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)


26-Day, Guided Group Tour – Pricing INCLUDES flights!

Unlike some others tour companies around  – our tour actually starts at the beginning of old 66 in Chicago – and finish at the end in LA. 

“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?

Simply because we work hard to offer a unique insight into this old highway. Route 66 is more than tail-fins and chrome, or burgers and drive thru’s. Much more…

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 a fantastic rental car for each couple, along with a well detailed Route book and navigational technology that’s produced by Gilligans, exclusively for our guests.

*Subject to availability



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!


2024 Tours: SOLD OUT!

NASCAR & Route 66 has been added for a SELF-DRIVE option with up to 10 other couples / cars.

DATES: 3rd July – 29th July


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2025 Tour Dates – HURRY! Selling now!

Spring Tour: April 2025 – SOLD OUT

Fall Tour: September 19th, 2025 – HURRY!   80% SOLD


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)
  • Car hire: Drive a late model Mustang (inclusive of Insurances and ‘One-Way’ fees)
  • Your own GPS unit – fully programmed with Gilligans’ exclusive ‘turn by turn’ programme
  • Welcome dinner in Chicago & Farewell dinner in LA
  • Additional Tours: Route 66 in Chicago, Abraham Lincoln’s home, plus a tour the Budweiser factory in St Louis!
  • 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