Aerial view of Montauk Point Long Island New York.

Long Island Guide: Planning Your Trip

••• Michael Orso / Getty Images

Long Island is a 118-mile long stretch of land jutting out from New York State and into the Atlantic Ocean, containing the state’s easternmost point. Just 47 miles from Manhattan, Long Island is a popular destination for New York City residents, either for a day trip, weekend getaway, or more extended stay—especially in the summer. It’s known for its wide, sandy beaches, surfing, wine country, and of course, the Hamptons, which draws everyone from celebrities to the wealthy to the merely curious. Long Island also has several historic sites and many estates and homes that previously belonged to some of America’s scions like the Vanderbilts and Roosevelts. Long Island also has an established art scene, excellent seafood, and miles of hiking trails.

Planning Your Trip

Best Time to Visit: Summer is high season, especially if you’re visiting the beaches, but spring and fall provide lesser crowds and milder temperatures.

Language: English

Currency: U.S. dollar

Getting Around: Although the easiest way to navigate Long Island is by car, if you’re headed to the East End, the intense amount of traffic there in summers can make driving undesirable. You can get between cities via the Long Island Railroad (LIRR), and within a city taxi, Uber or Lyft, and biking is also a good option within the Hamptons and North Fork. In Nassau County, the bus system is called NICE (Nassau Inter-County Express), and in Suffolk County, it’s called Suffolk Count Transit, or SCT. If you’re going to Shelter Island or Fire Island (which is car-free), you’ll need to take a short ferry ride. You can also use the Shelter Island Ferry to get between the North and South Forks.

Travel Tip: Long Island is more than just the Hamptons. The North Fork and Western portion are both worthy of visits and often host smaller crowds, even in summer. Shelter Island is a hidden gem between the two forks that’s a more casual alternative to the Hamptons as well. And for history buffs, Long Island can’t be beat.

Things to Do

While relaxing on the beach or surfing may be highlights of the area, there’s so much more to do in Long Island if you’re not a beach bum. Long Island is home to some incredible former estates and homes that are now open to the public, as well as other historic sites. It is also dotted with dozens of historic lighthouses, some of which have museums and allow you to climb them. Families will love the various amusement parks, aquariums, and children’s museums, while art lovers are sure to be impressed by the multiple museums with heralded collections. And of course, the wine country here is a must-see for oenophiles (and anyone who appreciates a nice glass of wine), with dozens of beautiful vineyards to visit. Finally, food lovers are far from forgotten, with seafood being a standout thanks to the ocean access. Don’t miss these activities:

  • Surfing: Head to Montauk and its famous Ditch Plains to see some of the world’s best surfers—and join in.
  • Wine Tasting: Make your way to the North Fork for some of New York State’s best pours at wineries like Lenz Winery, Macari Vineyard, and Pindar Vineyard. The South Fork has three wineries worth a visit: Channing Daughters, Wölffer Estate, and Duck Walk Vineyard.
  • Ogle Mansions: From gawking at massive homes in the Hamptons to entering some of the country’s most significant historic estates on the Gold Coast, Long Island is perfect for those who appreciate elegant homes. Head to Sagamore Hill, Teddy Roosevelt’s summer home, go inside the Vanderbilt Mansion, Museum, and Planetarium, and check out Old Westbury Gardens, the former home of the Phipps family. And don’t forget Oheka Castle, the second-largest residence ever built in the United States.

What to Eat and Drink

Long Island is known for its seafood, and you’ll find plenty of great ways that the local catch—from lobster to oysters to sea bass—is served. Lobster rolls are plentiful out here, and everyone will have an opinion on the best. Given its proximity to New York City, the bagels and pizza on Long Island are also very good. Classic diners are also a thing, and while the food might be average it’s worth a stop just for the experience. The amount of farmland on Long Island means that the local produce is bountiful, especially in summer and fall so look for restaurants that take advantage of it. Pies that use local fruits can be legendary, and some delicious doughnuts can also be found.

The wine on Long Island is excellent, with dozens of local vineyards around the region, especially on the North Fork. There are also plenty of local breweries and more than a few distilleries making everything from vermouth to gin to whiskey.

Explore our articles on the 10 Best Seafood Restaurants on Long Island You Must Try, Long Island’s Best Wineries, and The 10 Best Restaurants in Montauk.

Where to Stay

From high-end luxury hotels to charming bed and breakfasts and inns to beachfront resorts, Long Island has a wide array of accommodations to fit every style and budget, whether you’re alone, with friends, your significant other, or the entire family. The big brands are here, but mostly on the western end of Long Island—not in the Hamptons or North Fork. To save the most money, pitch your tent at more than a dozen campsites, from beachfront to wooded parks. Home rentals are plentiful, although many can be hard to book for less than a week in high season. They range from tiny cottages to full-blown villas, with everything in between.

Explore the best accommodation options for Long Island with our guides to The 9 Best Montauk Hotels of 2020, The 10 Best Hamptons Hotels of 2020, and The 6 Best Budget Hamptons Hotels of 2020.

Getting There

Most visitors to Long Island start their trip in New York City. The easiest way to get to Long Island from NYC is on the Long Island Railroad (LIRR). If you’re going to the Hamptons from Manhattan, you can also take the Hamptons Jitney, a bus service, or a Blade helicopter if you can splurge.

Long Island does have a small airport (Long Island MacArthur Airport in Ronkonkoma) with some domestic flights. Otherwise, you’ll probably fly into one of NYC’s two airports: John F. Kennedy International Airport and La Guardia International Airport, which are both about 45 miles away from Long Island. Newark Liberty International Airport is the farthest away from Long Island but is still an option.

You can also take a ferry to Long Island from New London, Connecticut (to Orient Point) and Bridgeport, Connecticut (to Port Jefferson). During the summer, Montauk Ferry runs between Montauk and Block Island, Rhode Island, and between Montauk and New London.

Money Saving Tips

  • Bring a bike with you if you can, instead of renting a car or taking lots of taxis. Bikes are allowed on the LIRR with a special $5 lifetime pass.
  • There are tons of public beaches that are free, and parking is free before Memorial Day and after Labor Day.
  • The Nassau County Museum of Art is free on weekdays. The African American Museum and Center of Education and Applied Art in Hempstead are also all free.
  • There are tons of hiking trails throughout Long Island that are free to access.

Learn more about the cheapest ways to have fun by exploring the best free things to do in Long Island.

Article Sources
TripSavvy uses only high-quality, trusted sources, including peer-reviewed studies, to support the facts within our articles. Read our editorial policy to learn more about how we keep our content accurate, reliable and trustworthy.
  1. Long Island Index. "What Is Long Island?"

  2. Metropolitan Transit Authority. "Taking your bike on MTA subways, buses, and trains."