Urban Exploration Tours & Cruises

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

Activities

Biking

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 $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 $15,890

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Complete Mississippi River

New Orleans - St. Paul - 23 Day Itinerary aboard American Melody

• Explore Natchez's Grand Homes
• Visit Oak Alley
• Delve into Baton Rouge's history
• Unravel Vicksburg's Civil War

Starts / Ends

New Orleans / St. Paul

Activity Level

Variable

Discover the Mighty Mississippi on a 23-day cruise covering 10 states aboard American Melody. Immerse in history, culture, and cuisine from New Orleans to Minneapolis, exploring charming ports along the way.

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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.

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from $7,275

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Mississippi Explorer

New Orleans - Memphis - 12 Day Itinerary aboard American Symphony

• Explore Natchez's Grand Homes
• Visit Oak Alley
• Delve into Baton Rouge's history
• Unravel Vicksburg's Civil War

Starts / Ends

New Orleans / Memphis

Activities

Adventure Options

Activity Level

Variable

Set sail on a 12-day Mississippi river cruise aboard the American Symphony, from New Orleans to Memphis, visiting Southern landmarks like Oak Alley, Houmas House, and Vicksburg National Military Park. Explore Baton Rouge's history, Natchez's antebellum homes, and Cleveland's musical heritage.

Cruise Details

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from $4,255

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Historic Mississippi River Cruise

New Orleans Roundtrip - 8 Day Itinerary aboard American Melody

• Explore the antebellum of Natchez
• Visit historic Civil War sites
• Discover Oak Alley's historic charm
• Visit charming ports and cities

Starts / Ends

New Orleans / New Orleans

Activity Level

Variable

The American Melody hosts this 8-day Mississippi River cruise from New Orleans. Explore historic plantations, Civil War sites, and charming towns. Immerse in the rich culture, cuisine, and music of the Deep South.

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

Activities

Wine Tasting

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 $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 $7,999

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Great Lakes and St. Lawrence Seaway

Montreal - Chicago - 13 Day Itinerary aboard Victory I

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

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.

Cruise Details

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from $6,295

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Niagara and the Great Lakes

Toronto - Milwaukee - 8 Day Itinerary aboard Viking Great Lakes

• Toronto Exploration
• Explore Mackinac Island
• Niagara Falls & Welland Canal
• Point Pelee Birdwatching
• Detroit’s Innovation Legacy
• Alpena’s Maritime Adventures
• Mackinac Island & Milwaukee’s Charm

Starts / Ends

Lake Ontario / Milwaukee

Activities

Hiking

Activity Level

Variable

On this 8-day Niagara and the Great Lakes cruise from Toronto to Milwaukee aboard the Viking Great Lakes, explore nature and culture. Navigate the Welland Canal, witness Niagara Falls, and spot migratory birds at Point Pelee. Visit Detroit’s Henry Ford Museum, kayak in Alpena, tour Mackinac Island, and explore Milwaukee’s waterfront history.

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

• 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.

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

• 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

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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

• 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 $5,999

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New England and Canada

Montreal to Portland - 10 Day Itinerary aboard Victory I

• Explore Montreal's European charm
• Visit Halifax’s Citadel Hill
• Stroll Portland’s historic streets
• Enjoy a scenic whale-watching

Starts / Ends

Montreal / Portland

Activity Level

Variable

Set sail on a 10-day cruise from Montreal to Portland aboard the Voyager 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.

Cruise Details

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from $6,355

Savings

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Columbia & Snake Rivers Cruise

Portland - Clarkston - 9 Day Itinerary aboard American Jazz

• Explore Astoria's Victorian charm
• Step ashore in Kalama
• Discover Richland's scenic trails
• Cruise the legendary Snake River

Starts / Ends

Portland / Richland

Activities

Local Market Visits

Activity Level

Variable

Embark on a 9-day cruise aboard American Jazz, navigating the Columbia & Snake Rivers. Cruise past Mount Hood and Mount St. Helens, reliving the golden age of riverboats. Explore Astoria's Victorian charm and visit Fort Clatsop. Journey through history in The Dalles, Richland, and Pendleton, culminating in the majestic landscapes of Hells Canyon.

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