Hamptons Winter Experiences | The Roundtree, Amagansett Skip to main content
Evening S'mores Event at The Roundtree, Amagansett, Hotel in Ham

Winter Hamptons

The storied Hamptons summer season may get all the attention, but we also love it as a destination in the winter. The crowds are gone, the weather rarely gets uncomfortably cold, and it’s an opportunity to appreciate the area’s authentic setting and scenic landscapes.

While the hubbub that exists from Memorial to Labor Day may be missing, rest assured that the Hamptons has plenty of diversions on offer in the winter months.

Winter Hamptons, The Roundtree, Amagansett, Hotel in Hamptons

Privately Guided Tours

We can arrange for privately guided hikes for guests of all fitness levels and ages in numerous areas - all equally picturesque and worth exploring. There are the seaside set trails in Montauk Point State Park, the serene wildlife dotted paths at the Elizabeth A Morton National Wildlife Preserve in Sag Harbor (a favorite for children, even toddlers) and more. 

Our guide Bruce is the former creative producer of the Radio City Rockettes and now calls the Hamptons home. 

The Hamptons Overview Tour

Take a journey from the past to the present in one engaging tour. Our licensed guide Bruce is your host on this unforgettable day. Travel with him in a chauffeur-driven car through the local villages or drive on your own and meet him at sites where you'll learn about the history of the colonists and summer settlers who established roots in the Hamptons and gave birth to the farming tradition that continues today. 

Our guide also shares his stories of how the region became a seaside getaway spot of choice for New York high society in the late 19th century. The culmination of the tour brings guests to present-day - a time when the Hamptons is an amalgamation of recreation, culture, the arts and food. Interactive, visual and story-filled, this tour can be tailored to your preference. 

Historical Amagansett, The Roundtree, Amagansett, Hotel in Hampt
Water Bottle, Hamptons Essentials, The Roundtree, Amagansett, Ho

Private Trainer-Led Workouts

Whether it’s yoga on our sprawling lawn, a boot camp on the beach or a strength circuit in the privacy of your room or at an indoor studio in East Hampton, our resident trainer Linda or someone on her team can lead you through your favorite workout during your stay here. Linda is a longtime Hamptons resident and certified personal trainer with a loyal local following. 

North Fork Winery Hopping

Home to more than 60 wineries, the North Fork is a dream for vineyard hopping. And, yes, most are open in the winter, although hours may be limited.  

Our favorites include Mattituck, open only by appointment and offering red blends, roses and whites. The winery has a new collection of heated tents for private tastings and also offers tastings on its heated covered deck. Mattabella has a tasting room in an early 20th-century barn where the staff proffers pours of the white, red and rosé varietals. Then there’s Paumanok, famous for its warm you up merlots and cabernet sauvignons. Our team can create a customized tour for you. Tell us what you like to imbibe on, and we’ll take care of the rest.

two glasses of wine in front of wooden barrel