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13 results | All Portland Tours

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Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

star-4.5
55
See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.
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  • 2 hours
  • Free Cancellation
From
$67.42
From
$67.42

Private Sunset Charter on a Vintage Lobster Boat
Likely to Sell OutLikely to Sell Out

Private Sunset Charter on a Vintage Lobster Boat

star-5
27
Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses and natural feature, and you're welcome to bring food and beverages, even the adult kind, on board.
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  • 2 hours
  • Free Cancellation
From
$600.00
per group
From
$600.00
per group

Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat
Likely to Sell OutLikely to Sell Out

Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

star-5
29
Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.
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  • 2 hours
  • Free Cancellation
From
$550.00
per group
From
$550.00
per group

Fall Foliage Private Sightseeing Cruise

Fall Foliage Private Sightseeing Cruise

star-5
4
Take in the famous autumn foliage of New England during a private 2.5-hour sightseeing cruise from Portland. With room for six people, it's an ideal intimate experience for couples, friends, or families. It’s also a great opportunity to photograph the leaves and wildlife from a unique perspective. Learn about the area from your private guide as you cruise at a gentle pace.
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  • 2 hours
  • Free Cancellation
From
$550.00
per group
From
$550.00
per group

2-Hour Private Sailing Charter

2-Hour Private Sailing Charter

There's something absolutely magical about traditionally-rigged wooden sailing vessels. Perhaps it's the epiphany that centuries-old technology can still be perfectly in harmony with our modern world. Or perhaps it's something else. Either way, we know you will fall under HESPER's spell the moment she sets sail. 2 hours will let you escape the hustle of the city and Portland Harbor, but still allow time for other activities. See lighthouses, historic stone fortresses, and the beauty of Casco Bay's islands. Relax on deck, or try your hand (with the help of our crew) at handling the rigging and learning how HESPER harnesses the wind. Book ONE TICKET for a group of up to 6.
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  • 2 hours
  • Free Cancellation
From
$550.00
per group
From
$550.00
per group

Portland, Maine Lighthouse Tour -2 hour Land Tour
Likely to Sell OutLikely to Sell Out

Portland, Maine Lighthouse Tour -2 hour Land Tour

star-5
364
Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Stop in downtown Portland, and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.
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  • 2 hours
  • Free Cancellation
From
$52.00
From
$52.00

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

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

star-5
615
Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.
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  • 1 hour 45 minutes
  • Free Cancellation
From
$57.00
From
$57.00

Vintage Fire Truck Sightseeing Tour of Portland Maine

Vintage Fire Truck Sightseeing Tour of Portland Maine

star-5
383
Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.
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  • 50 minutes
  • Free Cancellation
From
$35.00
From
$35.00

A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

star-5
227
Learn about Portland's history with this walking tour, which will take you through the Old Port, downtown, and waterfront areas. You'll see all sorts of historic attractions, including the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church, all with a professional guide on hand to share stories about the city's past.
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  • 2 hours
  • Free Cancellation
From
$49.99
From
$49.99

Around The Peninsula Bike Tour

Around The Peninsula Bike Tour

star-5
19
Explore the Portland Peninsula by bike with this guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of Portland's prettiest old brick buildings, and you learn the significance of local food, history and culture of this area.
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  • 3 hours
  • Free Cancellation
From
$79.00
From
$79.00

5 Lighthouse Bike Tour with XL Lobster Roll
Likely to Sell OutLikely to Sell Out

5 Lighthouse Bike Tour with XL Lobster Roll

star-4.5
35
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. We have made some modifications to the 5 Lighthouse tour in response to COVID-19. We have modified the tour to allow us not to have guests in our vehicles. As a result of this change, guests will begin biking from the Ocean Gateway and return to the Ocean Gateway by bicycle.  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
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  • 5 hours
  • Free Cancellation
From
$149.00
From
$149.00

Sunset Harbor Cruise

Special Offer

Sunset Harbor Cruise

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!
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  • 1 hour 30 minutes
From
$94.50
$105.00
$10.50 savings
From
$94.50
$105.00
$10.50 savings

Private Sunset Sailing Charter

Private Sunset Sailing Charter

This is the charter that needs no introduction. The name says it all and sells itself. Enjoy a great finish to your day in a way that only Maine can offer. There's a reason why sunset is the most popular time of day aboard all of our charter vessels. The light is just right, the harbor is less busy, and the world just seems to make more sense.
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  • 2 hours
  • Free Cancellation
From
$600.00
per group
From
$600.00
per group

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