Group Tours
NZ$13,995
per person – INCLUDES FLIGHTS
(26 days)
AU$13,995
per person – INCLUDES FLIGHTS
(26 days)
All pricing is based on TWIN SHARE
Includes economy airfares from:
- AKL / WLG / CHCH
- SYD / BRIS / MELB
To: Chicago – returning from Los Angeles.
(Pricing subject to change)
US$6,895
per person – LAND ONLY
Arrange your own flights from wherever you are in the world!
Arrive in Chicago
Depart from Los Angeles
26-Days | ‘The Official Tour’
“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 17-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 a TWO 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 and we won’t make you start in Los Angeles, to spend half of your vacation getting to Chicago, to eventually start Route 66 – all the way back to California…
The fully-guided ‘Official Tour’ provides guests with a comprehensive 28-day tour of Route 66.
We include economy flights to Chicago (returning from LAX) from major cities across the world.
Following an initial three nights in Chicago, you’ll collect your rental car and using our APP & compehensive Routebook – set off on a very special odyessey.
Route 66 is more than tail-fins and chrome; burgers and drive thru’s – it’s a history lesson in American culture and society.
“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 – 2027”
Our 2026 tours are all but fully booked.
DON’ MISS OUT! Join us on our 27-day odyssey in September 2027!
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 170+ 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 THREE nights away from Route 66 in Fabulous Las Vegas – PLUS, a day at the Grand Canyon!
What are you waiting for?
Get YOUR Kicks on Route 66 with Gilligans!
What’s included
- Return Economy airfares to the USA (not included in our Self-Drive Tours)
- 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
- Comprehensive Travel pack with Gilligans’ extensive Route Book – Yours to keep!
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