Experience a Long Weekend on Long Island, New York

A finger of land stretching out east from New York City, Long Island, New York, is often thought of as little more than a densely packed string of commuter towns giving way to posh seaside hamlets. But this area along the Atlantic is home to beaches and boardwalks, Gilded Age castles, tranquil ponds and verdant acres of vineyards.

More than 50 wineries add to Long Island’s charm and sophistication, and there’s no end to the natural beauty found in its bays, salt marshes and seaside plains.

And since it’s a stone’s throw from the biggest metropolitan center in the country, getting there is a breeze — hit the road straight from JFK International Airport, catch a train on the LIRR or grab the Hampton Jitney from Manhattan and you can make it there without missing a beat.

Here’s how to make the most of three days wining, dining and soaking up the sun on this little slice of paradise by the Big Apple. What on earth are you waiting for?

As always, check for travel restrictions and closures before planning your trip.

Friday: Beat the Weekend Crowds to the South Shore Beaches

No matter what time of year you find yourself visiting Long Island, the white-sand beaches are a must-see attraction. The South Shore of the island has so many choices, it’s impossible to go wrong, but for those looking to start the day with a stroll on the boardwalk, Long Beach can’t be beat. Rebuilt back to its full glory after Superstorm Sandy, Long Beach is a busy spot that gets crowded in peak season.

Pick up bagels at Max Bialystok and go for a Friday morning picnic before the New York City weekend crowds hit, to maximize your chance of getting a spot on the sand. Then ease into your getaway with sunbathing and beach reads until it’s time for your next meal.

With more than 2 miles of boardwalk, Long Beach has no shortage of beachy restaurants to choose from along the shore. Head up to Pop’s Seafood Shack for lunchtime staples like oysters and lobster rolls — if that breeze off the Atlantic is a bit chilly, outdoor fire-pit tables will keep you toasty as you nosh.

From here, make your way up to Fire Island, where your next stop is Robert Moses State Park. There you’ll find pristine Lighthouse Beach, historically a clothing-optional spot — nudity has been banned since 2013, with varying degrees of success.

Climb the 182 steps to the top of the Fire Island Lighthouse for panoramic ocean views. Built in the 1800s, it’s the tallest of the more than 20 lighthouses on Long Island.

Just down the road in Ocean Beach, the Island Mermaid is a Fire Island staple — go for crab tots, calamari and scallops (plus the obligatory burgers and wraps for the seafood-averse) by the water. Catch a drag show and dance the night away at Cherry’s on the Bay, an institution in the pioneering LGBTQ-friendly mecca of Cherry Grove.

Saturday: Unwind in the Hamptons

Hit the road early in the morning to trek to the east coast of Long Island, where you could easily while away the day rubbernecking as you drive past the multimillion-dollar homes lining the coast.

Grab coffee and a morning bite at Tate’s Bake Shop in Southampton — it’s nationally known for its addictively crunchy chocolate chip cookies, but this bakery is still killing it on the breakfast pastry front, too.

The Hamptons offer much more than celebrity sightings and exclusive parties. Top-rated Coopers Beach is a gem of scenic shoreline, with views of some of the area’s historic mansions. And East Hampton Main Beach is popular with visitors and locals alike — no doubt because those vacation-home property taxes mean it’s got top-notch amenities and impeccable upkeep.

Not in the mood for another seaside morning? Spend time wandering the quaint downtown areas of the hamlets within Southampton or East Hampton — or just post up on a sidewalk bench and people-watch as glamorous summer residents stroll past. If the weather puts the kibosh on time outside, duck into the Parrish Art Museum, a small but mighty collection of contemporary American art.

Snag a sidewalk table at 75 Main for a laid-back lunch of Niçoise salad and the famous prime-rib burger.

Next it’s on to Montauk, known in these parts as the End of the World, or simply “The End.” And fittingly so — it’s the easternmost point in all of New York state. Head to the end of the road and walk the windswept bluffs, scrubland trails and pebble beaches of Montauk Point State Park, home to the Montauk Lighthouse Museum.

For dinner, head to La Fin, a French spot with a rustic-glam vibe that feels right on point for Montauk. Lobster lettuce wraps are a house favorite, but an emphasis on local sourcing guarantees that no matter what you order it will be farm-fresh and satisfying. Weather permitting, skip the nightcap in favor of a sprinkle-dipped cone at John’s Drive-In, a beloved local ice cream spot with late-night hours.

Sunday: Wrap Up the Weekend Wine-Tasting in the North Fork

The vineyards on the North Fork offer New York’s best wine south of the Finger Lakes, with plenty of new purveyors to discover each time you return. Grab brunch today at Love Lane Kitchen — seasonal pancakes or the breakfast potato-and-egg bowl will lay a solid foundation for a day full of wine-tasting.

New Vine Wine Tours will set you up with a group-friendly ride and a private driver to escort you between vineyards, or if you trust your tolerance level, East End Bike Tours can lead you on a 5-hour, 13-mile circuit through the region’s top wineries, complete with a support vehicle to haul any cases you want to bring home.

If brunch doesn’t tide you over, make a detour to Modern Snack Bar, a 71-year-old North Fork institution, where, if the season is right, the battered and fried soft-shell crabs are a must-try.

Wind down your wine-filled day on the outdoor patio at Bedell Cellars, where you can look out over the manicured vineyard; they also feature live music and events in the taproom.

Then head to the historic seaport town of Greenport — an excellent spot to end your Long Island weekend. Stop by the historic 1920s carousel, and pick up a souvenir or two at small-batch distillery Matchbook, known for unusual — and utterly inspired — spirits.

Wrap up the night with a dozen bivalves at Little Creek Oyster Farm & Market, then walk down the road to Brix & Rye for a classic cocktail nightcap.