3 Days / 2 Nights
Theme: Americana luxury, countryside elegance
Inspired by the Hamptons’ rich equestrian heritage, this itinerary blends horseback riding, vineyard afternoons, charming villages, and timeless East End style. Think rolling fields, linen shirts, leather riding boots, and long summer evenings with a glass of rosé in hand.
Day One — Arrival & East End Elegance
- Check into Journey
- Explore East Hampton Village and nearby boutiques
- Leisurely afternoon to settle in and enjoy the property
- Dinner at Topping Rose House
- Fireside wine tasting to end the evening
Ease into the weekend with one of the Hamptons’ most iconic dining experiences before unwinding over wine and conversation. The pace is intentionally relaxed, setting the tone for the days ahead.
Day Two — Horses & Hamptons
- Private riding lesson at Deep Hollow Ranch
- Scenic horseback trail ride through preserved countryside
- Polo-inspired picnic lunch
- Afternoon shopping and gallery hopping in Sag Harbor
- Rosé tasting at Wölffer Estate Vineyard
- Dinner at your leisure in Sag Harbor or East Hampton
Few experiences feel more quintessentially Hamptons than a day spent on horseback followed by an afternoon of rosé and village wandering. From wide open landscapes to waterfront streets, this day captures the East End at its most timeless.
Day Three — Equestrian Tradition
- Leisure breakfast and slow morning
- Optional Hampton Classic Horse Show access (seasonal)
- Vineyard stop before departure
- Scenic drive through Bridgehampton and Sagaponack
If visiting during Hampton Classic season, spend the morning enjoying one of the country’s premier equestrian events. Outside of show season, enjoy a final vineyard visit and one last glimpse of the countryside before heading home.
Journey Recommendations
- Hampton Classic VIP experiences (seasonal)
- Private transportation
- Vineyard reservations
- Professional photography sessions
- Custom picnic experiences
- Luxury floral arrangements
Why We Love It
The Hamptons has long been synonymous with equestrian culture, from sprawling horse farms and riding trails to the internationally renowned Hampton Classic. This itinerary celebrates that legacy while pairing it with some of the East End’s most beautiful villages, vineyards, and dining experiences.