True Sailing offers private sailing charters, sailing lessons, and yacht management across four locations: NYC, Jersey City, the Hamptons, and the Caribbean. Led by Captain Nate, the business runs 2- to 8-hour private sailing trips on boats ranging from 6-passenger sailboats to 30-passenger vessels, along with weeklong luxury sailboat charters for up to 12 passengers in the Caribbean.
The Hamptons fleet, based at Long Wharf in Sag Harbor, includes Elizabeth (42-foot Catalina, up to 6 guests) and Hummingbird, both private charters covering Sag Harbor and surrounding waters, Cedar Point, Gardiners Bay, Coecles Harbor, and a full Shelter Island loop. Elizabeth pricing runs $900 for 2 hours, $1,225 for 3 hours, $1,550 for a half day (4 hours), $1,875 for 6 hours, and $2,500 for a full day (8 hours); Hummingbird runs slightly less, from $700 for 2 hours up to $2,000 for a full day. All charters are private (your group only), for up to 6 guests, with Captain Nate and all safety equipment included; holiday surcharges apply on July 4th and Labor Day weekend.
True Sailing emphasizes service, sustainability, and safety, running the motor as little as possible with a genuine “always be sailing” motto. Beyond charters, the business offers a sailing school and full yacht management services (haul-out, winterization, routine maintenance) for boat owners who can’t always be on-site.
Guest reviews are overwhelmingly glowing across dozens of testimonials, consistently praising Captain Nate (and crew members like Ken, Becca, and Bruce) for warmth, professionalism, deep local knowledge, and genuinely memorable experiences — from sunset sails and champagne brunch cruises to birthday celebrations and a treasured 60th anniversary sail.
For anyone in the Hamptons, NYC, Jersey City, or the Caribbean looking for a highly reviewed private sailing charter, sailing lesson, or yacht management service, True Sailing offers a well-established, multi-location operation with Captain Nate.
