East Coast Urban Exploration Cruises

from $13,940

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Grand New England Cruise

Roundtrip Boston - 15 Day Itinerary aboard American Patriot

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

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.

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

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

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.

Cruise Details

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from $13,285

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New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Glory

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

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.

Cruise Details

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from $6,710

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Maine Coast & Harbors Cruise

Portland - Bangor - 9 Day Itinerary aboard American Glory

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

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 Details

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from $7,070

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Hudson River Fall Foliage

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

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

Starts / Ends

New York / Catskill

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.

Cruise Details

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from $6,350

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Yankee Seaports

Boston - New York - 8 Day Itinerary aboard American Glory

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

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.

Cruise Details

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from $7,790

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New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty

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

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.

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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

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

Starts / Ends

Montreal / New York City

Activities

Whale Watching, 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.

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

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

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.

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from $12,670

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

Toronto - Boston - 13 Day Itinerary aboard Le Bellot

• Sail the scenic St. Lawrence Seaway
• Visit Montreal, a cosmopolitan city
• Explore Prince Edward Island
• Experience the Acadian culture
• Explore Nova Scotia and Lunenburg

Starts / Ends

Toronto / Boston

Activities

Wildlife Viewing, Urban Exploration, Village Visits

Activity Level

Variable

Explore eastern Canada and New England on a 13-day Smithsonian Journeys cruise. Sail from Toronto to Boston with stops in Quebec, PEI, Nova Scotia, and Cape Cod. Highlights include Montreal, Tadoussac, Magdalen Islands, Charlottetown, and Lunenburg. Includes expert talks and a shore excursion in each port.

Cruise Details

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from $17,100

EXPLORE

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

Toronto - Boston - 15 Day Itinerary aboard Le Champlain

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

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.

Cruise Details

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from $7,299

EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I

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

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.

Cruise Details

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from $7,299

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All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II

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

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.

Cruise Details

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from $7,299

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All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I

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

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.

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

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

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.

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

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

Starts / Ends

Toronto / Chicago

Activities

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 Details

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from $7,299

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All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II

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

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.

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from $7,999

EXPLORE

Great Lakes and St. Lawrence Seaway

Chicago - Montreal - 13 Day Itinerary aboard Victory I

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

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.

Cruise Details

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