Top 5 Boating Destinations on Long Island

There’s nothing quite like it. The air is so crisp, so fresh––you woke up to the smell of the grass this morning. The sun is out––it's hot, but it doesn’t burn. The perfect day to boat doesn’t come around often, but you’re a seasoned vet and you know today will be a day for the record books. Only one thing is holding you back: you don’t have a destination. I mean, you could pack sandwiches or other good meals to bring on. But there’s something about today that makes you want to expand your horizons, and sail to a new destination. Sound like you? You've come to the right place––here’s the boating destinations you won’t want to miss on Long Island.

Fire Island

You would be hard pressed to find a Long Islander that doesn’t have a story about Fire Island. Whether you are a college graduate or a senior couple enjoying their golden years, there is something here for everyone––and a community you can feel as soon as you step foot on its shores. Start your day strolling the 32 miles of white sand beaches, taking in the freshest sea air on the East Coast. When you get tired, head inland from wherever you ended up––you’ll be sure to be greeted with the same laid-back energy this island is known for no matter where you are. From restaurants boasting over 80 years of service like Flynn’s in Ocean Bay Park to beach clubs that would rival the best entertainment New York City has to offer, the hardest question you’ll have to ask yourself out here is, “What should I do next?”  Real locals will be enjoying a “Rocket Fuel” and we would advise any visitor to do the same. Composed of coconut milk, pineapple juice, and amaretto, the proportion might vary bar to bar but the secret remains the same––the rum must be 151 proof. Enjoy some delicious seafood (the Blue Point’s are our favorites) and unwind in a place that will have you thinking “Eden couldn’t be much better than this.”


Nestled in the North Fork of Long Island, this 19th century whaling port has been a favorite for those looking for a lowkey east-end alternative to the Hamptons experience. This quiet, one square mile hamlet is the perfect getaway for anyone craving those small-town, homely interactions. Regular activities include peaceful walks along neatly divided homes bursting with blooming hydrangeas and roses, coffee and a pastry from Blue Duck bakery and craft beers from Greenport Harbor Brewing Company. Continue to add to the magic with a visit to the town’s camera obscura; an ancient device preceding the modern camera, this structure demonstrates a natural effect of physics which produces an inverted photo realistic image onto the structure’s surface by bending light itself! Wind down from the excitement by walking to the town’s epicenter, Sterling Square, and lose yourself in a stylish oasis of restaurants and stores determined to give you the best the North Fork has to offer. Find a nice spot on the water, wrap up in your comfiest blanket and watch the sun come down in a place that could be mistaken for paradise.

Striano, Tara. The New York Times, 12 July 2018,

Democrat Point

Democrat Point is an inlet of Fire Island, and a popular destination for boaters, surfers, and 4x4 enthusiasts alike. When pulling up to Democrat Point on your vessel you’ll likely find yourself amongst other like minded boaters looking to enjoy the day just the same. Sore Thumb is another inlet that you would find the same hospitality at. The boating community within the Great South Bay is something special, and that same sense of companionship can be felt by all who venture into its waters. Being as the bay has some of the cleanest and clearest water you could jump in to, make your boat outing even more memorable with a sunset spent at Democrat Point––you'll be glad that you did!

Tenny, Kelly. A 4x4 At Robert Moses Beach.


Montauk is a first-rate destination on Long Island, a crown jewel that lies on the horizon of the East End. With miles of beaches and top dining and entertainment, this town invokes a sense of peacefulness to those that are fortunate enough to visit. There’s a rich history to this town, going back to the 1600’s. Climb the Montauk Lighthouse, a National Historic Site, 137 iron steps to the top for unbeatable views of some of the most beautiful scenery in the country.  Catch some sun at Ditch Plains and watch the surfers glide effortlessly over the water. Miles and miles of beach, dream inspiring cliff sides, it’s a place you’ll miss as soon as you leave! Food trucks dot the entrance for quality quick eats. Looking for something more substantial? Dining at a place like Navy Beach, you'll dine on the finest and freshest selection of seafood like squid, shrimp, local oysters, and that’s jusét the start. Feeling like having a drink? They have 3 different kinds of specialty house made rosé that are more than worth trying. Nightlife is also plentiful. With the opening of Common Ground MTK that blends dining entertainment and lodging, and staples such as Memory Motel and Ruschmeyers for more of a classic nightlife experience, descendants upon Montauk are in for a night of fun that they are sure to reminisce on upon their departure.

CNN, 2019, Accessed 2022.

Cold Spring Harbor

At one point being Long Island’s busiest whaling port, Cold Spring Harbor also has a rich history with the equal opportunity to run into a celebrity offhand. People from the likes of John Lennon to Lindsey Lohan have called this hamlet home, with premium destinations like Oheka Castle drawing global attention. For those planning ahead, a reservation at OHK within Oheka Castle is a restaurant that is second to none, and leaves none to the imagination. Headed by executive chefs Frank Monahan and Daniel Andreotti, their signature dishes paid with resident sommelier Samantha Bellando’s wine choices create a truly unique culinary experience. The oversized windows overlooking the grounds, coupled with the high ceilings within, lend to an opulent and luxurious feeling that is renowned the world over. As is popular with many coastal Long Island towns, quality fresh seafood is abundant. Walk down main street for endless shops to poke your head into whether you are looking for a candle or an antique––and for those interested in history there are two museums in Cold Spring Harbor as well.

Lambert, Audra, et al. “The Top 10 Secrets of Oheka Castle.” Untapped New York, 17 June 2021,

Jones Beach

One of the top beaches on Long Island Jones Beach is a favorite to many Long Island Locals, and it is easy to see why! From the 6+ miles of white sandy beaches, the expansive boardwalk, the Northwell Health Theatre that boasts a 15,000 seat-capacity, there are many opportunities to create memories well worthy of storytelling. One of the most visited beaches, Jones Beach has more than 6 million visitors every season. The waters are filled with boaters on weekends like July 4th, where many gather to watch the Fireworks Spectacular. There’s many different sport leagues to join like basketball, tennis, and beach volleyball, which run seasonally. Visitors can also ride bikes year-round on the boardwalk which has shops for food, drinks, and souvenirs. Besides the boardwalk and the Theatre across the parkway, there is relatively little commercial development, truly making Jones Beach feel like an escape from the hustle of everyday life. Be sure to spend a day in your boat off of Jones Beach if you get the chance this season!

ILoveNewYork, Accessed 2022.