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Portland Cruises

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Portland is one of North America's most beautiful and diverse cities, and there is no better way to explore it than on a cruise. Enjoy an up close and personal view of this vibrant city aboard a small ship cruise, that offers intimate sailing and the opportunity to watch whales, sea lions, and other wildlife along the coast. Admire the city's unique architecture, hike or bike in beautiful parks and forests, and enjoy panoramic views of the spectacular Oregon coastline. Start planning your Portland cruise today with Adventure Life.

Best Portland, Maine Cruises for 2026-2027

Beautiful seascapes in Maine

Maine Coast & Harbors Round-Trip Cruise

9 Days from $5,240
Explore Maine’s coast on a 9-day cruise from Portland aboard American Independence. Visit Bucksport, Bangor, Bar Harbor, Rockland, Camden, Boothbay Harbor, and Bath. Discover Fort Knox, Acadia National Park, maritime heritage, seafood traditions, and coastal communities across southern and midcoast Maine.
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Edgartown on Martha's Vineyard

Charm and heritage of the North American shores

9 Days from $7,180
Explore Canada and New England on a 9-day cruise aboard L'Austral. Visit Halifax, Lunenburg, Yarmouth, Eastport, Portland, Boston, Oak Bluffs, Newport, and New York. Discover maritime history, UNESCO heritage sites, coastal landscapes, iconic landmarks, and charming seaside towns throughout the voyage.
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Visit Portsmouth

New England and Canada

12 Days from $7,299
Experience a 12-day cruise from Portland to Toronto aboard Victory I and enjoy coastal views, local cuisine, and relaxing days at sea. This immersive journey blends Canadian culture, maritime history, and scenic waterways for a unique small-ship cruising experience.
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Stroll by the river running through Quebec City

Five Great Lakes + St. Lawrence Seaway: Portland to Toronto

13 Days from $7,299
Embark on a 13-day cruise Victory II and sail from Portland, Maine to Toronto, Ontario, calling at Nova Scotia, Prince Edward Island, Quebec City, and Montreal. This voyage links rugged Atlantic shores, deep glacial fjords, and Great Lakes channels into one seamless passage across North American coastal waterways.
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Fall Foliage on the St. Lawrence with Smithsonian Journeys

13 Days from $25,010
Sail Canada’s St. Lawrence Seaway on a 13-day cruise aboard Le Bellot. Visit Toronto, Montreal, Quebec, Tadoussac, Charlottetown, Magdalen Islands, Sydney, Lunenburg, Portland, and Boston. Enjoy whale watching, historic tours, cultural experiences, scenic landscapes, and regional cuisine throughout this journey.
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Colorful sunrise at Portland Head Lighthouse in Maine

East Coast: Jacksonville to Halifax

16 Days from $9,899
Sail from Jacksonville to Halifax aboard Victory I, visiting historic coastal ports in Georgia, South Carolina, North Carolina, Virginia, Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Nova Scotia. Explore waterfronts, museums, historic sites, mansions, naval landmarks, and lighthouses along the Atlantic coast.
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Portsmouth, New Hampshire

East Coast: Halifax to Jacksonville

16 Days from $9,899
Embark on a 16-day East Coast cruise aboard Victory I. Explore Halifax and Peggy’s Cove before visiting Portland, Portsmouth, Provincetown, Newport, and New London. Continue south to Norfolk, Wilmington, Charleston, Savannah, Brunswick, and Jacksonville. Experience New England’s coastal heritage, Southern history, and Atlantic scenery.
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Aerial View of Halifax Skyline

New England and Canada

10 Days from $5,999
Set sail on a 10-day cruise from Montreal to Portland aboard Victory I. Experience Montreal’s European charm and explore Quebec City’s historic streets. Enjoy whale-watching in Saguenay Fjord and discover Charlottetown’s coastal beauty. Sail through the Strait of Canso, visit Halifax’s bustling waterfront, and end in vibrant Portland, Maine.
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Charming Quebec City

Quebec City To Portland

12 Days from $6,799
Cruise from Quebec City to Portland on a 12-day cruise aboard Victory II, visiting Saguenay, Baie-Comeau, Gaspe, Charlottetown, and Halifax. Explore historic cities, coastal landscapes, the Saguenay Fjord, and maritime landmarks. Experience French Canadian heritage, Atlantic scenery, and historic ports across Canada and New England.
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Visit Portsmouth

5 Great Lakes + St. Lawrence Seaway: Montreal to Jacksonville

29 Days from $18,198
Embark on a 29-day voyage aboard Victory I, from Montreal to Jacksonville, linking the St. Lawrence Seaway with the Atlantic Seaboard. Walk Old Quebec, watch beluga whales in the Saguenay Fjord, and explore Halifax and Newport before reaching Florida.
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New England Travel Guide

Cruise the shores of New England

Top things to see and do on a New England cruise

From cycling to hiking to walking tours of cities, active travelers will enjoy all of the engaging activities that abound on a New England cruise, complemented by delicious seafood and wine and possibly opportunities to whale watch right from the deck of your small ship.
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The unique coastal town of Lunenburg.

How to choose the best New England cruise for you

What will your New England cruise be like? That depends on which one you choose! Each cruise is different, customized to what experiences you'd like to have, what sites you'd like to see, and how long you plan to travel.
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Explore the colors of fall

Best time to travel to New England

Whether you want to see the leaves in full transition in the Fall months of September and October or enjoy the summer months from May-August, find the perfect season to plan your New England vacation.
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New England in the fall

New England’s top cruise ports

As you journey through New England on our cruises, make stops in the top ports including Portland, Maine; Rockland, Maine; Bar Harbor, Maine; Boston, Massachusetts; Martha’s Vineyard, Massachusetts; Provincetown, Massachusetts; and Newport, Rhode Island, plus many others.
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Zakim Bridge reflection on the Charles River in Boston

Culture and history of New England

The culture of the New England region dates back hundreds of years and features some of the greatest historical highlights in North America's storied existence - our New England cruises highlight this culture and history.
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TrustScore 4.9 | 1050 reviews
TrustScore 4.9 of 5
total score
Based on 1050 reviews on
review score
21 hours ago
We just took our second trip arranged by Adventure Life. Their arrangements were perfect both times. The staff is incredibly knowledgeable and responsive. We will certainly work with them again.
Jennifer
review score
1 day ago
Perfect! UnCruise 2 Day Glacier Bay Adventure Cruise - arrangements made through Adventure Life. As we had traveled with Adventure Life previously I contacted them when we were interested in a small boat Alaska cruise. Adventure Life had the type of cruise we were interested and provided information, answered questions, and provided details. Emails received quick responses. We did the UnCruise 2 Day Glacier Bay Adventure Cruise which provided everything we wanted: small boat, activities (kayaking, hiking, ability to get close to nature. The UnCruise guides were terrific, knowledgeable and helpful. Safety was paramount. Expeditions were varied and long enough to be fun, short enough to be relaxing. Evening presentations were pertinent to what we saw or would be seeing. One evening included stories on the upper deck at sunset....wonderful. Food was excellent; the desserts were exceptional. The captain could be seen assisting kayakers into their kayaks, checking the skiffs, working with his crew. Scenery was unforgettable - from calving glaciers, sunrise on glaciers, whales alongside the vessel, This was an absolutely perfect trip.
Marian Alderman
review score
2 days ago
This was our 2nd Adventure Life trip. The information shared and the attention to details was appreciated. Everyone was very professional and worked hard to meet our trip requests. Communicating with the booking team was extremely easy.
Gordon
review score
4 days ago
Excellent planning help and the trip went smoothly.
Angela C
review score
6 days ago
If you go to the Galápagos, ask for James Sanchez as your guide he was fantastic! Very nice and extremely knowledgeable
Bob

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