What to Expect on a Private Sailing Charter

starting at $600 for couples, $700 for 3-6 guests
2 – 4 hours | flexible itineraries
catering menu | luxury amenities

A private sailing charter isn’t a ferry ride or a party boat packed with strangers. It’s something better: a polished, personal experience on the water that feels both exhilarating and effortless. Whether this is your first time sailing or your fiftieth, here’s what actually happens once you step aboard.

The Experience: Relaxing, Active, or Both

Sailing is whatever you want it to be.

Some guests settle into the cushioned seating, close their eyes, and let the rhythm of the harbor work its magic. Others want to steer, ask questions about the rigging, or stand at the bow while the boat cuts through the waves. There’s no script. Your captain adapts to your energy, not the other way around.

Different people in the same group often have completely different experiences—and that’s part of what makes a private charter feel genuinely yours. One person might lounge on the sun pad with champagne while another takes the wheel and learns to tack upwind.

You don’t need sailing experience. You don’t need to know port from starboard. You just need to show up and decide what kind of day you want to have.

What Sailing Actually Feels Like

There’s nothing quite like the sensation of wind-powered movement across water. When the sails fill and the engine cuts off, the change is immediate—the mechanical hum disappears, replaced by the sound of water rushing along the hull and wind humming through the rigging.

The boat responds to every gust and lull. You feel it heel slightly as the sails catch more wind, then level out as your captain adjusts the trim. There’s a quiet power to it—40 feet of fiberglass and carbon fiber moving across the harbor without burning a drop of fuel, responding to invisible forces most people never pay attention to.

It’s exhilarating without being intense. The motion is constant but gentle—more like gliding than driving. Some guests describe it as meditative. Others find it energizing. Most are surprised by how connected they feel to the environment—the breeze on their face, the warmth of the sun, the city skyline slowly rotating as the boat tacks across the harbor.

This is why people have been sailing for thousands of years. It’s not just transportation. It’s a way of moving through the world that feels fundamentally different from anything on land.

First-Time Sailors Welcome

Most guests have never sailed before, so if you’re new to this, you’re in the majority. There’s zero expectation that you’ll know nautical terminology or how a jib works. If you’re curious, your captain will explain everything and invite you to get hands-on. If not, you can sit back and enjoy the ride without a single question asked.

The private sailing charter experience is designed around comfort and ease, not credentials. Show up, relax, and let the wind do the rest.

Arrival and Boarding

Getting onboard is refreshingly simple. The marina entrance is steps from the sidewalk at Chelsea Piers—no long walks, no confusing terminals, no security theater. You’ll meet your captain at the marina gate, and they’ll guide you down a gently sloped ramp directly to the boat’s slip.

Boarding takes four steps up, then one step across to the deck. The whole transition from city sidewalk to sailboat happens in under two minutes, which is exactly how it should feel.

How You’ll Actually Use the Space

The sailboat has multiple zones, and guests naturally migrate between them throughout the charter.

Most of your time will be spent in the outdoor cockpit—the main gathering space where conversation flows easily, drinks are within reach, and you can watch the city unfold from every angle. The cushioned seating wraps around a central table, and the full shade system means you control how much sun you want.

When you want a different perspective, head to the sun pad at the bow. It’s where couples go for photos, where someone always ends up with their face to the wind, and where you feel most connected to the motion of the boat.

The interior cabin surprises people. It’s not cramped or dark—it’s wood-paneled, has wraparound windows, and feels like a sophisticated lounge. Some groups use it for champagne toasts. Others retreat there when conversation gets deep or when they need a break from the elements.

The bathroom (called the head) is clean, modern, and easy to use. Your captain will explain how it works during the safety briefing, but there’s no complicated pumping or confusing mechanisms like on older boats.

You’re encouraged to explore and use different spaces throughout your sail. There’s no “bad seat” on this boat—every spot offers something different, and most guests end up sampling them all.

Can You Move Around the Boat?

Yes, absolutely—just use a little common sense.

The crew moves around the deck like they were born at sea. For first-timers, it takes a moment to find your rhythm. Start by lounging, and when you’re ready to explore, there are handholds throughout the cockpit and cabin. Moving with the boat feels natural once you tune into its motion.

No athleticism required. No sailing knowledge expected. Just pay attention and move deliberately.

How Fast Does a Sailboat Go?

The Beneteau 40 is a performance cruising sailboat. She is built to feel smooth and responsive without sacrificing comfort. Speed depends on wind conditions and sail configuration, but most charters move at a relaxed pace perfect for sightseeing and soaking in the skyline.

Under engine power, the boat cruises at about 7–8 knots. With sails up, it naturally reaches hull speed around 7.8 knots and can go faster when conditions align. More speed usually means more heel—that gentle tilt you feel while sailing. Your captain can keep things calm and level for lounging and photos, or dial up the angle for guests who want a little thrill.

Food and Drinks

Elevate your private sailing charter with food and beverage service. You can order from our catering menu (brunch, lunch, champagne packages) or bring your own ($100 BYO fee). Either way, the crew handles setup, service, and cleanup—you just enjoy.

The Crew’s Role

Your captain and crew read the room. They’re happy to explain how sailing works, share harbor history, help with photos, or point out landmarks. They’re equally happy to step back and let you enjoy the moment uninterrupted. Service is attentive without hovering—professional but warm. Think hospitality, not narration.

If you want a hands-on sailing lesson, they’ll teach you. If you want silence and solitude, they’ll give you that too.