Route 66: The Great American Road Trip

Follow America's most legendary highway across the heart of the nation, with classic roadside Americana, unforgettable landscapes, and timeless small-town charm around every bend.

There's no road in America more legendary than Route 66. On this thoughtfully crafted journey from Chicago to Santa Monica, you'll experience the nostalgia, character, and enduring spirit of the Mother Road while traveling in the comfort of a custom-built Mercedes Sprinter designed specifically for small-group touring. Along the way, discover iconic roadside attractions, historic towns, classic diners, vintage motels, and some of the country's most remarkable landscapes, from the Painted Desert and Petrified Forest to the South Rim of the Grand Canyon.

Two memorable train journeys—including the historic Grand Canyon Railway—add another dimension to the adventure, while carefully selected hotels, exceptional sightseeing, memorable dining, and a relaxed pace allow you to fully savor the experience. From Chicago's Route 66 starting point to Santa Monica's famous "End of the Trail" sign, this is Americana at its most authentic and rewarding.


The UNCOMMON ROUTE 66 JOURNEY

  • The Mother Road: Experience the nostalgia, character, and timeless appeal of Route 66 from Chicago to the Pacific.

  • Travel Small, Travel Well: Enjoy a relaxed journey with just 24 travelers aboard a custom Mercedes Sprinter designed for comfortable sightseeing.

  • Icons of the American West: From Santa Fe and the Grand Canyon to the Painted Desert and Petrified Forest, discover some of the Southwest's most memorable landscapes and landmarks.

TOUR HIGHLIGHTS

  • Limited to just 24 travelers and fully escorted throughout, creating a relaxed, leisurely paced, and personal journey along America's most famous highway.

  • Follow historic Route 66 from Chicago to Santa Monica, tracing the legendary Mother Road across eight states and nearly a century of American history.

  • Experience classic American dining, from Chicago deep-dish pizza to iconic Route 66 diners to the famed Big Texan Steak Ranch.

  • Discover Route 66's most beloved roadside landmarks, including the Blue Whale of Catoosa, Cadillac Ranch, Pops 66, Roy's Motel & Café, and the Wigwam Motel.

  • Explore the Gateway Arch in St. Louis, America's soaring monument to westward expansion and one of the nation's most recognizable landmarks.

  • Spend two nights in enchanting Santa Fe, with time to enjoy its historic plaza, distinctive architecture, galleries, museums, and celebrated Southwestern culture.

  • Journey through the Painted Desert and Petrified Forest National Park, where colorful badlands and ancient fossilized forests create unforgettable scenery.

  • Overnight at historic La Posada in Winslow and stand on the famous corner immortalized by the Eagles.

  • Enjoy two nights in Williams and a full-day excursion aboard the historic Grand Canyon Railway to the South Rim of the Grand Canyon.

  • Travel one of the best-preserved stretches of Route 66 through Seligman, Peach Springs, and Kingman, where vintage Americana still thrives.

  • Celebrate your arrival at Santa Monica's iconic "End of the Trail" sign before a special farewell dinner marking the completion of an unforgettable American odyssey.

2027 JOURNEY Dates & PRICING

May 20 - June 1
October 14 - 26
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