Group Tours

Official tour stamp

Depart NZ: April 15, 2026:

NZ$13,495

per person – twin share

Depart Australia: April 15, 2026:

AU$13,395

per person – twin share

All pricing is based on TWIN SHARE

Prices* INCLUDE economy airfares from:

  • AKL / WLG / CHCH
  • SYD / BRIS / MELB

To: Chicago – returning from Los Angeles.

(*pricing subject to change)

Gilligans

The Centennial Tour:

Flights INCLUDED!

“Without question – THE best 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?

Because with Gilligans you actually drive what was Route 66 from Chicago to Los Angeles, and we spent 20-days doing it.   

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

We won’t start in Los Angeles only to end up back there. Route 66 started in Chicago – so do our tours.               

Route 66 is all about time over distance – we average just 145 miles a day from Chicago to Los Angeles (2,448 miles total) 

Consider those important factors with any other tour and you’ll soon discover that Gilligans works 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 three nights in Chicago, you will be allocated your rental car, 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. 

A Route 66 history that 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!

Route 66 Tour

April 2026:

Route 66 celebrates it’s 100th Birthday in 2026!

Secure the last places for our special ‘Route 66 Centennial Tour – departing April 15th, 2026!

 

Check out our “OFFICIAL TOUR” below!

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
Gilligans Brochure Cover

Contact us for a brochure