Self-Drive Route 66

received 394902791199056

20 days driving Route 66!


per person

Pricing includes:

All accommodation   (1 x night pre-tour included in Chicago)

Standard full-size rental car with insurances – upgrades available at additional cost – dependant on availability.

USA iPhone with our Turn by Turn navigation and unlimited calling back home.

Our extensive 130+ page tour book

20-Day: Self-Drive Route 66 Tour 

If our 26-day tour of the ‘Mother Road’ just isn’t an option for you – then why not do Route 66 the easiest way possible – Gilligans takes care of all the hard work and planning!

Our  brilliant 20-day, self-drive’ tour is designed for guests who prefer to travel Route 66 unaccompanied, or cannot make it along on one of our ‘Official Tours’.

You just choose the departure date from Chicago – and we provide everything you need to travel across Route 66 on your self-drive odyssey across the Mother Road to Los Angeles.

The package includes hotel accommodation on the night before departure downtown.

The next morning, you will be collected around 8:00am and taken to collect your rental car – Let the adventure begin!

You’ll absorb the history of a bygone era whilst enjoying all the modern creature comforts of our exclusive Route 66 Navigation APP, taking you across our chosen alignments of old 66!  

With a Gilligan’s ‘Self Drive’ tour you can be assured to see the best of Route 66, travelling the original road without the hassle of stopping to check road names, unravelling armful’s of maps, or trying to plan your vacation using a pile of books and written guides.

With the use of our exclusive turn by turn navigation system and Route Book, we detail each and every day of the journey for you.                         

Most days are planned around an 8:45am departure, which sees guests arrive at the end of each day around 4:30pm.       

We do all the hard work and you just enjoy each day as it appears out the windshield!

20 Day Self Drive Tour Pricing

  • 1 Vehicle, 2 people (twin-share): US$5,495pp
  • 1 Vehicle, 2 people (2 rooms): US$6,695pp


What’s included

  • Quality accommodation – including nearly all hotel breakfasts 
  • One nights accommodation in Chicago (prior to departure)
  • Car hire: Premium Class Full sized –  Inclusive of Insurances and ‘One-Way’ fees (upgrades available subject to availability)
  • Gilligans’ exclusive ‘turn by turn’ navigation programme across Route 66
  • Gilligans’ comprehensive Route Book with over 130 pages of town by town notes for your journey!
  • Pre-paid cellphone with unlimited international calls & texts!


  • Airfares to Chicago, and home from LA 
  • Rental car upgrades (if any) – subject to availability
  • Travel / Medical Insurance

  • Fuel costs (approx US$450 for the entire journey)
  • Lunches & Dinners + some breakfasts (eg. Las Vegas)


  • Driver/s must be over the age of 25 and hold a valid full driver’s license from your home country
  • All participants must have relevant travel insurance for the USA
Gilligans Brochure Cover

Contact us for a brochure