Travel Spotlight on Shelter Island, New York, and Its Top 14 Attractions

Hopper's travel guide to Shelter Island features its 14 best attractions, restaurants and hotels, and has travel tips and photos from local bloggers.

Hopper Editors - Oct. 26, 2017

A popular destination for New York summer vacationers, Shelter Island offers luxury and coastal beauty. It’s located a 2.5 hours west of New York City by car – although arriving by seaplane is a popular option for the moneyed, which takes just 45 minutes from Manhattan. The Sunset Beach Hotel in particular is a hotspot for luxury vacationers, many of which looking out for celebrity sightings. Visitors can also catch the Long Island Rail Road to Greenport, which takes them to the Shelter Island Ferry. The nearest Amtrak station and International airport is in New York City. Quieter and more family friendly than the trendy Hamptons party scene, Shelter Island maintains a beach community vibe and is a boating, beach and outdoors vacation spot.

There are beaches for all types of days out on Shelter Island

With 20 miles of coastline, there are quite a few beaches on Shelter Island, and those beaches are popular locations for celebrity spotting. Some beaches are quiet and perfect for laying low, while others are quite the opposite, such as Sunset Beach where you’ll find hot restaurants bustling with people popping open bottles of pricey champagne bottles.

Boating, sailing and kayaking are popular activities on Shelter Island

While at Shelter Island, what else are people going to do but dive straight in? Swimmers can kick their fins a bit, but visitors can also rent kayaks or sailboats and traverse the waters. Of course, the well-heeled will often elect to sail the seas on their own private boats and yachts, so the casual observer will be able to spot some pretty impressive vessels.

Go hiking in Mashomack Preserve

The Mashomack Preserve encompasses 2,100 acres of natural and diverse habitat where plants and animals can thrive. Although only 90 miles from New York City, the landscape couldn’t be more different: rather than tall, concrete skyscrapers that many call home, the preserve has a number of rare birds and plants, and the pine swamp area has been designated as an area of unique local importance.

Vine Street Cafe is country dining at its finest

Husband and wife duo, Pastry Chef Lisa & Chef Terry Harwood, are the owners and operators of this Shelter Island restaurant. They work with local farmers, fisherman and vineyards to source the very best local and seasonal produce for their constantly evolving menu. Aside from offering a beautiful country-style dining space, the restaurant also offers a small market out the back where people can grab a takeout order, ready-made salads and pastas or a few pantry items. They also offer specialty catering.

A few more restaurants to tickle your tastebuds in Shelter Island:

La Maison Blanche Hotel combines a country vibe with modern beach chic

Located close to Crescent Beach on Shelter Island, La Maison Blanche Hotel is an 1800’s property that has been lifted up with a modern beach chic touch. Facilities include a pool, patio, indoor and outdoor dining and a bar in the garden. Guests will also be delighted to visit their bakery, which offers daily-baked treats for the road. Decor-wise, expect to see crackling fireplaces inside, and beautifully manicured gardens outside.

See Shelter Island on the map:

Get the Hopper app to find the best deals.
You could save up to 40% on your next flight!