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

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

Averaging just 144 miles a day – You’ll cross eight states
and travel over 2,448 miles from the beginning in downtown Chicago to very end at the Santa Monica pier.

Our tour starts at the beginning in Chicago and follows some of the earliest alignments of Route 66!

26 Days | “The Official Tour’: 2026!

Departing: April 14th, 2026

Our  April 2026 “Official Tour” has room for just ONE MORE COUPLE!

Secure your place for 2026 NOW!

This tour includes return economy flights from wherever you live! 

28 -DAY  TOUR INCLUDES:

Return economy flights

All accommodation with most breakfasts

Premium car or SUV rental (with insurances and one-ways fees)

Spend a day at the Grand Canyon!

THREE great nights in fabulous Las Vegas!

PLUS MUCH MUCH MORE!

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!