True Sailing Hamptons

04/30/2026

There bigger boats and smaller boats, faster boats and slower boats, but this is the sailingest boat in Sag Harbor. We average around 40 gallons of diesel per season whilst taking hundreds of people out for memorable half day sailing excursions around Peconic and Gardiners Bay. We even go out to Orient and Montauk on occasion and we do it all with wind power. The stereo, fridge and starlink run on electricity almost fully provided by the sun via our solar panels making the cleanest and greenest charter option out there 🍃 🌬️

04/30/2026

The best place to get photobombed in the Hamptons
is on a sunset sail with 🌅

I can’t wait to be in the background of all of your pics
this summer 😁

04/09/2026

Our 42 foot “Elizabeth“ sailed over 3000 nautical miles this winter season in the Bahamas! 🇧🇸🩵🌊

03/09/2026

Sea breeze, turquoise water and nowhere else to be 🩵⚓️🌊

03/05/2026

Turns out I’m a pig guy 🐷

02/17/2026

Those Exuma blues sure make the winter a breeze 🌬️

09/13/2025

08/10/2025

we love our bachelorettes 😍 always the best vibes 🧜🏼‍♀️🎀🍇🌊🪭🩷

06/27/2025

The Season has started and we're excited to introduce you to our 2025 Charter Collection. Stay tuned to learn more about our new Merch, our True Sailing Yacht Club membership, our Yacht Management offers and lots of BTS ✨ Let the season begin ⛵️🌺👒🌅

11/13/2024

True Sailing has relocated to the Virgin Islands for the winter. Come join us for an unforgettable sailing adventure. World class snorkeling, exquisite meals served up by our talented chef and mind-blowing beaches are just a few of the highlights of a True Sailing Caribbean vacation. We’re also offering ASA courses up to 114 Catamaran Cruising aboard the mighty Ithaka.

09/09/2024

True Friends. True Fun. True Sailing ⛵️

Sometimes I think about coming up with a new slogan but this one truly sums up the True Sailing experience.

For best results bring tasty snacks for the crew 😋