Sailing in the Hamptons on a Sailo Yacht Charter

See and be seen on a sailing trip in Long Island

As one of the most popular getaways for well to do New Yorkers, the Hampton’s offer a great choice of opportunities for sailing. Find your perfect boat rental in Hampton, NY with Sailo and enjoy the best that this amazing destination have to offer.


The far eastern end of Long Island is dotted with pretty villages and towns, long sandy beaches and a whole plethora of desirable homes. It’s a beautiful place to pass some time, and easily accessible from downtown New York in just a couple of hours, it makes a great getaway from the city. Of course, one of the best things to do in the Hampton’s is jump aboard your own boat to enjoy the open seas. If you don’t have you own boat then you’ll find private Sag Harbor boat rentals and yacht charters in Montauk for the day, or longer, available in some of the most popular NY areas.


Sailo offers a fantastic choice of yacht rentals for you to browse, with an option of either a captained boat, or if you have the experience you can choose to rent a bareboat (just the boat with no crew). For those looking to enjoy a Montauk fishing party boats trip, a family outing, or just sailing Sag Harbor for a day by sailboat charter, you’ll find plenty of great things to do with a Sailo boat.


My Mate Charters Montauk Yacht Club


Three Mile Harbor Marina

Montauk Marine Basin

Uihlein's Marina & Boat Rentals

Gone Fishing Marina

Shagwong Marina

Ship Ashore Marina

Long Wharf Village Pier

Maidstone Harbor

Halsey's Marina Inc

Malloy Sag Harbor Cove East

Waterfront Marina

Conscience Point Marina

Harbor Marina

West Lake Fishing Lodge

Snug Harbor Motel & Marina

Southampton Yacht Club

Hidden Cove Marina Inc

Diamond Cove Marina

East Hampton Commercial Dock

Star Island Yacht Club & Marina

Strong's Marine of Southamtpon

East Hampton Marina

Sunset Cove Marina

Montauk Sportsmans Dock

East Lake Marina

Montauk Lake Club Marina

East Hampton Point Marina

Three Mile Marina

Breakwater Yacht Club

Sag Harbor Marine Park

The Lobster Inn

Sag Harbor Yacht Yard

Three Mile Harbor Boat Yard

Sag Harbor Launch, Moorings & Services

Westlake Marina

Sag Harbor Cove Yacht Club

Offshore Sports Marina

Bullhead Yacht Club Inc

Gardiner's Marina

Captain's Cove Marina

Montauk and the lighthouse


Setting sail in the Hamptons, you’ll likely pass Montauk lighthouse. The fourth oldest in the US, and the oldest in New York state, the lighthouse is today the location of a fascinating museum which features fascinating exhibits and incredible panoramic views.

Montauk itself is a fairly sleepy village that is popular in the summer. The surrounding area is home to excellent beaches and is also a great place to pick up your Sailo motor yacht, sailboat or catamaran charter.

Sail around Shelter Island


Nestled in between the forks at the end of Long Island, Shelter Island is easily accessible by sailboat or motor yacht charter from Sag Harbor or any other town on the north or south fork. The island itself is home to Mashomack Preserve, a marshy coastal nature reserve. The island is also dotted with homes and quaint marinas, inviting you to stop by for some food or drink. Shelter Island is a popular place to explore by yacht charter in the Hamptons. 

    Suggested Boats

  • 36ft Vintage Yacht Charter in Sag Harbor, New York
    $900 (per ¼ day)

    36ft Vintage Yacht Charter in Sag Harbor, New York
    Sag Harbor, NY

    View More
  • A Fine Yacht with an Experienced Captain
    $750 (per ¼ day)

    A Fine Yacht with an Experienced Captain
    Sag Harbor, NY

    View More

Watersports in Sag Harbor


The village of Sag Harbor was originally established as a fishing community, but today you’re more likely to find the well heeled relaxing on the water. The village is home to celebrities and is a popular hangout for New Yorkers, with some stunning homes. Visitors will find some of the best things to do in Sag Harbor include renting a sailboat in the Hamptons, or indulging in some watersports. Wakeboarding and waterskiing are popular things to do around these parts, with many boat owners offering watersports activities.

    Suggested Boats

  • Beautiful 40' catamaran available for charter in Sag Harbor
    $9,120 (per day)

    Beautiful 40' catamaran available for charter in Sag Harbor
    Sag Harbor, NY

    View More

Fishing trips from Montauk and East Hampton


The south fork offers several opportunities for fantastic days out fishing. Charter a boat from East Hampton or do Montauk sailing and head out into the Atlantic to see what you can catch. The area is home to striped bass and false albacore, a member of the tuna fish family, and as one of the best things to do in the area, fishing is a popular activity with plenty of boat rentals to choose from. Whatever you catch, you’re sure to have a spectacular day on a fishing trip from the Hamptons. 

    Suggested Boats

  • We will take you to a new era of sport fishing!
    $1,100 (per day)

    We will take you to a new era of sport fishing!
    Montauk, NY

    View More
  • Fish the beautiful waters of Long Island's South Fork
    $475 (per ½ day)

    Fish the beautiful waters of Long Island's South Fork
    East Hamptons, NY

    View More
  • Amazing day fly fishing!
    $675 (per day)

    Amazing day fly fishing!
    East Hampton, NY

    View More

Plum Island and Gardiners Island


These two outlying islands are easily to reach by private yacht from the Hamptons, however anchoring/docking is prohibited on both of them. Gardiner’s Island is privately owned and Plum Island is home to a research center, which is due to close within the next few years. So as fascinating as it might be to sail past these two mysterious islands, you can’t set foot on them… For now. But if you’re looking for a fun day out on the water, they make a great waypoint on your sailing trip from the Hamptons.

Experience the Good Life


Many celebrities, titans of business, and New Yorkers call The Hamptons their home each weekend during the summer months. Luxury cars dot the parking lots, and high-end stores line the main streets. Why not experience a taste of the good life for the day by chartering a luxury yacht to explore the local waters and sites. Anchor in a cove and enjoy the water toys, or watch the sunset from the aft deck. You will feel like you have entered the Forbes 500 when you charter a yacht out East.

    Suggested Boats

  • Indulge in Luxury and comfort aboard Sundancer 32
    $3,710 (per ½ day)

    Indulge in Luxury and comfort aboard Sundancer 32
    Sag Harbor, NY

    View More

Also, check out these destinations: