Expansive and historic, Route 66 sparks feelings of excitement and freedom in the hearts of avid travellers everywhere. This iconic route spans eight states — Illinois, Missouri, Oklahoma, Texas, New Mexico, Arizona, Nevada, California — and a total of 2, 400 miles. Route 66 is famous for old-school diners and motels, quirky roadside attractions, memorabilia gift shops, and the mythical landscapes. A Route 66 road trip requires considerable preparation from staying safe on the road to where to stay, eat, and sightsee. Here’s how to plan the your road trip of a lifetime.

Staying safe

Embarking on your road trip with a reliable vehicle is of utmost importance. If you drive the entire route from Chicago to LA, you’ll be on the road for up to four weeks depending on how much time you spend exploring. Battery problems, engine failure, and tire damage were the most common reasons for breakdowns on the road last year. So, take your car in for servicing beforehand to make sure it’s in good working condition. Also pack a first kit, spare phone chargers, and a flashlight. While America is generally safe, crime does happen — particularly late at night. Keep your valuables hidden, your doors locked, and use common sense like you would anywhere else.

Where to stay

There are plenty of big-chain hotels en route, however a more authentic experience awaits you in the motels and independent hotels. Open since 1939, the iconic Blue Swallow motel in New Mexico has a giant neon sign and a classic car parked outside. Inside, you’ll find art-deco features, 1950s furniture, and even old-fashioned telephones. Or stay at the El Rancho Hotel in Gallup, New Mexico, just like Western movie stars like John Wayne, Errol Flynn, Gregory Peck, and Humphrey Bogart once did. In Tulsa, the Campbell Hotel offers classic comfort in a beautiful historical building dated 1927. It also has an ultimate Route 66 suite featuring vintage road signs. Always book in advance to avoid disappointment.

What to see

Famous must-see attractions include the Willis Tower in Chicago, the Gateway Arch in St. Louis, and Angel & Vilma’s Route 66 gift shop in Arizona. Book a guided tour through Missouri’s Meramec Caverns where infamous outlaw Jesse James once sought refuge. You can also catch a movie in Missouri’s open-air 66 drive-in theater. Smaller sights also offer huge intrigue. For example, booking a ghost tour through Maggie Mine in California will take you back in time to the Wild West.

Where to eat 

Stop at the famous drive-ins and diners along the route and enjoy classic American cuisine. For example, Carl’s Drive-In in St. Louis has been popular with both locals and visitors for its crispy-edged burgers and creamy root beer since 1959. To celebrate reaching the halfway mark, stop at Midpoint Cafe in Adrian, Texas for some homemade pie. When you reach Los Angeles, Fair Oaks Pharmacy and Soda Fountain in South Pasadena sells nostalgic ice cream floats, phosphates, egg creams, and lime rickeys since 1915 — along with retro-style Route 66 memorabilia.

Finally, the route winds up at Santa Monica Pier. Snap a photo of the sign and ride the world-famous Ferris wheel. Watching the sunset over the Pacific Ocean is a nice way to finish your trip. No matter which drive you take, Route 66 will provide a lifetime of memories.