10 Best North America Multiday Tours in May 2026

Southwest USA Canyons & Cultures - May 2026

No booking fees

Best price guaranteed

Discover the Southwest's most spectacular canyons and rich indigenous cultures on this unforgettable journey. Starting in Las Vegas, watch the sunset over the rim at the Grand Canyon. Head to Monument Valley and discover the sacred landscape and enjoy an evening around the campfire listening to stories and traditional music. Then journey deep into Canyon de Chelly with a Navajo guide who'll share traditional stories and insights into their living culture. Visit Mesa Verde National Park's UNESCO World Heritage cliff dwellings and trace the footsteps of Ancestral Puebloan civilization. Explore Durango's Mountain town atmosphere, then continue to Colorado Springs to see Garden of the Gods' dramatic red rock formations before ending your trip in vibrant Denver.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Lodge

Age Range

15-99 yrs

Operated in

english

Destinations

Las Vegas, Grand Canyon National

Las Vegas, Grand Canyon National Park, Monument Valley, Canyon De Chelly National Monument, Durango, Colorado Springs , Denver

Duration8 days

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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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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

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Patriot Trails - May 2026

Trip customizable

Best price guaranteed

Trace the footsteps of history and culture on the Patriot Trails trip, a 9-day guided adventure perfect for families, seniors, and curious young travelers. Starting in Boston, this tour winds through the heart of Eastern USA and Canada, including stops in Quebec City, Montreal, Ottawa, Toronto, Niagara Falls, Gettysburg, Washington D.C., and culminating in the vibrant metropolis of New York City. From the cobblestone streets of Boston to the thundering waters of Niagara Falls and the storied battlefields of Gettysburg, this easy-paced tour package immerses you in a rich tapestry of landmarks and local stories. Enjoy comfortable accommodations, group camaraderie, and seamless transportation as you explore a blend of heritage, natural beauty, and urban excitement. What makes this trip truly special? Its diverse, cross-border itinerary that brings together multiple cultures and iconic sites in a single, well-orchestrated journey—ideal for those seeking both enrichment and relaxation.

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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Walking in Jersey, Guernsey and Sark - May 2026

No booking fees

Best price guaranteed

For those who appreciate coastal beauty and slow travel, the "Walking in Jersey, Guernsey and Sark" tour unveils the charms of the Channel Islands in a way that rewards every step. This 7-day self-guided hiking adventure is tailored for experienced explorers seeking both relaxation and discovery. Breathe in salty breezes as you traverse Jersey’s dramatic coastline and Guernsey’s flower-draped cliff paths. Delight in Sark’s car-free tranquility, where the only traffic is horse-drawn or on foot. Meander through wooded valleys, quaint fishing villages, and along marinas dotted with inviting pubs. The unique selling point of this tour package is the rare chance to explore three distinct islands, each with its own character, at your own pace. With included accommodations, meals, and transport, it’s a refreshing escape into a world where time slows down and nature takes center stage.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

New York, Jersey, Guernsey

Duration7 days

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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

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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

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Maya Homestay Experience 2D/1N - May 2026

No booking fees

Best price guaranteed

Step off the beaten path and discover Guatemala’s living heritage with the "Maya Homestay Experience 2D/1N." Beginning in Panajachel and concluding at Iglesia de San Jorge La Laguna, this cultural tour package is perfect for young adults and seasoned explorers eager for an authentic connection. Spend two days immersed in the vibrant world of San Jorge La Laguna, where you’ll stay with a local Maya family and experience daily life firsthand. The relaxed pace of this trip allows you to fully engage with the community: learn traditional crafts, sample homemade Guatemalan dishes, and join guided visits to historic sites and bustling local markets. Each activity offers a window into the traditions, beliefs, and artistry of the Maya people. A highlight of this journey is the unique homestay, providing a rare opportunity for genuine cultural exchange and deep personal connections—something few travelers experience. All accommodations, transport, and meals are thoughtfully arranged, letting you focus on absorbing every moment of this immersive adventure. This tour’s USP is its authentic, community-focused approach: by living, learning, and sharing alongside your hosts, you gain a meaningful understanding of Guatemala’s indigenous culture—a truly unforgettable getaway for the curious traveler.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Home-stay

Age Range

18-99 yrs

Operated in

english

Destinations

Panajachel, San Jorge La Laguna

Duration2 days

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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

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Raramuri Tour - May 2026

Trip customizable

Best price guaranteed

Begin your Raramuri Tour in Mexico City and journey across a stunning tapestry of landscapes and cultures. This self-guided, five-day art and architecture trip introduces seniors and history lovers to the magic of El Fuerte, the engineering marvel of the train ride to more than 2400 meters elevation, and the rich heritage of the Tarahumara (Raramuri) people. Marvel at breathtaking canyons and unique natural beauty, experiencing one of Mexico’s finest tourist routes. The trip’s unique selling point lies in its seamless blend of indigenous culture, awe-inspiring scenery, and a train journey acclaimed for its engineering. This tour is perfect for those eager to discover authentic Mexico at a gentle, relaxed pace.

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

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North America Tours in May 2026

Page 31 of 558 Trips in North America during May 2026 with 73,136 Reviews

Southwest USA Canyons & Cultures - May 2026

Touring the East Coast end Toronto - May 2026

Unmissable Canada with East Coast - May 2026

Page 31 of 558 Trips in North America during May 2026 with 73,136 Reviews

Patriot Trails - May 2026

Walking in Jersey, Guernsey and Sark - 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

Maya Homestay Experience 2D/1N - May 2026

Unmissable Canada, Niagara and Chicago - May 2026

Raramuri Tour - May 2026

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North America Tours in May 2026

Page 31 of 558 Trips in North America during May 2026 with 73,136 Reviews

Page 31 of 558 Trips in North America during May 2026 with 73,136 Reviews