Route 66 Escorted Road Tour
Gilligans ' 27-Day Escorted Tour departing 17 September 2026
As you can imagine, the last few months have been pretty chaotic in regards to world travel, but throughout the ever-changing face of the world, we have continued to travel Route 66 and show our guests what makes heartland America so special, and despite perceptions: The USA remains a wonderful country to visit.
Given the fact 2026 marks the 100th Birthday of Historic Route 66 – we thought we’d add ONE LAST opportunity to drive Route 66 in 2026!
Our 27-Day “Official Tour” arrives in Chicago on SEPTEMBER 17th.
You’ll enjoy a 3-night stay in this fantastic city, before collecting your rental car and making your way out to the Santa Monica pier via old Route 66.
Averaging just 145 miles a day – you’ll experience a few of the oldest alignments (some that remain unsealed to this day) of this famous highway, stopping and visiting at historic places of interest along the way. You’ll meet some great locals, enjoy nights out with new friends and find your way easily with our supplied iPhone & APP, along with our 190+ page Route Book.
The tour includes a day to visit the Grand Canyon along with a fun three-night side trip to Fabulous Las Vegas!
If this tour isn’t an option – our next available tour is SEPTEMBER 2027. All are filling up – so use the button ablove to get all the information!
We hope you can join us on the road!
Chicago to Los Angeles 27 Day Tour NZ$10,995
Chicago & Los Angeles
The start and finish of the Road Tour

Chicago
Tour includes three nights accommodation

Santa Monica Los Angeles
Options to addon accommodation before your fliht home.
Averaging just 3 hours of driving a day – you’ll spend more time exploring, discovering and talking with the people who live and work across Historic Route 66.
Inclusions
Accommodation, rental car, route book
- Our guide supports the group each and every day – ensuring you get the very best Route 66 experience. You’ll see things and meet people you never would have on your own!
- Quality accommodation: Some modern hotels – some authentic Route 66 motels (most with breakfasts included)
- Premium Rental Car / SUV hire: (inclusive of Insurances and ‘One-Way’ fees)
- Gilligans’ exclusive ‘turn by turn’ navigation APP programmed with easy to use daily files
- Welcome dinner in Chicago & Farewell dinner in LA!
- Additional short-tours: Route 66 in Chicago, Abraham Lincoln’s home, & MORE!
- USA mobile phone with unlimited international calls & texts!
- Hand-held radios for communication between cars & your guide
- Las Vegas Side-trip: (3 x nights) Enjoy free time in the ‘Entertainment Capital of the World: Las Vegas!
- Spend a day visiting the Grand Canyon
What’s NOT included
- Flights
- Upgrades: rental car or hotel upgrade costs requested.
- Fuel: This is additional – allow approx US$400.
- Admission to museums, Route 66 sites etc
- Personal Travel / Medical Insurance (a MUST for travel to the USA)
- Cost for lunches, dinners and a few breakfasts
- Personal / discretionary spending
Conditions
- Driver/s must be over the age of 25 and hold a valid full driver’s license from your home country
- All participants must have relevant travel insurance for the USA
“We thought about doing Route 66 on our own… It quickly became obvious it wasn’t easy to plan and it wouldn’t have saved us any money!
Gilligans have been doing this for 11 years and we’re proud to offer what we believe to be: ‘The very best tour of Route 66 in the world!’
Yes, they know – it’s a bold statement! However,they genuinely believe that they provide their guests with the most comprehensive, detailed and with it; the best value for money tour of this historic highway.
Why? Because they work hard to tell the story of Route 66 in a way they feel it should be. With authenticity and by engaging with the people you’ll meet.
Since 2014, Gilligans has welcomed guests from New Zealand, Australia, Belgium, South Africa, Germany, Spain and the UK!
All have complimented Gilligans for their experiences, the memories and new found friends they earned during their odyssey across heartland America.
Since established a designated highway in November of 1926, Route 66 underwent multiple realignments over it’s lifetime and with Gilligans you can be sure to drive the best of them.
I will book your Gilligan's Route 66 Road Tour along with the International flights.
Email robert.schroder@whitestartravel.co.nz
Accredited Travel Broker for Mondo Travel TAANZ Bonded Agency
robert@mondotravel.co.nz
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