Beaches, Vineyards, and Waterfront Dining: The Bostonian’s Guide to a Summer Getaway on Long Island, NY

If you’re looking for the perfect summer destination, look no further than Long Island, New York. Home to world-class beaches, Gatsby-era mansions, an award-winning wine region, and championship golf courses, Long Island promises endless fun and adventure for the whole family.

Long Island offers convenient access by air, rail, land, and sea. A short Long Island Railroad ride from Manhattan, two ferry services from New England, and easy access via JFK International, LaGuardia, and MacArthur Airports, Long Island combines the convenience of a big city with the charm and affordability of a quaint coastal town. A four-hour road trip away from Boston, Long Island will be the trip of a lifetime—and one you’ll want to make again and again.

Be a Foodie

From scenic waterfront dining and celebrity chef-owned restaurants to some of the best pizza and bagels you’ll find in the country, it’s no wonder why Long Island is a foodie’s paradise. Whether you’re planning unforgettable family dinners or romantic date nights, the region’s culinary scene has something for every occasion.

Get a taste of Long Island’s maritime culture with sea-to-table cuisine, including everything from oyster shucking to iconic lobster rolls. Choose to dine at charming beach shacks where you can listen to live music and chat with friendly locals, or at upscale seaside restaurants with stunning sunset views.

Don’t miss the chance to explore the region’s award-winning “Wine Country,” home to over 60 vineyards, where you can sip and savor locally crafted wine while soaking up the sun against beautiful landscapes. Stop by one of the many local farm stands for fresh produce year-round and famous homemade pies that will have you coming back for a second slice.

Be Adventurous

Long Island is the perfect destination for travelers of all kinds, each corner of the region offering a unique experience. With plenty of exciting attractions, amusement parks, museums, and historical landmarks on Long Island, there is no shortage of fun activities that ensure year-round entertainment for all ages.

Experience a nautical adventure at the Long Island Aquarium, with stunning marine life, hands-on experiences, and quaint boat tours down the Peconic Bay. If you’re seeking thrill and excitement, head to Splish Splash water park or Adventureland for amusement rides and hours of fun and entertainment. For the thrill-seekers and nature enthusiasts, WildPlay takes you to new heights. Treetop obstacle courses, zip lines, and breathtaking aerial challenges await while overlooking the Atlantic Ocean.

Your Journey Starts Here

From stunning Gatsby-era mansions and lush vineyards of the North Shore to the pristine sandy beaches and The Hamptons villages of the South Shore, Long Island is made up of six distinct regions filled attractions, adventure, and fun.

The Gold Coast – Visit the Gold Coast to explore mansions, castles, and gardens from the 1920s, built by industry tycoons including the Vanderbilts and Guggenheims. If some of these properties look familiar to you, it’s because the Gold Coast has served as the backdrop for several Hollywood productions, including Taylor Swift’s “Blank Space” music video and the hit TV series “Succession.”

Local Favorites: OHEKA Castle, Opus Steakhouse, Old Westbury Gardens, The Vanderbilt Museum & Planetarium, Restaurant PRIME

North Shore – Luxury and legends abound on the North Shore where revolutionary history was shaped and harborside villages offer local flavors and New England-style charm. The North Shore includes beaches offering breathtaking views across the Long Island Sound, along with waterfront dining, plenty of culture attractions, and shopping.

Local Favorites: The Northport Hotel, Curry Club at SaGhar, Washington Spy Trail, John W. Engeman Theater at Northport, Del Vino Vineyards, Danfords Hotel & Marina

South Shore – Featuring some of Long Island’s best white sand beaches and iconic New York State Parks, the South Shore is a water lover’s paradise, and provides a perfect coastal escape for surfing, boating, and fishing.

Local Favorites: The Bellport Inn, Drift 82, Bohdi’s Beach Shack, WildPlay Jones Beach, Tiki Boat Long Island

Fire Island – A car-free destination with 17 different communities, Fire Island is known for its pristine beaches, family friendly villages, and iconic LGBTQ+ communities like The Pines and Cherry Grove. If you’re feeling adventurous, be sure to try Fire Island’s signature drink, “Rocket Fuel,” but don’t say we didn’t warn you!

Local Favorites: The Palms Hotel, Dune Point, Housers Bayfront Bar and Grill, Fire Island Lighthouse, Kismet Beach, Sunken Forest at Sailors Haven

North Fork – Known as “Wine Country,” or “NOFO” by the locals, the North Fork is one of the largest agricultural regions in New York, offering over 60 wineries, as well as seasonal farm stands, breweries, and craft distilleries. The North Fork provides a picturesque escape and celebrates the changing of the seasons, from fall leaf-peeping to fields of lavender and sunflowers in the spring and summer.

Local Favorites: The Shoals Suites & Slips, Sound View Greenport, The Haylard, Harbes Family Farm, Lenz Winery, Sparkling Pointe Vineyard, Lavender By the Bay

Shelter Island – For a tranquil step back in time, this charming and magical island nestled between the North Fork and South Fork is accessible by car ferry. This scenic retreat has over 2,000 acres of natural preserves that combine casual charm with exclusive privacy.

Local Favorites: Sunset Beach, The Pridwin Hotel & Cottages, Weakfish, The Terrace, Mashomack Preserve

South Fork – This world-famous region features coastal communities and Long Island’s most premier summer destinations: The Hamptons and Montauk. Enjoy chic boutiques and gourmet dining just steps from iconic beaches and historic art collections on the South Fork.

Local Favorites: Baron’s Cove, Gurney’s Montauk Resort & Seawater Spa, Duryea’s Montauk, Calissa Hamptons, Montauk Lighthouse, Wölffer Estate Vineyard

 

This is a paid partnership between Discover Long Island and Boston Magazine