Group Tours

APRIL 2025 TOUR

ONE CAR NOW AVAILABLE – Departs April 16, 2025:

Due to a late cancellation, we now have room for ONE COUPLE to join us, for the upcoming ‘Spring Tour across Route 66 – next April!

Get in touch TODAY to secure your dream of driving across Route 66 in just a few months time!

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!

Contact us for a brochure