The Romantic Getaway Itinerary

4 Days / 3 Nights

Theme: Coastal romance, intimacy, elevated leisure

Day One

  • Check into Journey and settle into a slower weekend pace
  • Beachfront picnic at golden hour with coastal bites and ocean views
  • Afternoon stroll through East Hampton Village and Newtown Lane
  • Dinner at Dopo La Spiaggia for candlelit Italian by the coast

Day Two

  • Couples massage and wellness experience at Shou Sugi Ban House
  • Slow lunch at Wölffer Estate Vineyard beneath the vines
  • Afternoon to relax at the beach or explore Sag Harbor together
  • Private sunset sail charter departing from Sag Harbor
  • Stargazing setup on the beach to end the evening

Day Three

  • Scenic drive out to Montauk along the coast
  • Gurney’s BathHouse spa circuit and oceanfront relaxation
  • Optional stops at Shadmoor State Park, Camp Hero, or Ditch Plains
  • Sunset cocktails at Crow’s Nest — one of the East End’s iconic golden hour spots

Day Four

  • Slow breakfast at Carissa’s Bakery
  • Morning stroll through Sag Harbor’s harborfront and boutiques
  • Coffee, antiques, bookstores, and a final quiet morning before departure