Sailing Behind Assateague
All the Chill of Sailing, Without the Uncertainty of the Atlantic
So you want to experience real sailing—sails up, engine off, wind doing the work—but you’re not sure about what the Atlantic Ocean might serve up? This is your trip.
Alyosha is a 50-foot sailing catamaran that has crossed oceans and logged over 50,000 nautical miles. She’s the real deal. When conditions are right throughout the season, the tides and currents behind Assateague Island create the most pleasant sailing conditions you can imagine. We head south with a strong current running into the predominantly south winds, which gets Alyosha down to the Verrazano Bridge pretty quickly. Then we turn around and the magic happens: a long, beautiful spinnaker run with those south winds behind us, into the current. Flat sailing, no motors, and you and your family or friends take in the scenic views from a choice seat on the trampoline or on Alyosha’s spacious deck.
If you’ve been searching for sailing charters near Ocean City, Maryland—this is the one that delivers a genuine sailing experience without asking you to bet your stomach on the Atlantic!
Who Is This Trip For?
Anyone who loves the idea of sailing but maybe not the actual seas and boat movement that come with the open ocean. You get everything that makes sailing special—the quiet, the wind in the sails, the feeling of moving across the water under nature’s power—without the swells and chop of the Atlantic.
If you are celebrating a special event like a birthday or anniversary let us know!
What to Expect on Your Bay Sailing Trip
This is actual sailing—not a motor cruise along the bay. When conditions are right, Alyosha will be under sail for the majority of the trip. The ride south is quick and exhilarating as we work against the current and into the wind. The ride back is pure bliss: a downwind spinnaker run where the boat glides flat and quiet and you can just… be. In some cases, and the seas are calm, we may head out into the ocean. You can check our homepage to see if that is an option.
Along the way, you’ll take in the scenery of Assateague Island and the surrounding bay. Keep an eye out for wildlife on the shoreline—including the wild ponies. And because we’re in the protected waters behind the island, the water stays flat the entire time.
A Note on Motion Sickness
This is one of the best sailing trips we offer for people who are concerned about seasickness. The bay waters are flat and calm, and because the sailing here is primarily downwind, the boat stays level and comfortable. You get the full sailing experience—sails up, engine off, wind in the sails—without the rocking and rolling that can come with ocean sailing. It is fantastic.
Weather & Cancellation
This trip is weather dependent. If the captain feels there’s any risk—mainly lightning—the trip will be cancelled and you’ll receive a full refund, no questions asked.
We need a minimum of 4 people for this trip to go out. If your party is fewer than 4, go ahead and book anyway—you’ll receive a full refund if the trip doesn’t go forward.
What to Bring
Feel free to bring any food or drinks you’d like onboard. Alyosha has plenty of bottled water for customers. There’s plenty of room to spread out: trampolines built for lounging and cushioned seating for an additional 6 people.
There are restrooms (“heads”) aboard for customer use—just keep in mind the toilets on a sailboat are a little more sensitive than the ones on land. For sun protection, the real action is outside on deck, so we recommend plenty of sunscreen and sunglasses. Alyosha also has a roomy salon area and cabins if you need a break from the sun.
Yes — that’s the whole point. When conditions are right, we cut the diesel and let Alyosha do what she was built to do. You’ll hear the sails fill and feel the boat move under wind power alone. It’s a completely different experience from a motor cruise.
A spinnaker is a large, downwind sail — ours happens to be the colors of the Maryland flag, so you can’t miss it. On this trip, we head south into the wind and then turn around for a long, beautiful spinnaker run back with the wind behind us. It’s the highlight of the trip and the moment most people grab their cameras.
Not at all. This is a passenger experience — Captain Steve handles everything. You just find a good spot on the trampoline and enjoy the ride. It’s actually one of the best first sailing experiences we offer.
Getting to Our Ocean City Sailing Charters
Trips depart promptly at the scheduled time from Olde Towne Marina (307 Dorchester Street, Ocean City, MD 21842), right next to Oyster & Scales in downtown OC. Parking can be limited, so plan to arrive a few minutes early. You can’t miss Alyosha—we’re the only sailing vessel around.