Tell Me Where: 3 Perfect Days on Shelter Island
My favorite summer beach town.
My family’s love affair with Shelter Island began in 2015 when we visited The Chequit Inn on a random summer weekend. Until then, we had only day-tripped to Sunset Beach for a fun dinner or boozy brunch. But we fell in love with Shelter Island that summer, and for the last 10 years, have been finding any excuse to return.
Shelter Island is an 8,000-acre island tucked in the middle of Gardiners Bay, between the North Fork and the Hamptons. Accessible only by ferry (you drive your car on), it feels worlds away—beautiful, secluded and just the right level of chill. On the southern end, you drive through the Hamptons to the South Ferry, and on the Northern end, you drive through Greenport to the North Ferry. While the ride is less than five minutes from either route, once you arrive on Shelter Island, it’s a world unto itself.
What I love most about Shelter Island is that it feels like a classic New England coastal town. You can bike anywhere, past weathered shingled houses, roadside farm stands and plenty of small, quiet inlets to call your own. There’s beach in every direction. It’s the kind of place where flip-flops are the dress code, and a perfect day might involve nothing more than a beach towel, a good book and a soft-serve cone. Life moves slowly. There’s not a single traffic light on the island. But if you’re jonesing for high-key Hamptons lunch or night out, you have it just across the bay. I think Shelter Island drums up memories of my childhood summers spent on lakes throughout New England. I think it’s also why I love a bay. I am a Bay Bae. I’m not here to boogie board. I love calm water. I also love parking my car, hauling out a chair and walking 10 feet to the beach. None of this Moses in the Desert nonsense.
Since coming to Shelter Island, we’ve stayed at nearly every hotel and eaten at nearly every restaurant. We’ve stayed at The Pridwin, Shelter Island House, The Ram’s Head Inn, The Chequit, West Neck Guesthouse, the list goes on…..But for five years, we’ve been hanging our hats at Seven on Shelter Island—a stylish seven-room inn just up the street from Crescent (aka Sunset) Beach. It’s close to the action but feels worlds away.
I met Seven owner Beth Swanström in 2020 while reporting a story on tourism during Covid, and we became fast friends. Now I help her out however I can just for a way to get back. Beth totally nails the vibe. It’s a French-inspired breakfast spread each morning, wine in the fridge, art everywhere, luxe bed linens, a well-appointed gym and large pool with red Marcel Wanders loungers. It’s everything you’d want out of a lowkey but stylish beach inn. Beth is a former New York art gallerist and art interiors expert and she curates the scene accordingly.
While each hotel has its charm, opt for Seven if you’re with a friend, a significant other or maybe another couple. The Pridwin is best for families. The Chequit is great as it’s right in town, but it’s not near the beach. I’d rather bike or drive to town and walk to the beach. Dering Harbor Inn and Ram’s Head Inn are nice options if you’re on a multi-generational trip with grandparents and small kids. They have tennis and other amenities, but I like being walking distance to Sunset Beach. While the restaurant attracts a scene, it’s also really fun to have around. My kids play ping pong and cornhole there during the day. There’s a food truck stationed outside and people playing beach volleyball. Its energy makes the beach all the more fun.
Now that the kids are at camp, Evan and I sneak out of the city at around 8pm on Thursday and stay through Monday. What we get in return: three perfect, easygoing days on Shelter Island. So I laid out a visitor’s itinerary - the one we return to again and again.
Friday
I start my day with a workout at Seven’s gym or a nice long run around Crescent Beach. I’ll relax by the pool before biking or driving into town for lunch. The first stop is always Marie Eiffel - a lovely French market with to-die-for tuna salad. So it’s the tuna, a loaf of crusty bread, quart of fresh gigante beans and a tomato. You can eat outside on the Dering Harbor marina or take it to the beach. Either way, you win.
Then we head to Crescent Beach. I just like it there. If you want to grab an iced coffee or a frosé, you’ve got Sunset Beach right there. Plus you can rent paddleboards, get a massage or walk to the Pridwin for a late afternoon cocktail on the patio. If you have small kids in tow, family-friendly Wades Beach is worth checking out. Ask your hotel for a beach pass for your car. It is essential.
After your beach day, head to dinner at Léon 1909, a rustic, French-inspired bistro housed owned by Robert Mnuchin and his daughter Valerie. The vibe is unfussy but cool, with lofted ceilings, exposed beams and a 14-foot open hearth where much of the menu is cooked. Order the half-chicken, grilled local fish or anything kissed by the flames. Léon is a Shelter Island fixture—laidback and local, yet special enough to anchor a summer evening.
If you’re looking for something cultural, check out the Perlman Music Program, founded by Toby Perlman and led by her husband, world-renowned violinist Itzhak Perlman. Tucked away on a waterfront campus, the program brings together exceptionally talented young musicians from around the world for summer study. Think band camp but for future first chairs at the New York Philharmonic. The concerts are open to the public and held under a tent overlooking Crescent Beach (see video below from its annual summer gala we attended in 2022). The shows are intimate and magical and you’ll leave wondering why you never enrolled your child in violin. The Pridwin is next door for a post-show drink.
Saturday
Start your Saturday with a morning hike at Mashomack Preserve—a 2,350-acre nature sanctuary that covers nearly a third of Shelter Island. The trails wind through coastal woodlands, salt marshes and quiet creeks, with the occasional osprey soaring overhead. It’s peaceful, shaded and vast. We accidentally did 10 miles last weekend! (wouldn’t recommend). After your hike, head to Maria’s Kitchen for a gigantic salad or freshly made burrito that’s as hearty as it is flavorful. Right next door is Shelter Island Craft Brewery. Grab a cold beer and cool off at a picnic table in the back garden before heading to the beach.
Try a new stretch of sand today: bike over to Shell Beach and Hay Beach, both of which offer quieter vibes and stunning views. If you’re up for it, swing by White Oak Wine Garden for an afternoon tasting and game of bocce in its lovely garden before ending the day with dinner at Vine Street Café - a Shelter Island classic. It’s the kind of place you’d go with your parents to celebrate their anniversary. At the helm is Chef Terry Harwood and his wife Lisa Murphy-Harwood. Expect thoughtful and seasonal fare, with standout dishes like the fresh pastas, local fish and the cult-favorite crispy duck confit. Don’t pass on the warm bread and butter and french fries. Saturday night can be a good vibe at Sunset Beach for an after-dinner drink.
Sunday
Start your day with a bike ride to Dering Harbor for a tennis lesson or yoga class at the Dering Harbor Inn. Dering Harbor is a tiny village tucked into the northeast corner of the island. It feels like a world unto itself, with grand old homes, manicured hedges and quiet streets that make for the most scenic ride.
After your lesson, cruise the neighborhood and admire the architecture. Stop in town for a smoothie at Stars Cafe or pancakes and eggs at the Shelter Island Pharmacy. That’s right. The town pharmacy has a 12-seat counter where locals go for greasy-spoon style breakfasts and burgers on the cheap. Everyone knows each other and most are trading stories from their wild night before at Sunset Beach or Isola, an Italian restaurant down the street that transforms into a live music bar with karaoke (usually on Fridays).
Then it’s back to Crescent Beach—because Sunday is Sunset Beach Sunday. Go hang at the beach and when you get an inkling for a drink or a bite, pop on in. You don’t need a reservation or even a full meal to soak in the scene. Grab a small table in the front, order a few bites and people-watch for a while. The scene is a sh*t show in the best possible way: dudes stepping off their boats chatting about crypto, 20-somethings snapping selfies and wearing Pinterest board versions of “boho chic” attire. Magnums of rose….it’s all there. If you can get past the inherent cheesiness of the place, it’s really fun. It caters to people of all ages who want to have a good time. Pro tip: the more you look like you came off the beach, the cooler you’ll feel. But whatever you’re wearing, it’s welcoming and fun.
We like to end the weekend with a picnic on Crescent Beach rather than heading out to eat. If you manage to escape the Sunset Beach vortex, call in a pickup order at Commander Cody’s (order by 2pm). It’s a beloved, no-frills roadside shack that serves up some of the island’s best fish, fried chicken and authentic Southern sides. Everything is freshly made by Commander Cody and his mom, Linda, and it tastes even better barefoot on the beach, with a bottle of rosé and the sun going down.
Great article 😃