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Swimming, fishing, tubing, and beach hopping are just a few of the possibilities for a day out on Hummingbird. This boat really goes anywhere you want to be. Located on the dock in Three Mile Harbor, we are just a short ride to great swimming spots and several bars and restaurants to dock up at including Bostwicks, Sisi and Sunset Harbor. Three Mile Harbor is a pristine oasis of sparkling, placid water right in the middle of East Hampton. There we can deploy the toys including our floating lounge and giant unicorn, flamingo and pineapple floaties and have a perfect day of fun without heading into open water. For fishing and water sports we will exit the harbor into Gardiners Bay where the striped bass, bluefish and porgies are jumping and we can let that Yamaha purr at a spritely 30kts of boat speed. Tubing is currently available and wake board, water skis and scurf board coming soon. All of our captains are USCG licensed masters and trained for safety and the highest level of professional seamanship. Capt. Nate has been working on boats of all sizes for nearly 20 years and is enthusiastically bringing you the safest and most fun boating experiences on the East End.


We offer private charters, sailing lessons, and sailing courses aboard our 42-foot Catalina sailboat, 35 foot classic sailboat, and 20 foot center console, all based in Sag Harbor. Capt. Nate began sailing professionally in 2007 and started True Sailing in NYC in 2017. He moved his operation to the Hamptons amid the chaos of the Covid pandemic in 2020. Since then he and his crew have taken out hundreds of groups on sailing charters and fishing charters on the stunning waters of Peconic and Gardiner's Bays. With all the toys, swim floats, paddle boards, noodles, and fishing rods at their disposal, along with the numerous delicious catering options on offer in the Village of Sag Harbor, True Sailing has been one of the communities favorite and most reliable boating options for many years. Come join us and see for yourself what experienced crew and beautiful boats we have at your service. We look forward to sailing with you soon. - The True Sailing Team
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Free cancellation up to 5 days before your trip.