New York - Oyster Yachts Insider Sailing Guide

Friday, 25th September 2020


If you keep your boat in Newport Rhode Island, the chances are that your cruise plans usually involve turning east once you’ve left Newport. After all, with such a range of popular and picturesque cruising destinations such as Block Island, Martha’s Vineyard, Cuttyhunk and Nantucket to choose from, heading away from the mainland seems the obvious choice. But how about going the other way and making the Big Apple your cruising goal?

According to those who have spent time afloat in the centre of the city, be it in North Cove alongside Ground Zero, or across the water in New Jersey at Liberty landing where you can look across the Hudson River at the Manhattan skyline, this is a destination that should be on everyone’s bucket list. As should sailing past the Statue of Liberty.

Yet, New York often doesn’t make it into the season’s cruising itinerary. To many, it is reverse commuting where heading towards the city would mean sacrificing time spent in a number of wonderful harbours and anchorages among picturesque islands.

But Oyster’s Will White doesn’t buy into this line of thinking. He claims that while heading east presents a well established cruising ground that is popular for good reason, there are also some great places to visit in a relaxed trip to the city and back. “The Connecticut shoreline and Long Island offer some great cruising locations which, when you string them together, make for a really interesting and easy going cruise to New York. The beauty is that the distances aren’t huge and there are so many available destinations that you can weave your way there and back with no real pressure on time while making best use of the weather. This means you don’t have to have a fixed plan to cover the miles, just an understanding of the areas that you could use as stepping stones.” So here are Will’s five tips for a cruise to the Big Apple and back.


Starting from Newport Rhode Island, taking three nights to get to New York, two nights in the city and a further two stopovers to get back would form a basic and easily manageable cruise plan.

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


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.

Oyster Yachts News Discover New York Insider Sailing Guide Tips | Thimble Islands

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.

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

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.

Oyster Yachts News Discover New York Insider Sailing Guide Tips | Nesbitt

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.

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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.


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. 


Rich Morano – Oyster 62 Venture

“For those who don't mind New York City transferred to a beach town Sag Harbor is OK.  However, we prefer staying in 3 Mile Harbour which is very well protected and is very quiet. You can easily head into the Hamptons with an Uber.” 

Will White

Will grew up in Bristol, Rhode Island and from a young age spent every free moment out on the water. Later he worked his way up from deckhand to engineer and finally captain. After running an Oyster 56 for Oyster’s founder, Richard Matthews, Will joined our USA office in Newport, Rhode Island, and has spent the last 17 years helping our US based owners with their commissioning and customer service enquiries.

Important note:

These cruise guides are intended as food for thought only based on the experiences of those who have been there and do not form a definitive guide. The locations should always be studied using the appropriate pilots and charts.

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