Musement
Mt. Hood Waterfall tour with lunch and wine tasting
On this tour, you'll enjoy a visit to Timberline Lodge on Mt. Hood, wine tasting, and a stop at Multnomah Falls, the tallest waterfall in Oregon.
8 hours
Portland, United States
Free cancellation
Instant confirmation
From
$155
No similar experiences found
Viator
Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll
Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthouses, and Portland’s history. Groups will generally see only 4 lighthouses (Bug Light, Spring Point, Portland Head Light, and Ram Island Ledge). Lunch will be provided by the award-winning "Bite into Maine" Food Truck
4.8(153)
5 hours
Portland, United States
Free cancellation
Likely to sell out
From
$165
No similar experiences found

Musement

7 Wonders of the Gorge Jetboat Adventure

3 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$90

Viator

New Hampshire White Mountains Day Tour

5.0(2)

6 hours - 8 hours

Portland, United States

Free cancellation
Private tour

From

$325

Musement

Portland Culture Tour With Local Guide

4 hours

Portland, United States

Free cancellation
Instant confirmation

From

$95

Viator

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

5.0(2)

2 hours

Portland, United States

Free cancellation
Private tour

From

$675

Musement

Portland bike and local food carts tour

3 hr 30 min

Portland, United States

Free cancellation
Instant confirmation

From

$79

Viator

Casco Bay Morning Windjammer Sail

4.9(29)

2 hours

Portland, United States

Free cancellation

From

$61

Musement

Mt. Hood Waterfall tour with lunch and wine tasting

8 hours

Portland, United States

Free cancellation
Instant confirmation

From

$155

Viator

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

4.8(153)

5 hours

Portland, United States

Free cancellation
Likely to sell out

From

$165

Transportation & transfers in Portland

Airport pickups, point-to-point transfers, and city transport

See all

Viator
Private Portland Lighthouses and Kennebunkport Tour - 12 Pax
All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van that can take up to 12 passengers. We’re happy to customize the experience to match your interests. This particular tour covers all the major sights in Portland, followed by a visit to the South Portland lighthouses, including admission to Fort Williams Park to see the Portland Headlight. After exploring Portland, you'll journey down the highway to Kennebunkport, a charming coastal village that served as the summer retreat for former President George W. Bush and his family. While we have a standard route, as a private tour, we can personalize the itinerary to suit your preferences.
5.0(4)
6 hours
Portland, United States
Private tour
From
$1,508
No similar experiences found
Viator
Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse
This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your pace, and a relaxed day along Maine’s scenic shoreline. Visit historic York’s colonial landmarks, walk through the Old Burying Ground, and enjoy views from John Hancock Wharf before stopping at Cape Neddick Light, one of New England’s most photographed lighthouses. Continue to Ogunquit for time at Perkins Cove, with the option for a short scenic stroll along the Marginal Way overlooking the Atlantic. In Kennebunkport, enjoy unhurried time in Dock Square to browse shops, walk the harbor, and dine at a local restaurant of your choice. A scenic stop at The Colony Hotel adds classic New England charm and sweeping coastal views. Because this tour is private, the experience remains flexible and comfortable, allowing you to explore at your own pace and focus on the scenery and stories that interest you most.
5.0(3)
6 hours - 8 hours
Portland, United States
Free cancellation
Private tour
From
$300
No similar experiences found
Viator
Private EBike Tour Portland Maine
Some cities are best seen from a car window. Portland, Maine is not one of them. On this fully private e-bike tour, it's just your group, a local guide, and five hours of spectacular coastal scenery — with a Maine lobster roll along the way. Ride through the Old Port's cobblestone waterfront and fishing piers. Climb to Fort Allen Park for sweeping Casco Bay views. Cruise the Eastern Promenade before crossing to South Portland to walk the breakwater to Bug Light, designed by the architect of the U.S. Capitol dome. Continue to Spring Point Ledge — the only lighthouse of its kind you can reach on foot — then Portland Head Light, commissioned by George Washington in 1791. Finish on the Western Promenade, a hidden hilltop park with views to the White Mountains that most visitors never find. Lunch is a fresh Maine lobster roll at a waterfront spot worthy of the occasion. No strangers, no set pace — just your group and the best of coastal Maine.
5.0(1)
5 hours
Portland, United States
Free cancellation
Private tour
New
From
$349
No similar experiences found
Viator
Large Group Private Wooden Boat Sightseeing & Lighthouse Charter
100% Private Charter for Groups up to 15 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate experience on Casco Bay. Unlike crowded public cruises, your group of up to 15 guests will enjoy the full comfort and charm of one of our classic wooden vessels—all to yourselves. Cruise past iconic lighthouses, historic granite forts, and stunning stretches of Maine’s coastline, with opportunities to spot harbor seals, seabirds, and other local wildlife along the way. Whether you’re celebrating a special occasion or simply gathering with friends, this charter offers a personalized, relaxed way to experience the best of coastal Maine. Feel free to bring your own food—we provide all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard. Due to our liquor license, we do NOT permit outside alcoholic beverages on board.
4.8(5)
2 hours
Portland, United States
Free cancellation
Private tour
Likely to sell out
From
$850
No similar experiences found
Viator
6 Hours Private Lighthouses and Kennebunkport Tour in Portland
All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.
4.7(20)
6 hours
Portland, United States
Private tour
From
$735
No similar experiences found
Viator
Private Portland Head Light & Midcoast Explorer
Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.
4.5(14)
6 hours - 8 hours
Portland, United States
Free cancellation
Private tour
From
$350
No similar experiences found
Viator
Camden, Rockland, Pemaquid, and Belfast Private Tour
Join us for an exciting Private Coastal Tour from Portland to Camden, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is Camden Hills State Park, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie. We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!
8 hours - 12 hours
Portland, United States
Free cancellation
Private tour
From
$350
No similar experiences found
Viator
Portland Jetport (PWM) to Portland - Arrival Private Transfer
Book your private Arrival transfer from Portland International Jetport (PWM) to Portland hotels. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.
15 minutes
Portland, United States
Free cancellation
Private tour
From
$86
No similar experiences found

Viator

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

5.0(4)

6 hours

Portland, United States

Private tour

From

$1,508

Viator

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

5.0(3)

6 hours - 8 hours

Portland, United States

Free cancellation
Private tour

From

$300

Viator

Private EBike Tour Portland Maine

5.0(1)

5 hours

Portland, United States

Free cancellation
Private tour
New

From

$349

Viator

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

4.8(5)

2 hours

Portland, United States

Free cancellation
Private tour
Likely to sell out

From

$850

Viator

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

4.7(20)

6 hours

Portland, United States

Private tour

From

$735

Viator

Private Portland Head Light & Midcoast Explorer

4.5(14)

6 hours - 8 hours

Portland, United States

Free cancellation
Private tour

From

$350

Viator

Camden, Rockland, Pemaquid, and Belfast Private Tour

8 hours - 12 hours

Portland, United States

Free cancellation
Private tour

From

$350

Viator

Portland Jetport (PWM) to Portland - Arrival Private Transfer

15 minutes

Portland, United States

Free cancellation
Private tour

From

$86

Private & luxury experiences in Portland

Private guides, VIP access, after-hours tours, premium small-group

See all

Viator
Sunset & Scenic Private Boat Tour of Portland & Casco Bay
Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline. Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.
5.0(19)
2 hours
Portland, United States
Free cancellation
Private tour
From
$650
No similar experiences found
Viator
Private White Mountains Tour with Mount Washington Cog Railway
Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region. The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum. The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.
5.0(6)
6 hours - 8 hours
Portland, United States
Free cancellation
Private tour
From
$395
No similar experiences found
Viator
Kennebunkport, York and Portsmouth NH Private Tour
Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean views, and savor local flavors. With a personalized itinerary, this tour offers the flexibility to explore at your own pace, while an expert guide provides insights into each destination. Enjoy a relaxed atmosphere with included snacks, bottled water, and lunch to keep you energized throughout the day. - Private tour lasting approximately 7 to 8 hours - Customizable itinerary to suit your interests - Included lunch, snacks, and bottled water - Pickup from your location in an air-conditioned vehicle
5.0(2)
7 hours - 9 hours
Portland, United States
Free cancellation
Private tour
From
$325
No similar experiences found
Viator
Self-Guided Audio Tour of Portland’s Historic Old Port District
Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom Trail, which honors the city’s fight for freedom and civil rights. The tour showcases the Old Port’s architectural charm and its transformation from a bustling shipping hub to a cultural center. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalization efforts of the 1970s. Join fellow history enthusiasts for a memorable journey through Portland’s past and present. — Explore the historic Old Port district, a cultural and commercial hub — Walk along the Portland Freedom Trail, learning about civil rights — Discover stories of resilience, fire, and maritime life — Ideal for history lovers and those curious about Portland's heritage
5.0(1)
2 hours - 2 hr 30 min
Portland, United States
Free cancellation
Private tour
From
$10
No similar experiences found
Viator
Private Sunset Charter on a Vintage Lobster Boat with Drinks
Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset. We’ll navigate through the islands of Casco Bay, passing by Portland’s most iconic coastal sights, including historic 19th-century forts, lighthouses, and the stunning Maine coastline. This experience is perfect for families and small groups, offering a completely private and personalized tour just for you. First round of alcoholic drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the view!
5.0(42)
2 hours
Portland, United States
Free cancellation
Private tour
Likely to sell out
From
$407
No similar experiences found
Viator
Private Sightseeing Charter on a Vintage Lobster Boat with Drinks
100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning Maine coastline. Charters depart from Portland’s Old Port and are perfect for families and small groups. Each charter is completely private for up to 6 guests, and all ages are welcome! First round of drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the breathtaking views!
4.8(66)
2 hours
Portland, United States
Free cancellation
Private tour
Likely to sell out
From
$380
No similar experiences found
Viator
Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks
Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It doesn’t get any more “New England” than this! This private charter is a flat rate for up to 6 guests—all ages welcome! Step aboard MONHEGAN, our sturdy lobster boat, equipped with rollable side canvas for comfort even if the autumn air is crisp. Cozy up with the blankets we provide and enjoy an authentic New England experience. To make your tour even more special, we’re including a round of drinks—choose from locally brewed Portland, Maine beer or a glass of wine as you soak in the breathtaking scenery.
4.6(11)
2 hours
Portland, United States
Free cancellation
Private tour
From
$380
No similar experiences found
Viator
Portland Maine Self-Guided Walking Audio Tour
Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picturesque coastal city as you traverse the cobblestone streets of Old Port and downtown. Learn about the city’s long, embattled history as you pass the myriad of shops, bars, and eateries which have put it on the map. And discover secrets only locals know! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.
4.5(12)
1 hour - 2 hours
Portland, United States
Free cancellation
Private tour
Special offer
From
$12
No similar experiences found

Viator

Sunset & Scenic Private Boat Tour of Portland & Casco Bay

5.0(19)

2 hours

Portland, United States

Free cancellation
Private tour

From

$650

Viator

Private White Mountains Tour with Mount Washington Cog Railway

5.0(6)

6 hours - 8 hours

Portland, United States

Free cancellation
Private tour

From

$395

Viator

Kennebunkport, York and Portsmouth NH Private Tour

5.0(2)

7 hours - 9 hours

Portland, United States

Free cancellation
Private tour

From

$325

Viator

Self-Guided Audio Tour of Portland’s Historic Old Port District

5.0(1)

2 hours - 2 hr 30 min

Portland, United States

Free cancellation
Private tour

From

$10

Viator

Private Sunset Charter on a Vintage Lobster Boat with Drinks

5.0(42)

2 hours

Portland, United States

Free cancellation
Private tour
Likely to sell out

From

$407

Viator

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

4.8(66)

2 hours

Portland, United States

Free cancellation
Private tour
Likely to sell out

From

$380

Viator

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

4.6(11)

2 hours

Portland, United States

Free cancellation
Private tour

From

$380

Viator

Portland Maine Self-Guided Walking Audio Tour

4.5(12)

1 hour - 2 hours

Portland, United States

Free cancellation
Private tour
Special offer

From

$12

Portland tour FAQs

Common questions about booking Portland experiences through SimilarTours

When's the best time to visit Portland for boat tours?

Summer and early fall (June through September) offer the most reliable weather and consistent tour schedules. Many operators do run year-round, but check before you go - some tours shift to weekends only in shoulder seasons, and winter sailings can be sparse.

How far ahead should I book a private boat charter?

For summer weekends, aim for at least 2-3 weeks out if you want a specific date. Weekday tours usually have more availability, and shoulder seasons are far more flexible. If you're flexible with timing, you'll have better luck.

Are the private yacht and sailboat tours actually worth booking over group options?

If you want to control the pace and focus - say, spending extra time at one lighthouse or timing it perfectly for sunset - private charters absolutely deliver. You're paying for that flexibility and a smaller group (many cap at 6-12 people). For a casual day on the water, group sails work fine too.

What's typically included in a Portland lighthouse or boat tour?

Most include the boat, captain, and narration about local history and the lighthouses you're seeing. Some are bare-bones cruises, others include drinks or snacks - check the individual listing before you book. Bring layers; it's cooler on the water than you'd expect.

Can I get around Portland without taking a boat tour?

Yes - the downtown waterfront is walkable, and you can see some lighthouses from shore. But the real experience of Portland's coast only happens when you're actually out on the water where these lighthouses sit. Most visitors who come for the scenery end up booking a charter or sail.

Are these tours good for families or people who get seasick?

Casco Bay itself is relatively sheltered, so motion is usually gentle - much calmer than open ocean sails. For nervous swimmers or very young kids, confirm vessel size and safety features before booking. If seasickness is a real concern, take medication beforehand and sit amidships where motion is least.

How do I get to the docks for a Portland boat tour?

Most tours depart from downtown Portland's waterfront, which is walkable from hotels and parking lots nearby. Check your confirmation for the exact dock location and arrival time - some require 15-30 minutes for check-in before departure.