Vine Street Café

The Pridwin on Shelter Island is an adorable, quaint retreat that operates as a true escape from the Hamptons—but with all the luxurious amenities you'd expect. New this summer: a cocktail menu designed by Dante (one of NYC's trendiest bars), a Tammy Fender residency at the spa, and access to a Hinckley charter through Barton & Gray. With additional activities like yoga on the lawn, tennis, croquet, weekly barbecues, and movie nights—you could blissfully spend your entire vacation enjoying the hotel’s onsite offerings.

André Balazs's Sunset Beach Hotel is a lovely property that sidles right up next to the ocean. The 20 guest rooms all have private porches looking out onto the water. There’s easy access to the beach, which makes activities here especially nice—bikes are complimentary, and the hotel will happily arrange for beach chairs, paddleboards, and boats so guests can waterski, fish, or explore the area by sea. Good to know: The beach here is west-facing, so it's a great place to watch the sunset.

At the heart of this dining experience is a wood-burning hearth. The Provençal-inspired menu features shareable plates like bluefin tuna belly, slow-fired chicken, dayboat scallops, and striped bass. The wine list is filled with plenty of approachable, reasonably-priced bottles that pair beautifully with the simple, delicious dishes. It's our favorite in the fall for the cozy factor, but it makes for a great summer evening, too.

As at any André Balazs hotel, the scene at Sunset Beach is on point—with a great little European-style restaurant and a bar that brings in some of the area's best DJs. It's a fun spot for a long, boozy lunch (best with a big group) or a romantic dinner overlooking the sunset, and for the most glamorous entrance, you can arrive by boat.

The adjoining market to Vine Street Café, where you can take a bit of the magic home with you—expect fresh to-go foods alongside sauces, pastas, and a slew of gourmet pantry essentials.

Marie Eiffel Market is the best spot on Shelter Island for fresh baked goods, organic produce, sandwiches, salads, prepared meals, and catering. Take it home, or stay and enjoy the dockside water view from out back—our favorite is the terrace, where you can watch the boats pass by. She also keeps a small, curated shop of women's apparel and jewelry. It's a true Shelter Island favorite.

When in need of a nature fix, go straight to Mashomack Preserve on Shelter Island. The 2,039-acre preserve—often called the "Jewel of the Peconic"—is a stunning mix of ecosystems, home to eagles, ospreys, river otters, and more. The 11 miles of coastline also so many lovely trails to wander and enjoy.