Coastal Living at Its Best in Shelter Island, New York

When you want to get away from it all, the seaside is the best place to go. There’s just something magical about the sea air that helps us slow down, relax, and enjoy life. And the East Coast doesn’t only have some of America’s most beautiful beaches; it’s also rich in culture and history. So no matter what kind of vacation you’re craving, whether it’s exploring or unwinding, you’ll be able to find it at the ocean.

Set in the iconic Hamptons, Shelter Island, NY, is home to some of the East Coast’s best vacation experiences. Our scenic waterfront has a stunning new view around every corner that will take your breath away. From dining to accommodation, this venue encompasses every element of a top-notch vacation. And no matter your budget, there’s plenty of fun to be had outdoors or inside. Alternatively, if retail therapy is more your speed, we’ve got you covered too.

The laid-back Shelter Island community is ready to welcome you for your next memorable stay.

Best Outdoor Activities on Shelter Island, NYC

With weather like ours, the outdoors is the best place to be, and there’s so much to do!

Boating is pretty much a way of life here on Shelter Island. Live the high life on a chartered yacht or rented boat and take to the seas to explore nearby Gardiners Bay or Coecles Harbor. You can’t get much further from the hustle and bustle of modern life than spending an afternoon sailing the big blue. And who could resist a romantic sunset cruise?

At The Rams Head Inn, we have an assortment of water-based activities for the whole family, from paddle boards to kayaking. It’s a wonderful opportunity to visit the island’s waterways, creeks, and inlets. You never know what magical marine life you might spot as you paddle across the clear waters.

Of course, it wouldn’t be an island vacation without a trip to the beach. Splash around in Rams Head Cove right in front of our inn and then take a stroll or laze on the beach to soak up some sun – we’ll take care of the beach blankets.

There’s even more to do outside of the water. At the inn, we offer several games to keep the whole family entertained, from pickleball, to bocce ball, to cornhole, and croquet. There’s even trivia nights for those who’d like to test their general knowledge alongside our other guests. Or why not take lunch outside to one of the stunning picnic spots?

Nearby Shelter Island Attractions

The Mashomack Preserve is an absolute must-visit when you’re on Shelter Island. Although it’s just 90 miles from New York City, it’s said to be one of the richest habitats in the northeast. Encompassing woodlands, marshes, and tidal creeks. You can hike along the trails that run through the reserve from dawn until dusk. Keep an eye out for the vibrant wildlife that live there, from red-tailed hawks to painted turtles.

Many of Shelter Island’s hotels are situated close to the island’s many historic attractions. The island’s rich history is lovingly documented at the Shelter Island Historical Society. The museum houses a collection of artifacts and documents that spans back to the island’s earliest inhabitants, the Manhanset tribe. At the Sylvester Manor Educational Farm, you can step back in time to the island’s plantation past. Besides the manor house itself, each of their walking trails allows you to explore a different part of the farm property.

Shelter Island is set in the Hamptons, which means that there’s no shortage of things to do and places to see very close by. Take in the magnificent collection at the Parrish Art Museum, which is home to masterpieces by Picasso, Jackson Pollock, and many other artists. Why not climb to the top of the Montauk Lighthouse, the oldest lighthouse in the state of New York? It takes 137 steps to get to the top, but the view is worth it. The Sag Harbor Historic District is also well worth a visit – if history is your cup of tea, don’t miss the Sag Harbor Whaling & Historical Museum.

Dining & Local Cuisine

Shelter Island is home to a wide variety of restaurants to please almost any palate. The first place to start is The Rams Head Inn Restaurant, of course. Whether you’re in the mood for brunch, dinner, or a sweet treat, we pride ourselves on our fresh, seasonal ingredients from our very own vegetable garden. Relax and sip a glass of wine or try one of our specialty beverages.

Other Shelter Island restaurants include seafood eateries overlooking the waterfront and farm-to-table options. Quality is the watchword, and wherever you go, you’re sure to enjoy food prepared with love and attention to detail. As with many coastal communities, you can enjoy the kind of high quality you only get when your seafood is fresh from the ocean.

One of the most popular breakfast spots on the island is the Shelter Island Heights Pharmacy. Don’t be fooled by the same – they operate in the old tradition of the pharmacy being a gathering point, lunch counter, and soda fountain for the community. You can mingle with the locals picking up their usual orders while you wait for your own simple, wholesome food.

Getting to Shelter Island

Now that you’re ready to plan your trip, the last thing you need to know is how to get here!

You might be asking yourself how far Shelter Island is from NYC. We have some good news – in just a few hours, you could be sitting on the Rams Head Cove beach sipping a cocktail. There are a few ways to get to Shelter Island, but perhaps the most convenient is simply taking a train or bus straight from NYC to the ferry terminals on the mainland. This convenient connection makes the transition seamless.

The ferry ride to the island is just the start of your next wonderful vacation.