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The Top 10: Fall Weekend Getaways

The autumnal season, when the air turns crisp and trees flaunt vibrant hues, is a particularly lovely time to travel, whether on a quick escape or long weekend trip overseas. As the countryside blossoms with fall produce and the wine harvest begins, many hotels offer special experiences exclusive to the fall season. From Tuscany to Tennessee, here are ten of our favorite destinations—and hotels—for fall weekend getaways.

Contact Indagare for assistance planning a fall getaway. Our specialists can book you at the hotels that are right for you, plan great meals and activities, arrange behind-the-scenes access and introduce you to our favorite guides.

Related: Melissa’s Picks: Where to Go in September

1. Tuscany; Rosewood Castiglion del Bosco

This fall, the Ferragamo-owned Castiglion del Bosco offers grape-picking excursions and tastings at the hotel’s vineyard, Tuscan BBQs, grape-infused treatments at the spa and helicopter tours of the region.

Related: Italy Dreaming: Florence and Tuscany

2. Tennessee; Blackberry Farm

This rustic-luxe retreat in rural Tennessee is particularly festive in the fall. The amber-colored Appalachian mountains surrounding Blackberry Farm draw active types looking to spend a weekend hiking, biking and fly-fishing, and foodies can delight in the hotel’s culinary offerings, including cooking classes, apple and pumpkin picking and harvest festivals with music and crafts.

Related: Countryside Getaways

3. Vermont; Twin Farms

This historic farmhouse tucked in the Vermont mountains is surrounded by crimson, gold and green foliage during the fall months. A hideaway for couples, the all-inclusive Twin Farms is a bucolic getaway for enjoying nature walks, fly-fishing at the hotel’s pond, gourmet harvest feasts and late-night bonfires. 

Related: Top 10: Fireside Cocktails

4. California Wine Country; Farmhouse Inn, Sonoma and Meadowood, Napa

California’s renowned wine valleys flourish in autumn with the ripening of the grapes and the anticipation of new varietals. Two exceptional properties, Farmhouse Inn in Sonoma and Meadowood in Napa, are luxe properties to retreat to after a fall getaway spent at local vineyards, touring wineries and visiting harvest-themed fairs. In partnership with Round Pond Estate, Meadowood Napa also offers olive oil–themed weekends, during which guests can tour a nearby olive mill and learn about how the oil is produced.

Related: Napa Wineries

5. Bordeaux; Les Sources de Caudalie

A magnificent French country estate set amongst grapevines and gardens, guests of Les Sources de Caudalie can learn about French wines without leaving the property. The on-site and renowned Château Smith Haut Lafitte hosts wine tastings, grape harvest workshops and tours that can be enjoyed with French fare from one of the hotel’s three restaurants.

Related: Bordeaux Wine Country: A Tale of Two Banks

6. Nantucket; Greydon House and White Elephant

Nantucket is known for its buzzy summer season, but the autumn months—which boast breezier weather and fewer tourists—are equally charming. Families who want to be within walking distance to town should opt for the luxurious White Elephant, while couples should retreat to the atmospheric Greydon House, which boats exquisite nautical décor and an acclaimed restaurant. Both resorts are elegant bases from which to enjoy fall weekend festivals (the Cranberry Festival over Columbus Day Weekend is particularly fun) and days spent picking fresh produce or sampling seasonal ales at island institutions like Bartletts Farm and Cisco Brewers, respectively.

Related: First Look: Greydon House

7. Provence; Villa La Coste

A modern art wonderland in a blissfully remote corner of Provence, this boutique hotel and open-air museum boasts sleek, sophisticated rooms, an on-property vineyard, a Francis Mallmann restaurant and hundreds of acres studded with works of contemporary art. Visit the winery, Château La Coste, for tastings and wander through the grounds to observe the exhibits debuting this fall with works from Jeppe Hein and Giuseppe Penone.

Related: Fall in Provence

8. Hudson Valley; Glenmere Mansion

Only an hour from Manhattan, this romantic estate is set in the spectacular Hudson Valley, which is particularly beautiful during October. The region has much to offer for fall weekend getaways, including wineries, apple orchards, farm-to-table restaurants and the plein air Storm King Art Center.

Related: Exploring the Hudson Valley

9. Rioja; Marques de Riscal

Oenophiles and aesthetes alike will be delighted by Rioja’s many riches: premiere wineries, architectural masterpieces like Ysios Winery and the Frank Gehry–designed Hotel Marques de Riscal, medieval villages and UNESCO sites. During the fall season, the Spanish region is abuzz with wine festivals and special events at the Dinastia Vivanco wine museum and vineyard.

Related: Spanish Escape: San Sebastian & La Rioja

10. Aspen; The Little Nell

A glamorous ski resort come winter, Aspen also draws active types in the fall. The chic Little Nell is centrally located at the base of Ajax Mountain, making it the prime address for visitors looking to spend the majority of their time hiking, mountain biking and horseback riding. The hotel also offers helicopter rides and Jeep tours, which provide stunning views of the glorious foliage and Rocky Mountains.

Related: Aspen’s Best Seasons

Contact Indagare for assistance planning a fall getaway. Our specialists can book you at the hotels that are right for you, plan great meals and activities, arrange behind-the-scenes access and introduce you to our favorite guides.

– Kira Reinke on September 13, 2017

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