Portland
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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)
1h 30m
Portland
- Free cancellation
- Likely to sell out
From
$69
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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
- Free cancellation
- Private tour
From
$650
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Viator
Sea Kayak to an Island Tour in Casco Bay
Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay! Often we paddle south to the end of Mere Point for a photo op and then on to visiting an island for a stretch break, snacks, and shoreline exploring. Then we paddle back on a different route close to an island to our launching point. Your Master Maine Guide will share history of the area while adapting the tour to paddling conditions and participants abilities. Sea kayaking is an easy, fun way to sightsee from the water. We often see different kinds of sea gulls, cormorants, ducks, great blue herons, snowy egrets, osprey and sometimes bald eagles. If we are lucky, we will see a seal. Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. This a family-oriented experience. Single and double kayaks are used on this guided tour by a Master Maine Guide.
5.0(8)
3 Hours
Portland
- Free cancellation
From
$89
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Viator
Portland Lighthouse 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.
5.0(5)
1h 30m
Portland
- Free cancellation
From
$137
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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)
2h 30m
Portland
- Free cancellation
From
$92
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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
- Free cancellation
- Private tour
From
$675
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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
- Free cancellation
- New
From
$149
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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
- Free cancellation
From
$54
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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.
5.0(21)
2 Hours
Portland
- Free cancellation
From
$61
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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(41)
2 Hours
Portland
- Free cancellation
- Private tour
- Likely to sell out
From
$407
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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.
4.8(104)
2 Hours
Portland
- Free cancellation
- Likely to sell out
From
$60
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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(65)
2 Hours
Portland
- Free cancellation
- Private tour
- Likely to sell out
From
$380
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Viator
Sunset Lighthouse Cruise Along Casco Bay
Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!
4.8(37)
1h 30m
Portland
- Free cancellation
From
$69
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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(65)
2 Hours
Portland
- Free cancellation
From
$119
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Viator
Morning 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.
4.8(58)
1h 30m
Portland
- Free cancellation
From
$59
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Viator
Sunset Lighthouse Cruise Tour from Casco Bay
This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the bay at dusk. Enjoy evening breezes and city lights on this fully narrated tour of Casco Bay. A great way to end a hectic day or begin a romantic evening!
4.8(141)
1h 45m
Portland
- Free cancellation
From
$56
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Viator
Harbor Lights and Sights Cruise
Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that guide mariners into Portland Harbor.
4.8(718)
1h 45m
Portland
- Free cancellation
From
$57
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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
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
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
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
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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