4 Days / 3 Nights
Theme: Old-school Hamptons leisure culture
Inspired by the timeless traditions of summer on the East End, this itinerary blends championship golf, waterfront lunches, beach afternoons, and sunset cocktails. It’s a weekend built around leisure in its finest form—where the days are active, the evenings are social, and there’s always time for one more round.
Day One — Arrival & Clubhouse Classics
- Check into Journey
- Afternoon exploring East Hampton Village
- Cocktails and dinner at East Hampton Grill
Ease into the weekend with one of the Hamptons’ most beloved dining institutions. Think classic cocktails, polished service, and the kind of atmosphere that never goes out of style.
Day Two — Montauk Links & Coastal Leisure
- Morning tee time at Montauk Downs Golf Course
- Rosé lunch following your round
- Afternoon at the beach or a nearby beach club
- Time to relax and recharge before the evening
- Whiskey and cigar experience
Spend the day enjoying one of the East End’s most scenic public courses before transitioning into a leisurely afternoon by the water. It’s a balance of sport, relaxation, and classic summer tradition.
Day Three — Golf & Golden Hour
- Morning round at Sag Harbor Golf Club
- Lunch in Sag Harbor Village
- Spa recovery treatments or massage
- Sunset cocktails at Gurney’s Montauk or Crow’s Nest
- Dinner at your leisure in Montauk or East Hampton
From historic fairways to oceanfront sunsets, this day captures the effortless luxury that has long defined Hamptons summers.
Day Four — One Last Morning
- Leisurely brunch before departure
- Optional stop at Wölffer Estate Vineyard
- Scenic drive through Sagaponack and Bridgehampton
A slow final morning offers the perfect ending to a weekend centered around leisure, great company, and some of the East End’s most beautiful landscapes.
Why We Love It
The Hamptons has always been a destination built around leisure. This itinerary combines championship golf, coastal dining, village exploration, and waterfront relaxation into a weekend that feels both classic and distinctly East End.