3 Days / 2 Nights
Theme: Intentional slowing down
Despite its name, the Coastal Grandmother lifestyle isn’t about age—it’s about embracing simple pleasures, beautiful surroundings, and the art of slow living. Think garden afternoons, fresh flowers, well-loved books, beach walks with coffee, and leisurely days spent enjoying the very best of the East End.
Day One — Arrival & Village Wandering
- Check into Journey
- Coffee and pastries from Carissa’s Bakery
- Explore East Hampton Village at your own pace
- Browse local home, lifestyle, and book shops
- Sunset beach walk at Indian Wells Beach
- Dinner at Topping Rose House
The first day is all about settling into a slower rhythm. Wander without an agenda, linger over coffee, and embrace the kind of afternoon that feels increasingly rare.
Day Two — Gardens, Books & Beautiful Things
- Morning visit to LongHouse Reserve
- Browse Sag Harbor Books and independent shops along Main Street
- Lunch in Sag Harbor
- Antique shopping throughout the village
- Afternoon at Madoo Conservancy
- Linen picnic setup or garden reading afternoon
- Sunset tea service overlooking the coast
From sculpture gardens to antique stores and charming bookstores, the day is filled with the small rituals that make the Hamptons feel timeless.
Day Three — Farm Stands & Farewell
- Leisure breakfast and coffee
- Visit Round Swamp Farm for local provisions and seasonal treats
- Optional pie baking or cooking workshop
- Scenic drive through Sagaponack and Bridgehampton
- Departure
A final morning spent exploring farm stands, gathering fresh flowers, and taking the scenic route home is the perfect ending to a weekend centered around simple pleasures.
Suggested Stops
- LongHouse Reserve
- Round Swamp Farm
- Sag Harbor Books
- Carissa’s Bakery
- Madoo Conservancy
- East Hampton Village
- Sag Harbor Main Street
Why We Love It
Despite its name, the Coastal Grandmother lifestyle isn’t about age—it’s about a way of living. A love of fresh flowers, well-set tables, meaningful rituals, and afternoons spent outdoors. This itinerary captures the softer side of the Hamptons through gardens, books, beaches, and the luxury of unhurried time.