Portland
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Viator
Port City Lights Cruise
A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many as four lighthouses can be seen including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse.
4.8(260)
1 Hour
Portland
- Free cancellation
From
$39
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Viator
Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine
Learn about Maine's most famous crustacean and the men and women who make their living from trap to table. Stroll along Portland's vital working waterfront , view lobster boats often unloading their catch and visit Old Port and waterfront district destinations for a progressive, iconic Maine lunch. - This walking tour is appx. 1 - 1.5 miles visiting local favorites with plenty of food, and food for thought - lots of time for Q/A. - There's always a whole lobster roll, a New England clam or seafood chowder, local craft beer (or soda) plus a whoopie pie or other Maine sweet, and a surprise seafood taste or two along the way. This is our most “classic heritage” Maine experience with a bit of modern flare.
4.8(148)
3 Hours
Portland
- Free cancellation
- Likely to sell out
From
$160
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Viator
Discover Portland City and Lighthouse Tour
The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland peninsula. Towards the end of the tour, we make a 20-30 minute stop out at Portland Head Light in Cape Elizabeth.
4.8(1041)
1h 45m
Portland
- Free cancellation
- Likely to sell out
From
$57
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Viator
Sunset Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine 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. 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.
4.8(144)
2 Hours
Portland
- Free cancellation
From
$77
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Viator
Mobsters and Lobsters -True Crime in Portland's Old Port
Step into the shadows of Portland’s past on this thrilling true crime tour, where secrets lurk behind historic facades and cobblestone streets whisper tales of corruption, violence, and vice. From ruthless mobsters and bootleggers to power-hungry bosses and shocking scandals, this tour unveils the darker side of Maine’s largest city. Walk the very streets where speakeasies thrived, deals were made in the dead of night, and blood was spilled in the name of power. Led by expert guides, this journey through Portland’s underworld will leave you with spine-tingling stories you won’t soon forget. Dare to explore the city’s past? Book now—if you’re brave enough.
4.8(4)
1h 30m
Portland
- Free cancellation
From
$56
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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, making it easy to sip, savor, and soak in the scenery.
4.8(4)
2 Hours
Portland
- Free cancellation
- Private tour
- Likely to sell out
From
$850
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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
- Private tour
From
$735
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Viator
Small Group Afternoon Lighthouse Boat Cruise With Local Drinks
Have you seen these iconic beacons from the water? Now is your chance! Board the Elizabeth Grace to cruise around Portland Harbor on this one of a kind sightseeing cruise. It is the perfect way to see the lighthouses, historic stone forts, and rocky islands that make Casco Bay a world-renowned destination. Relax with a drink as you take in the scenery! GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!
4.7(55)
1h 30m
Portland
- Free cancellation
From
$87
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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
- Free cancellation
- Private tour
From
$380
No similar experiences found
Viator
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — 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). 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 ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.
4.6(186)
2 Hours
Portland
- Free cancellation
From
$69
No similar experiences found
Viator
Around The Peninsula Bike Tour
Discover the rich history and stunning architecture of the City of Portland . Only 3.5 miles long and 3/4 miles wide, the Portland peninsula is packed full of food, history, and culture. This 2.5-hour tour will show you the best of the peninsula.
4.6(43)
3 Hours
Portland
- Free cancellation
- Likely to sell out
From
$89
No similar experiences found
Viator
Small Group Sunset Lighthouse Boat Cruise With Local Drinks
Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep your eyes open for potential seal sightings, as well as the multiple lighthouses, islands, and forts you will see while cruising around. We will turn the bow toward Portland so you can take in a Maine sunset from the water and then cruise through Portland Harbor as the city’s nighttime skyline illuminates. You won’t find a more spectacular experience in Maine! GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!
4.6(96)
1h 30m
Portland
- Free cancellation
From
$97
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Viator
Walk With Ghosts in Portland
The most immersive way to see Historic Portland is on foot. Our 1 hour 15 minute walking tour takes you down the cobblestone pathways of our historic city in search of spirits that linger from times long past. Our knowledgeable guides will enchant you with tales of Portland’s most renown ghosts as well as the area's vast and rich history. You’ll hear fascinating and spooky tales from the first European settlement in 1632 right up to the present day. Discover the many times Portland has fallen and risen anew, and hear about the restless spirits who remain, unable or unwilling to move on. Follow our guides as they lead you by lantern-light sharing the ghost stories, legends, and folklore of this beautiful city.
4.6(75)
1h 15m
Portland
- Free cancellation
From
$33
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Viator
Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.
4.6(236)
2 Hours
Portland
- Free cancellation
From
$101
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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(11)
1 Hour - 2 Hours
Portland
- Free cancellation
- Private tour
From
$13
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Viator
2-Hour Portland Old Port Ghost Walking Tour
Step back in time to the bustling 18th Century port, where shipbuilding, trade, and whispers of strange occurrences at sea filled the air. Known for its picturesque waterfront, historic architecture, and vibrant arts scene, Old Port reveals its darker side at night. Supernatural tales include apparitions, psychic phenomena, and a sea serpent nicknamed Cassie.
4.5(38)
1h 30m - 2 Hours
Portland
- Free cancellation
From
$29
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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
- Free cancellation
- Private tour
From
$350
No similar experiences found
Viator
Portland's World of Flavors Tour
Introducing Portland’s World of Flavors Walk highlighting hidden gems and great flavors that give Portland its cosmopolitan flair. Enjoy this walkable city with a big palate on our international journey, tasting locally sourced foods prepared with the recipes, customs and spices from other lands. On this 2.5-3 hour tasty romp through Portland’s historic Old Port and waterfront, you will enjoy the flavors while learning their food pathways and the owners journeys to Maine. Portland’s World of Flavor serves up a diversity of tastes and ethnicities in a compact area, packing a punch of flavors you will love. All tour experiences are highly educational and entertaining with trained, local guides.
4.5(6)
3 Hours
Portland
- Free cancellation
From
$160
No similar experiences found
Viator
Afternoon Lighthouse Cruise Along the Coast of Portland Maine
Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.
4.4(66)
1h 30m
Portland
- Free cancellation
From
$64
No similar experiences found
Viator
Audio Guided Walking Tour from Old Port of Portland, Maine
On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.
4.2(54)
1 Hour - 1h 30m
Portland
- Free cancellation
- Private tour
From
$8
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Viator
Seven Portland Lighthouses Tour
As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This historic beacon, with its striking architecture and stark coastal backdrop, is a sight to behold from the perspective of the Atlantic Ocean as seafarers have done for more than 200 years. After photos and information about this iconic lighthouse, we continue the ride along the rocky shores of Cape Elizabeth to Two Lights State Park, whose twin lighthouses perch atop dramatic cliffs. Our best chance for wildlife comes during the next leg of the ride as we cruise open waters to Halfway Rock Lighthouse, a true maritime relic. Standing proudly on a remote ledge in the open ocean, it has guided mariners through thick fog and turbulent waters for over a century. Seals are often found hanging on the rocks and feeding in the nutrient-rich waters.
4.1(28)
2 Hours
Portland
- Free cancellation
- Likely to sell out
From
$109
No similar experiences found
Viator
Ultimate Portland Self-Guided Driving GPS Audio Tour
Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock full of shops, restaurants, and bars, all complemented by the sparkling bay. Dive into the city’s long and embattled history at a church still sporting British cannonballs. See iconic Maine lighthouses and visit pristine beaches. Portland may be a small city, but it packs a big punch! Purchase one tour per car, not per person. Everyone listens together! 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.
4.0(59)
1 Hour - 2 Hours
Portland
- Free cancellation
- Private tour
From
$17
No similar experiences found
Viator
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone streets and admire old brick architecture by the waterfront. Visit bustling neighborhoods like Old Port and the Art District, stop at shops and restaurants whenever you please, and breathe in the coastal air. Then take a drive out to the east and west promenades, before swinging down to the famous Portland Head Light lighthouse. It’s the most comprehensive way to experience this unique, quirky city! 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.
4.0(8)
3 Hours - 5 Hours
Portland
- Free cancellation
- Private tour
From
$25
No similar experiences found
Viator
Maine Whale Watching Tour in Portland
Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board a comfortable vessel equipped for a thrilling marine adventure. As we cruise along the rugged coastline, keep your eyes peeled for the majestic giants of the sea – humpback whales, fin whales, and minke whales are frequently spotted in these waters. Our experienced naturalist guides will be with you every step of the way, providing fascinating insights into the behavior and biology of these incredible creatures. The tour also offers the opportunity to observe a variety of other marine life, including seals, porpoises, and a wide range of seabirds. Don't forget to bring your camera, as you'll want to capture these unforgettable moments.
4.0(45)
3h 30m
Portland
- Free cancellation
- Likely to sell out
From
$129
No similar experiences found
