The Ultimate Long Island Boating Guide: Best Places to Sail, Dock & Dine, Anchor and Fish

There may be no better way to experience Long Island than from the water.

With the Long Island Sound to the north, the Atlantic Ocean to the south, the Great South Bay, Peconic Bay, Gardiners Bay and countless harbors, coves, canals and inlets in between, Long Island offers an incredible variety of destinations for sailors, powerboaters and fishermen.

You can spend the morning fishing, drop anchor for an afternoon swim, cruise into a waterfront restaurant for dinner and watch the sunset from your boat — all without leaving Long Island.

Whether you're a lifelong Long Island boater or thinking about getting out on the water for the first time, here are some of the best places to sail, boat, anchor, eat, drink and fish around Long Island, New York.

Best Places to Sail on Long Island

1. Huntington Harbor & Huntington Bay

For sailors on the North Shore, Huntington is hard to beat.

Protected Huntington Harbor opens into Huntington Bay and eventually the Long Island Sound, giving boaters the option of staying relatively protected or heading into open water.

The area around Lloyd Neck, Eaton's Neck and Centerport makes for a beautiful day on the water, while Huntington Harbor offers marinas, moorings and easy access to town.

Why boaters love it:

• Protected harbor
• Beautiful North Shore scenery
• Access to Long Island Sound
• Plenty of marinas and marine services
• Great jumping-off point for longer Sound trips

For sailors, a run out of Huntington Harbor and across Huntington Bay is one of those quintessential Long Island summer experiences.

2. Port Jefferson Harbor

Port Jefferson is another outstanding North Shore destination.

The large harbor provides considerably more protection than the open Long Island Sound and makes Port Jefferson a natural destination for cruising sailors.

Once inside, you're also within walking distance of downtown Port Jefferson's restaurants, bars, shops and waterfront.

For someone planning a longer North Shore sailing itinerary, combining Huntington, Northport, Port Jefferson and eventually Mattituck or Greenport can make for an incredible trip.

3. Northport Harbor

Northport has a classic small-harbor atmosphere that makes it perfect for a relaxed afternoon sail.

Cruise through Northport Bay, explore the waters surrounding Eatons Neck and Centerport, or make Northport part of a longer trip along Long Island's North Shore.

The combination of calm harbor scenery and a walkable village makes this an especially nice destination for couples and families.

4. Greenport & Shelter Island

If you're looking for one of Long Island's premier boating destinations, put Greenport and Shelter Island near the top of the list.

The waters around Shelter Island connect Peconic Bay, Gardiners Bay and the North Fork, creating seemingly endless possibilities for sailing.

A boating weekend here can include Greenport, Shelter Island, Sag Harbor and the surrounding North Fork.

Greenport itself is particularly attractive because you can get off the boat and immediately enjoy restaurants, bars and shops.

One of the waterfront landmarks is Claudio's Waterfront, a classic Greenport destination with waterfront dining and a lively summer atmosphere.

Great boating itinerary:

Greenport → Shelter Island → Sag Harbor → Greenport

It's difficult to find a more quintessential East End boating weekend.

5. Great South Bay & Fire Island

The Great South Bay offers an entirely different boating experience.

Protected from the Atlantic by Fire Island, the bay provides miles of cruising territory stretching along much of Long Island's South Shore.

Destinations include:

Ocean Beach
Kismet
Atlantique
Davis Park
Watch Hill
Sailors Haven
Fire Island Lighthouse

Ocean Beach is particularly fun because you can arrive from the water and walk into one of Long Island's most famous summer communities.

Island Mermaid is a waterfront Ocean Beach restaurant known for sunset dining and a lively bar atmosphere.

Best Long Island Restaurants & Bars to Visit by Boat

One of the best parts about boating on Long Island is being able to dock and dine.

Instead of driving to dinner, you arrive from the water.

Here are several places worth putting on your boating list.

Claudio's Waterfront — Greenport

Claudio's Waterfront

Greenport is already one of Long Island's great boating towns, and Claudio's waterfront location makes it a natural stop for boaters exploring the North Fork.

Come for seafood, drinks and the waterfront atmosphere, then spend some time walking through Greenport.

Island Mermaid — Ocean Beach, Fire Island

Island Mermaid

For Great South Bay boaters, Ocean Beach is one of the ultimate summer destinations.

Island Mermaid sits right on the bay and combines waterfront dining, cocktails and a lively Fire Island atmosphere.

Dockers Waterside — East Quogue

Dockers Waterside Marina & Restaurant

Dockers is located on Dune Road in East Quogue and combines a marina, waterfront restaurant and bar.

It's a great destination when cruising the waters around Shinnecock Bay and the Hamptons.

Canal Cafe — Hampton Bays

Canal Cafe

Located inside Hampton Watercraft Marina along the Shinnecock Canal, Canal Cafe is another natural boating stop.

The canal itself is one of the most interesting boating areas on Long Island because it connects Shinnecock Bay with the Peconic system.

On The Docks — Aquebogue

On The Docks

North Fork boaters should also know On The Docks, located along Meetinghouse Creek in Aquebogue.

Its marina setting, outdoor deck and waterfront atmosphere make it an easy addition to a North Fork boating day.

The Wharf — Oakdale

The Wharf

Located at Nauti River Marina on the Connetquot River, The Wharf is a convenient South Shore destination for boaters exploring the Great South Bay area.

The waterfront setting and sunsets are a big part of the appeal.

Tiki Bar at Sunset Harbour — East Patchogue

The Tiki Bar At Sunset Harbour

For something more casual and lively, this seasonal marina destination offers drinks, food, waterfront views and a classic summer boating atmosphere.

The Buoy Bar — Point Lookout

The Buoy Bar

Western Long Island boaters shouldn't be left out.

The Buoy Bar sits on Reynolds Channel in Point Lookout and offers a waterfront deck, drinks, food and beautiful sunset views.

Pier 95 — Freeport

Pier 95 Restaurant & Marina

Freeport's extensive canal system and proximity to the South Shore bays make it another popular boating area. Pier 95 combines marina scenery with a more upscale waterfront restaurant experience.

Boating tip: Docking policies, transient slips, water depths and dock availability can change. Always contact a restaurant or marina before assuming you'll be able to pull up and dock.

Best Places to Anchor Around Long Island

Sometimes the best destination isn't a restaurant or marina.

It's simply finding a protected spot, dropping the hook and spending the afternoon on the boat.

Great South Bay

The Great South Bay offers numerous areas where boaters can find protected water depending on wind and weather.

A typical summer afternoon might mean anchoring near Fire Island, swimming, having lunch aboard and watching hundreds of boats move through the bay.

Hemlock Cove

Often associated with the boating scene around Captree and Fire Island, this area can become a major summer gathering place for recreational boaters.

It's the kind of destination where the boat itself becomes your beach house for the afternoon.

Northport Bay

For North Shore boaters, the Northport area provides beautiful scenery and several opportunities for spending a relaxing afternoon on the water.

Huntington Bay

Huntington Bay also provides plenty of room to explore outside the harbor before heading back in for the evening.

Shelter Island

The protected waterways and coves surrounding Shelter Island make this one of Long Island's most interesting cruising areas.

You can spend an entire weekend exploring without feeling like you're boating the same water twice.

Peconic Bay

The Peconic system offers enormous amounts of cruising territory between the North and South Forks.

For sailors especially, this is one of the most rewarding areas of Long Island to explore.

Important: Never choose an anchorage solely from an online recommendation. Check current NOAA charts, water depth, tides, bottom conditions, weather, local restrictions and marine forecasts before anchoring.

Best Fishing Areas on Long Island

Long Island is surrounded by productive saltwater fishing grounds, and what you'll target changes throughout the season.

Popular species include striped bass, fluke, porgy/scup, bluefish, black sea bass, tautog/blackfish and weakfish.

New York's seasons, possession limits and minimum sizes change, so always check the current NYS Department of Environmental Conservation regulations before fishing. Anglers age 16 and older fishing New York's Marine and Coastal District generally must also enroll in the state's Recreational Marine Fishing Registry.

Montauk

It's impossible to discuss Long Island fishing without Montauk.

The waters surrounding Montauk Point are legendary because the Atlantic Ocean and Block Island Sound converge around the eastern tip of Long Island.

New York State Parks describes Montauk Point as offering some of the world's best surf fishing.

For boat fishermen, the surrounding waters can produce everything from striped bass and bluefish to offshore opportunities farther from land.

Fire Island Inlet

Fire Island Inlet is one of the South Shore's most important fishing areas.

The moving water around the inlet can attract baitfish and predators, making the surrounding waters popular with fishermen targeting species such as striped bass, bluefish and fluke.

Navigation deserves serious respect here, however. Conditions around South Shore inlets can change significantly with tide, wind and sea conditions.

Captree & Great South Bay

Captree is practically synonymous with Long Island fishing.

Captree State Park sits near Fire Island Inlet and provides access to the Great South Bay and Atlantic.

New York State Parks calls Captree home to the largest public fishing fleet on Long Island, with open and charter boats operating from its boat basin. The park also has fishing piers, a boat launch, bait and tackle and transient berthing.

Long Island Sound

The Sound provides excellent fishing opportunities along the entire North Shore.

Depending on season and location, anglers pursue striped bass, bluefish, porgies, blackfish and other species around structure, rocky bottoms, channels and points.

Areas around Huntington, Northport, Port Jefferson, Mount Sinai and Orient Point are all worth learning.

For fishermen exploring Mount Sinai Harbor, Ralph's Fishing Station is a useful marina and fishing-oriented stop with bait, tackle and boating services.

Orient Point

The eastern end of the North Fork produces strong currents where Long Island Sound meets the waters toward Plum Island and Gardiners Bay.

Those currents and changes in underwater structure make the area particularly interesting to experienced fishermen.

This isn't an area where inexperienced boaters should blindly follow coordinates from the internet. Tides, current and commercial traffic need to be understood.

Shinnecock Bay & Shinnecock Inlet

Shinnecock gives South Fork boaters access to protected bay fishing as well as the Atlantic.

It also makes Hampton Bays an excellent home base for someone who wants a combination of boating, fishing and waterfront restaurants.

A Few Long Island Boating Trips Worth Trying

North Shore Day Trip

Huntington Harbor → Huntington Bay → Northport → Eatons Neck → Huntington

Great for sailing, sightseeing and a relaxing afternoon.

Fire Island Day

Great South Bay → Fire Island → anchor/swim → Ocean Beach → dinner → sunset cruise home

This is about as "Long Island summer" as boating gets.

North Fork Weekend

Mattituck → Greenport → Shelter Island → Sag Harbor → Greenport

A fantastic multi-day itinerary combining sailing, restaurants and some of the East End's most beautiful waterfront communities.

Fishing + Lunch Day

Captree → Fire Island Inlet fishing → Great South Bay → waterfront lunch → afternoon cruise

Captree's location provides direct access toward both the State Boat Channel and Fire Island Inlet.

When Is the Best Time to Boat on Long Island?

Long Island's main recreational boating season generally runs from late spring through early fall.

May and June can offer beautiful boating before the peak summer crowds.

July and August bring warm water, busy waterfront restaurants and the full Long Island summer boating atmosphere.

September may be one of the most underrated boating months. The water remains relatively warm, crowds begin thinning out and early fall fishing can be excellent.

Weather and marine conditions matter far more than the calendar, however. Always check the marine forecast, wind, tides and small-craft advisories before heading out.

Long Island Boating Safety

Long Island's waterways can change dramatically from one location to another.

A calm afternoon inside a protected harbor can be very different from conditions in Long Island Sound, an ocean inlet or offshore Atlantic waters.

Before heading out:

• Check the marine weather forecast.
• Review tides and currents.
• Carry properly sized life jackets for everyone aboard.
• Keep updated navigation charts aboard.
• Know your boat's draft.
• Watch channel markers carefully.
• Carry a VHF marine radio.
• Monitor fuel.
• Don't mix boating and alcohol for the operator.
• File a float plan when making longer trips.
• Give South Shore ocean inlets extra respect.

Sandbars and channels can shift, particularly around inlets and shallow South Shore waters. Local knowledge and current charts are invaluable.

Know the Fishing Regulations Before You Go

New York recreational saltwater fishing regulations can change during the season.

As of 2026, the NYSDEC maintains separate seasons, size limits and possession limits for popular Long Island species, including fluke, striped bass, black sea bass, scup, bluefish and tautog. The state notes that regulations are subject to change.

Before keeping any fish, check the current regulations directly with the New York State Department of Environmental Conservation.

Current NYS Recreational Saltwater Fishing Regulations

Why Long Island Is Such an Incredible Place to Own a Boat

One of the underrated benefits of living on Long Island is just how much access we have to the water.

You can live in central Suffolk County and be within a short drive of either the Long Island Sound or Great South Bay. Head farther east and you gain access to Peconic Bay, Gardiners Bay, Shelter Island, the North Fork, the Hamptons and Montauk.

For someone who loves sailing, fishing or simply spending weekends on the water, Long Island is difficult to beat.

And for homebuyers who make boating part of their lifestyle, choosing where to live can be just as important as choosing the boat.

Communities throughout Nassau and Suffolk County offer everything from neighborhood marinas and yacht clubs to waterfront homes with private docks and condominium communities offering boat slips.

As Long Island real estate professionals — and people who appreciate everything that makes living here special — The Galluzzo Team at Compass helps buyers and sellers throughout Long Island find the community and home that fits the way they want to live.

Whether that means being minutes from your marina, searching for a waterfront home with a dock, or simply finding the right Long Island neighborhood to call home, we're always happy to help.

The Galluzzo Team at Compass
Helping Homes Find Their People.
631-774-3333

Frequently Asked Questions About Boating on Long Island

Where are the best places to sail on Long Island?

Some of the best sailing areas include Huntington Bay, Northport Bay, Port Jefferson Harbor, Long Island Sound, Great South Bay, Peconic Bay, Shelter Island and Gardiners Bay.

Where can you take a boat to restaurants on Long Island?

Popular waterfront boating destinations can be found throughout Greenport, Fire Island, Freeport, Point Lookout, Oakdale, East Patchogue, Hampton Bays, East Quogue and Aquebogue. Always call ahead to confirm current transient docking availability.

Where is the best fishing on Long Island?

Popular areas include Montauk, Orient Point, Long Island Sound, Great South Bay, Fire Island Inlet, Shinnecock Bay and Shinnecock Inlet. The "best" location depends heavily on species, season, tide and conditions.

Is the Great South Bay good for boating?

Yes. The Great South Bay is one of Long Island's major recreational boating areas and provides access to numerous South Shore communities and Fire Island destinations.

Can you boat to Fire Island?

Yes. Boating is one of the best ways to experience Fire Island, with numerous communities and boating destinations accessible from the Great South Bay.

Do you need a fishing license to fish in saltwater on Long Island?

New York handles marine recreational fishing differently from a traditional saltwater fishing license. Anglers age 16 and older fishing in New York's Marine and Coastal District generally need to enroll in the free Recreational Marine Fishing Registry. Additional permits apply to certain species and activities. Always verify current NYSDEC requirements before fishing.