No highway gets more recognition and praise than America’s Mother Road, & few know it better than Gilligans.

We’re the experts in delivering world-class, self-drive tours of this journey into America’s heart and soul.

With Gilligans, you get the full Route 66 immersion, following the original route crossing eight states
and covering over 2,448 miles from the beginning in downtown Chicago right to Los Angeles and the Pacific Ocean, on the Santa Monica pier.

“Route 66 – Group Tour”

April 15th – May 9th, 2026

HURRY!  Join us in April 2026 for the Route 66 Centennial Tour a special tour to celebrate Route 66’s 100th Birthday!

Our hugely popular Group Tour – known as ‘The Official Tour’ is now SOLD OUT for both April & September, 2025… 

Includes return economy flights, accommodation with breakfasts, rental car & TWO great nights in fabulous Las Vegas!

SELF-DRIVE ROUTE 66

Want to enjoy Route 66 by yourselves?

Perhaps our group tour dates don’t fit with your plans?

Check out our 20-day SELF-DRIVE tour across Route 66! You choose the start date from Chicago and we plan the rest!

What to expect with Gilligans:

Route 66 was 2,448 miles started in Chicago and finished in Los Angeles.

With Gilligans, you’ll start at the very beginning, and spend TWENTY DAYS on Route 66, from Chicago to LA.

• Start in Chicago & finish on the Santa Monica pier at the ‘End of Route 66’ sign
• We include your rental car* with insurances and one-way fees included
• Tours average just 144 miles a day from Chicago to LA – less than any other!
• Guests enjoy Gilligan’s EXCLUSIVE navigation system, our comprehensive Route Book and a US mobile phone
• Drive some of the oldest alignments including some that remain unsealed to this day!
• Stay at superior hotels and enjoy nights at some iconic Route 66 motels along the way!

(*rental car type, make or model are always subject to availability)

Gilligan’s doesn’t provide a ‘tour’ in the true sense of the word. We provide you with a personal experience across America’s greatest highway – an immersion into the tapestry of heartland USA and an opportunity to encounter the people who live and breathe Route 66.

A true Route 66 experience starts and finishes with Gilligans.

We look forward to welcoming you to the USA!