Group Tours
US$6,995
per person – 27 days
(door to door return – excludes flights)
All pricing is based on TWIN SHARE
Flights Details:
ARRIVE: Chicago, Illinois (18th September 2026)
DEPART: Los Angeles (10th October, 2026)
(Pricing subject to change)
SEPTEMBER 2026 – HURRY!
27-Days | ‘The Official Tour’
A trip across heartland America is a rewarding and insightful experience into the tapestry of the USA.
What’s different with Gilligans?
Put simply, we offer a tour that focusses solely on Historic Route 66 and the people, history and stories that have made it so very famous.
Compare our itinerary with any other, and you’ll soon understand why business owners and Route 66 experts recommend Gilligans.
Route 66 began in Chicago – so does our tour.
Route 66 ended in Los Angeles, and thats exactly where you’ll end up after 21 outstanding days across America.
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.
The people are great, the stories meaningful and the history – well, thats the best part…
“Without question – This is the BEST, Self-Driving Tour of Route 66 available in the world” – Kevin Mueller (Blue Swallow Motel Owner – 2019)
We’re not being boastful – that’s what many of the business owners along Route 66 tell our guests.
Why?
Most importantly, travelling across Route 66, is all about time over distance – Put simply:
“How many days are actually spent on what was Historic U.S 66 – Chicago to Los Angeles? (2,448 miles)
With Gilligans, we spend 21-days travelling from Chicago to L.A which is an average of just 144 miles a day – much less than other tours. This means you’ll experience more, see more, enjoy more.
In addition, you’ll spend THREE nights in Chicago before the tour, another full day exploring the Grand Canyon, and then relax, with a THREE day side-trip away from 66, visiting the Entertainment capital of the World: Fabulous Las Vegas!
Route 66 started in Chicago – so do our tours.
We won’t have you on the four-lane Interstate highway between towns to save time.
Finally, we won’t have you start in Los Angeles – ask you to spend half of your vacation driving to the start line in Chicago – only to then turn around to begin a hasty tour back to L.A…
The fully-guided ‘Official Tour’ provides guests with a comprehensive 27-day tour of Route 66.
Following an initial THREE nights in Chicago, you’ll collect your rental car and using our APP & comprehensive Routebook – set off on a very special odyssey, across America’s Greatest Highway; U.S 66.
Our tour is more than tail-fins and chrome; burgers and drive thru’s – it’s an outstanding history lesson in American culture, society and progression.
“A story of Route 66 history is best told with Gilligans”
Tour Format:
Following breakfast, your day usually starts with a morning briefing to outline the day ahead, give an overview about the areas visited and to answer questions.
The group generally departs around 8:30am, and often arrives at the hotel at about 4:30 each afternoon. Some days are shorter – others slightly longer. Time spent driving is approx 2.5-3hrs per day, which allows more time to see what you came to see: Route 66!
Along the way, guests use our GPS platform and extensive Route Book to learn about towns and notable sites as you drive.
We travel as a group – although not in a ‘convoy’ as such – giving guests more freedom to stop for more or less time (dependent on interests) at the places we visit.
Your guide/s also have a few stops planned each day of the tour that really will add value to your Route 66 experience!
27 Days | “The Official Tour – 2026”
Our tour of Route 66 is world-leading for a reason: We start in Chicago and our guests drive the very best of Route 66 all the way out to Los Angeles!
You’ll be behind the wheel enjoying the freedom to explore; but with the bonus of a guide, a 190+ page Route Book and an exclusive APP for turn-by-turn navigation across the very best of Route 66.
Even better? You’ll experience the adventure with new friends, doing just the same as you!
Limited to approximately 15 cars/couples, our guided ‘Official Tour’ makes for the most memorable Route 66 adventure available.
Includes a THREE night ‘side-trip’ away from Route 66 in Fabulous Las Vegas!
A full day at the Grand Canyon!
Get YOUR Kicks on Route 66 with Gilligans!
What’s included
- 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 / Travel: Travel is easily arranged on your behalf. Arrive in Chicago – depart from Los Angeles.
- Upgrades: Any flight, 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
Contact us for a brochure