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 finish point at Santa Monica pier, overlooking the Pacific Ocean.

2025 Tours – ON SALE NOW!

Planning to drive America’s greatest Highway – Route 66?

Join us in either April or September of 2025!

Our ‘Spring Tour’ in April includes being part of the annual Route 66 Fun Run: A massive classic car event in Arizona, which features over 900+ cars on a drive across Route 66.   

As a guest of Gilligans – you’ll be there and be a part of it!

Self Drive Route 66

If our “Official Tour” simply isn’t an option – then why not take a tour of Route 66 using our highly-regarded “Self-Drive 66 Tour”.

You choose the departure date from Chicago and we’ll take care of all the details!  

Spend 18 days driving what was old Route 66 from Chicago to Los Angeles!

If you have never visited Fabulous Las Vegas! Why not add 2 additional nights for just US$195pp?

What to expect

• Drive what was Route 66!
• Start in Chicago & finish on the Santa Monica pier at the ‘End of Route 66’ sign
• We include your rental car* (insurances and one-way fees included *rental cars subject to availability)
• 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!

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!