CHOOSE YOUR Experience on Elizabeth
Whether you're looking for a relaxing afternoon sail or a unique, themed experience, Elizabeth offers something for everyone. Choose from our flexible time options or our curated experiences designed to create lasting memories.
Two Hour
The perfect quick getaway on the water. Feel the breeze on this 2-hour sailing adventure, taking in the views of Sag Harbor and the surrounding coastline before getting back ashore for your evening plans.
Three Hour
Sail across the bay towards Cedar Point and Gardiners Bay, passing the historic lighthouse to starboard. Enjoy a snack, float in the water, and soak in the scenery before returning back ashore.
Half Day (Four Hours)
Perfect for lunch plus a swim. Sail out past the lighthouse and into Shelter Island’s Coecles Harbor or Redneck where we’ll anchor, deploy the water toys for a fun swim and enjoy a picnic before catching the wind back to harbor.
Full Day (Eight Hours)
Explore The Hamptons in style. Set sail for a full day adventure, with stops at Shelter Island, Montauk, or Greenport. Enjoy a swim, beach time, and a delicious waterside lunch before sailing back at your own pace.
Sailing Zen & Yoga
On this 4-hour trip, we combine the tranquility of sailing with a serene Yin Yoga session on the bow or beach, followed by a refreshing dip and time to enjoy the boat with snacks and boat-made iced tea.
Sunset Sail & Sips
Sail into the sunset on a 2-hour voyage with a bottle of Veuve Clicquot Champagne or a locally sourced Brut. Settle in as the sky transforms and the water reflects the glow of the evening.
Sail & Sketch
Immerse yourself in creativity on this 4-hour sailing trip. We provide canvases, paint, brushes, an art guide and stunning ocean views. Return to shore with a unique art piece—a lasting memory of your time at sea.
Sunrise Meditation Sail
Set out just before dawn on this 3-hour sail. Enjoy a peaceful guided 20-min meditation at sea while watching the sunrise. Take a refreshing morning dip, savor breakfast from our catering menu, and return feeling refreshed and renewed.
Paddle & Sail Excursion
Set off on a 6-hour adventure combining sailing and paddle boarding. Sail to an anchorage, and enjoy a guided paddleboard tour for all skill levels. Afterward, a delicious lunch will be waiting back on the boat before sailing back to shore.
Wine tasting cruise
Indulge in an elegant 4-hour wine tasting experience aboard a sailing yacht. A sommelier from a local vineyard will guide you through a selection of fine wines while you sail smoothly along the coast. Perfect for wine lovers seeking a unique sailing experience.
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?
