10 Best North America Multiday Tours in September 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.

Premium Mexico In Depth - September 2026

22% OFF TODAY

Cyber Monday Super Sales

Premium Mexico in Depth - September 2026

No booking fees

Best price guaranteed

Journey through Mexico City, Puebla and Oaxaca on this 15-day Premium adventure. Weave your way through award-winning restaurants and hidden street food stalls, uncover the ancient secrets of the Teotihuacan, Cholula and Mitla ruins, and relax on the white sand beaches of Tulum. Explore the Chichen Itza archaeological site, visit the historic town of Merida and learn about traditional craft industries on an Exclusive Experience. Visit the Celestun Bird Sanctuary, stay in a 17th-century mansion and enjoy plenty of free time to explore Playa del Carmen at your own pace.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Mexico City, Tulum, Chichen Itza

Mexico City, Tulum, Chichen Itza, Merida, Puebla, Oaxaca, Puerto Morelos, Valladolid

22% OFF TODAY

Duration15 days

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22% OFF TODAY

Cyber Monday Super Sales

Best of Mexico - September 2026

No booking fees

Best price guaranteed

Raise a margarita to the beauty and culture of Mexico on this adventure. Discover Maya history at the incredible Chichen Itza ruins and visit Indigenous communities near the charming San Cristobal de las Casas. Indulge in a traditional pibil feast (slow roasted pork) with a Maya family and learn about Zapotec culture over lunch in a local home. Stroll the charming streets of Merida, be charmed by the alebrijes of Oaxaca and chill out on the beaches of Playa del Carmen. From museums and ruins to canyons and waterfalls, this journey will give you a taste of Mexico’s best.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Mexico City, Playa Del Carmen, P

Mexico City, Playa Del Carmen, Palenque, Merida, Oaxaca, Salina Cruz, San Cristobal De Las Casas

22% OFF TODAY

Duration15 days

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Cyber Monday Super Sales

The Grand East - September 2026

Trip customizable

Best price guaranteed

Visit cosmopolitan cities and state-of-the-art places like the Kennedy Space Center which exhibits modern space-age technology. Gaze upon the many monuments and museums the American capital is famous for in Washington D.C. Stay in historic Quebec City and cosmopolitan Montreal and stop in Canada’s elegant capital Ottawa including Toronto, the largest city in Canada. Visit the musical cities of Nashville and Memphis before a stop in the jazz city of New Orleans. Travel to the Gulf Coast to Florida, stopping in Orlando, and ending in sunny Miami

AdventureCity 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

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Cyber Monday Super Sales

New England's Fall Foliage, a Women-Only Tour - September 2026

No booking fees

Best price guaranteed

With a tapestry of vibrantly coloured leaves at every turn, New England in the autumn is a sight to behold. On this eight-day guided women-only tour, explore Boston, one of the oldest cities in the U.S., walking part of the red-brick Freedom Trail and seeing the hall that housed the country’s first-ever town meeting. Marvel at the bronzing leaves of Vermont’s trees as you travel to Stowe and visit the women-owned and -managed Bread and Butter Farm. In Montpelier, delight in a visit to a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ascend a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and join a MAKE TRAVEL MATTER® Experience for an insightful talk by a woman who is an expert on the North Woods' wildlife and ecology. With your small group of like-minded travellers, celebrate your trip with a decadent lobster dinner.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Boston, Saratoga Springs, Stowe

Boston, Saratoga Springs, Stowe, North Conway, Portland, ME

Duration8 days

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Cyber Monday Super Sales

Canadian Capitals with Chicago and the entire West Coast - September 2026

No booking fees

Best price guaranteed

Experience the grand sweep of North America’s diverse cities with the 'Canadian Capitals with Chicago and the entire West Coast' tour package, tailored for senior travelers seeking comfort and discovery. Over 20 leisurely days, this guided sightseeing trip begins in Montreal and winds through the vibrant capitals of Canada, the dynamic streets of Chicago and Detroit, and the iconic attractions of the West Coast before concluding in San Francisco. Carefully crafted for those who appreciate a relaxed pace, this journey offers accessible walks and plenty of rest, making it especially appealing for seniors. The itinerary covers noteworthy destinations such as Ottawa, Los Angeles, and multiple cities across both the USA and Canada, with all hotel accommodations, transport, and meals seamlessly included. What sets this tour apart is its harmonious blend of urban exploration and scenic journeys, providing a comprehensive North American experience with all the ease and comfort senior guests deserve.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

San Francisco, Montreal, Chicago

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

Duration20 days

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Georgia History Trail To Nashville - September 2026

22% OFF TODAY

Cyber Monday Super Sales

Georgia History Trail to Nashville - September 2026

No booking fees

Best price guaranteed

Uncover the history, culture and cuisine of the southern states on this eight-day adventure from Atlanta to Nashville. With a passionate local leading the way, you’ll take in the Southern gothic glory of Bonaventure Cemetery, walk the historic streets of Savannah and hear stories behind the landmarks of Charleston. Head to the Appalachian Mountains for a visit to Biltmore House in Asheville, the United States’ largest home. Then finish your adventure in the toe-tapping heartland of country and western music. If you want to do more than just see the sights, this immersive historic tour is calling your name!

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Atlanta, Savannah, Charleston, A

Atlanta, Savannah, Charleston, Asheville, Nashville

22% OFF TODAY

Duration8 days

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Cyber Monday Super Sales

Premium Mexico City to Oaxaca - September 2026

No booking fees

Best price guaranteed

When it comes to vibrant culture and varied cuisine, there’s nowhere quite like Mexico. Get a taste of the country’s best on an eight-day Premium adventure through Mexico City, Puebla and Oaxaca. Join expert local guides to uncover the ancient secrets of Teotihuacan, Cholula and the Mitla ruins and see the world’s widest tree, over 1500 years old! Take your taste buds on a trip, from the beckoning street food stalls of the capital to a home cooked Zapotecan lunch and a creative dining experience in Oaxaca and attend some local artisan workshops, working with obsidian and beeswax. Your experienced local leader will show you the heart of a country that is sure to leave you captivated.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Mexico City, Oaxaca, Puebla

Duration8 days

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Cyber Monday Super Sales

Canadian Capitals with Chicago and West Coast - September 2026

No booking fees

Best price guaranteed

Ready to uncover the best of Canada and the USA in comfort? The 'Canadian Capitals with Chicago and West Coast' tour offers a 16-day city sightseeing adventure, starting in Montreal and winding up in the dazzling lights of Las Vegas. Designed specifically with seniors in mind, this group tour balances gentle exploration with enriching experiences, taking you through Toronto’s lively streets, the architectural marvels of Chicago, and the natural beauty of Flagstaff. With accommodations, meals, and all transport arranged, you can immerse yourself in each destination without worry. The unique highlight of this tour is its effortless combination of Canada’s cultural hubs and America’s vibrant cities, making it ideal for seasoned travelers eager for diversity and ease.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Las Vegas, Montreal, Quebec City

Las Vegas, Montreal, Quebec City, Ottawa, Toronto, Niagara Falls, Detroit, Chicago, Los Angeles, Flagstaff

Duration16 days

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Cyber Monday Super Sales

Mexico Highlights (from Mexico City) Travel Pass - September 2026

No booking fees

Best price guaranteed

Discover Mexico’s vibrant culture and stunning landscapes with an unforgettable adventure starting in Mexico City. This immersive journey takes you to iconic landmarks like Teotihuacan’s pyramids, Oaxaca’s rich heritage, and breathtaking waterfalls in Palenque. You'll enjoy authentic culinary delights, explore historic cities, and experience Mexico’s diverse ecosystems firsthand. Perfect for culture enthusiasts and nature lovers, this tour offers unparalleled experiences, from ancient ruins to local traditions, delivering a comprehensive and captivating exploration of Mexico’s most celebrated highlights.

Snorkeling

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Mexico City, Cancún, Merida, Tul

Mexico City, Cancún, Merida, Tulum, Playa Del Carmen, Oaxaca, Puerto Escondido, Pochutla, San Cristobal De Las Casas

Duration17 days

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Cyber Monday Super Sales

Toronto, Niagara, and Chicago with Western Classics - September 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

View Tour

Hi there

North America Tours in September 2026

Page 7 of 122 Trips in North America during September 2026 with 785 Reviews

Premium Mexico in Depth - September 2026

Best of Mexico - September 2026

The Grand East - September 2026

New England's Fall Foliage, a Women-Only Tour - September 2026

Canadian Capitals with Chicago and the entire West Coast - September 2026

Georgia History Trail to Nashville - September 2026

Premium Mexico City to Oaxaca - September 2026

Canadian Capitals with Chicago and West Coast - September 2026

Mexico Highlights (from Mexico City) Travel Pass - September 2026

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

Page 7 of 122 Trips in North America during September 2026 with 785 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 September 2026

Page 7 of 122 Trips in North America during September 2026 with 785 Reviews

Page 7 of 122 Trips in North America during September 2026 with 785 Reviews