Top Long Island On the Water

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while soaking in views of the harbor views and local wildlife from a spacious deck. Feel the wind in your hair as you help raise the sails or take a turn at the helm, all while admiring the stunning craftsmanship of this traditional tall ship. You're welcome to bring any snacks and food you want, however all drinks consumed onboard must be purchased from our onboard bar.

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.

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!

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!

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspective. Professional Guidance: Captain Steve is an experienced sailor who knows the area well. He can provide you with professional guidance on how to sail and show you the best places to visit. Relaxation: Sailing is a relaxing activity that can help you unwind and forget about the stresses of daily life. Captain Steve's provides a peaceful and calming environment that allows you to escape from the hustle and bustle of city life. Adventure: Sailing with Captain Steve's Sailing Experience is an adventure. You can experience the thrill of sailing on the open water and explore new places.

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.

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

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.