10 Best North America Multiday Tours in May 2026

Western Discovery - May 2026

No booking fees

Best price guaranteed

Fifteen days of exploration await on the Western Discovery trip, a group adventure designed for young adults and families with a passion for the great outdoors. Journey through the towering canyons and vibrant valleys of California, Nevada, Utah, and Arizona—making time for soulful towns and historic landmarks along the way. Highlights include sun-soaked days in San Diego, awe-inspiring vistas in Zion and Monument Valley, and the laid-back charm of California’s coastal cities. The trip’s easy pace ensures you have time to soak up each destination, while the standout feature is the balance of iconic sights and off-the-beaten-path experiences—perfect for those seeking both adventure and relaxation in one trip package.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Resort, Lodge

Age Range

18-75 yrs

Operated in

english

Destinations

Los Angeles, Modesto, San Franci

Los Angeles, Modesto, San Francisco, Napa Valley , Central Coast, Phoenix, Grand Canyon, Lake Powell, Bryce Canyon, Las Vegas, Fresno, CA

Duration15 days

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Mexico City to Cancun (via Guatemala & Belize) Travel Pass - May 2026

No booking fees

Best price guaranteed

Traverse the heart of Central America on the Mexico City to Cancun (via Guatemala & Belize) Travel Pass—a 30-day self-guided odyssey. Discover ancient Mayan ruins, colonial towns, and dazzling cenotes, while absorbing the vibrant cultures of three countries. This relaxed-paced trip is perfect for young adults and seasoned explorers seeking adventure blended with history. Accommodations, transportation, and meals are included, ensuring a smooth journey. The USP: unparalleled variety and depth, delivering cultural immersion and scenic discovery from bustling Mexico City to the tranquil beaches of Cancun.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Home-stay

Age Range

18-99 yrs

Operated in

english

Destinations

Mexico City, Cancún, San Jorge L

Mexico City, Cancún, San Jorge La Laguna, Panajachel, Antigua, Lanquin, Rio Dulce, Flores, San Ignacio, Oaxaca, Belize City, Caye Caulker, Chetumal, Bacalar, Tulum, Playa Del Carmen, Puerto Escondido, Pochutla, San Cristobal De Las Casas

Duration30 days

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Chicago to LA - May 2026

No booking fees

Best price guaranteed

Set out on a landmark adventure from the Windy City to the West Coast on the Chicago to LA trip, an 11-day journey crafted for young adults and families. Start with a lively day in Chicago, exploring its arts, dining, and nightlife, then hit the open road to discover the rugged beauty of Badlands National Park and the Black Hills. Continue through Wyoming’s mountain landscapes, trek the trails of Yellowstone, and marvel at the Grand Canyon’s grandeur. The trip concludes in the glitz of Las Vegas and the laid-back vibes of California. The USP here is the coast-to-coast exploration, offering a dynamic mix of city life, national parks, and classic American road trip appeal.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

18-75 yrs

Operated in

english

Destinations

Los Angeles, Chicago, Las Vegas

Los Angeles, Chicago, Las Vegas, Sioux Falls, Rapid City, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon National Park, Flagstaff

Duration11 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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New York to Hollywood - May 2026

Trip customizable

Best price guaranteed

From the vibrant streets of New York City to the glitz of Hollywood, the 'New York to Hollywood' tour offers a sweeping 17-day city sightseeing adventure across the USA. Designed for travelers of all ages—families, seniors, and young adults—this easy-paced trip covers iconic highlights including the historic landmarks of Philadelphia, the monumental sights of Washington D.C., the presidential faces of Mount Rushmore, and the natural wonders of Yellowstone National Park. Cruise along legendary Route 66, cross the Mojave Desert, and experience the high-octane energy of Las Vegas before arriving in sunny Los Angeles. The unique selling point of this tour package is its comprehensive, coast-to-coast exploration, offering a seamless blend of urban excitement and natural beauty, all with the comfort of guided group travel.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Lodge

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Los Angeles, Californi

New York, Los Angeles, California, Cody, Yellowstone National Park, Salt Lake City, Bryce Canyon, Flagstaff, Las Vegas, Washington D.C., Niagara Falls, Detroit, Chicago, Sioux Falls, Rapid City

Duration17 days

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Real Guatemalan Group Experience 8D/7N - May 2026

No booking fees

Best price guaranteed

Unlock the spirit of Guatemala with the "Real Guatemalan Group Experience 8D/7N." This immersive adventure tour, crafted for young and experienced travelers, takes you from the colonial charm of Antigua to the ancient wonders of Tikal. Trek volcanic peaks, browse colorful markets in Chichicastenango, and engage with local communities for genuine cultural connection. Each day is packed with active discovery and meaningful interactions, making this tour package ideal for those who crave authenticity and vibrant landscapes in one of Central America’s most captivating countries.

AdventureExplorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Guatemala City, Antigua, Chichic

Guatemala City, Antigua, Chichicastenango, Tikal

Duration8 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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Western Landscapes - May 2026

No booking fees

Best price guaranteed

Set out on a 13-day journey through the American Southwest with the Western Landscapes trip, perfect for young adults and families eager for adventure. Starting and ending in Los Angeles, this tour introduces you to the majestic national parks—like Bryce Canyon and the Grand Canyon—as well as lively cities and quaint backcountry towns. Optional activities, such as night tours and a wine-tasting in Napa Valley, add a personalized touch to your experience. The beauty of this trip lies in its ability to deliver daily variety: from star-studded nights in charming small towns to the dynamic pace of urban centers. The USP is its well-rounded itinerary, offering both natural wonders and local culture in a relaxed and engaging format.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Resort, Lodge

Age Range

18-75 yrs

Operated in

english

Destinations

Los Angeles, San Francisco, Napa

Los Angeles, San Francisco, Napa Valley , Central Coast, Phoenix, Grand Canyon, Lake Powell, Bryce Canyon, Las Vegas, Fresno, CA, Modesto

Duration13 days

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Riviera Maya Cenote Tour: Explore Yucatan And Quintana Roo (9 Days) - May 2026

Trip customizable

Best price guaranteed

With the Riviera Maya Cenote Tour, dive into the crystalline waters of Yucatán and Riviera Maya coast, and have a vacation full of unique and diverse activities! Arrive in Cancun and discover the Caribbean Sea basking in the warmth of the sun’s caress on Paradisiac Holbox Island’s pristine sandy shores. Also, refresh in multiple cenotes, and natural freshwater ponds formed by collapsing limestone, and immerse yourself in Mayan culture at the majestic world-famous archeological sites. In addition, admire the stunning bluish 7-color lagoon of Bacalar, savor the essence of tequila at a local factory, and wander through the charming colonial towns of Merida and Valladolid. This is the perfect getaway for island and beach enthusiasts eager to dive into Mexican history, culture, and nature. Come join our adventure trip to Cancun, Yucatán, and Riviera Maya wonders!

BeachAdventureLocal boat rides

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

12-69 yrs

Operated in

spanish, english

Destinations

Cancún, Holbox, Valladolid, Meri

Cancún, Holbox, Valladolid, Merida, Uxmal, Bacalar, Tulum, Playa Del Carmen

Duration9 days

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Mexico Youth Adventure - 14 days - May 2026

No booking fees

Best price guaranteed

GROUP TOUR (FOR AGES 18 to 49): Journey from Mexico City to Playa del Carmen on this 14-day Mexico group tour, taking in the best of the country's tropical beaches and historic sites. Take in the sights of Mexico City, enjoy leisure time in Oaxaca and enjoy a mezcal tasting in Tehuantepec. Spot monkeys on a boat cruise at the Sumidero Canyon, explore San Cristobal de las Casas and meet local communities in Zinacantan. Then fly to Cancun, gateway to the Yucatan Peninsula. Relax on the beaches of Isla Hoblox and Playa del Carmen, take a day trip to Tulum and enjoy an included visit to Chichen Itza, one of the New Seven Wonders of the World.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-49 yrs

Operated in

english

Destinations

Mexico City, Playa Del Carmen, I

Mexico City, Playa Del Carmen, Isla Holbox, Chichen Itza, Oaxaca, Tehuantepec, San Cristobal De Las Casas, Cancún

Duration14 days

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Hi there

North America Tours in May 2026

Page 9 of 161 Trips in North America during May 2026 with 233 Reviews

Western Discovery - May 2026

Mexico City to Cancun (via Guatemala & Belize) Travel Pass - May 2026

Chicago to LA - May 2026

Patriot Trails - May 2026

New York to Hollywood - May 2026

Real Guatemalan Group Experience 8D/7N - May 2026

Maya Homestay Experience 2D/1N - May 2026

Western Landscapes - May 2026

Riviera Maya Cenote Tour: Explore Yucatan And Quintana Roo (9 Days) - May 2026

Mexico Youth Adventure - 14 days - May 2026

Page 9 of 161 Trips in North America during May 2026 with 233 Reviews

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

Hi there

North America Tours in May 2026

Page 9 of 161 Trips in North America during May 2026 with 233 Reviews

Page 9 of 161 Trips in North America during May 2026 with 233 Reviews