• True Sailing
    hamptons

CHOOSE YOUR Experience

We offer charters for two hours, three hours, half day and full day. Longer durations mean more possibilities for adventure.

Two Hour

These charters are the shortest we offer and provide an amazing opportunity to see Sag Harbor and the surrounding waters. Feel the wind in your hair, enjoy a refreshing drink, and get back in time for dinner ashore.

Three Hour

A great option for an afternoon or evening sunset sail to celebrate an occasion, entertain, or simply relax. We sail you across the bay and out towards Cedar Point and Gardiners Bay where you’ll see the old lighthouse pass us to starboard.

 

Half Day (4 Hour)

Perfect for a picnic plus a swim. We’ll sail out past the lighthouse and on to Shelter Island’s pristine Coecles Harbor where we’ll drop anchor, deploy the water toys and go for a dip before packing up and sailing back home.

Full Day (8 Hour)

Prepare to explore The Hamptons in style. Swimming, beach hopping and waterside restaurant dining are all possible on the full day sail. Itineraries may include a loop around Shelter Island with a stop at Sunset Beach Bar or a sail out to Montauk or Greenport.

 

Meet your boat

Our 42-foot, American-built Catalina is a fully equipped sailing yacht designed for comfort, performance and safety. The cockpit comfortably seats six passengers for dining or relaxing, complete with surround sound speakers. The foredeck provides plenty of room for laying out and catching some rays. The interior has a large dining table, lounge, kitchen, and a bathroom for our guests. The entire boat is child proofed and surrounded by three-foot high lifelines to keep even the most adventurous little sailors onboard and safe.

Meet your captain

Meet Nate, a captain with 15 years of professional sailing experience. Nate started sailing a sunfish at age 9 with his brother at summer camp and on the Schuykill River in his hometown of Philadelphia. After high school he went to maritime school and started working on an America’s Cup race boat before diving deep into the super-yacht industry, working primarily on large sailboats.

Now he splits his time between the Hamptons, Brooklyn, and the Caribbean. He is a certified ASA instructor and is very passionate about sailing and introducing people to the sport. When he’s not sailing, he enjoys paddle boarding, biking, playing guitar, and riding his motorcycle into the sunset.

 

WHY TRUE SAILING

Sailing is our passion and we want to share it with as many people as possible. We offer 2 to 8 hour private sailing trips on several different sailboats in New York Harbor and the Hamptons. Some of our boats take up to 6 passengers and others up to 30 passengers. We also offer weeklong private charters on luxury sailboats for up to 10 passengers in the Caribbean.

We maintain a strong emphasis on service, sustainability, and safety. Our staff will attend to all of your needs and keep you safe as we sail as much as possible and run the engines as little as we can. Our motto: “always be sailing”.

WHAT ARE PEOPLE SAYING ABOUT TRUE SAILING?

Contact us.