East End Boating Series: Greenport

Greenport: North Fork Favorite 

The Village of Greenport has seen many roles during its recorded history of more than 300 years. It served as a long term reservation for Native Americans, an early home to whaling fleets and the ship building industry, a site of rum running, an established “navy” boasting volunteer boat patrols seeking Nazi submarines, and most recently, as a summer destination for tourists.

Large vessels are a common sight in Greenport. 

Located on the north fork of Long Island, Greenport is one of the area’s oldest villages, having been settled in 1682. The folksy town, overlooking Shelter Island, is a favorite among boaters, with its access to a number of local harbors and marinas. 

The three harbors around Greenport include Greenport Village, Stirling Harbor and Gull Pond.  While there are not designated anchorage opportunities, Greenport is a wonderful destination for boaters seeking to enjoy a pleasant ride, or enjoy some land borne activities.

Greenport Village

For daily visitors, the harbor at Greenport Village offers dock space through the town or at a local marina. The water is deep and open, and many larger vessels can be seen transiting. Greenport has one of the east coast’s busiest seaports, so boaters should schedule in-season trips accordingly.

The village marine area is directly across from Dering Harbor on Shelter Island.  The water in front of the village is very deep and can accommodate some very large commercial and private vessels. Smaller boats should be cautioned: while there are no real sand or obstacle hazards in the village entry, larger vessels can create large wakes, and the boat traffic can be intimidating. All boats are urged to adhere to the posted speed limit of 5 mph. 

This is the heart of the village, where transient boaters can tie up and visit Greenport’s friendly streets and purchase provisions or just soak up the engaging maritime atmosphere.  Visitors can enjoy recreational activities, shopping, sailboat tours, museums, and more.

Visitors seeking a meal can choose from more than a dozen eateries, including the historic restaurant Claudio’s, which was established in 1870.

Greenport offers beachgoers tranquil surrounds. 

Stirling Harbor

Stirling Harbor is located just east of the village docks and inside Young’s Point, at the base of the Greenport's Jetty. Unlike the village entry, the Harbor provides greater protection from boat traffic and prevailing winds. Visitors can tie up and walk the short distance into the village.

Upon entry into the Harbor, boaters will note there is ample water. Its entry also displays a memorial to remember those lost at sea.

Visitors will note access to three marinas within the harbor.  The western shoreline is the home of several other local marinas and fishing boats.  On the east shoreline are Stirling Harbor’s largest marinas.  Eastern Long Island Hospital is visible along the northern shoreline.

Many of the smaller marinas don’t allow transients on a regular basis.  Stirling Harbor Marina, Brewers Yacht Yard and Townsend Manor Marina are the only marinas that accept transient boats.

Gull Pond

Gull Pond is located just to the east of the Greenport Jetty and is the home of many local boats. 

There are no marinas or designated anchorages in the pond, but the area is a fun place to visit. Peaceful and serene, Gull Pond is ideal for exploring by dinghy. The pond is home to large vessels and a number of beautiful residences.   

One of the best times to visit Greenport is in the early fall, during the Annual Maritime Festival – September 19-21 this year. It’s a terrific opportunity to visit Greenport’s historic sites, enjoy live music, observe the Festival parade, check out craft vendors and artisans, watch live maritime demonstrations, and sample some of the best food around the area. Modern Yachts will be on hand to display also! Mark your calendars and see the best of what Greenport offers. 

East End Boating Series: Sag Harbor

Land of Whales, Sails and....Sales 

The Village of Sag Harbor boasts a proud history as a former thriving whaling port, as well as the first official port of entry in New York State for large vessels. The village’s strategic maritime importance is well-documented throughout its 300-year history.

A two-square mile village with two harbors, Sag Harbor is a beautiful and popular destination for boaters. The village is a popular destination for celebrities, and upscale shopping, fine dining and cultural activities abound. Boaters should expect to see large vessels and yachts in port throughout the season.

Boaters approaching Sag Harbor should take care as the currents can run swiftly, and rocks are just 2 – 3 feet, only marked by lobster buoys. Shallows are off Mashomack Point; also note there are fishing nets around Majors Harbor near Shelter Island.

Village of Sag Harbor
The charming Village of Sag Harbor is the most popular local destination for boaters. The harbor is usually calm with little wake throughout, since the adjacent jetty protects the harbor from boats that cruise past in Gardiners Bay and Shelter Island Sound. 

You can expect a fairly busy and tight channel at Sag Harbor. Transient dockage is available on a

Sag Harbor beaches and harbors offer lovely views. 

first come, first served basis. There are marinas, transient dockage with pilings and a town boat ramp within the harbor limits. After docking, visitors can enjoy the town’s many amenities, conveniences and activities on land, including shopping, dining, theaters and museums. The windmill on land houses the tourist office, where visitors can ask for maps and town event schedules.

Northwest Harbor
The Northwest Harbor's anchorage is tranquil and offers fantastic views.  Peaceful and lovely, Northwest is fairly well protected, and offers an anchorage in the northeast corner of the harbor. With limited disturbances, and about eight feet of water throughout the entire anchorage, the area is wonderful for a quiet excursion, but Cedar Point County Park limits access to commercial amenities. It's a tranquil destination and for many, a welcome contrast to the busier part of Sag Harbor waters. 

East End Boating Series: Shelter Island

Shelter Island Cruising 

Beautifully preserved and wonderfully welcoming, Shelter Island offers ample dockage and moorings for boaters. The island is only accessible by boat or by ferry, and much of the 8,000-acre island is protected.

Lovely private homes dot the island and a number of historic sites offer a glimpse into the island’s nearly 400-year documented history.

Shelter Island offers an escape from life’s rapid pace, but still offers recreational opportunities like kayaking, biking, shopping or exploring local surrounds. The island also features about a dozen eateries.

Shelter Island's laidback beaches and water-only access makes it
a popular destination for boaters. 

In particular we are fans of the restaurants Salt and the Pridwin Hotel. Salt is fantastic for traditional dishes with a contemporary twist. Its laidback atmosphere, fresh menu choices, crafty cocktails and live music are great reasons to go.

The Pridwin is a fabulous choice for fresh seafood catches (courtesy of the hotel proprietor’s ambitious fishing endeavors!). The Pridwin also offers an array of traditional dining choices, and has a “young diners” menu that will please youthful palates. Wednesday nights are celebrated with cookouts on the lawn, and live music abounds. Hurry – only through Labor Day!

Boaters heading to Shelter Island may enjoy a basic primer on the island's harbors: 

Coecles - Eastern section

Buoys on inside and outside harbor are privately maintained; locations can shift and navigation can be tricky, especially for boats with deep drafts. We would advise caution around the mooring near Reel Point, where a sand bar can wreak havoc. 

The southern shoreline is undeveloped and protected as part of Mashomack Nature Preserve. The northern shoreline is developed, and features beautiful homes.

Mashomack – Southeast section

Almost the entire coast of Machomack is dedicated as a preserve. Here, boaters can enjoy the sights of ospreys and various other types of wildlife. While there is no access to commercial amenities, two harbors offer boaters access to beautiful beaches. 

Majors Cove, located on the southeast point of Shelter Island, is a quiet harbor and offers a good holding ground for favorable anchorage. Majors Cove overlooks Sag Harbor, but is well protected from passing boats.

Major Cove is just east of Smith's Cove, another harbor that provides good anchorage opportunities. Smith's Cove is more exposed to boating traffic but it is protected from prevailing southwesterly breezes. Anchoring here on summer afternoons can be a challenge because of the heavy traffic to and from Sag Harbor. The Cove does offer plenty of depth and provides a lovely view of Mashomack Preserve. Anchoring along the western Shoreline offers quite good protection. 

Along the eastern shore of Smith's is Split Rock, a wonderful place to swim and walk the beach.

Dering Harbor – Northwest section

The most popular harbor on Shelter Island, Dering Harbor is located directly across from Greenport.  It offers boaters convenient and easy access and is populated by several restaurants, stores, stately private homes, mansions, and of course, marinas. Overnight visitors can request accommodations at a local hotel or B and B – well in advance of a stay, since they are often booked.

Dering Harbor is the most popular harbor for commercial activity,
including shopping, dining and sightseeing on the island. 

West Neck Harbor – Southwest section

On the southwest corner of Shelter Island is West Neck Harbor. While the harbor is well protected, it has several shallow areas that boaters should watch for. On the harbor’s south side, there are good opportunities for swimming and relaxing at Shell Beach. Wades Beach is across from Shell Beach and also offers a relaxing beach day. Not to be forgotten, many boaters also enjoy exploring by dinghy around West Neck Harbor. 

East End Boating: East Hampton

Long Island’s greatest gift to its natives is its accessibility to beautiful beaches, bays and many other waterways. In fact, when boaters ask us for tips on cruising, we are happy to comply and provide our recommendations for east end boating destinations.  

We’ve prepared a short list for various eastern Long Island boating destinations that provide opportunities for fun, for tranquil relaxation, for fishing, or for exploration.

We’ll start with East Hampton and make our way through the list in days ahead. Please feel free to share your thoughts. And if you have a boating destination that you enjoy, send it along to us.

East Hampton Cruising

The town of East Hampton offers ideal areas for cruising, fishing and exploring by boat. With a south side flanked by the Atlantic, north side by the sound, and several creeks, harbors and bays throughout, the town offers ample boating opportunities. East Hampton also offers a plethora of land-based fun. 

Three Mile Harbor

The most boater friendly harbor in East Hampton town is inarguably Three Mile Harbor. Nestled between Amagansett and Sag Harbor, Three Mile is a well-protected harbor. It offers its share of marinas, restaurants and generous anchorage for boaters. Other activities permitted within the area include watersports (kayaking, water skiing, tubing, paddle boarding and fishing) but jet skis are prohibited within the harbor area. Take heed, though: while it is a very long harbor, its west side is narrow with sand bars along the channel.

Springs

Springs, located on the west side of the peninsula, is home to Acabonack Harbor and East Harbor. Both are tranquil and offer a quiet opportunity to view wildlife and to explore the natural area. This harbor, however, does not provide boating amenities or access to commercial establishments. Overnight anchoring is prohibited in Springs.

Hog Neck Creek
Hog Neck Creek is a shallow harbor not recommended for transient boaters. While it is beautiful for a short exploration, it appears to be used by locals and does not offer access to restaurants, marinas or other commercial businesses. No anchorage is available in Hog Neck.