10 Best North America Multiday Tours in May 2026

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Cyber Monday Super Sales

Toronto, Niagara, and Chicago with Western Classics - May 2026

No booking fees

Best price guaranteed

Iconic cities and breathtaking scenery await on the "Toronto, Niagara, and Chicago with Western Classics" guided city sightseeing tour. Perfect for seniors, this 16-day group adventure starts in Toronto and ends in San Francisco, with stops in Fresno, San Francisco, and several other North American gems. Enjoy easy-paced exploration with included hotels, meals, and transport. The unique selling point of this trip is its dual-country itinerary, offering a rare blend of Canadian and American highlights within a single, expertly organized package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, San Francisco, Niagara

Toronto, San Francisco, Niagara Falls, Detroit, Chicago, Los Angeles, Las Vegas, Flagstaff, Bakersfield, Fresno, CA

Duration16 days

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Cyber Monday Super Sales

Essential East Coast and Western Classics - May 2026

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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Cyber Monday Super Sales

Magic Chiapas - May 2026

Trip customizable

Best price guaranteed

Join our 4-day tour and go in the track of the world´s oldest civilization that ever existed in our history. Explore the unique archaeological site of Palenque, and unveil the heritage of the Ancient Mayan culture. Sail down the Sumidero Canyon and admire the gems of local nature, before you walk down the picturesque streets of San Cristobal de las Casas and enjoy its vibrant atmosphere in San Juan Chamula and Zinacantan. This trip is full of a rich and exciting adventure that will leave you with stories to tell for years!

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Tuxtla Gutiérrez, San Cristobal

Tuxtla Gutiérrez, San Cristobal De Las Casas, Palenque, Villahermosa

Duration4 days

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Cyber Monday Super Sales

Touring the East Coast end Toronto - May 2026

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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Cyber Monday Super Sales

Unmissable Canada with East Coast - May 2026

No booking fees

Best price guaranteed

Uncover the charms of Canada and the USA on the 'Unmissable Canada with East Coast' sightseeing tour, spanning 13 days from Montreal to New York. Designed for senior travelers, this guided group trip covers highlights such as Toronto and Montreal, as well as the vibrancy of New York and other select cities. With all logistics taken care of, you’re free to enjoy the journey at your own pace. What sets this tour apart is its focus on both Canadian warmth and American dynamism, providing a balanced and memorable exploration.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Montreal, Washington D

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

Duration13 days

View Tour

Cyber Monday Super Sales

Patriot Trails - May 2026

Trip customizable

Best price guaranteed

Embark on an unforgettable Eastern USA and Canada tour starting from the historic city of Boston and winding your way through fascinating destinations, including Quebec City, Montreal, Ottawa, Toronto, Niagara Falls, Gettysburg, Washington D.C., and concluding in the vibrant metropolis of New York City. This journey will take you through a blend of cultures, history, natural wonders, and iconic landmarks, providing a diverse and enriching travel experience

Adventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Massachusetts, Boston

New York, Massachusetts, Boston, Quebec City, Montreal, Toronto, Niagara, Amish Country, Washington D.C.

Duration9 days

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Cyber Monday Super Sales

Best Of Chiapas & Yucatan With The Maya Train, Italian-speaking Guide - May 2026

Trip customizable

Best price guaranteed

Experience the wonders of Chiapas and Yucatán on this unforgettable seven-day journey, highlighted by a scenic ride aboard the Maya Train, an innovative new rail route through the heart of the Yucatán Peninsula. Discover a perfect blend of ancient civilizations, dramatic landscapes, and vibrant colonial heritage. Stand in awe before the towering cliffs of Sumidero Canyon, immerse yourself in indigenous traditions, and cool off with a refreshing swim beneath the stunning waterfalls of Chiapas. Wander the cobbled streets of charming San Cristóbal and timeless Mérida, each echoing with history and local color. Explore majestic Mayan ruins at Palenque, Uxmal, and Chichén Itzá, icons of a mysterious past rising from the jungle. Conclude your adventure with a comfortable and memorable journey aboard the Maya Train to Cancún Airport.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

italian

Destinations

Cancún, San Cristobal De Las Cas

Cancún, San Cristobal De Las Casas, Palenque, Campeche, Merida, Chichen Itza

Duration7 days

View Tour

Cyber Monday Super Sales

Best Of Chiapas & Yucatan With The Maya Train - May 2026

Trip customizable

Best price guaranteed

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Cancún, San Cristobal De Las Cas

Cancún, San Cristobal De Las Casas, Palenque, Campeche, Merida, Chichen Itza

Duration7 days

View Tour

Cyber Monday Super Sales

Unmissable Canada, Niagara and Chicago - May 2026

No booking fees

Best price guaranteed

Journey from French-speaking Montreal to the towering skyline of Chicago on the 11-day 'Unmissable Canada, Niagara and Chicago' sightseeing trip. Tailored for seniors, the itinerary features Montreal, Toronto, Quebec City, Niagara Falls, and more, offering a rich selection of North American highlights. Group guidance, comfortable hotels, and all meals and transport are included for an effortless experience. This tour’s unique benefit is its blend of Canadian culture and American city life, promising a vivid and accessible adventure.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chicago, Montreal, Quebec City

Chicago, Montreal, Quebec City, Ottawa, Toronto, Niagara Falls, Detroit

Duration11 days

View Tour

Cyber Monday Super Sales

Raramuri Tour - May 2026

Trip customizable

Best price guaranteed

Start your journey in the magical town of El Fuerte and finish in the historic and colonial city of Chihuahua. Nominated as one of the best tourist routes. Travel from sea level to a height of more than 2400 meters. The train route is considered a masterpiece of Mexican engineering. Enjoy the views of incredible canyons and endemic natural beauty and get to know the Tarahumara culture.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, spanish

Destinations

Mexico City, Chihuahua, El Fuert

Mexico City, Chihuahua, El Fuerte, Divisadero, Creel

Duration5 days

View Tour

Hi there

North America Tours in May 2026

Page 10 of 209 Trips in North America during May 2026 with 1,898 Reviews

Toronto, Niagara, and Chicago with Western Classics - May 2026

Essential East Coast and Western Classics - May 2026

Magic Chiapas - May 2026

Touring the East Coast end Toronto - May 2026

Unmissable Canada with East Coast - May 2026

Patriot Trails - May 2026

Best Of Chiapas & Yucatan With The Maya Train, Italian-speaking Guide - May 2026

Best Of Chiapas & Yucatan With The Maya Train - May 2026

Unmissable Canada, Niagara and Chicago - May 2026

Raramuri Tour - May 2026

Page 10 of 209 Trips in North America during May 2026 with 1,898 Reviews

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Hi there

North America Tours in May 2026

Page 10 of 209 Trips in North America during May 2026 with 1,898 Reviews

Page 10 of 209 Trips in North America during May 2026 with 1,898 Reviews