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Route 66: Classic American Road Trip

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April 9, 2025 - April 16, 2025 $1,999
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Route 66: Classic American Road Trip
1999

New! – Embark on a classic journey along Route 66. Enjoy quirky roadside attractions, vintage diners, and historic landmarks like the Gemini Giant and Route 66 Museum. Cross into Missouri and discover St. Louis, where the Gateway Arch welcomes you to the Mississippi River. This nostalgic road trip blends history, Americana, and scenic views into an unforgettable adventure.

Click here to view flyer & registration form

Highlights & Inclusions:

  • 8 Days | 7 Nights
  • 18 Included Meals
  • Vito’s Vault Speakeasy Dinner Theatre
  • Downtown Chicago Tour
  • Jacob Henry Mansion
  • Rialto Square Theatre
  • Abraham Lincoln National Cemetery
  • Gemini Giant Phot Stop
  • Polka Dot Drive-In Lunch
  • Wally’s: Home of the Great American Road Trip
  • American Giant’s Museum
  • World’s Largest Covered Wagon
  • 66 Motorheads Entertainment Complex
  • Abraham Lincoln Museum and Library
  • Maldaner’s Restaurant
  • Route 66 Neon Light Exhibit
  • Virden Square
  • Pink Elephant Mall
  • National Great Rivers Museum
  • Old Chain of Rocks Bridge
  • Gateway Arch Museum and Shop
  • Stay at The Palmer House
  • Stay at Drury Inn Union Station
  • Round Trip Motor Coach Transportation
  • Professional Tour Leader

Day 1
Wednesday, April 9

Depart Michigan anticipating the celebration of historic Route 66. The “Mother Road” was one of the U.S. first continuous stretches of paved highway. This week visit the iconic drive-ins, signs, museums and other quirky attractions that have made this road famous. On the way, stop at the Indiana Welcome Center for lunch, gift shop and exhibits. Arrive this afternoon at the Palmer House Hilton, a beautifully restored and decorated historic hotel right in the center of Chicago. Dinner and show this evening at Chicago’s only speakeasy dinner theater, Vito’s Vault. (L, D)

Day 2
Thursday, April 10

After breakfast at a local favorite restaurant, take a leisurely walking tour from Millennium Park to Buckingham Fountain, stopping at the “Begin” and “End Route 66” signs. Enjoy a light lunch at Del Rhea’s Chicken Basket, then head to Joliet, IL for the “First One Hundred Miles of Route 66” exhibit. End theday with a gourmet dinner and a tour of Jacob Henry Mansion, well-known for its beauty, Old Victorian Charm and furnishings. (B, L, D)

Day 3
Friday, April 11

Visit the historic Rialto Square Theatre, then continue to the Abraham Lincoln National Cemetery. Photo stop at the famous Gemini Giant in Wilmington. Enjoy lunch at the Polka Dot Drive'In before visiting various historic stops along Route 66, including the Ambler-Texaco Gas Station, two-cell jail, and the Old Route 66 Family Restaurant in Dwight. End the day in Pontiac, exploring the Historical Museum and the swinging bridges. This evening we'll stop at Wally's: Home of the Great American Road Trip for a bite to eat as well as fun shopping for kitschy Route 66 souvenirs. (B,L)

Day 4
Saturday, April 12

After breakfast, travel down Memory Lane, an original stretch of Route 66. This morning's activity includes a scavenger hunt at local sites such as the American Giant's Museum before lunch at the Country-Aire Restaurant in Atlanta, IL. Continue to Lincoln to see the World's Largest Covered Wagon and visit The Mill, a Route 66 Museum. End the day in Springfield with dinner and overnight accommodations. (B,L,D)

Day 5
Sunday, April 13

Start the day with a visit to 66 Motorheads Entertainment Complex. After lunch, make a pohoto stop at the Lauterbach Giant on our way to visit the Abraham Lincoln Museum and Library, where you can explore Lincoln's life from boyhood to presidency. Enjoy dinner at Maldaner's Restaurant, Springfield's oldest and finest. End the evening with a visit to the Illinois Fairgrounds to see the Route 66 neon light exhibit. (B,L,D)

Day 6
Monday, April 14

Travel down a brick-paved section of Route 66 to Virden Square and learn about the Virden Mine Battle. Visit the welcome center in Litchfield, IL, and enjoy lunch at a local restaurant. A stop at the Pink Elephant Mall might results in your best finds on the trip! Stop at the Skyview Drive-In Theatre befor heading to Alton, IL, for dinner at the Terrace at Aerie's Resorts, the best view in the Midwest! Overnight in Alton, IL. (B,D)

Day 7
Tuesday, April 15

After breakfast, visit the Robert Wadlow statue, a life-sized statue of the tallest man in the world. A stop at the National Great Rivers Museum lock and dam showcases the Mississippi River and its influence on our history. After lunch, stop at the old Chain of Rocks Bridge for a photo op and short stroll. Last stop: St. Louis, MO. Spend some time at the Gateway Arch and Museum and shop with an option to go to the top (or not!) Kick back evening snacks included at the Drury Inn located in the iconic Union Station. (B,L,D)

Day 8
Wednesday, April 16

Our journey home includes plenty of rest stops and an exciting lunch venue in Indianapolis wheree choices abound. Arrive home early evening with fun memories and plenty of photos to celebrate the Mother Road: Route 66!

Trip Facts

  • April 9-16, 2025
  • $1,999
  • $2,599
  • $1,819
  • $1,729