Join us for a once-in-a-lifetime journey along the legendary Route 66 as we mark its 100th anniversary. From classic diners and vintage neon to historic landmarks and charming small towns, this tour captures the heart and soul of America's most iconic highway. With curated stops, cultural experiences, and plenty of photo-worthy moments, it's a nostalgic road trip adventure you’ll never forget. A $200 REFUNDABLE DEPOSIT holds your spot until April 2026. Limited to only 30 fun friends.
Day 1 After crossing the border, our first stop is for a fascinating visit to the Henry Ford Museum of American Innovation. After exploring this treasure trove of automotive and cultural history, we continue on to Chicago to kick off our Route 66 journey. Hampton Inn Majestic, Chicago IL
Day 2 Start the day with an included breakfast at the iconic Lou Mitchell’s, a legendary stop for Route 66 travelers. Enjoy a free day to shop or stroll the Windy City. Tonight, we dine at the historic Berghoff Restaurant — a Chicago institution since 1898. (B,D)
Day 3 We hit the road with a scenic drive to Joliet for a stop at the Joliet Area Historical Museum. More Route 66 photo ops pop up as we head to Pontiac, famous for its Murals. After a day filled with small-town charm, we check into our hotel. Hampton Inn, Pontiac IL (B,L)
Day 4 Today we visit the Ace Sign Co., home to a fun collection of vintage signage. After a cozy lunch, we tour the Route 66 Experience at the Illinois State Fairgrounds. This self-guided exhibit features vintage billboards, a drive-in theater, Legends Neon Sign Park, and a tribute to the famous muffler men. Our day ends in St. Louis. Pear Tree Inn, St. Louis MO (B,L)
Day 5 Explore the historic Chain of Rocks Bridge, ride to the top of the famous Gateway Arch, and cruise the mighty Mississippi River. It’s a day of discovery in St. Louis as we dive deeper into Route 66 lore and the spirit of the Midwest. (B,L)
Day 6 Take a relaxed drive into the Ozarks as we head for Springfield, Missouri. Our hotel embraces the region’s natural beauty and connection to the Wonders of Wildlife — the perfect place to unwind. Angler’s Lodge, Springfield MO (B)
Day 7 Step back in time this morning with Hot Rods & High Heels, a retro show full of music, memories, and 1950s flair. After lunch, enjoy a guided Golf Cart tour through the breathtaking Top of the Rock Lost Canyon. The late afternoon is yours to explore the massive Grandaddy Bass Pro Shop or the nearby Wonders of Wildlife Museum. (B,L)
Day 8 Our journey continues with more classic photo stops along the way before we arrive at the stunning Coleman Theatre — a beautifully restored 1929 vaudeville and movie palace. We visit the Will Rogers Memorial Museum, dedicated to one of Oklahoma’s most beloved sons. We end the day in Catoosa for a restful evening. Hampton Inn, Catoosa OK (B,L)
Day 9 We begin with a guided city tour of Tulsa, showcasing its rich history and vibrant culture. Then it’s time for a casual lunch at the Mother Road Market, a buzzing food hall filled with local flavors and Route 66 energy. Continuing along the route, we make our way to Oklahoma City, where we settle into the lively Bricktown District for a two-night stay. Residence Inn, Oklahoma City OK (B,D)
Day 10 Today we honor the resilience of the human spirit at the Oklahoma City National Memorial Museum, followed by a fun and fascinating visit to the American Banjo Museum, celebrating this uniquely American instrument. Tonight, enjoy a cowboy inspired dinner. (B,L,D)
Day 11 As we turn northeastward, we make a can’t-miss pit stop at Buc-ee’s — famous for clean restrooms, endless snacks, and quirky souvenirs. We soon arrive near St. Louis where Route 66 nostalgia meets roadside Americana. Holiday Inn Route 66, St Louis MO (B)
Day 12 This morning, we stop in Casey, Illinois, where small-town charm meets Guinness World Record-holding roadside attractions — from giant rocking chairs to oversized pencils. After some great photo ops and a bit of whimsy, we journey into Ohio just in time to relax at our hotel with a cheerful Happy Hour. Drury Inn & Suites, Dayton OH (B,HH)
Day 13 Time to say farewell to the Mother Road, carrying home memories of vintage signs, great food, and the enduring spirit of Route 66. Until next time, happy trails! (B)
Includes Deluxe Motor Coach Transportation, 12 Nights’ Accommodations, 12 Breakfasts (B), 6 Lunches (L), 3 Dinners (D), 1 Happy Hour (HH), Sightseeing & Visits as outlined, Carbon Offset, Services of Tour Director, and All Taxes
Price Per Person Twin $5495 Single $7275
Departs From: Waterloo, Kitchener, Cambridge