IllinoisDay tour
3 trips in 8 states
Route 66 classic car tours
Route 66 the way it looked in the postcards: from behind the wheel of a restored 1960s convertible, with the roof down and a mechanic following in a chase truck.
- Trips
- 31 end to end
- States
- 8Along Route 66
- Length
- 1 to 14 daysSmall groups
- From
- $249Per person
Classic car drives
Route 66 classic car tours: what to expect
On our convertible trips you drive yourself. The fleet is a small group of restored 1960s convertibles, among them Ford Mustangs and Chevrolet Impalas, maintained in Amarillo by our road captain Mike Tillman, who has rebuilt more carburetors than he can count. Two guests share each car and swap at every stop, so both of you get to drive and both get to look around.
The group drives in a loose convoy of up to six cars. A road captain leads in the first car with a radio in each vehicle, and a mechanic follows in a chase truck that also carries the luggage, because a 1965 trunk holds less than you think. Day 1 includes a full briefing: manual roofs, drum brakes on some models, and how far you can trust a sixty-year-old fuel gauge.
We run two convertible trips: the full road from Chicago to Los Angeles in 14 days, and an 8-day Southwest drive from Amarillo to Flagstaff, which covers the best open road on 66 with the Santa Fe loop and the Painted Desert. Drivers must be 25 or older with a valid license.
If you would rather ride than drive, our Chicago to Pontiac day trip puts three guests in each chauffeured classic, driven by members of a local car club who are happy to talk engines all day.
Fuel for the convertibles is included, and the chase truck carries spare parts, a fridge with cold drinks and a set of umbrellas for the photo stops. Cars are allocated by drawing names on the first evening, and pairs who want to try a different model can swap halfway.
Route 66 classic car tours: trips for 2026 and 2027
Per person sharing a double room. Optional flights to the start and home from the end are priced on each trip.
IllinoisDay tour
Illinois to California8 statesRoute 66 Convertible Tour: Chicago to LA in a Classic Car
Next departureAvailable
From$6,890per person
Texas to Arizona3 statesRoute 66 Southwest Road Trip by Convertible: Amarillo to Flagstaff
Next departureAvailable
From$4,590per person
Stops on our Route 66 classic car tours
The places these trips stop at most often. Each links to its section on the state page.
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Chicago and the Begin signIllinois, from $249
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PontiacIllinois, from $249
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Amarillo and Cadillac RanchTexas, from $2,290
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Albuquerque and Central AvenueNew Mexico, from $2,390
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GallupNew Mexico, from $2,390
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Petrified Forest and the Painted DesertArizona, from $2,890
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WinslowArizona, from $2,890
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Adrian, the midpointTexas, from $3,190
4 questions
Route 66 classic car tours: your questions answered
Do I need experience with old cars?
No. If you are comfortable driving a modern car you will manage. The briefing covers what is different, and the first morning is on quiet roads so you can get used to the steering and brakes.
What happens if a car breaks down?
The mechanic in the chase truck fixes most problems at the roadside within an hour. If a car needs longer, you ride in the chase truck or with another pair, and we swap in a spare car the next morning where we can.
Can a solo traveler come?
Yes. We pair solo guests in one car if they agree, or you can have a car to yourself for a supplement, shown as the single price, which also covers a single room.
Is there air conditioning?
Some cars have it, most do not, and the roof is usually down. We plan driving in the cooler hours and avoid July and August in the desert.
Free advice, no obligation
Route 66 classic car tours: which trip suits you?
Tell us the month, how many days you have and your budget. A trip advisor replies with the trips that fit.