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

27 Days

Just 15 Vehicles

Averaging 144 miles a day, from Chicago to Los Angeles.

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

September 2027 Tour

27 Days “The Official Tour”

If a true Route 66 experience has been on your bucket list, then Gilligans here to turn your dream into reality!

The majority of our guests are from New Zealand and Australia – but if you’re from elsewhere: You’re just as welcome on this odyssey across America’s Greatest Highway.

We provide everything you need to travel the road, seeing all that you’ve read and heard about: The famous stops, the old motels, the old sections of this famed highway. With Gilligans – you’ll do it all.

We provide the accommodation, the rental vehicles and our 190+ page Route book, iPhone and Navigation APP make it easy & enjoyable, giving you a real life history lesson across heartland USA!

Our tour is designed to allow guests the closest way of driving Route 66, as if you were doing it on your own.

We do the planning – you do the driving!

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 21-Days driving across on Route 66, from Chicago to LA.

(Our ‘Group Tour’ is 27 days total – that includes 3 x nights in Chicago along with travel to and from the USA)

• Start in Chicago & finish on the Santa Monica pier at the ‘End of Route 66’ sign
• Stay at superior hotels and enjoy nights at some iconic Route 66 motels along the way!
• We include your rental car* with insurances and one-way fees included (or use your own)
• 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 if you’re from outside of the USA.
• Drive some of the oldest alignments including some that remain unsealed to this day!

(*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!