The Ultimate Guide For a Bostonian’s Long Island Getaway: Beaches, Vineyards, and Seaside Dining

Looking for the perfect summer destination? You’ll find it on Long Island, New York. From world-class beaches and Gatsby-era mansions to an award-winning wine region and championship golf courses, Long Island offers endless opportunities for fun, relaxation, and family adventure.

Getting here is simple. Whether you take the Long Island Rail Road from Manhattan, hop on one of two ferries from New England, or fly into JFK, LaGuardia, or MacArthur Airport, Long Island is as accessible as it is unforgettable. It’s where the convenience of a big city meets the charm and affordability of a coastal escape.

Just a four-hour drive from Boston, Long Island is close enough for a weekend getaway, but packed with experiences that will keep you coming back. Make it the trip of a lifetime, again and again.

Be in the Game

This September, the eyes of the golf world will turn to Long Island as Bethpage Black hosts the Ryder Cup for the first time in history. Renowned for its difficulty and prestige, Bethpage Black is a true bucket-list course and the centerpiece of Bethpage State Park, famously known as “The People’s Country Club.” As one of the most celebrated public golf destinations in the country, it proudly represents the spirit of accessible, championship-level play.

Long Island is home to a wide range of prestigious courses, both public and private, offering everything from legendary greens to stunning ocean-view fairways. The famous Shinnecock Hills Golf Club, an exclusive private course, is known for its classic links-style design which has been the backdrop of several U.S. Open tournaments and is set to host the famed major once again in 2026. For those looking for a similar experience of coastal premier play, but on the public side, Montauk Downs is the perfect option with a blend of historical significance, challenging course layout, and natural beauty. Whether you’re chasing legendary fairways or discovering a new, standout course, Long Island invites golfers of all levels to experience world-class play in a setting where every round is one to remember.

Be Adventurous

From scenic shorelines to action-packed attractions, Long Island is the perfect destination for travelers of all interests—each region offering something unique. With amusement parks, museums, and historic landmarks across the island, there’s no shortage of exciting activities, making it a year-round getaway for visitors of all ages.

Embark on a nautical adventure at the Long Island Aquarium, where you’ll encounter stunning marine life, hands-on exhibits, and relaxing boat tours along the Peconic Bay. For classic thrills, head to Splish Splash water park or Adventureland, packed with rides and family-friendly fun. Craving more excitement? Soar through the trees at WildPlay Jones Beach, where zip lines, aerial challenges, and treetop obstacle courses come with sweeping views of the Atlantic Ocean. Whether you’re seeking high-flying adventure or coastal charm, Long Island delivers unforgettable experiences at every turn.

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 with 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,” and inspired the setting of F. Scott Fitzgerald’s iconic novel The Great Gatsby.

Local Favorites: OHEKA Castle, Opus Steakhouse, Old Westbury Gardens, The Vanderbilt Museum & Planetarium, Prime: An American Kitchen & Bar

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, a variety of cultural attractions, and shopping. In 2026, the region will celebrate Long Island 250, honoring its pivotal role in the American Revolution with special events, historic experiences, and community pride on full display.

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. Pair your beach day with a stroll through one of the many charming downtowns, where you’ll find local shops, waterfront dining, lively nightlife, and scenic parks to explore.

Local Favorites: The Bellport Inn, WildPlay Jones Beach, Tiki Boat Long Island, Besito West Islip, Blue Point Brewery, Nicky’s on the Bay, The James

Fire Island – A car-free destination accessible only by ferry, Fire Island is home to 17 unique communities and known for its pristine beaches, family-friendly villages, and iconic LGBTQ+ destinations like The Pines and Cherry Grove. Feeling adventurous? Try Fire Island’s signature cocktail, the “Rocket Fuel”—just don’t say we didn’t warn you!

Local Favorites: The Palms Hotel, Dune Point, 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, Sound View Greenport, Harbes Family Farm, Lenz Winery, Sparkling Pointe Vineyard, Lavender By the Bay, North Fork Sights, Bites, and Flights

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, Mashomack Preserve, Ram’s Head Inn, Shell Beach

South Fork – This world-famous region is home to Long Island’s most iconic summer destinations: The Hamptons and Montauk. Explore coastal communities filled with chic boutiques, gourmet dining, historic art collections, and more, all just steps away from stunning beaches. And be sure to keep an eye out for celebrities—you might just spot one or two!

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

 

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