Shelter Island Mini Guide: The Perfect Day Trip from the Hamptons
Not quite the Hamptons… but just close enough.
Shelter Island sits quietly between the North and South Forks of Long Island, just a quick ferry ride from Sag Harbor or Greenport. While it’s technically not part of the Hamptons (depending who you ask), its charm, ease, and salty magic make it one of my favorite summer escapes.
Whether you’re heading over for a laid-back day trip or planning a weekend getaway, this guide covers where to eat, what to do, and how to soak up all the little things that make Shelter Island special.
Best Restaurants on Shelter Island
Shelter Island might be small, but its food scene is mighty. These are the places I find myself coming back to again and again:
Vine Street Cafe
A beloved favorite for refined comfort food in a cozy, cottage-like setting. Seasonal, fresh, and consistently delicious.
SALT Waterfront Bar & Grill
A go-to for seafood and cocktails on the dock. Come by boat or drive over—either way, stay for the view.
Sunset Beach Restaurant
If you want a side of glamour with your rosé, this beachside spot delivers. Great for people-watching, French fare, and a fun afternoon.
Leon 1909
Chic and intimate with a European twist. The vibe is romantic, and the food never misses.
Marie Eiffel Market
A charming café and market where you can grab a great sandwich, coffee, or snacks for the beach.
The Terrace at The Pridwin
Come for dinner and stay for the sunset. The setting is elegant but relaxed—perfect for a golden-hour meal.
The Ram’s Head Inn
A timeless Shelter Island classic with Adirondack chairs, lawn games, and a menu that keeps it simple and satisfying.
Top Things to Do on Shelter Island
When you’re not eating (or sipping something chilled), here are my favorite ways to spend the day:
Beach Day at Crescent Beach
Calm water, soft sand, and a casual vibe that’s perfect for families or a relaxed swim.
Bike Around the Island
There’s no better way to explore. Rent bikes and discover winding back roads, shaded lanes, and secret water views.
Go Antiquing
Check out Marika’s Eclectic Boutique or Dworkin & Daughter for vintage treasures with soul.
Watch the Sunset at The Pridwin
Nothing beats a Shelter Island sunset. Grab a drink and settle into one of the lawn chairs—you’ll never want to leave.
Go on a Sailing Trip
Whether you charter a boat or bring your own, a day on the water is the ultimate Shelter Island experience.
Play a Round at Shelter Island Country Club
Nicknamed “Goat Hill,” this relaxed nine-hole course has sweeping views and just the right amount of nostalgia.
