An insider’s sailing guide to New York

An insider’s guide to sailing New York


Setting out from Newport, Stonington makes a good destination for the first night. While there is dockage available in this quaint New England town, the chances are that you will decide to take a mooring. It’s what most people do and there’s a good launch service. Once ashore, take a drink at the Dog Watch within the marina before heading downtown, to walk around a selection of restaurants and coffee shops. Nothing huge, just a quiet and attractive spot to spend your first night.

Alternatively, you could press on to Mystic and Noank. These are a bit further to the west so they would present a longer sail to get from Newport, however they also would make good options for the return trip. The Mystic River is beautiful. A trip to the Mystic Seaport Museum, further up the river is well worth a visit. Arriving by water into the seaport is like going back in time.

Thimble Islands

The unique geography of the Thimble Islands on the Connecticut shoreline make this archipelago another key place to visit. This area is more exposed to weather from the south so it’s important to keep an eye on conditions if you plan to stay overnight. If you’re passing through from Stonington heading west, these islands make a perfect midway stop for lunch.

Huntington & Oyster Bay 

Back on the Long Island side, Huntington is a convenient stopover before heading into New York. Getting the tide right from here on is key, so this is a great place to stopover and prepare for the leg into New York’s East River. Huntington Bay and the harbour are both big areas with plenty of places to stop so it’s pretty easy to find somewhere to moor or drop anchor.

Alternatively, slightly further to the west is Oyster Bay, home of the Seawanhaka Yacht Club. This elegant and prestigious club, (which claims to be one of the oldest yacht clubs in the western hemisphere), has a long and proud history for racing. Among the many places to stop, Cold Spring Harbour or Oyster Bay Marine Centre are popular.

New York City

From Huntington / Oyster Bay you can time your arrival into the East River to catch the south going tide that will take you to Manhattan. It’s important to get this right as the tide running past Astoria Park and Randall’s Island runs fast – it’s nicknamed Hell’s Gate so you definitely want to be going with it rather than against it! From there you head down to the tip of Manhattan from where there are three key choices as you turn north into the Hudson River.

The first is North Cove Yacht Harbour. This is on the Manhattan side and is very close to Ground Zero. Just a little further to the north is Chelsea Piers. On the New Jersey side Liberty Landing is the third option. This is the most popular for many as it provides a spectacular view across the water to the Manhattan skyline, but it is still easy to get into town using the water shuttles or the subway.

Now you are in New York, sailing past the Statue of Liberty is a must – it never disappoints. If you have time on your hands and want to explore further, head over to Sandy Hook Bay. While there’s nothing on Sandy Hook to go ashore for, it’s an impressive place to anchor and hang out as you take in the view. It’s also a handy place to spend the night before setting out east if you plan to return to Newport in one hit by sailing to the south of Long Island.

Oyster Yachts News Discover New York Insider Sailing Guide Tips | Stonington
Oyster Yachts News Discover New York Insider Sailing Guide Tips | Silken

Oyster yachts

Explore our award-winning, rally-proven fleet of luxurious bluewater sailing yachts

Montauk & Sag Harbour

At the eastern end of Long Island, Montauk is famous for its sports and commercial fishing. Its position at the very tip of the island makes it a remote and often windswept place, great if you are after that wilderness feeling. 

Alternatively, a little further to the west, Sag Harbour offers a very different experience. Well known for being where the rich and famous like to hang out, there are beautiful bays with beaches and sand dunes and small islands.

There are plenty of places to pull up and anchor and the bustling cosmopolitan town has plenty to offer. From both Montauk and Sag, getting over to the south coast of the island takes you to some spectacular, seemingly endless beaches which are popular for walking and surfing. Alternatively, renting a paddle board on one of the salt water ponds also makes a fantastic family activity.

Cruise Tips 

Because Long Island Sound is protected from weather coming from the south, it’s generally an easy and comfortable place to cruise, it’s New York itself that can be the issue. In the height of the summer it can be pretty hot so the best times to visit are either side of this, spring/early summer and the late summer/fall.

The closer you get to the city, make sure you plan your trip around the tides. Plugging into a foul tide can make life unnecessarily hard whereas the opposite can make the trip a breeze.

A copy of the Eldridge Tide & Pilot Book is essential. 

Oyster Brokerage Used Sailing Yachts For Sale Oyster 66 Rivky Cruising In Action

Related Stories

Looking for inspiration? Get inspired with our insider sailing guides informed by our owners insights and real-life adventures.