Summer may have ended, but that doesn’t mean vacation season has to. Throughout the fall, many top destinations still feature lovely weather and plenty of ways to fill an itinerary. The Inspirato Collection includes more than 900 vacation options in 175+ destinations, so there are plenty of places to visit for a great vacation with the club this fall. Below, find five of our favorite places for a fall vacation and start planning today.

Wailea, Maui, Hawaii

Hawaii’s peak season is summer, but with beautiful weather year-round, Maui’s Wailea area is still a great place to visit in the fall. With kids back in school, this season is perfect for a romantic couple’s getaway among the island’s picturesque tropical scenery. Inspirato’s residences in Wailea are located within our resort partners, Fairmont Kea Lani, Ho’olei at Grand Wailea, and Andaz Maui at Wailea; all offer plenty of entertainment throughout the season, with activities such as traditional canoe experiences, hula lessons, and luaus.

Telluride, Colorado

After bustling summer festivals and before always-popular ski season, fall is one of Telluride’s best kept secrets. All across the San Juan Mountains surrounding Telluride there are dozens of hikes that offer stunning views of the gorgeous fall foliage, and fly fishing on one of the area’s four rivers is good throughout the year. Telluride’s Friday Farmer’s Market runs through October 13, offering fresh produce, pastries, meats, crafts, and more, all sourced from within 100 miles of town.

Peninsula Papagayo, Costa Rica

Fall might be the rainy season on Costa Rica’s exclusive Peninsula Papagayo, but it’s arguably the most beautiful, as well. The precipitation helps bring out the rainforest’s natural beauty in lush hues of green. Don’t let the forecast scare you away: most often, days are warm and sunny, interrupted only by brief showers in the afternoon. That makes great conditions for a round of golf or a snorkeling expedition in the morning, followed by an afternoon of relaxation at the beach club.

Real del Mar, Mexico

Temperatures in Real del Mar stay nice and warm throughout fall, so it’s still a great time for water activities such as swimming, boating, and fishing — in fact, big-game fishing season extends all the way from early summer through January. Back on land, the renowned Festival Gourmet International takes place in November in Puerto Vallarta, which is only about a 30-minute drive from Inspirato’s residences in Real del Mar.

What a wonderful time we had in Real del Mar! From the home-cooked breakfasts prepared by our talented housekeeper and served poolside, to the lazy days floating around the private infinity pool, our group rated our stay as 'perfection.'

Jane AngelichInspirato Member

Florence, Italy

As one of Europe’s most-visited cities, Florence is almost always packed with visitors, but fall months are much less busy than most. That means it’s easier to get a front-row glimpse at iconic sites such as the Uffizi, the Accademia Gallery, the Ponte Vecchio, and of course, Florence’s endless array of delicious restaurants. Bonus: Fall is harvest season in the Tuscan countryside, so we highly recommend a day trip (or longer) to any of the area’s wineries or olive oil producers — or for something more exotic, a rare truffle-hunting expedition.

For more articles about destinations like these, as well as stories about how Inspirato Members travel and experience the world, subscribe to IN the Details.

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