Living on Long Island comes with a lot of perks, one of which is the chance to explore the island’s waterways and shoreline sites by boat, which are spread out along the north and south sides. Throughout the summer, boaters can go on a variety of exciting experiences. Before you go, be in mind that the rivers on Long Island have various navigational standards. Before going, make sure to check with local marinas or dockage facilities to learn about space availability, size accommodations, and docking fees. In this article, I will list the best boating destinations in Long Island so as to help you choose one or all of them. So, keep reading!

Old Saybrook and Essex, CT

In the fall, swallows swarm, bald eagles nest in the winter, and shad school in the spring. The Connecticut River is all about boating on Long Island Sound in the summer. Some great anchoring locations may be found in the southernmost towns. One of the unusual anchorages in Old Saybrook is above the highway bridge between Ferry Point and Calves Island. In the harbor north of Calves Island, the town of Old Lyme maintains two transient moorings. Also, there is a short-term site east of Nott Island near Essex. But, shoaling has been reported so watch your depths.

Stamford, CT

Carefree Boat Club of Southern CT has a facility in Stamford, which is a thriving metropolis. If you’re boating out of Stamford or visiting, there are numerous fantastic restaurants on the water and just a short walk from the docks, where there are also many shops. The Crabshell Restaurant, where you can tie up on their private docks, is highly recommended. A mirage appears along the shore as you approach Stamford from the Sound. A mini-Manhattan rises out of the green lovely hills, complete with modern buildings lining a shore littered with marinas galore. However, this isn’t your normal cruising spot. It’s not quite like taking a boat to Manhattan, and it’s certainly not an ideal, calm harbor, but it’s still a worthwhile excursion.

Hamburg Cove and Selden Creek, CT

As you travel up the Connecticut River, the shores become ever more picturesque. Hamburg Cove in Lyme has always attracted visitors seeking peace and quiet or hoping to meet up with friends. Because it is currently full of moorings, you should call the harbormaster to discuss your choices. Selden Creek, to the north, makes you feel like you’ve stepped back in time. It is a popular hurricane hole for locals due to its natural safety. Although the creek that flows around Selden Island has deep water for anchoring, many people find it too small for swinging. Stay at a marina in Deep River or Chester Point Marina to properly appreciate the surroundings.

Fishers Island, CT

Fishers Island, which is nine miles long and mostly private, has a colorful history as a refuge for the affluent and famous. It is a hamlet in New York that is often confused with adjacent Connecticut. You may enjoy the beauty of this small island by anchoring outside the mooring field in the approved anchorage at West Harbor. You’ll generally find plenty of space, and transients are welcome to utilize the Fishers Island Yacht Club’s dinghy dock. The east side of Flat Hammock, which is uninhabited, is a lovely area for a swim, and you may dinghy to shore. For smaller vessels, East Harbor can be a peaceful haven.

Westport and Milford, CT

The Saugatuck River and historic Westport make for a great boating destination, as well as one of Carefree Boat Club of Southern Connecticut’s locations. Explore the nice stores downtown while cruising the river past luxurious houses. There are also numerous excellent eateries to suit any taste or budget. While visiting, members can call Carefree’s Westport Dock Master for free dockage. Milford has Connecticut’s longest coastline and is only a short walk from Milford Harbor, the country’s second-longest Green. Milford’s Green, located just behind Boston Common, is surrounded by restaurants, shops, and other attractions. Charles Island, which is connected to the mainland by a sandbar, is home to Silver Sands State Park.

The Sand Hole at Lloyd Point, NY

With the exception of one private 20,000-square-foot Tudor villa, this protected dual-basin just north of Huntington was excavated into the spit and is bordered by Caumsett State Park. On weekends, it attracts a large number of sailors. If you go exploring in your dinghy, keep in mind that the surrounding area is mostly a bird refuge and private land. Keep in mind that the entrance is difficult to find. Deeper draft vessels should only enter at high tide, and if it’s your first trip, you might wish to follow another boat in. Keep an eye out for the bar to the north of the entryway. A short waterway connects the two basins on the inside. Both basins have strong retaining ground, but the southern basin has more depth.

West Harbor, Bayville, NY

You might wish to head beyond the charming tiny hamlet of Oyster Bay and into West Harbor, a popular protected anchorage not far from the Sand Hole. In the harbor, a 5 mph speed limit is strictly enforced to ensure safety. These waterways are part of the Oyster Bay National Wildlife Refuge, which serves as a wintering location for waterfowl such as black ducks, canvasback ducks, and long-tailed ducks. During the summer, they are replaced by a different type of water enthusiast: boaters. Although there isn’t much in the way of shore access, the area is peaceful. Even in the hotter climates, there are plenty of feathered pals to be found, with the protected piping plover being one of them.

Montauk Point, NY

When totally controlling their sailboat, many boaters are quickly drawn to “The End.” They are drawn by history and beauty to the flame that is the beacon atop the Montauk Point Lighthouse and Museum. Montauk is also a great place to go fishing, whether for tiny fish near the beach or for big games like tuna, marlin, and sharks further out. Montauk has miles of gorgeous coastal beaches ashore. Explore Hither Hills State Park or one of the five state, county, or local parks, as well as a burgeoning summer nightlife.

Fire Island, NY

If you want to avoid the hustle and bustle then you will enjoy all that Fire Island has to offer. Visitors can dock at Watch Hill, Ocean Bay Park, or Ocean Beach, where cars are prohibited but there are still various eateries and services. Davis Park, a mile from Watch Hill, has a lovely coastline and excellent service at its main restaurant/bar, while Kismet is the westernmost party hotspot. The main seaside dining and dancing spot is the Surf’s Out restaurant. However, Ocean Beach has the most concentration of bars, restaurants, and shopping.

Fort Pond Bay, East Hampton, NY

This location features a great underwater attraction for snorkelers and divers, as well as a spectacular view of the bluffs. The bay’s entrance lies right opposite Gardiners Island in Napeaque Bay, west of Lake Montauk and east of Hither Hills State Park. Culloden Point is located on the bay’s east side entrance, where the H.M.S. Culloden, an English frigate that sank in 1871, lies moored about 150 feet offshore. Pay attention to depth and don’t get too near to the beach because deep water drops off swiftly.

Port Jefferson and Mt.Sinai Harbor, NY

On the North Shore of Long Island, near Black Rock Harbor and Captain’s Cove Seaport, Port Jefferson is deep water, protected boating location. Restaurants on the ocean and inland, shopping, art galleries, markets, a children’s museum, and parks are just a few of the attractions in the region. Mount Sinai Harbor is a bustling little port with plenty of things to see and do. Cedar Beach features a beautiful sandy beach bordered by a thicket of cedar trees. A variety of local eateries are located right on the sea, as well as in nearby small communities.

Eaton’s Neck, Northport, NY

As you reach Huntington Bay, a long stretch of sand wraps around Eaton’s Neck Basin, a gorgeous anchorage surrounded by nothing but nature and home to one of the country’s oldest Coast Guard stations. The land is now a bird sanctuary, so you can’t get ashore. The Coast Guard station as well as the historic Eaton’s Neck Lighthouse are still operational. The entrance is narrow, and there are no buoys marked on the map (be sure to pay attention to them, though). Inside, there are plenty of depths. The fog adds a vibrant touch to this gunkhole, with the Coast Guard station and lighthouse bell blasting above you.

Cold Spring Harbor and Oyster Bay, NY

Cold Spring Harbor is currently a bustling summer resort town with a whaling museum and aquarium. There are great local eateries and attractions like the Harbor Mist Restaurant. What a charming small hamlet, nestled at the mouth of gorgeous Oyster Bay on Long Island Sound. Cold Spring Harbor is a beautiful former whaling harbor tucked on the North Shore of Long Island Sound along scenic Route 25A in the Town of Huntington. This small, charming village now has a plethora of shops and two museums, ensuring that a weekend stay will not be boring.

Oyster Bay is home to a large population of bluefish as well as good cruising and coastal exploration conditions. Beautiful sandy beaches and a profusion of restaurants and stores await visitors on the beach. The waters of Oyster Bay are protected by Centre Island, which offers boaters tranquil weather and beautiful anchorages.

Zachs Bay, NY

This anchorage is easily accessible from both east and west. The harbor is highly protected and normally quite peaceful, located just off the State Channel and east of Wantagh Parkway (where Sloop Channel meets the State Channel). It does, however, fill up with other boaters looking for peace and quiet or a place to raft up and chat, so arrive early. Jones Beach Theater is a landmark in the bay’s northeast corner, however, it’s not normally a free listening venue.

Mattituck Inlet, NY

Mattituck Creek is a beautiful flowing creek that is home to wetlands, wading birds, and osprey. However, don’t get too distracted by the scenery, as you must keep an eye on the buoys in the small waterway. The lovely village of Mattituck awaits you at the end of your voyage boating on Long Island Sound. Just off Strong’s Water Club and Marina is a federal anchorage. You have the option of landing your dinghy at the town port or temporarily docking at the resort-style marina. The region is right across Peconic Bay, and a short walk or bike ride will take you to a hamlet with restaurants and stores, as well as wineries.