CHOOSE from our fleet of Boats
Whether you're looking for an exciting day on the water or a peaceful sail, we have the perfect boat for your adventure. Select your ideal vessel for your private charter to match the experience you're craving.
Spacious, elegant, and designed for comfort, Elizabeth is a 42ft Catalina sailing yacht that offers a luxurious and relaxing experience on the water.
For thrill-seekers and watersports enthusiasts! With a powerful 150hp engine, this 20ft Center Console is perfect for watersports, fishing, and swimming.
"Elizabeth" Catalina 42 Sailboat
"Elizabeth" Catalina 42 Sailboat
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.
Two Hours
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 Hours
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 Hours)
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 Hours)
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.
"Hummingbird" 20ft center console motorboat
"Hummingbird" 20ft center console motorboat
Hop aboard Hummingbird, our 20-foot center-console motorboat equipped with a Yamaha 150, and enjoy an idyllic time on the water. Perfect for water sports, fishing or zipping out to a secluded beach for a day of swimming and frolicking. Each charter is private and tailored to your preferences, ensuring an unforgettable experience for you and your guests.
Watersports
Choose from wakeboarding, wakesurfing, tubing and waterskiing. Between activities take a break, relax and enjoy a delicious prepared lunch with options from our exclusive catering menu. Perfect for creating unforgettable memories on the water!
Fishing
Embark on a fantastic fishing trip to all of the best spots inside Gardiner’s and Peconic Bays. We have everything you need from quality gear, fresh bait, and expert fishing advice from your captain. Expect stripers, bluefish, porgies and lots of fun.
Paddle Board Adventure
Set out on a guided paddleboard adventure, exploring pristine waters with an expert leading the way. Along the journey, we’ll help you perfect your form and show you some back water gems you’ve never seen before.
Swimming & Beach Hopping
This is our mainstay offering aboard Hummingbird. We’ll zip around within Three Mile Harbor or venture out into Gardiners Bay and beyond, stopping at the stunning beaches and hidden coves of the East End. Included: drinking water and standard floaties.
Water Taxi
Get around in style with our convenient water taxi service. Whether you're heading to a nearby beach, a restaurant, or just exploring, we’ll get you there quickly and comfortably, offering a seamless experience on the water.
Powerboat Lessons
Learn the ropes of powerboating with hands-on lessons from an experienced captain. Whether you're a beginner or looking to refine your skills, our lessons provide you with confidence on the water and eligibility to join our exclusive boating club.







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 12 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”.

