Sort by:

Departure date

Trip duration

Day trip
Multiple days
(Less than 1 week)
Weekly trip
Boat Details

Boat type

Boat length: 5ft -

Price: $ - $



Boat model


Boat build year: -


137 Boat Rentals & Yacht Charters in Oyster Bay, NY

1 - 18 of 137 boats

Rent a Boat Charter in Oyster Bay, NY with Sailo!

Looking for a boat rental in Oyster Bay, NY? There’s no better place for a seaside getaway than Oyster Bay, the gem of the northeast coast. This charming Long Island town is a must-see for anyone looking to explore the rich history and gorgeous seaside views of New York. This is a commonly visited area for those vacationing in New York City or Sag Harbor, but Oyster Bay offers so much that it’s worth it to make a full weekend trip out of your sailing experience on a Sailo boat. From fishing charters to sunset cruises and some of the most delicious seafood around, adventure awaits you in Oyster Bay.


Types and locations of boat rentals

With sailboats, motor boats, and party boats, we offer a variety of daily boat rentals on Sailo, so you can charter a yacht for two to eight hours per day while on your Oyster Bay vacation. You can rent a boat from three different areas in Oyster Bay (Port Washington, Mamaroneck, and Greenwich), all of which offer plenty of rental options for any occasion or party size.


Port Washington area is one of Oyster Bay’s excellent boat rental locations. From here, you can enjoy gorgeous views of the New York City skyline as you set sail to explore everything Long Island has to offer. We recommend booking a fishing charter so you can experience the spirit of the east coast while trying your hand at one of the most popular activities in the area.


Renting a boat from Mamaroneck area will give you a tranquil escape from the hustle and bustle of the city. If you’re looking for romance and relaxation on your Oyster Bay getaway, Mamaroneck is the perfect location for your boat rental. Couples looking for romance on their east coast vacation can book a gorgeous sunset cruise from Mamaroneck after indulging in a delicious harborfront meal. For families, we recommend having some fun in the sun and checking out the nautical-themed Harbor Island Park.


Greenwich area is one of the most visited east coast boating destinations, so it’s no surprise we recommend you charter a yacht here on your trip to Oyster Bay. You can access all of the beauty and adventure Long Island has to offer from the harbors of Greenwich, CT. Rent a boat from Greenwich and visit all of Oyster Bay’s nearby destinations, from The Hamptons to Montauk. From half-day sails along the coastline to full-day fishing charters and fun for the whole family, you can choose your own adventure.


Visiting Oyster Bay

This area of the east coast has so much to offer visitors. Oyster Bay extends from the Long Island Sound of the north to the waters of South Oyster Bay and the Atlantic Ocean, so there’s plenty to explore by land and by sea. The coastal villages of Oyster Bay feature classic east coast architecture and rich history, so be sure to spend some time meandering the area’s beaches, museums, and quaint neighborhoods during your visit.

Oyster Bay is conveniently located within close proximity to other amazing northeast destinations, including New York City, East Hampton, Southampton, Sag Harbor, and Montauk. Rent a boat in the morning and set sail on a full day of adventuring through the east coast. From Oyster Bay, charter a yacht to The Hamptons to soak in some history and feast on some unforgettable waterfront dining.


What to keep in mind on your trip

When booking your Oyster Bay vacation, it’s important to keep in mind the weather, what to pack, and what you plan to do on your trip to make sure you have an enjoyable time. The Long Island sailing season generally runs from spring through fall, and the most popular time to visit Oyster Bay with the most temperate weather is the summertime between June and September. During those months, temperatures tend to range from the mid-70s to low-80s during the day. As you plan your trip, we recommend packing according to the weather (including bringing additional layers of clothing aboard your boat rental if you plan to sail in the early morning or at sunset) and bring plenty of sunscreen and water during those warm summer days.

Ready to book your Oyster Bay boat rental? Cruise around beautiful Long Island aboard this sailboat!

Popular locations to rent a boat on the North East Coast:

Popular boat types among renters: