While summer might get all the attention, fall is a wonderful time to take a road trip in the United States. The weather is still lovely throughout most of the country, fewer cars are out and about, and with a colorful display of changing leaves, the scenery is even more beautiful. The Inspirato Collection includes numerous residences and luxury hotel partners in the best destinations for hitting the road and soaking in everything fall has to offer. Rent a car or bring your own for these suggested itineraries.

Southern California

Start in beautiful San Diego, where Inspirato Members can stay in a beautiful residence just steps from La Jolla beach. Then, drive about two hours north to Dana Point, one of the most treasured vacation destinations in Orange County. At Monarch Beach Resort, members have access to amenities such as a private beach, preferred tee times, and kids’ programs. From there, it’s an easy drive up to the Rancho Palos Verdes peninsula, home of Inspirato Member-favorite Terranea resort. Finish up the trip in sunny Palm Springs with a round on the area’s 100+ golf courses.


New York City is a perfect start: indulge in fine dining, a Broadway show, and a stay with one of Inspirato’s luxury hotel partners. Next, escape the city and head to idyllic Cape Cod; the sandy beaches and calm water will have you relaxed in no time. It’s only a 90-minute drive from the Cape to Boston and Inspirato’s partner, The Lenox Hotel. Hop out of the car and tour the hotel’s historic Back Bay neighborhood on foot. Your final stop offers another break from urban life, in the mountains of Stowe, Vermont. Your itinerary might include hiking or golfing, but no matter what activities you schedule, make time to gaze at New England’s iconic autumn foliage.


Inspirato Members love this coastal region of South Carolina for its old-fashioned charm and family-friendly appeal, so this is a great road trip to take with kids in tow. Enjoy laid-back Isle of Palms before making the roughly 90-minute drive to Kiawah Island, another peaceful slice of coastal beauty. Make it an extended stop and play the island’s five championship golf courses. Next, keep heading down the shoreline to Hilton Head Island, ranked the best island in the continental United States by Travel + Leisure on multiple occasions. End back on the mainland in Palmetto Bluff and explore its perfectly manicured grounds.

Rocky Mountains

Colorado’s mountains are beautiful any time of the year, but from mid-September through October, they’re particularly breathtaking, blanketed in stunning hues of orange, red, and yellow as the leaves change. Start in lush Steamboat Springs at Inspirato’s spacious lodge-inspired residence, then drive through stunning scenery en route to always-popular Vail and Beaver Creek. White River National Forest is the backdrop for your next leg as you drive to Aspen and Snowmass; here, the area’s gorgeous namesake trees surround visitors at every turn. The final drive to Telluride is a bit more complicated, but the reward is worth the effort: unspoiled Rocky Mountain beauty with far fewer crowds to compete with.

These four trip ideas are only a few ways to make the most of Inspirato’s collection of more than 900 vacation options around the world. Explore all of the club’s destinations and get inspired for your own adventure, and subscribe to IN the Details content to stay up to date on Inspirato Members’ experiences traveling the globe.


  • Jane Norris says:

    Consider a cross country trip on the Lincoln Highway.

    • Madie says:

      If you are a beach fan, or golfer might be a consideration, but sounded boring to me. Colorado Mts was the most intriguing choice. Going to a big city sounds more like a long week-end trip, mostly for adults with golfing, broadway shows and fine dining. Grand Canyon, Yellow Stone, Beach Cottages, Skiing and even Family Cruises would be more intetesting to kids, I think. I did not forget Amusement Parks, those are usually 2 or 3 days excursions planned specifically for the Park. Sometimes 1 day.

  • Sierra says:

    I live at the western end of U.S. 50 and think it would be fun to drive it coast to coast! Also Route 66!

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