8 Off-Season Fall Destinations (and Where to Stay)
Fall is our favorite time to travel — foliage, harvest, crisp air, and way fewer crowds. Our fall departures (and holiday trips!) are already starting to fill up, so if there's a trip on your mind, now's the time to reach out.
Here are eight destinations we're loving this season, along with our hotel picks for each.
Portugal — Douro Valley
Fall is harvest season in the Douro Valley, one of the oldest wine regions in the world, so you'll catch grape picking, treading festivals, and vineyard tours at their most authentic. Temperatures settle into a comfortable 60s-70s°F, a relief after summer's heat and crowds in Lisbon and Porto.
Where to stay:
Six Senses Douro Valley — A restored 19th-century manor house on the riverbank, widely regarded as the region's standout luxury property, with a spa, wine library, and multiple dining venues surrounded by terraced vineyards.
Vintage House — A classic riverside pick in Pinhão, ideal if you want to be centrally located near the heart of the valley's wine estates.
Casa de São Domingos — A quieter, boutique option near Régua for travelers who want a low-key, nature-immersed stay.
Tuscany, Italy — Siena & San Gimignano
Fall brings olive and grape harvests, white truffle season, and rolling hills in gold and burgundy tones, all with a fraction of summer's tour-bus crowds.
Where to stay:
Rosewood Castiglion del Bosco — An ultra-luxury estate near Siena with its own vineyards, a private golf course, and a Michelin-starred restaurant — one of the most celebrated properties in all of Tuscany.
Hotel Certosa di Maggiano — A former monastery turned luxury retreat, walkable to Siena's historic center.
Hotel La Collegiata — A converted 16th-century convent just outside San Gimignano, with panoramic countryside views and a classic Tuscan feel.
New England — Vermont & New Hampshire
Peak foliage typically hits early-to-mid October, when sugar maples turn the Green and White Mountains into a patchwork of red, orange, and gold. Traveling slightly off the peak weekend, or sticking to weekdays, helps you dodge the leaf-peeper traffic.
Where to stay:
Woodstock Inn & Resort (Woodstock, VT) — An iconic, walkable-to-town luxury inn with a spa and gardens that burst with color in October.
The Pitcher Inn (Warren, VT) — An intimate luxury property where each room has its own distinct design, set in one of Vermont's most picturesque villages.
Omni Mount Washington Resort (Bretton Woods, NH) — A grand, historic resort at the base of Mount Washington with sweeping mountain views.
Slovenia — Lake Bled & the Julian Alps
Slovenia gets overshadowed by neighboring Italy and Austria, which works in your favor: the same dramatic alpine scenery with a fraction of the tourist volume, plus crisp, clear fall air that's ideal for hiking before winter closures.
Where to stay:
Grand Hotel Toplice — A historic lakefront hotel with a private beach and boathouse, right on Bled's main promenade.
Vila Bled — Once Tito's summer residence, this secluded lakeside property offers a private swimming area and classic, elegant interiors.
Adora Luxury Hotel — A smaller, design-forward boutique option with panoramic lake views, ideal for couples.
Cape Town, South Africa
Because the seasons flip in the Southern Hemisphere, fall travel here actually lands in spring: mild temperatures, blooming wildflowers, and Winelands vineyards in full swing, without summer's beach crowds.
Where to stay:
The Silo Hotel — A striking, design-led property in the V&A Waterfront with panoramic harbor and mountain views.
Mount Nelson, A Belmond Hotel — Cape Town's historic "Pink Lady," known for its gardens, afternoon tea tradition, and central location.
Delaire Graff Lodges & Spa — For a Winelands base, this Stellenbosch estate combines luxury accommodations with some of the region's best wine tastings and mountain views.
Patagonia — Torres del Paine
This is spring in the Southern Hemisphere, considered one of the best windows to visit all year: wildflowers carpet the steppe, glaciers actively calve, and trails are open without the peak-season crowds of December through February.
Where to stay:
Explora Torres del Paine — The original luxury lodge in the region and the only one located inside the national park boundary, with unobstructed views of the famous granite towers.
Tierra Patagonia — A striking, architecturally distinct lodge on Lake Sarmiento just outside the park, all-inclusive with daily guided excursions.
Awasi Patagonia — Private villas with a dedicated guide and vehicle per villa, offering a more personalized, flexible itinerary.
Jackson Hole, Wyoming
This is the sweet spot between summer's Yellowstone and Grand Teton crowds and winter's ski season: aspens turn brilliant gold against the Tetons, wildlife is highly active during the fall rut, and trails are nearly empty.
Where to stay:
Amangani — An adults-focused, spa-forward property with sweeping views of the Teton Range, known for its understated, minimalist luxury.
Four Seasons Resort Jackson Hole — Ski-in access at the base of the resort, with strong shoulder-season rates and availability before winter's peak.
Rusty Parrot Lodge — A smaller, boutique option in the town of Jackson itself, walkable to restaurants and galleries.
Asheville, North Carolina
Widely considered the best base for Blue Ridge fall foliage, with the Blue Ridge Parkway offering some of the most scenic leaf-peeping drives in the country, typically peaking mid-to-late October. The Biltmore Estate also runs seasonal harvest events during this window.
Where to stay:
The Omni Grove Park Inn — A historic, Arts and Crafts-era resort with sweeping mountain views and a well-known subterranean spa.
The Inn on Biltmore Estate — For guests who want to stay directly on the Biltmore grounds, with easy access to the estate's fall programming.
Kimpton Hotel Arras — A stylish, walkable option in downtown Asheville for travelers who want to be close to the city's restaurant and brewery scene.
These fall departures won't stay open long. Reach out today and let's start planning your trip.