East Coast Urban Exploration Cruises

from $13,940

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Grand New England Cruise

Roundtrip Boston - 15 Day Itinerary aboard American Patriot

Starts / Ends

Boston / Boston

Activity Level

Variable

Set sail on a 15-day cruise aboard American Patriot. Discover historic seaports and savor New England's charm with a Maine lobster bake.

• Explore Portland iconic lighthouses
• Discover Bath historic shipyards
• Explore Bangor Victorian mansions
• Discover Portsmouth architecture

Cruise Details

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from $11,030

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New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Independence

Starts / Ends

Portland / New York

Activity Level

Variable

Cruise the New England coast on a 16-day cruise from Portland to New York aboard American Independence. This journey delivers history, culture, and natural beauty through iconic destinations, guided tours, and onboard enrichment—all while experiencing the region’s fall colors and crisp sea air.

• View Cape Elizabeth lighthouses
• Discover Nantucket whaling history
• Walk Portland’s Old Port
• Visit Maine Maritime Museum

Cruise Details

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from $13,285

Savings

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New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Glory

Starts / Ends

Portland / New York

Activities

Wine Tasting

Activity Level

Variable

Sail the coast of New England on a 16-day New England Fall Foliage cruise aboard American Glory, visiting historic cities and scenic harbors from Maine to New York. This cruise blends history, coastal charm, and iconic landmarks with smooth sailing and guided excursions.

• Walk Portland’s working waterfront
• Tour Newport’s seaside mansions
• Walk at cobblestone streets
• Visit Gloucester’s Maritime Museum

Cruise Details

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from $6,710

Savings

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Maine Coast & Harbors Cruise

Portland - Bangor - 9 Day Itinerary aboard American Glory

Starts / Ends

Portland / Bar Harbor

Activity Level

Variable

Cruise Maine’s coast for 9 days aboard American Glory. Sail Casco Bay, visit a Bath oyster farm, explore Boothbay’s gardens, enjoy a Rockland lobsterbake, tour Acadia National Park in Bar Harbor, and walk its quaint downtown.

• Cruise through Casco Bay
• Sample fresh oysters in Bath
• Visit Boothbay Harbor's garden
• Taste a traditional lobsterbake

Cruise Details

0

from $7,070

Savings

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Hudson River Fall Foliage

New York - New York - 8 Day Itinerary aboard American Glory

Starts / Ends

New York / Catskill

Activities

Village Visits

Activity Level

Variable

Embark on a scenic Hudson River 8-day cruise from New York to Albany aboard American Glory. Visit historic sites in Sleepy Hollow, West Point, Kingston, Hyde Park, and Catskill. Enjoy scenic views, onboard enrichment, and cultural landmarks. Experience the beauty and history of the Hudson River on this unforgettable journey.

• Visit Sleepy Hollow landmarks
• Tour West Point Academy
• Discover Hyde Park’s history
• Admire Vanderbilt Mansion

Cruise Details

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from $6,350

Savings

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Yankee Seaports

Boston - New York - 8 Day Itinerary aboard American Glory

Starts / Ends

Boston / New York City

Activity Level

Variable

Join this 8-day Yankee Seaports cruise from Boston to New York aboard American Glory. Explore historic Boston before visiting picturesque Plymouth, MA, and the grandeur of Newport. Dive into maritime history in New London, Mystic, and Essex, CT. Lastly, enjoy an evening cruise around New York Harbor.

• Visit the Massachusetts Maritime
• Explore the Mystic Seaport Museum
• Travel to Old Saybrook
• Stroll around Sag Harbor

Cruise Details

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from $7,790

Savings

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New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty

Starts / Ends

Nantucket / Newport

Activity Level

Variable

Embark on an 8-day cruise aboard American Liberty through New England, exploring maritime history from Providence to Newport. Indulge in lobster bakes, visit whaling museums, and wander charming cobblestone streets.

• Enjoy Block Island's beaches
• Explore Whaling Museum New Bedford
• Discover Martha's Vineyard's towns
• Learn whaling legacy and maritime

Cruise Details

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from $8,600

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Montreal to New York, NY

Montreal - New York - 12 Day Itinerary aboard Silver Shadow

Starts / Ends

Montreal / New York City

Activities

Whale Watching, Wildlife Viewing, Kayaking

Activity Level

Variable

Embark on a 12-day cruise from Montreal to New York on the Silver Shadow, exploring Canada's Atlantic coast and New England's charm. Highlights include Quebec City, Prince Edward Island, and excursions like hikes and heritage walks, offering a blend of culture and relaxation.

• Discover Montreal’s landscape
• Explore Quebec City historic charm
• Experience Saguenay’s wilderness
• Stroll Charlottetown’s streets

Cruise Details

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from $7,299

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New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I

Starts / Ends

Portland / Toronto

Activity Level

Variable

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.

• Explore Portland
• Watch whales in Saguenay Fjords
• Walk Old Quebec streets
• Explore Charlottetown history

Cruise Details

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from $17,100

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Fall Foliage on the St. Lawrence: Québec to the Canadian Maritimes – with Smithsonian Journeys

Toronto - Boston - 15 Day Itinerary aboard Le Champlain

Starts / Ends

Toronto / Boston

Activity Level

Variable

On this 15-day Fall Foliage cruise from Toronto to Boston aboard Le Champlain, explore the stunning coastlines of eastern Canada and northern New England. Sail the St. Lawrence Seaway, visiting cities like Montréal, Québec City, and Charlottetown. Discover Nova Scotia's history in Baddeck, Louisbourg, and Lunenburg before concluding in Boston.

• Sail the scenic St. Lawrence Seaway
• Visit Montreal, a cosmopolitan city
• Visit Old Quebec, a UNESCO site
• Colonial seaport of Charlottetown

Cruise Details

0

from $7,299

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All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I

Starts / Ends

Chicago / Toronto

Activity Level

Variable

Embark on an 11-day Great Lakes cruise from Chicago to Toronto aboard Victory I, exploring cities, islands, and historical sites. Enjoy scenic sailings and unique excursions.

• Discover Michigan's Upper Peninsula
• Explore Detroit's Henry Ford Museum
• Stroll Chicago’s Navy Pier
• Visit Niagara Falls up close

Cruise Details

0

from $7,299

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All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II

Starts / Ends

Chicago / Toronto

Activity Level

Variable

Embark on an 11-day All Five Great Lakes cruise aboard Victory II, visiting iconic cities such as Chicago, Detroit, and Toronto. Discover scenic wonders like Mackinac Island and Niagara Falls, exploring rich history and culture along the way.

• Visit car-free Mackinac Island
• Sail through the Soo Locks
• Explore the Henry Ford Museum
• Visit Escanaba's lighthouse

Cruise Details

0

from $7,299

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All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I

Starts / Ends

Toronto / Chicago

Activities

Biking, Local Market Visits

Activity Level

Variable

Embark on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard Victory I, exploring vibrant cities and stunning natural landscapes. Enjoy historical tours and scenic sailing on this unique cruise through the heart of North America.

• Discover the diverse food scene
• Enjoy the vibrant nightlife
• Visit Niagara Falls
• Explore Niagara Peninsula

Cruise Details

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from $6,799

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All Five Great Lakes

Toronto to Chicago - 11 Day Itinerary aboard Victory I

Starts / Ends

Toronto / Chicago

Activity Level

Variable

Cruise the Great Lakes from Toronto to Chicago on an 11-day cruise aboard Victory I. Explore museums, historic districts, and natural wonders while enjoying relaxing scenic days at sea.

• See powerful Niagara Falls
• Explore Cleveland’s rock history
• Tour Milwaukee’s lakefront gems
• Visit peaceful Mackinac Island

Cruise Details

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from $6,799

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All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II

Starts / Ends

Toronto / Chicago

Activities

Urban Exploration, Archaeological Site Visits

Activity Level

Variable

Embark on an 11-day All Five Great Lakes cruise aboard Victory II and explore cultural hubs like Cleveland and Detroit, visit Niagara Falls, and relax on car-free Mackinac Island. Enjoy scenic days on Lake Ontario, Erie, Huron, Michigan, and Superior.

• Cruise all five Great Lakes
• Visit Niagara Falls up close
• Tour Cleveland’s museums
• Visit Mackinac Island

Cruise Details

0

from $7,299

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All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II

Starts / Ends

Toronto / Chicago

Activity Level

Variable

Set sail on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard a Victory II. Explore Toronto, Niagara Falls, Cleveland, Detroit, and Mackinac Island, experiencing unique landmarks and vibrant cultures.

• Explore Toronto
• Experience Niagara Falls
• Visit Henry Ford Museum
• Enjoy a horse-drawn carriage tour

Cruise Details

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from $7,999

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Great Lakes and St. Lawrence Seaway

Chicago - Montreal - 13 Day Itinerary aboard Victory I

Starts / Ends

Chicago / Montreal

Activity Level

Variable

Sail from Chicago to Montreal on a 13-day cruise aboard Victory I, exploring iconic cities, engineering marvels, and natural wonders. Scenic lake crossings offer time to unwind between dynamic destinations.

• Visit Willis Tower in Chicago
• Explore the Henry Ford Museum
• Visit Rock and Roll Hall of Fame
• Discover Toronto's culture

Cruise Details

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from $7,999

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Great Lakes and St. Lawrence Seaway

Montreal - Chicago - 13 Day Itinerary aboard Victory I

Starts / Ends

Montreal / Chicago

Activity Level

Variable

Embark on an unforgettable 13-day cruise from Montreal to Chicago aboard the Victory I, exploring all five Great Lakes. This voyage combines scenic sailing with onshore excursions, offering a unique blend of urban exploration and natural wonders.

• Discover the city of Toronto
• Visit the Henry Ford Museum
• Visit Lake Huron
• Savor local delicacies

Cruise Details

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