Group Tours

Official tour stamp

26-days Route 66 – WITH FLIGHTS!


per person – twin share


per person – twin share

All pricing is based on TWIN SHARE

Prices* INCLUDE economy airfares from:

  • AKL / WLG / CHCH

To: Chicago – returning from Los Angeles.

(*pricing subject to change)


Guided Group Tour:

26-Days – Price INCLUDES flights!

“Gilligans provides the very BEST tour of Route 66″ available.”  

We’re not being boastful – that’s what many of the business owners along Route 66 tell our guests. Why?

Because with Gilligans you actually drive what was Route 66 from Chicago to Los Angeles.                                             

We won’t have you on the four lane Interstate between Route 66 towns to save time and cover the miles.             

We won’t have you visiting other states to get to Chicago to start the tour, and you won’t average more than 145 miles a day. 

Consider those important factors with any other tour and you’ll soon see we work harder than the rest to offer a unique insight into this old highway.         

Our fully guided ‘Official Tour’ provides guests with a comprehensive 26-day tour of Route 66.

We include flights to Chicago (returning from LA) from major cities across the world!

Following 3 nights in Chicago, you will be allocated your rental car for each couple, along with a well detailed Route book and navigational technology that’s produced by Gilligans, exclusively for our guests.

Route 66 is more than tail-fins and chrome, or burgers and drive thru’s – it’s a history lesson in American culture and society – conveyed to you via the front seats, for over 2,448 miles of America’s Greatest Highway!



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!


September 2025! 

Spaces remain for just FOUR more couples in 2025!

DATES: September 19th – October 14th, 2025.


2026 Tours – Selling Now!

Spring Tour: Departs April 16th, 2026


Check out our “OFFICIAL TOUR” below!

What’s included

  • Return Economy airfares to the USA (not included in Self-Drive Tours)
  • Quality accommodation – including breakfasts (except for Las Vegas)
  • Rental Car hire: (inclusive of Insurances and ‘One-Way’ fees)
  • Gilligans’ exclusive ‘turn by turn’ navigation APP programmed from Hotel to Hotel.
  • 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!


  • 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
Gilligans Brochure Cover

Contact us for a brochure