A Dreamy Hamptons Weekend — Planned for You
A weekend in the Hamptons should feel effortless, not overscheduled. The air is salty, the dress code is linen, and the best plans leave room for last-minute rosé. Whether you’re staying in East Hampton, Montauk, or Sag Harbor, this Hamptons weekend itinerary blends the perfect mix of beach time, local flavor, and low-key luxury — all with real-life timing.
Friday: Arrival + Sunset Dinner in Sag Harbor
Arrive by late afternoon to avoid peak traffic on Route 27. If you’re driving in from the city, stop at Round Swamp Farm in East Hampton to pick up snacks and fresh flowers for your Airbnb or rental cottage. Their lemon bars, shrimp salad, and blueberry muffins are iconic.
Check into your stay ideally something near town but walkable to the beach. Freshen up, toss on a breezy shirt dress or button-down, and head to Sag Harbor for dinner at The Beacon. Sit outside if you can. Order the tuna tartare, the lobster rigatoni, and a grapefruit martini. Watch the boats. Breathe. You’re here.
If you’re still awake, take a short stroll down to the pier and soak in the warm harbor breeze before calling it a night.
Saturday: Sunrise, Sea, and Montauk Vibes
Start your day early with a bike ride or walk through East Hampton Village, stopping for iced coffee and a cardamom bun at Carissa’s Bakery. If you’re the yoga type, head to a beach class with Yoga Shanti for a grounding hour in the sand.
Next stop: Montauk. Grab breakfast at Bluestone Lane or Left Hand Coffee, then head to Ditch Plains Beach for surfing or sunning. The vibe here is more surf shack than Upper East Side, and that’s exactly the point.
Around midday, head over to Duryea’s Montauk for a casual dockside lunch. Order the lobster cobb salad or grilled octopus, sip some chilled rosé, and enjoy the breeze. If you’re more of a picnic type, stop at Amber Waves Market in Amagansett on the way and build your own beach spread.
After lunch, explore Shadmoor State Park for a scenic hike along Montauk’s dramatic bluffs. You’ll feel like you’ve left New York entirely.
Dinner can be back near home base: try Cove Hollow Tavern or Bostwick’s Chowder House in East Hampton for fresh seafood and relaxed coastal vibes. If you’re in the mood for ice cream, Scoop du Jour is a local favorite.
End the day with a slow drive down Further Lane to admire the houses and hydrangeas. Or light a beach bonfire (where permitted) and listen to the waves.
Sunday: Slow Mornings + Local Markets
Sleep in. Seriously. Let the salt air and seagulls wake you up naturally. Make coffee at home or stroll to Jack’s Stir Brew Coffee in Amagansett for a vegan donut and strong iced latte.
Spend the late morning at Main Beach get there by 10 a.m. for easy parking. Bring a towel, a paperback, and not much else. Main Beach is simple and stunning, with gentle waves and postcard views.
Before heading back to the city, swing by the Sag Harbor Farmers Market if it’s open (typically Sunday mornings) to grab honey, fresh peaches, or wildflowers. It’s a little reminder of summer to take home with you.
If you need one last bite before the road, brunch at Estia’s Little Kitchen hits the spot with huevos rancheros, smoothies, and baked goods that rival the best in the city.
Final Notes for a Perfect Weekend
The Hamptons isn’t just about status or crowds — it’s about finding your own rhythm among the dunes, shops, and small-town magic. This itinerary gives you a flexible but inspired path through the weekend, leaving room for detours, naps, and roadside lemonade stands.
Pack light. Leave space in your schedule. And don’t forget: some of the best Hamptons moments happen when nothing is planned at all.
More from Healthy Living Magazine
Additional Resources
The Beacon Sag Harbor
Carissa’s Bakery
Yoga Shanti
Amber Waves Farm Market
Scoop du Jour
Roz Mattei
Roz Mattei is Healthy Living Magazine’s Travel Correspondent, reporting from the crossroads of culture, wellness, and global living. With a deep love for slow travel, natural beauty, and the rituals that connect people to place, Roz explores how different cultures around the world nourish mind and body.
When she’s not discovering herbal hammams in Istanbul or learning olive oil tasting techniques in Crete, you’ll find her sipping espresso in a tucked-away piazza or journaling by the sea. Roz brings the soul of travel to every article she writes.
