Why Fall Might Be the Most Underrated Travel Season
Summer often gets all the attention.
It’s the season of family vacations, beach trips, and packed itineraries. But after years of helping clients plan everything from bucket-list adventures to relaxing getaways, I’ve come to appreciate a different season altogether.
Fall.
There’s something about autumn that changes the way we travel. The weather softens, the crowds begin to disappear, and destinations seem to reveal a more authentic version of themselves. It becomes less about checking attractions off a list and more about savoring the experience.
Some of my favorite fall destinations couldn’t be more different from one another, yet they all share that same feeling.
In Montana, the landscape begins to transform as the leaves turn shades of gold against a backdrop of rugged mountains. Whitefish becomes a peaceful retreat, offering easy access to Glacier National Park without the crowds of peak summer. It’s the kind of place where mornings start with a cup of coffee overlooking the lake and evenings end around a fire. For travelers looking for a luxury mountain escape, I love recommending The Lodge at Whitefish Lake, where the setting is every bit as spectacular as the service.
Across the country, New England enters the season it was made for. There is a reason travelers from around the world flock to Vermont, New Hampshire, and Maine each fall. Winding roads, charming villages, and brilliant foliage create a landscape that feels almost cinematic. For those looking for an extraordinary stay, Twin Farms in Vermont offers an intimate all-inclusive experience that blends luxury, exceptional dining, and some of the most beautiful scenery in the country.
Meanwhile, in California’s Napa Valley, harvest season is underway. The vineyards are alive with activity, the weather is nearly perfect, and the entire region seems to glow in autumn light. Whether it’s a milestone anniversary, a romantic getaway, or simply an excuse to enjoy incredible food and wine, fall is one of the most rewarding times to visit. Auberge du Soleil remains one of my favorite recommendations, offering sweeping vineyard views and an atmosphere that feels effortlessly elegant.
Not every fall getaway has to revolve around mountains or wine country. Some travelers are drawn to places where slowing down is the main attraction.
That’s where Blackberry Farm comes in.
Tucked into the foothills of Tennessee’s Smoky Mountains, Blackberry Farm has become one of the most celebrated luxury resorts in America. Guests spend their days horseback riding, fly fishing, hiking, enjoying spa treatments, or simply sitting on a porch overlooking the countryside. The farm-to-table dining is exceptional, but what truly makes the property special is the sense of calm that settles over everything. During the fall, when the surrounding hills are painted in shades of amber and crimson, it’s easy to understand why so many travelers return year after year.
For those who prefer history, culture, and incredible dining, Charleston offers an entirely different kind of autumn escape. Once the summer heat fades, the city comes alive. Historic homes, waterfront walks, and some of the South’s best restaurants create the perfect setting for a long weekend. My favorite luxury recommendation is The Dewberry Charleston, a sophisticated hotel that blends Southern hospitality with modern design and places guests right in the heart of the city.
What I love most about fall travel isn’t necessarily where you go.
It’s how you experience it.
There’s less rushing and more lingering. More scenic drives. More conversations over dinner that stretch long into the evening. More opportunities to slow down and truly enjoy the destination in front of you.
While everyone else is thinking about summer vacations, seasoned travelers are already looking ahead to autumn. And honestly, they may be onto something.
Because some of the most memorable trips aren’t taken during the busiest season.
They’re taken just as the leaves begin to change.