Sail in style and comfort on the North Fork classic wooden sailing yacht "Surprise”. East End Charters "Surprise” was designed for comfort, stability, and elegance. Custom built in 1967, her spacious decks and friendly crew provide the perfect sailing experience. Available for private day sails, sunset cruises and multi-day excursions. Experience the beauty of the East End with wind in your hair and leave your worries behind.

Easterly Sailing in Greenport offers hands-on sailing aboard the J100 YIKES, tours in and around Greenport Harbor, and exquisite sunset sails. Take the helm and feel the wind in your hair and connect with the beautiful East End – a sailors paradise. Knowledgable North Fork native Captain Paul Kreiling and First Mate James Lockley will ensure you have a great experience. Your sailing adventure awaits.

Glory Harbor Tours owns and operates GLORY, America’s premier environmentally-friendly solar-powered passenger vessel. Captain David Berson has delighted adults and children alike with whisper-quiet and fume-free tours of the nooks and crannies of Greenport and Stirling Harbors and the Peconic Bay since 1999. He is a navigating treasure trove of Greenport maritime history and guarantees a fun-filled, relaxing day. Leaves from Preston’s Dock.

Kingfisher is an American classic – a 50’ 1959 Huckins Corinthian, lovingly restored to its grand glory. They specialize in providing the elegant yachting lifestyle customized for business entertainment, family celebrations, culinary and brand immersion experiences. Entertain in style on the beautiful waters of the East End. Kingfisher collaborates with a variety of culinary creators, including Anker, to make your experience truly sublime.

Make memories with the ones you love! Let Layla's crew take care of your every need as we cruise through the bay under the silence of sails. Captain Liz earned her captain's license sailing in the USVI, Hawaii, and even sailed across the Atlantic Ocean. She brings this dedication back to her home waters, to share her love of the sea with guests of all experience levels. Kick back, enjoy and let the wind blow through your hair. Layla Sailing is female-owned and a member of 1% for the Planet. 

Presented by the Greenport Village BID with the East End Seaport Museum, the annual Maritime Festival in Greenport celebrates the nautical heritage of the East End while entertaining and educating all generations to leave a lasting legacy. Each year during the last weekend of September, the always vibrant Greenport community hosts a truly unique two day event kicked off by the Land & Sea Gala.

Captain Rob and North Fork Adventures Charters offers a custom fishing experience backed by more than 30 years navigating local waters – tailored to work with your time and location – and target available fish species for the maximum fun potential. All fishing and excursions can accommodate parties of 1-6 people. Start your adventure today and enjoy the beauty and bounty of the North Fork. Perfect for a group day out or family celebration!

The North Fork Foodie Tour Sunday, September 11th, 2022 – presented by the North Fork Reform Synagogue. Visit a variety of North Fork farms and producers, learn and support local makers including artisanal wine & beer, cheese & dairy, meat & poultry, fruit & vegetables, seafood, specialty foods including chocolate, baked goods & sweets, herbs, horticulture and more. Start the tour at any of the participating farms or producer locations, or begin at Charnew’s Farm in Southold.

The fast, modern aluminum fleet of boats sailing out of Greenport daily offers full day fishing in season, special sunset cruises and lighthouse visits. Afternoon and evening charters available. The 150 passenger Peconic Star Express is an amazing vessel – fully equipped with the latest safety and communications gear, fish finders, sonar, radar, a huge sundeck and plenty of personal comforts and conveniences for the whole family. Their knowledgeable, friendly crew will make every day one to remember.

Peconic Water Sports is the premier water sports company on the East End. They provide a world-class menu of water sports activities including wakeboarding, waterskiing, wakesurfing, tubing, fishing charters, boat rentals, a boat club, and more. They can teach kids of all ages so they can experience the pure joy of active life on the water. Make memories with friends and family to cherish for a lifetime.