Route 66 Tour

Chicago, IL. to Los Angeles, CA.
15 day vacation


Tour Date (2 dates available)

May 14, 2019 - May 29, 2019
Sep 14, 2019 - Sep 29, 2019
  • May 14, 2019 - May 29, 2019
  • Sep 14, 2019 - Sep 29, 2019


Vehicle Rental see vehicle rental chart

Route 66 Tour

     Everyone has a wish list of roads and trips they have to take at some point in their lives. Route 66 is somewhere on that list for most people. If you're going to drive R66 then you need to do it with River Pilot. Most tours are hurried and visit towns and cities that aren't part of the R66 experience. River Pilot has perfected the tour and we stay on the road to see all of it. We have paced this tour to allow enough time to meet all of the interesting characters and see the attractions you have waited all this time to see. This is the tour all of the guides and experts wanted. We now bring it to you.

River Pilot Tours Route 66 Map     Incepted in 1926, Route 66 crosses America through 8 states giving travelers a chance to see America and all that it is. Driving this road gives one a chance to meet real Americans going about their day to day lives while viewing some of the most majestic scenery west of the Mississippi. The road twists and turns at over 2,288 miles and still offers folks the chance to recapture the past. What’s even more exciting is the road is coming back. Folks are establishing business catering to Route 66 travelers, new attractions are being created and the road is still in drivable condition if you have the right information and guide.

     Route 66 originally started out as a group of roads strung together that followed farm roads, railroad tracks, the Ozark Trail, Santa Fe Trail and the National Old Trails Hwy. As time and traffic progressed, the road became the artery for travelers looking to move westward in search of a new beginning. The stories that folks still tell of helping car loads of families with broken down cars, flat tires, in need of a place to sleep are fascinating. One gets a sense of how important this road was to fulfilling people’s hopes and dreams if they could just follow it westward.

     Why would you ride with anyone else? We know you've waited a long time to ride R66 and we expect to deliver the experience of a lifetime. WhyRoute 66 Tour Guide Training Facility are we better than all the other operators and rental companies? Easy. Were not in the rental business and not trying to get you out on the road to accumulate rental days. River Pilot Tours is based in the U.S. When others are in their home country in the off season, we're here exploring the road, maintaining relationships and researching every bit of R66. We invented the worlds first commercial use GPS for Route 66. We work with the trusted experts and authors who wrote the books on Route 66. We just do it better than everyone else. We really like Route 66 and that passion and knowledge for the road comes through on our tours that you won't find anywhere else.

     Join River Pilot Tours in exploring this road and all that is has to offer. Our experienced team will guide you to attractions and icons of the road that you’ve heard about as well as many of the lesser known that you may not have. River Pilot Tours - "Come Along For The Ride"

15 Day Vacation

Day 1
Chicago Arrival
Day 2
Chicago, IL. to Springfield, IL.
Day 3
Springfield, IL. to Cuba, MO.
Day 4
Cuba, MO. to Springfield, MO.
Day 5
Springfield, MO. to Tulsa, OK.
Day 6
Tulsa, OK. to Clinton, OK.
Day 7
Clinton, OK. to Amarillo, TX.
Day 8
Amarillo, TX. to Santa Fe, NM.
Day 9
Santa Fe, NM.
Day 10
Santa Fe, NM. to Gallup, NM.
Day 11
Gallup, NM. to Williams, AZ.
Day 12
Williams, AZ.
Day 13
Williams, AZ. to Needles, CA.
Day 14
Needles, AZ. to Victorville, CA.
Day 15
Victorville, CA. to Los Angeles, CA.
Day 16
Los Angeles Departure

Note: The final day in the tour itinerary is the departure day. No activities are planned unless otherwise specifically included at time of booking.

  • Professional tour guide(s)
  • Support vehicle for additional luggage storage
  • 15 nights, 3 star hotel accommodation, double occupancy
  • Unlimited mileage
  • Full coverage vehicle or motorcycle insurance
  • Daily breakfast
  • Welcome dinner
  • Water and ice
  • Parking
  • Park entrance fees
  • Helmet for driver and passenger
  • Taxes, surcharges, fees

What's Not Included

  • Airfare
  • Fuel and oil
  • Food, snacks, beverages, alcohol
  • Personal travel, accident and medical insurance
  • Museum entrance fees
  • Gratuities, tips, personal spending money
  • Personal souvenirs, gifts, purchases
  • Delivery charges for participating vehicles
  • Cost for replacement of lost or stolen keys or equipment
  • Optional excursions or extras
  • Any other items not specifically included in tour price
  • Note: Car and Motorcycle Selection Subject To Availability

Approximate Total Miles: 2,416

Average Miles Per Day: 150, longest is 280

Riding Conditions: Paved, gentle sweeps, maintained roads

Riding Difficulty: Easy

Exploring Days: Santa Fe, Grand Canyon

Highlights: Authentic Route 66 roads and spurs, downtown Chicago, Gay Parita Sinclair, original gas stations, muffler men, Route 66 museum, western vistas, Winslow AZ, Snow Cap Drive-In Seligman AZ, Grand Canyon, Santa Fe, Hackberry Store, Oatman  AZ, Santa Monica Pier

Optional activities: Helicopter tours of Grand Canyon $250, Universal Studios Hollywood $129, Disneyland $90 per day, Hollywood Tour $60 PP

Tour Departure: 5 or more

Included Motorcycle: Harley Davidson - Other make and model motorcycles may incur additional charges.