Is Route 66 on your bucket list?

Route 66 BW Shield 1

   You’ve come to the right place

Is Route 66 on your bucket list?

Route 66 BW Shield

You’ve come to the right place

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.

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Gilligans Route 66 Map WEB

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.

NASCAR & Route 66:  July 3rd-29th, 2024

LAST  CALL  FOR  CHICAGO!

A special, one-off, July 2024 Tour which coincides with the Chicago NASCAR event!   It all starts in Chicago with Independance day celebrations, followed by a weekend of NASCAR in Chicago!   Leaving Chicago – you’ll enjoy the next 20-days driving Route 66 from Chicago to L.A!

Includes return flights, Accomodation with breakfasts, rental car & TWO great nights in fabulous Las Vegas! Visit the Grand Canyon, & the Hoover Dam all with ease – using Gilligans’ exclusive Route Book and navigation APP.

Limited to just 10 cars/couples!

29 Day Tour: Just NZ$13,995pp – twin share!

 

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2025 Route 66 Tours:

April 2025:  Departs April 16th –  TWO places available!

September 2025: HURRY!  80% SOLD

NASCAR & Route 66:  July 3rd-29th, 2024

LAST  CALL  FOR  CHICAGO!

A special, one-off, July 2024 Tour which coincides with the Chicago NASCAR event!   It all starts in Chicago with Independance day celebrations, followed by a weekend of NASCAR in Chicago!   Leaving Chicago – you’ll enjoy the next 20-days driving Route 66 from Chicago to L.A!

Includes return flights, Accomodation with breakfasts, rental car & TWO great nights in fabulous Las Vegas! Visit the Grand Canyon, & the Hoover Dam all with ease – using Gilligans’ exclusive Route Book and navigation APP.

Limited to just 10 cars/couples!

29 days: Just NZ$13,995pp – twin share!

2025 Route 66 Tours:

April 2025:  Departs April 16th – HURRY!  Just TWO places available!

September 2025: HURRY!  80% SOLD

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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!

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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* with insurances and one-way fees included                            (*rental car type, make or model are always 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!