3 Days / 2 Nights
Theme: Vineyard hopping, local flavors, and slow autumn afternoons
Fall is the perfect time to explore the Hamptons’ wine country. With golden vineyard views, crisp coastal air, and fewer crowds, the East End offers an inviting setting for a weekend of wine tasting and seasonal dining. From the celebrated vineyards of Sagaponack and Bridgehampton to cozy meals and sunset beach walks, discover a more relaxed side of the Hamptons with Journey East Hampton as your home base.
Day 1: Arrive, Unwind & Explore
Afternoon | Check In at Journey East Hampton
Settle into your accommodations at Journey before heading out to explore the East End. Take advantage of the slower pace of the season and enjoy an afternoon discovering East Hampton and Amagansett.
Evening | Dinner at Il Buco al Mare
Head to Il Buco al Mare for a memorable dinner featuring coastal Italian flavors and seasonal ingredients. It’s a fitting start to a fall weekend centered around great food and wine.
Day 2: A Taste of Hamptons Wine Country
Morning | Breakfast at Carissa’s Bakery or Tutto Caffè
Start the day with fresh pastries and coffee at Carissa’s Bakery or Tutto Caffè before making your way west toward the vineyards.
Late Morning | Wölffer Estate Vineyard
Visit Wölffer Estate Vineyard for a tasting of locally produced wines overlooking the vines. The vineyard’s autumn landscape makes it one of the most scenic places to experience fall in the Hamptons.
Afternoon | Channing Daughters Winery
Continue to Channing Daughters Winery, known for its distinctive wines and creative approach to winemaking. Enjoy a tasting while discovering another side of Long Island wine country.
Late Afternoon | Duck Walk Vineyards
Round out your vineyard tour at Duck Walk Vineyards, where a selection of local wines and scenic surroundings make for a relaxing final stop. Advance reservations and a designated driver are recommended.
Day 3: Coffee & a Coastal Farewell
Morning | A Slow Start at Journey
Enjoy a leisurely morning before checkout, then explore the local shops and cafés of Amagansett.
Afternoon | One Last Beach Walk
Before heading home, take a peaceful walk along the shoreline. Fall brings a special kind of quiet to the Hamptons beaches, making it the perfect way to close out your wine country getaway.