Gilligans Tours

09/26/2026

We’re underway and on the road!

Route 66: Chicago to L.A.

We begin the tour at the start in Chicago - we finish in LA!

Day one was fantastic - it’s been a great run from Chicago, that included some of the coolest little stops in Illinois!

Finished the day with visits to museums in one of the most recognizable, and famous little towns on Route 66: Pontiac, Illinois

09/15/2026

We’re about to set off next week from Chicago for our next Route 66 adventure.

This will be a great tour - lots of new experiences await!

08/20/2026

For guests, there are a number of highlights that stay with them well after their Route 66 adventure finishes.

One of them is our visit to Visit Joplin MO each and every tour since early 2014.

For one of our early tours, the trolley booked for out group's tour around town was either temporarily out of commision, or too small to take everyone. Patrick Tuttle - Director at Visit Joplin MO called with some concern... The only available vehicle was a yellow school bus.

Ever since, we've taken hundreds of happy New Zealand and Australians who had only ever seen the yellow American school buses on TV, or in movies.

Patrick has given his time to us graciously for many years - turning up after hours to do an evening tour around town on a noisy, non-airconditioned - yet absolutely perfect, Yellow School Bus.

Patrick is set to retire after a stella career this December, and on behalf of all the past guests - THANK YOU.

Your humour, knowledge and enthusiasm is not only valuable for Joplin - but the respect you've earned across Route 66 is to be commended.

Enjoy retirement, but I hope and think that perhaps you might be able to join us a couple nights a year in the future.

Best wishes Patrick!

https://www.newstalkkzrg.com/2026/08/19/patrick-tuttle-director-of-joplin-convention-and-visitors-bureau-announces-plans-to-retire/?fbclid=IwY2xjawTzr5ZwZG9mBWV4dG4DYWVtAjExAGJyaWQRMVVlRUNmekN0bk9Na2tMNnBzcnRjBmFwcF9pZBAyMjIwMzkxNzg4MjAwODkyAAEe5wcP-k8SqZnmOHPAkXBGNq6ZDLLgk_TavTTyS0CbAsa56Pme5MRRrNnS-D0_aem_lzzsuVm0pMT_nDxcVF4EgA

07/31/2026

Join us to see all off what 66 has to offer !

Thirty years after first documenting the Mother Road, filmmaker John Paget returns to discover what’s still out there—and finds a centennial portrait of everyday heroes and enduring towns along this legendary highway. ROUTE 66: THE MAIN STREET OF AMERICA travels through all eight Route 66 states...

07/02/2026

Today Greg completed his 'Self-Drive' Tour of Route 66 with Gilligans. He enjoyed a final stop with Ian at Santa Monica.

Greg arrived from Australia in early June, and has spent the time and effort to explore all of the stops we provide as part of the trip (and there are MANY!)

Route 66 is all about time over distance - there is no shortcuts.

Our self-drive tour is 21 days, but as Greg and past guests know: You need each and every one of them to do it justice.

We spoke each and every day of the tour on the phone, and it's fair to say we've found another friend in Greg.

Congratulations Greg & safe Travels home!

06/26/2026

We can certainly vouch for the credibility in this recognition.

One of Oklahoma’s most famous food joints received national recognition recently. Sid’s Diner in El Reno was ranked as a Top 15 Roadside Restaurant by Southern Living.

06/25/2026

Join us this September on a newly added tour across the Mother Road!

06/25/2026

If there is ever a year to travel Route 66: The centennial season is it!
Route 66 was officially designated a highway in November 1926 and you could be part of the celebrations!

This newly added 27-day tour, starts in Chicago and finishes in Los Angeles, driving some of the oldest alignments of this historic road.

No matter where in the world you live, we can have you in Chicago for a trip of a lifetime!

If Route 66 has been on your bucket list - tick it off this September!

Check out the website or call for more information!

LIMITED TO JUST 15 CARS

05/09/2026

The last stretch of Route 66 from Arizona and into California:

Two great days as we left Arizona and crossed the Mohave desert into our stay on historic 66 near Pasadena.

The final morning saw us take a short drive out to Santa Monica and the welcome sight of the Pacific Ocean !

It was an emotional night at our farewell dinner - saying goodbye to new friends is never easy, made worse by the fact that our time on Route 66 had come to an end.

We arrived in Chicago on April 15 and over the last few weeks we’ve met some incredible people across the country.

Thanks to everyone who stopped to talk to the group, that showed interest and gave up some time to share stories.

If an authentic Route 66 adventure is on your bucket list - reach out to get your memorable adventure underway!

05/07/2026

A sensational last few days across the Mother Road.

Leaving New Mexico, we drove the Petrfied Forest and Painted Desert through into Arizona.

The Grand Canyon, the Route 66 Fun Run and an outstanding side-trip in Vegas.