Learn more about our Route 66 Car Caravans

The Basics:

All participants will meet in Chicago for a Welcome Reception. (Unless you choose to start later in the trip)

During this reception, we’ll discuss the overall itinerary, answer questions, and prep for our adventure. Of course, we’ll also have you sign a liability waiver.

The next morning, we’ll gather for a “Drivers’ Meeting,” something we’ll do most mornings. These brief meetings will go over the day’s itinerary, any special considerations, and any changes that may have developed.

After each morning’s meeting, we’re off! We’ll have designated time windows for each stop on our itinerary and suggestions for any free time you may have.

Everything included:

We've taken care of all the "hard" parts of planning this trip. Plus, we've added some extras that'll make your trip even better than if you were doing it on your own.


  • Lodging in a standard room

  • Admission/parking/tickets for any group activity on the itinerary

  • Trip drawstring tote bag

  • Trip guidebook

  • Lead-car guide

  • 13 breakfasts

  • 2 lunches

  • 3 dinners

  • Digital souvenir photo

  • Gift bags and special daily treats

  • Custom Spotify playlist tailored to each day's journey

What's not included:

  • Your vehicle (car, truck, or a rental car!)

  • Gas (Budget $300-500 for fuel depending on vehicle)​

  • Any meals not expressly mentioned in the itinerary

  • The boat-load of gifts and souvenirs you’re going to buy everywhere

  • Hotel “incidentals” (aka if you raid the mini-bar)

Vehicle Requirements

For the safety and smooth operation of our trips, any vehicle on the trip must meet the following criteria:

  • Capable of traveling at highway speeds (70 MPH)

  • Safe and good working condition with no known major issues

  • Operable windows

  • Operable headlights, wipers, and all other standard features reasonably expected to be present on a street-legal vehicle.


Keep in mind, this trip is over 2,400 miles long, so be sure to choose a vehicle that you feel comfortable with for both comfort and mechanical reliability. If you have questions, contact us at austin@2laneamerica.com

If your vehicle breaks down, we'll try to assist, but ultimately- the show goes on.

Registering and Payment

To register, simply fill out this form and pay a $250 per person deposit. (To register by phone, call 513-827-8273)

After registering, you'll receive a digital Welcome Packet and an invoice for the remaining balance due. The invoice is due 30 days before your trip. (Partial payments can be made anytime!)

Refund and Cancellation Policy:

A full refund will be issued up to 30 days prior to your trip departure. After that, a full refund will be issued minus the $250 deposit amount.

If you should leave the trip early for any reason, no refunds will be issued.


If a trip is cancelled by Two Lane America at any time, a full refund will be issued.

Preparing for your trip

Between the time you register and your trip, we'll reach out with any major updates if need be. You'll just want to plan to be in Chicago by the afternoon of the 1st day. You'll also want to make any plans for your return trip for the day after the last day. (or later)

We will also reach out at 2 specific times:

  • 45 days prior to the trip

    • Remind everyone to pay their invoices​

    • Offer folks a chance to book pre or post nights in Chicago/LA at our group rates.

    • Give any updates that may impact the trip

  • 15 days prior to the trip

    • Parking and any other arrival instructions fo Chicago​

    • Any other last-minute updates


Of course, we're always available by phone or email anytime.

Travel Insurance

We highly encourage all guests, especially if traveling from overseas, to purchase travel insurance. For travel insurance providers, visit Insure My Trip.

We'll also provide our preferred partner in the Welcome Packet.

Itinerary and Trip Changes

Two Lane America does not guarantee any particular activity, meal, hotel, or experience listed in the itinerary. Places can open, close, and change at a moments notice. If something changes, we'll always try to replace it with something comparable. We firmly believe we handle any changes fairly and with an extreme emphasis on guest satisfaction.

What are the hotels like?

We stay in a mixture of different “brands” of hotels, but each has been hand-selected from our years of experience. Each hotel includes hot breakfast. Some hotels feature full, sit-down buffets while others are hot breakfasts, but less robust. Most are 3 or 4-star properties and many are less than 5 years old or recently renovated.

Whenever possible, the hotels are all within close walking distance to restaurants, nightlife, etc.


We do not stay at any vintage motels, but we do VISIT multiple vintage motels on the trip such as the Blue Swallow, Roadrunner, Wagon Wheel, and more.

I’m part of a car club or large group, and we’d like to do the trip as a group! Do we need to register each car individually?

We love groups! We happily offer group rates and can even offer custom dates if the group is large. Email austin@2laneamerica.com for more info.

How much driving is there each day?

Some days, almost none. Most days, anywhere from 3-6 hours.

We typically never go more than about 2 hours without a stop, so you'll always be able to stretch your legs, see some sights, and use the restroom on our longer driving days.

What if my car breaks down?

Two Lane America does not offer any major roadside assistance. We suggest checking with your insurer to see if you have roadside protection and/or getting AAA. We can help to a certain degree, but it is ultimately your responsibility to make it to each new day.

What if it rains?

The weather, is, well, the weather. As a general rule, we will roll each day- rain or shine. If incliment weather impacts safety, your tour director may take a break until the weather clears.

Can you do this in a rental car?

Sure can. In fact, it may be a great option for you. We purposely spend the final night near the airport, so you can drop off the rental and fly home easily.

What happens when we get to LA?

After our farewell dinner, we return to the hotel. The next day, you can either fly home, stay in LA later, or make your way home anyway you'd like. You're on your own, but we're happy to help you route a fun trip home.

Can I bring my pet?

We love pets, but sadly, no. Not all of our hotels allow pets.

How much of Route 66 is still there, and how much of it do we drive?

Roughly 80% of Route 66 still exists. We split time between it and the interstate to help us see as many attractions as possible. We also avoid the spots where the road might be rough on your vehicle.

Have more questions? Email austin@2laneamerica.com.

We’ve taken our experiences from solo, rally, and bus travel to create a structured trip that still allows some freedom to explore on your own.