Illinois to California8 statesRoute 66 Tour Chicago to Santa Monica: 15 Days End to End
Next departureGuaranteed
From$5,890per person
Guided Route 66 road trips in small groups
16 guided trips in 8 states, 1 to 15 days, from $179 per person. The whole road from Chicago to Santa Monica or one stretch at a time, by small coach, classic convertible or motorcycle.
Often searchedFull routeGrand CanyonNeon signsMotorcycleNew MexicoDay tours
Per person sharing a double room. Flights to the start and home from the end are optional and priced on each trip.
Illinois to California8 statesNext departureGuaranteed
From$5,890per person
Illinois to California8 statesNext departureAvailable
From$6,890per person
Illinois to California8 states
New Mexico and Arizona
Oklahoma to New Mexico3 states
New Mexico
Illinois and MissouriNext departureAvailable
From$2,190per person
OklahomaDay tourNext departureAvailable
From$179per person
The places our guests ask for most, with the lowest price of a trip that stops there.












We drive the surviving two-lane alignments, brick and concrete included, and use I-40 only where 66 is gone.
Fourteen guests at most, twelve on convertible and motorcycle trips and ten on photography trips.
8 road captains who live along the route they lead. You know who meets you before you pack.
We book the restored 1930s to 1960s motels where we can, and good hotels in the cities.
The next date of each trip with seats. Prices per person, double room.
Real dates with real seats. Offers apply to new bookings only.
Last minuteUp to $350 off 13 departures with seats left: Arizona, California, Kansas, New Mexico, Oklahoma. From $159 per person.
See last-minute dates
Early bookingEvery 2027 departure of a multi-day trip with seats, booked by January 31, 2027. The deposit stays $300, and the price is fixed when you book.
How early booking works
Solo travelers4 spring 2027 departures where a room of your own costs nothing extra, while those rooms last.
See solo datesGift certificates from $100, or for a whole trip, sent by email as a printable PDF on the date you choose. Valid for three years on any departure.
Told by our guests and shared with their permission, with first names only. We do not publish star ratings.
I had seen the Blue Whale of Catoosa in a hundred pictures and expected to be underwhelmed. Earl timed it so we arrived in the last light, with the pond like glass, and it was lovely. The whole Oklahoma stretch was like that: he knew when to get somewhere, not just where. The onion burgers in El Reno were the best thing I ate all year.
Linda K., Ohio
Route 66 in OklahomaWe did the whole road for our 40th anniversary. Ray had a story for every town and never told the same one twice. Highlights for us were the Chain of Rocks Bridge, the night at the Blue Swallow and standing at the end of Santa Monica Pier after two weeks. The motels were small but spotless, and the coach always had cold water.
Robert and Ann M., Minnesota
Route 66 in IllinoisI live in Texas and thought I knew this road. I did not. The Neon and Diners trip showed me signs I had driven past at 70 miles an hour for years. The evening walk in Tucumcari with the motel owner explaining how the tubes are bent was a highlight, and so was the MidPoint Cafe pie.
Carol D., Texas
Route 66 in New Mexico
Grand CanyonRoute 66 to the Grand Canyon: Williams or Flagstaff as a base, the Grand Canyon Railway, how much time you need and the best sunset viewpoints.
MuseumsRoute 66 museums worth a stop in small towns, from the Hall of Fame in Pontiac and Galena's old station to the state museums in Clinton and Elk City.
FoodBest diners on Route 66, state by state: Lou Mitchell's, the Cozy Dog, Ted Drewes custard, onion burgers in El Reno, MidPoint pie and green chile.
Only guided small-group trips on Route 66: the whole road from Chicago to Santa Monica in 14 or 15 days, five section trips of 5 to 7 days, themed trips of 7 to 9 days, a Grand Canyon add-on and two day tours. Every trip has a road captain from start to finish.
A professional driver with a commercial license drives the coach, and the road captain looks after the group. The road captain never drives and guides at the same time.
Email [email protected] with the trip and date. We hold a seat for 72 hours, a $300 deposit per person confirms it, and the balance is due 60 days before departure. Day tours are paid in full when you book.
No, prices are for the trip itself. We can book flights into the start city and home from the end city, from 10 US cities, at the price shown on each trip page.
Up to 14 guests on coach trips, 12 on the convertible and motorcycle trips and 10 on the photography trip. The day tours take up to 14 and 12.
Driving, motels, heat, flights and more in the full FAQ.