Sailing Trips In Ocean City, MD
Nine Ways to Get on the Water — From Calm Bay to Open Ocean
Sailing trips in Ocean City start here. Alyosha is a 50-foot sailing catamaran — the real thing, not a party barge. She’s crossed oceans, circumnavigated the globe, and logged over 50,000 nautical miles with Captain Steve at the helm. Now she runs out of Olde Towne Marina in downtown Ocean City, Maryland, and she can take you just about anywhere: through the inlet and onto the Atlantic, behind Assateague Island into the flat, calm bay, or out into the open Atlantic for a full day offshore.
We offer nine distinct sailing trips in Ocean City. Some are designed for first-timers and families who want a beautiful, easy morning on the water. Others are for people who want real sailing — sails up, engine off, wind doing the work. A few are reserved for guests who’ve already been out with us and want to go further.
The guide below will help you find the right one.
HOW TO PICK YOUR SAILING TRIP
Start here: Are you worried about seasickness?
If yes — or even if you’re just not sure — look at the Assateague sailing trips first. They all take place on the flat, calm waters of Sinepuxent Bay, behind Assateague Island. No ocean swells, no dramamine required. Seriously.
If you’re comfortable on the water and want real sailing — wind in the sails, the Atlantic under you — start with Ocean Sailing on Alyosha. It’s the right introduction to what Alyosha can really do.
And if you’ve already been out with us and want more: the Advanced sail, Hands On Sailing, The Big Blue, and the Moonlight Cruise are all waiting.
Ocean City Sailing Trips at a Glance
| Trip | Duration | Time | Sails? | Max Guests | Best For | Seasick Risk | Min to Run |
|---|---|---|---|---|---|---|---|
| Morning Assateague Tour | ~2 hours | Morning | No | 12 | Families & early risers | None | 4 |
| Sunset Cruise | ~65-75 min | Evening | Possibly | 12 | Couples, celebrations | None | 4 |
| Sailing Behind Assateague | ~2 hours | Varies | Yes | 12 | Sail lovers, calm water | None | 4 |
| Yoga on Alyosha | ~2 hours | Morning | No | 8 | Wellness seekers & yogis | None | 6 |
| Ocean Sailing | ~2 hours | Varies | Yes | 12 | First-timers & everyone | Some | 4 |
| Ocean Sailing Advanced | ~3 hours | Varies | Yes | 12 | Return sailors wanting more | Some | 4 |
| Hands On Sailing | ~3 hours | Varies | Yes | 6 | Doers & aspiring sailors | Some | —* |
| The Big Blue | ~6 hours | Full day | Yes | 6 | Experienced adventurers | Plan for it | —* |
| Moonlight Cruise | ~2 hours | Evening/Night | Yes | 8 | Couples, adults (16+) | Low/None | 4 |
* Prior booking with Sail Alyosha required for Advanced, Hands On, and The Big Blue.
Assateague Island Sailing Trips
Four sailing trips in Ocean City, one spectacular backdrop. The protected waters behind Assateague Island are where you go when you want beautiful scenery, wildlife, and zero seasickness risk. Wild ponies, ospreys, bald eagles — and a 50-foot catamaran with two restrooms and plenty of room to spread out.
Our Assateague Trips:
Morning Assateague Tour
Scenic 2-hour bay cruise
Assateague Sunset Cruise
Evening magic on calm water
Sailing Behind Assateague
Real sailing without ocean swells
Yoga on Alyosha
Guided yoga at anchor in the bay
Atlantic Ocean Sailing Trips from Ocean City
Out through the OC Inlet and onto the open Atlantic. Four sailing trips in Ocean City ranging from a 2-hour introduction to a 6-hour offshore adventure 20 miles from shore. Dolphins, real sailing, and the kind of experience most people only read about.
Our Ocean Trips:
Ocean Sailing
The starting point. 2 hours, open to everyone
Ocean Sailing Advanced
3 hours for return guests wanting more
Hands On Sailing
You crew the boat. Learn about sailing
The Big Blue
6 hours, 20 miles offshore. The ultimate
Assateague Sunset Cruise
Calm bay water, gorgeous views, and the Ocean City skyline lighting up on the way back. Perfect for birthdays and anniversaries
Moonlight Cruise
The adults-only option (no one under 16). This trip only runs when everything is right — the moon, the wind, the sea — which means it happens only a handful of times each summer. Either Atlantic Ocean or behind Assateague depending on conditions. Intimate, magical, unforgettable
What All Our Ocean City Sailing Trips Have in Common
Every trip runs on Alyosha — a 50-foot St. Francis catamaran with two restrooms, a roomy salon, cushioned seating, trampolines built for lounging, and enough deck space that nobody’s on top of each other. You’re welcome to bring food, snacks, and drinks (including alcohol) on every trip. We’ll have bottled water aboard.
All trips depart from Olde Towne Marina (307 Dorchester Street, Ocean City, Maryland). Parking can be tight — arrive a few minutes early.
Not Sure Which Sailing Trip Is Right for You?
If you’re nervous about the ocean, start with any of the Assateague trips — you can’t go wrong. If you want real sailing and you’re feeling confident, start with Ocean Sailing on Alyosha. And if you’ve got specific questions, reach out — Captain Steve is happy to help you figure out the right fit.
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.