How to Have a Relaxed, Casual (and fun) Summer Vacation in the Hamptons
After 25 years of living and working in the Hamptons, I've come to learn a thing or two about what makes a truly great summer out here. Whether you're renting for a week, staying the whole season, or just popping in for a long weekend, the secret to a memorable Hamptons summer is finding the perfect mix of casual charm, low-key adventure, and a deep mental reset.
Here’s how to do summer in the Hamptons the right way—relaxed, easygoing, and full of unexpected fun.
Start with the Right Morning Ritual
Skip the frenzy and lean into the slow. Grab a coffee and a sticky bun from Carissa’s in East Hampton or the Montauk Bake Shoppe (yes, the jelly croissants live up to the hype), and take a walk on the beach. Trust me, there’s nothing like an early morning barefoot stroll at Main Beach or Indian Wells to reset your brain and set the tone.
Reset Body and Soul
Summer isn’t just a season—it’s an opportunity to recalibrate. The Hamptons has quietly become a haven for those looking to restore their mental well-being. Start your day with sunrise yoga on the beach or a guided meditation class at The Class by Taryn Toomey in East Hampton. Try a sound bath at Mandala Yoga in Amagansett or book a Reiki session for a little energetic alignment.
Need to clear your head? Nature does wonders. A solo walk through the Elizabeth Morton Wildlife Refuge or an unplugged hour on the beach can feel like a total nervous system reboot. And if you really want to go all-in, a digital detox day without your phone might just be the most luxurious indulgence of all.
Make It About the Water
Don’t just look at the ocean—get out on it. Paddleboarding at Georgica Pond, kayaking through the coves in Sag Harbor, or even whale watching out of Montauk (yes, whales!) offers a whole new perspective.
One of the best ways to experience the East End from the water is with Paddle Diva in Springs. They make stand-up paddleboarding feel accessible and empowering, especially for beginners, and offer guided excursions that double as core workouts and peaceful meditations.
For adrenaline seekers, try windsurfing or kitesurfing at Napeague or jet skiing in Three Mile Harbor. And of course, charter a casual boat with friends for a sunset cruise—bonus points for bringing rosé and a playlist.
Casual Food with Serious Flavor
The best meals are the ones that don’t take themselves too seriously. A few of my staples:
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Bostwick’s Chowder House for lobster rolls, fried clams, and beachy vibes.
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Duryea’s Montauk for sunset dining with grilled branzino and rosé.
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La Fondita in Amagansett for fish tacos and margaritas under the string lights.
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The Dock in Montauk—a true salty staple. No frills, all character.
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Elaia Estiatorio in Bridgehampton for when you want fresh Mediterranean in a casual-chic setting.
Events That Keep It Interesting
This isn’t just a beach town. Summer in the Hamptons brings art, culture, and community together in a way that always feels spontaneous and stylish.
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The Parrish Art Museum in Water Mill hosts open-air concerts and film nights.
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Guild Hall in East Hampton mixes local theater, big-name speakers, and gallery shows.
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The Hampton Classic is a late-summer staple—go for the horses, stay for the people-watching.
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Sag Harbor Cinema is a gem for indie films and smart programming.
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Don’t miss local musicians playing at Stephen Talkhouse in Amagansett, The Surf Lodge in Montauk, or impromptu acoustic sets at beach bars and backyard parties. This place hums with live music if you know where to listen.
Architecture That Tells a Story
Part of the Hamptons vibe is how it looks and feels—timeless, human-scaled, and full of character. Take a stroll through Sag Harbor to see beautifully preserved whaling captain’s homes, their wide porches and weathered shingles whispering stories from the 1800s. In East Hampton, the historic cottages, white picket fences, and wind-swept hydrangeas offer that quintessential Hamptons charm. These are the kinds of places that make you want to slow down, breathe deeply, and just...be.
Hit the Landmarks (But Do It Your Way)
Yes, the Montauk Lighthouse is iconic. Yes, it’s worth it. But go early or late to avoid the crowds and bring a picnic. Likewise, a bike ride along Further Lane or a walk through the walking dunes in Napeague will leave you feeling like a local in the know.
Live Like You Belong
The best way to enjoy the Hamptons? Don’t over-plan it. Let your days unfold. Strike up a conversation at the farmstand, try a pop-up yoga class on the beach, linger at the farmer’s market. This place rewards spontaneity and curiosity.
After two and a half decades of calling the Hamptons home, I can tell you this: The real magic isn’t in the scene—it’s in the vibe. Relaxed, breezy, beautiful. Just like summer should be.
To make the most of your visit or move to this enchanting area, consider reaching out to Bill Williams for expert guidance. Let Bill Williams help you uncover the best of what The Hamptons has to offer.
