1. Chicago, Illinois
Start your road trip at Lou Mitchell’s Restaurant, a local institution where Route 66 officially begins. Then head over for a leisurely walk in the 319-acre Grant Park and check out some museums or marvel at the enormous Buckingham Fountain. At the end of the day, take advantage of this two-bedroom apartment in the Magnificent Mile area, just a few minutes from Wrigley Field or Sox Park. Situated on the 45th floor, the private balcony offers a killer view.
2. St. Louis, Missouri
Built on the banks of the mighty Mississippi River, St. Louis offers a rich history and lots to see. Take a ride to the top of world-famous 630-foot Gateway Arch for a spectacular view, then head over to Ted Drewes Frozen Custard, serving a variety of flavors and toppings along Route 66 since 1929. After you’ve had your fill, unwind in this charming guesthouse where you can soak your bones in the outdoor hot tub overlooking the garden (available year-round), or get out and explore the urban and eclectic Central West End neighborhood.
3. Tulsa, Oklahoma
After passing through the 13-mile stretch of Kansas, explore the gentle plains of Oklahoma. Stop in Tulsa to check out local attractions like the 76-foot Golden Driller statue, or cool off in the swimming hole that also serves as home to the kitschy Blue Whale of Catoosa. After getting a glimpse of American Indian and Old Western art at the nationally celebrated (and possibly haunted) Gilcrease Museum, you can get a taste of country life for yourself at this farmhouse, complete with its own barn.
4. Amarillo, Texas
As you cruise through the Texas Panhandle, the open prairies start to give way to desert canyons, and Amarillo’s Palo Duro Canyon State Park offers majestic views. You can check out quirky local attractions like the famous Cadillac Ranch or the RV Museum, but the landscape here is the real star. This cabin offers amazing canyon views right from the porch and is close enough that you can hike down into the canyon a couple of times a day and still come back to enjoy a snack in the expansive kitchen.
5. Albuquerque, New Mexico
Albuquerque’s Southwestern architecture reflects New Mexico’s Spanish and Native American heritage, and Historic Old Town is an excellent example—walk the cobblestone streets and browse the shops in authentic adobe buildings. Afterward, ride the Sandia Peak Tramway for an awe-inspiring panorama of the area. Bunk down for the night in the perfect home away from home. This one-bedroom bungalow is in Nob Hill, a quiet neighborhood yet still very close to a brisk nightlife scene.
6. Flagstaff, Arizona
Set near the San Francisco Peaks, the rocky desert badlands of the Painted Desert, and one of the largest Ponderosa Pine forests in the country, Flagstaff has no shortage of scenery to take in. Of course, with the Grand Canyon and the 3,900-foot-wide Meteor Crater not too far away, you might have to prioritize! After you’ve taken all the pictures you want, retire to this luxury forest retreat and soak in the hot tub overlooking the woods. If you’re still wanting more of the great outdoors, hiking and biking trails are just out the back door.
7. Pasadena, California
As you make your way to the City of Roses, be sure to notice the Arroyo Seco Parkway, the first freeway built in the Western United States—especially the Colorado Street Bridge, rising 150 feet above the canyon below since 1913. Old Town offers plenty of shopping and entertainment options, as well as the Wrigley Mansion, home to the Tournament of Roses Association. Then enjoy some peace and quiet (and a breathtaking view) at this nearby artist’s retreat, complete with a Zen garden and two decks overlooking the woods.
8. Santa Monica, California
At the end of the Santa Monica Pier, a sign indicates the end of the road. Your journey is complete! Walk the boardwalk and take a ride on the iconic Ferris wheel. Kick your shoes off and feel the sand in your toes or walk down to Venice Beach for a more unconventional beachgoing experience. You can rent a bike and cruise the beach trail or grab a souvenir at one of the shops at the Third Street Promenade, just minutes away. This spacious cottage (and historic landmark) is perfectly located in the middle of it all.