Group Tours

2026 – 100 Years Tour: September 2026

27-Days | ‘The Official Tour’

A trip across heartland America is a rewarding and insightful experience into the tapestry of  the USA – and what better year to travel Route 66 – than during the roads 100th Birthday!

What’s different with Gilligans?

Put simply, we offer a tour that focusses solely on Historic Route 66 and the people, history and stories that have made it so very famous.

Compare our itinerary with any other, and you’ll soon understand why business owners and Route 66 experts recommend Gilligans.

Route 66 began in Chicago – so does our tour. 

Route 66 ended in Los Angeles, and thats exactly where you’ll end up after 21 outstanding days across America.

Averaging  just 3 hours of driving a day – you’ll spend more time exploring, discovering and talking with the people who live and work across Historic Route 66.

The people are great, the stories meaningful and the history – well, thats the best part…

“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 21-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 then relax, with a THREE 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.

Finally, we won’t have you start in Los Angeles – ask you to spend half of your vacation driving to the start line in Chicago – only to then turn around to begin a hasty tour back to L.A…

The fully-guided ‘Official Tour’ provides guests with a comprehensive 27-day tour of Route 66.

Following an initial THREE nights in Chicago, you’ll collect your rental car and using our APP & comprehensive  Routebook – set off on a very special odyssey, across America’s Greatest Highway; U.S 66.

Our tour is more than tail-fins and chrome; burgers and drive thru’s – it’s an outstanding history lesson in American culture, society and progression. 

“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!

Contact us for a brochure

Check out our “OFFICIAL TOUR” below!