Sailing

Featured Sailing Charters

Sag Harbor Sailing

Offering Sailboat rentals, charters, and instruction, Sag Harbor Sailing boasts hundreds of graduates from its award-winning sailing education programs and its fleet of well maintained 23' keel boats.

Email: sailingsagharbor@optonline.com

Phone: 631-725-5100

Address: 51 Pine Neck Avenue, Sag Harbor, NY 11963

Website: www.sailingsagharbor.com

Catamaran Mon Tiki

Sail aboard a US Coast Guard Certified eco-conscious catamaran
inspired by traditional Polynesian designs on one of our daily scheduled sailing trips in Montauk or create your own. Day sail, Sunset cruise, Summer sail & swim, Events, and small group (1-4 people) and private charters.

Phone: 631-668-2826

Dock Location: Sam’s Star Island Yacht Club and Marina, Montauk, NY11954

Website: www.sailingmontauk.com

East Hampton Sailing Charters

Little Dutch Sailing Charters

Sail aboard a 1985 Whitby 42' Ketch Sailboat accommodating up to four overnight guests

Phone: 917-513-5724

Email: captmissy@littledutchsailing.com

Website: www.littledutchsailing.com

Dock Location: East Hampton, NY 11937

Sail East Charters

Crewed private or individual trips. Sail aboard the beautiful J/42 yacht Truant, a deep-keeled, 42’, sloop-rigged yacht for full-day, half-day and Sunset sails up to four people

Phone: 646-388-2669

Email: ewa@saileastcharters.com

Website: www.saileastcharters.com

Dock Location: Halsey’s Marina, 73 Three Mile Harbor, Hog Creek Rd, East Hampton, NY 11937

Greenport/North Fork Sailing Charters

East End Charters

Private charters on fully-crewed sailing and motor yachts on the flagship yacht Surprise for 1-6 people or one of their vessels in their partner fleet

Phone: 631-268-6528

Email: info@eastendcharters.com

Website: www.eastendcharters.com

Dock Location: Multiple locations in Hamptons and Greenport

Layla Sailing

Female-owned and operated, Layla Sailing was voted Best Sailing Charter on the North Fork by Dan’s Papers in 2019. Offers crewed Morning Sails, Half-day, Full-day and Sunset sails

Phone: 631-319-0161

Email: liz@laylasailing.com

Website: www.laylasailing.com

Dock Location: 1410 Manhanset Ave, Greenport, NY 11944

Nautical Dreamer Sailing Charters

Join Captain Ron aboard Nautical Dreamer II, a Beneteau 50' sailing yacht, on a number of skippered yacht charters including Full-day, Half-day, Sunset cruise (overnight) and custom charters

Phone: 631-767-0149

Email: captainronh1@aol.com

Website: www.nauticaldreamercharters.com

Dock Location: 500 Beach Rd, Greenport, NY 11944

Sail Deliverance

Sail with Captain Dan and the 11th generation sailing tradition of the Hallock family in the serene and protected waters of Peconic and Gardiner’s Bay from Greenport

Phone: 631-680-6199

Website: www.sail-deliverance.business.site

Dock Location:102 Main St, Greenport, NY 11944

Montauk Sailing Charters

MTK Cruises

Offering scheduled daily sails, a Stargazer cruise, Harbor lake & History tour, Sunset sail, Lake Eco tour, and Eleanor’s Pearl Sail and Beach tour

Phone: 631-668-8079

Email: montaukcruises@gmail.com

Website: www.cruisemontauk.com

Dock Location: 484 W Lake Dr, Montauk, NY 11954

Sail Montauk

Private Sailing Lessons, Intro into Sailing, and Basic Sailing Packages available

Phone: 631-522-5183

Email: sailmontauk@gmail.com

Website: sailmontauk.com

Address: 440 Queens Street #96 • Syosset, NY 11791

Dock Location: Gurney’s Star Island Resort & Marina, 32 Star Island Rd. Slip 412 Montauk, NY 11954

Sag Harbor Sailing Charters

Delphine Sailing Charters

Multi-day crewed charters from long weekends to weeklong trips. aboard the Delphine, a sailing catamaran. Day trips available out of Sag Harbor in the summer and fall

Phone: 631-335-2747

Website: www.delphinecharters.com

Dock Location: Sag Harbor, NY 11963

Lelanta

Crewed charter available for Full-day, half-day, and Sunset sails

Phone: 843-683-0449

Email: info@sylelanta.com

Website: www.sylelanta.com

Dock Location: Waterfront Marina, Bay St #1A, Sag Harbor, NY 11963

Sailacat

Private luxury sailing yacht charters and top-rated catamaran boat rentals in the Hamptons and Bahamas

Phone: 631-682-8288

Email: info@sailacat.com

Website: www.sailacat.com

Dock Location: 1 Long Wharf, Sag Harbor, NY 11963

Sailo

Explore 80+ private boats in the Hamptons and rent directly from owners

Phone: 631-682-8288

Email: info@sailo.com

Website: www.sailo.com

Dock Location: 1 Long Wharf, Sag Harbor, NY 11963

Sail Hamptons Luna and Starlight

Private Luxury Sailing from Sag Harbor, Shelter Island, Greenport and Points East aboard Schooner Luna and Sailing Yacht Starlight for up to 41 guests.

Phone: 917-399-0686

Email: info@sailhamptons.com

Website: www.sailhamptons.com

Dock Location: Multiple locations

Sea Escapes Sag Harbor

Offering half-day, full-day, sunset and custom sailing tours, as well as captain services from Sag Harbor native, Captain Eric Skilbred

Phone: 631-259-1033

Email: info@SeaEscapesSagHarbor.com

Website: www.seaescapessagharbor.com

Dock Location: Sag Harbor, NY

SV Dove Boat Charters

Full-day, Half-day trips, Sunset Cruises, Bachelorette Parties

Phone: 631-901-8928

Email: probabar@hotmail.com

Dock Location: 27 Bay St. Sag Harbor, NY 11963

Valkyrie Sailing Charters

Climb aboard the sailing catamaran Valkyrie with the largest deck area in the Hamptons. At 60’ long by 30’ wide and a total of 1800 square feet of open deck. Specialty cruises are 4 hour sails from Sag Harbor Wharf around Shelter Island. Also operates in NYC/Chelsea Piers and Miami
Phone: 917-613-1765

Email: captainpaul@valkyriesailing.com

Website: www.valkyriesailing.com

Dock Location: 51 Division St Unit 1-117, Sag Harbor, NY 11963