Boston City sightseeing Trips in 2025/2026

Touring the East Coast end Toronto

No booking fees

Best price guaranteed

Picture yourself journeying from the heart of the USA to Canada’s cosmopolitan hub on the 'Touring the East Coast end Toronto' trip. Over 12 days, this guided city sightseeing tour leads you from Washington D.C. through Ottawa and Toronto, as well as several other key cities. Created for seniors, the pace is gentle and the logistics seamless: comfortable hotels, included meals, and group transport ensure a smooth experience. The unique advantage of this tour is its focus on both American and Canadian highlights—offering a cross-border adventure packed with cultural discovery and relaxation.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Washington D.C., New Yo

Toronto, Washington D.C., New York, Boston, Montreal, Quebec City, Ottawa

Duration13 days

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Essential East Coast and Western Classics

No booking fees

Best price guaranteed

Explore the cultural treasures of North America on the 16-day 'Essential East Coast and Western Classics' tour, starting in New York and concluding in San Francisco. Designed with seniors in mind, this guided journey takes you through Montreal, Los Angeles, Bakersfield, and other vibrant cities. Enjoy leisurely sightseeing of historic and religious landmarks, all while staying in comfortable hotels and enjoying inclusive meals and transportation. What makes this tour stand out is its seamless blend of cultural heritage and modern cityscapes, ideal for those who appreciate both history and the comforts of well-organized group travel.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Los Ang

New York, San Francisco, Los Angeles, Bakersfield, Fresno, CA, Boston, Montreal, Quebec City, Ottawa, Toronto

Duration16 days

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From Washington to San Francisco

No booking fees

Best price guaranteed

From the historic streets of Washington D.C. to the iconic hills of San Francisco, the "From Washington to San Francisco" guided city sightseeing tour delivers an 18-day journey ideal for seniors. With stops in Montreal, San Francisco, and a range of vibrant American cities, this group adventure ensures comfortable accommodations, seamless transport, and included meals. The relaxed pace and varied itinerary make it an excellent choice for travelers seeking a thorough cross-country experience. Its USP is the rare opportunity to traverse the breadth of the USA while enjoying expert guidance and camaraderie.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., San Francisco

Washington D.C., San Francisco, Toronto, Los Angeles, Bakersfield, Fresno, CA, New York, Boston, Montreal, Quebec City, Ottawa

Duration18 days

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Essential East Coast, Niagara and Chicago

No booking fees

Best price guaranteed

From the bright lights of New York to the architectural wonders of Chicago, the 'Essential East Coast, Niagara and Chicago' tour is a 14-day city sightseeing trip designed for seniors. This guided journey covers Detroit, Toronto, and other key destinations, with all logistics managed for your ease. The highlight is its comprehensive route, encompassing both historic and modern marvels in an itinerary that balances excitement with comfort.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Chicago, Niagara Falls

New York, Chicago, Niagara Falls, Detroit, Boston, Montreal, Quebec City, Ottawa, Toronto

Duration14 days

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Essential East Coast

No booking fees

Best price guaranteed

Discover the best of the East Coast on a 7-day journey from New York to Quebec City with the 'Essential East Coast' city sightseeing tour. Travelers will enjoy stops in Boston, Quebec City, and New York, with all hotels, meals, and transport handled. This trip is especially suitable for seniors, with a relaxed pace and well-planned itinerary. The special feature is its concise yet thorough exploration of the region’s cultural highlights.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Quebec City, Boston, Montreal

Duration7 days

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East Coast Essential End Toronto

No booking fees

Best price guaranteed

The 'East Coast Essential End Toronto' tour invites you on a 10-day city sightseeing journey from New York to Toronto, stopping in Montreal, Quebec City, Ottawa, and more. Perfect for seniors, the trip is paced for comfort, with included accommodations, transport, and meals. Its unique selling point is the curated route through some of eastern North America’s most fascinating cities, offering both cultural depth and ease of travel.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Toronto, Boston, Montr

New York, Toronto, Boston, Montreal, Quebec City, Ottawa

Duration11 days

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Discover Eastern US and Canada

Trip customizable

Best price guaranteed

Imagine a journey that weaves together the cosmopolitan energy of New York, the historic charm of Quebec, and the natural spectacle of Niagara Falls—all in one unforgettable tour. "Discover Eastern US and Canada" is an 11-day guided city sightseeing trip designed for those who appreciate both cultural highlights and scenic wonders. Starting in New York City, experience its legendary vibrancy before heading to Boston, a cradle of American history. Journey into Canada to explore Quebec’s old-world streets, Montreal’s festive spirit, Ottawa’s lush parks, and Toronto’s iconic skyline crowned by the CN Tower. Marvel at the thundering Niagara Falls before crossing back into the US, where you’ll delve into the Amish way of life in Pennsylvania Dutch Country. Visit the poignant Gettysburg Civil War Memorial Battleground, then immerse yourself in the political and cultural heartbeat of Washington D.C. Round out your adventure in Philadelphia, home to Independence Hall and the Liberty Bell. With all accommodations, transport, and meals included, this trip offers a blend of guided discovery and relaxed travel. The unique selling point is its comprehensive itinerary, which merges the best of American and Canadian cities with natural marvels—making it perfect for travelers seeking a seamless, all-encompassing North American tour package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

New York, Washington D.C., Montr

New York, Washington D.C., Montreal, Boston, Quebec City, Toronto, Niagara Falls, Gettysburg

Duration11 days

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Essential East Coast and Unmissable West

No booking fees

Best price guaranteed

Curious about the ultimate North American odyssey? The 'Essential East Coast and Unmissable West' tour delivers 23 days of city sightseeing from the bustling avenues of New York to the scenic charms of San Francisco. Crafted for seniors, this journey promises a relaxing pace through a dozen destinations, including Detroit, Chicago, and Los Angeles, as well as key cities in Canada. With comfortable hotels, group transport, and meals included, every detail is managed so you can focus on enjoying each locale. The standout feature is the tour’s extensive itinerary, offering a rare opportunity to experience both coasts and everything in between, all in one seamless trip package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Niagara

New York, San Francisco, Niagara Falls, Detroit, Chicago, Los Angeles, Las Vegas, Flagstaff, Bakersfield, Fresno, CA, Boston, Montreal, Quebec City, Ottawa, Toronto

Duration23 days

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From Washington to Las Vegas

No booking fees

Best price guaranteed

Set off on a grand adventure from the nation’s capital to the entertainment capital of the world with the "From Washington to Las Vegas" city sightseeing tour. Spanning 21 days, this group trip covers Boston, New York, and 10 other destinations throughout the USA and Canada—crafted for seniors who value comfort and cultural immersion. With hotels, transport, and meals seamlessly included, you can relax and enjoy the journey’s diverse highlights. The tour’s unique selling point is its extensive, cross-country route, allowing you to experience a remarkable variety of cities and landscapes in one cohesive package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Las Vegas, Toro

Washington D.C., Las Vegas, Toronto, Niagara Falls, Detroit, Chicago, Los Angeles, Flagstaff, New York, Boston, Montreal, Quebec City, Ottawa

Duration21 days

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The Grand East

Trip customizable

Best price guaranteed

From the skyscrapers of New York to the palm-fringed shores of Miami, The Grand East tour delivers a sweeping panorama of North America in 20 days. This group adventure is perfect for families and travelers eager to blend cosmopolitan city life with cultural discovery. Visit Washington D.C.’s monuments, marvel at modern marvels like the Kennedy Space Center, and soak up the historic ambiance of Quebec City and Montreal. Journey through the musical capitals of Nashville, Memphis, and New Orleans, then unwind on Florida’s Gulf Coast before finishing in vibrant Miami. The trip’s unique selling point is its diverse itinerary—uniting iconic cities, world-class attractions, and a rich medley of American and Canadian experiences in one unforgettable tour package.

Adventure City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Roanoke, Gatlinburg, N

New York, Roanoke, Gatlinburg, Nashville, Memphis, New Orleans, Pensacola, Orlando, Miami, Boston, Quebec City, Montreal, Toronto, Niagara, Amish Country, Mount Washington, Washington D.C.

Duration20 days

Boston City Sightseeing Trips 2025/2026

Design your own personalized City sightseeing trip to Boston with help from a local expert.

Page 2 of 22 City sightseeing Trips in Boston with 119 Reviews

Page 2 of 22 City sightseeing Trips in Boston with 119 Reviews

Touring the East Coast end Toronto

Essential East Coast and Western Classics

From Washington to San Francisco

Essential East Coast, Niagara and Chicago

Essential East Coast

East Coast Essential End Toronto

Discover Eastern US and Canada

Essential East Coast and Unmissable West

From Washington to Las Vegas

The Grand East

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

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Boston City Sightseeing Trips 2025/2026

Design your own personalized City sightseeing trip to Boston with help from a local expert.

Page 2 of 22 City sightseeing Trips in Boston with 119 Reviews

Page 2 of 22 City sightseeing Trips in Boston with 119 Reviews