Cuffing Season is Here

Cuffing season extends from October to Valentine’s Day. It’s the time of year when the temperature drops, sweaters are donned and coziness reigns. By necessity, more time is spent inside. As a result, it’s a popular time to couple up — hence the “cuffing.” 

For new and existing couples (or throuples, or friend groups, or relationships with anyone you love), cuffing season is also the perfect time for a cozy domestic getaway. Below, I've listed five of my favorites, from luxury mountain escapes to posh New England estates.

When you’re ready, reach out to plan and book your dream romantic trip.

White Barn Inn, New England

White Barn Inn, in Kennebunk, Maine, is the epitome of New England charm. You and your significant other will love its cozy, rustic-chic, preppy vibe. Another plus, it’s one of the only local properties within walking distance to the beach and downtown. Although, if you’re not up for a walk (about 10 minutes), they offer complimentary shuttles to and from the beach.

Every day, take advantage of trips to nearby vintage and antique shops. A savvy local tastemaker will point you in the right direction. Back at the hotel, schedule a treatment at the spa, which offers Eminence facials and rejuvenating treatments incorporating Native American traditions and alternative healing components like tuning forks and aromatherapy. Afterward, play chess by the fire, or learn how to make beeswax candles and seasonal floral arrangements with an in-house expert, a former TV producer for Martha Stewart.

Spend the evening at the hotel’s eponymous restaurant. Choose from a locally sourced prix fixe menu, a lobster tasting menu, or an elaborate eighth-course “blind tasting,” where the chef takes you on a culinary journey (you can trust him). It feels fancy and romantic. For something a bit more casual (but no less delicious), opt for Little Barn, where you can indulge in elevated classics like lobster rolls and crispy brussel sprouts. End the night by the fire pits, and make use of your complimentary daily s’mores kit.

Alila Ventana, Big Sur

There’s something especially romantic about Big Sur, where mountains meet rugged coastline. And the all-inclusive, adults-only Alila Ventana is the alpine-rustic-chic cabin you always wanted. Knotty exposed wood, heavy blankets, leather, and spacious balconies amid the redwoods make each of the 54 suites feel extra welcoming. The romance is dialed up further by the in-room record players (and there’s a record library in the lobby).

Even better, because of the property’s cliffside location, you’ll be able to see above the foggy marine layer blanketing the ocean each morning. 

The main restaurant is Sur House. Here, meticulously crafted dishes use ingredients sourced from the on-site garden and local producers. The wine list, too, highlights local, small-scale producers. Every evening begins with a complimentary cocktail hour and ends with post-dinner s’mores.

In between hikes and meals, learn how to make a knife, cold plunge in a mountain stream, go on a trail run, or partake in “Wine Down Yoga” (a flow followed by wine).

Blackberry Farm, Smoky Mountains

Anyone looking for a foodie-wellness getaway should head to Blackberry Farm, in Tennessee’s Great Smoky Mountains. The 4,200-acre property hosts a variety of activities, from fly fishing and mountain biking to yoga and meditation. There are numerous opportunities for adventure here, but if you’re really up for an active romantic getaway, consider starting your trip at the Farm’s sister property, Blackberry Mountain, and ending at the Farm.

Several things set Blackberry Farm apart, but they really shine when it comes to food and hospitality. As for the food, savor farm-to-table Appalachian cuisine at the James-Beard-award-winning Barn, which offers over 9,000 wines and 300 brandies and whiskies. Expect an elegant, dimly lit atmosphere with sterling silver and delicate linens. It’s the perfect spot for an elevated, fancy evening.  For a more casual, shorter prix fixe menu, try The Dogwood. You’ll have breakfast and lunch — biscuits and gravy, griddle cakes, hearty salads — at the Main House. 

The Inn of the Five Graces, Santa Fe

At The Inn of the Five Graces, set in the historic Barrio de Analco, the oldest neighborhood in the United States, suites and guest rooms are built into historic homes dating back to the 1600s, using earthy, traditional adobe mud plaster, and decorated with sacred and tribal art, precious stone mosaics, and offering signature amenities & unparalleled service.

A few favorite nearby attractions include the 400-year-old San Miguel Chapel, just across the street and the neighboring community theater, Santa Fe Playhouse. But don’t miss what’s offered on site — like the spa. 

In addition to treatments inspired by the various cultures along the Silk Road, you’ll also find a meditation and shrine room, a soaking pool and a sun-and-moon deck. In the evenings, grab a drink (especially something containing tequila or mezcal) at the Dragon Room. (Robert Redford and Georgia O’Keeffe were regulars.) End the night with a romantic farm-to-table dinner at Pink Adobe, the inn’s elevated New Mexican-Cajun restaurant.

The Roundtree Amagansett, Hamptons

The 14-room Roundtree Amagansett is a dreamy, sophisticated Hamptons hideaway. Choose from coastal-chic rooms and suites in the property’s restored century-old barn; a two-story historic home that sleeps up to eight; and a chic, modern private beach house a few minutes away from the main property.  

Everything here is whimsical and playful. Embracing your inner child is very much encouraged. There is afternoon tea and bonfires complete with s’mores, made-to-order late-night snacks (popcorn, sundaes), and ice cream happy hour featuring scoops from a local creamery. 

Hop on one of Roundtree’s complimentary bikes to explore the nearby museums and galleries, or to head down to the beach for a leisurely stroll with your plus-one. Cuffing season is the perfect time to visit; cozy activities abound. Go apple or pumpkin picking, go wine tasting, or curl up in a blanket with a cup of hot chocolate. After a day soaking up all the the homey vibes, retreat to your zen oasis of a room, and wash the day away with the beautifully aromatic Grown Alchemist bath amenities.