Top Long Island On the Water

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. Unlike private charters that are widely offered in the area, this ticketed sail allows you to get on the water at a more affordable price.

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is meticulously maintained and equipped with modern amenities. Features include a fully shaded cockpit with an integrated swim platform, Bluetooth stereo, refrigeration, YETI soft cooler, and folding cockpit table. Private sailing charters are perfect settings for celebrating special occasions, enjoying a relaxing day on the water with family and friends, or hosting memorable client events. Those coming from NYC can take the Long Island Railroad (LIRR) from Penn Station to the Oyster Bay stop, which is steps to the marina!

Sail the Long Island Sound on this private sailing tour. Tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point, and spot the multi-million-dollar mansions that line the coast. As you enter Long Island Sound, catch views of New York City's skyline. See the Throgs Neck Bridge, Hart Island, and the Steppingstone and Execution Rocks lighthouses.

Sip on Long Island wine or cider while visiting the area’s renowned vineyards, including Osprey's Dominion Vineyards and Duck Walk Vineyards, all in one indulgent, private tour. With round-trip transit from your preferred Long Island location and included tastings (with a lunch upgrade option available), enjoy simplified logistics and an enjoyment-focused experience.

Set sail aboard the Bonnie Lynn for a delightful 2-hour public schooner experience in Greenport. Departing from Stirling Harbor, this sail offers the opportunity to enjoy the scenic beauty of the waters while indulging in a BYOB policy and light picnics (no large coolers). Suitable for guests aged 5 and up, this adventure is perfect for families and friends looking to relax and connect with nature. Limited spots are available, so get your tickets early for this memorable nautical journey!

Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard WINDSWEPT, a Jeanneau 36i. This charter offers flexible departure times, allowing you to choose a start time that suits your schedule. Private charters are perfect for celebrating special occasions with friends and family, client outings, or learning to sail. Your charter includes a licensed US Coast Guard OUVP Captain with decades of sailing experience. Bottled water and ice are included, and you're welcome to bring your own food and drinks for a relaxing day on the water. Enjoy scenic views of the waterfront mansions that line the bay, help sail the boat, take in a spectacular sunset, or take a refreshing swim - you are free to choose your own adventure! - Private sailing charter for up to 6 guests - Flexible departure times to fit your schedule - Includes bottled water, ice, and onboard refrigeration - Perfect for sunset cruises or leisurely harbor tours - Swimming is permitted

This is a premier tour with experienced ACA (American Canoe Association) guides that have been paddling these waters for over 15 years. They will be with you out on the water at all times. All equipment is in excellent condition and your trip might include the following tour sites: - 140 yr. old, Cold Spring Harbor Labs. CSHL is ranked among the leading basic research institutions with Thomson Reuters ranking it #1 in the world in molecular biology. - The private home of James Watson, an American molecular biologist. In 1953, he co-authored with Francis Crick the academic paper proposing the double helix structure of the DNA molecule. - The former home of Beatles John Lennon - Tiffany Tower in Laurel Hollow - You are just a few minute walk to the historic Village of Cold Spring Harbor, where you may visit the shops & restaurants. - Take a hike at CSH State Park. Hiking and parking is free, and the (2) trails are some of the most popular and highly rated hikes on Long Island.

Set sail for an unforgettable 2-hour journey on the Peconic River and Orient Harbor, accompanied by live music that enhances the serene atmosphere. With only 20 tickets available, this intimate experience allows you to relax and enjoy original Folk-Pop tunes with a Celtic twist performed by Driving Route 9, hailing from East Haddam, CT. This limited-time event is perfect for music enthusiasts and those looking to enjoy a unique night on the water. Don't miss out on this special opportunity to combine beautiful scenery with captivating melodies.