Ocean Sailing "Advanced"
Sail the Boat That Sailed the World
A longer bit of sailing for customers who have sailed with us before and know they love the sailing action on Alyosha. This is 3 hours on the water—more time to really get out there, more time under sail, more of what made you fall in love with it the first time around.
This experience is only available to those who have a prior booking with us. We know you, you know us, and you’re ready for it. If you haven’t sailed with us before, please start with our 2-hour ocean sailing experiences offered throughout the week, or the sunset cruise offered nightly.
We also have other ocean adventure trips here.
What to Expect on Your Advanced Adventure
Prepare yourself for a very different Ocean City attraction. This is not the jetboat Osprey! Sailing on the Atlantic Ocean is sometimes very exciting and often very relaxing, depending on the conditions. Don’t worry—you’ll have a great time either way.
The adventure begins promptly at the scheduled start time and Alyosha heads out for an unforgettable sail on the Atlantic. The fun really begins when the diesel engines cut off and the boat moves along effortlessly under nothing but sail power. Pods of dolphins often swim right off the bow—a once-in-a-lifetime natural experience. There’s plenty of room aboard Alyosha for you to spread out: claim a spot on the wide trampolines at the front of the boat for lounging, or settle into the cushioned seating on deck.
If the Atlantic is too rough, the captain may decide to stay inside the inlet for a tour along Assateague Island instead. Either way, you’re in for a great day on the water.
Who Is This Trip For?
Return sailors who’ve been on Alyosha before and were left wanting more. You know what ocean sailing on a catamaran feels like, you know you love it, and now you want a deeper experience. Three hours gives you time to really settle in, watch OC fade into the horizon, and enjoy the Atlantic.
If you are celebrating a special event like birthday or anniversary let us know!
A Note on Motion Sickness
Alyosha is a big, stable sailing catamaran, and she sails flat. But there can be motion in ocean sailing, and if you’re prone to seasickness, you should plan to take preventative medicine before we leave the dock. Once you’re feeling sick, it’s too late. We recommend Bonine or Dramamine.
If you’re on the fence, take a look at our Seasickness Guide!
Weather & Cancellation
This trip is weather dependent. If the captain feels there’s any risk given the day’s conditions—including a forecast that doesn’t look promising—the trip will be cancelled and you’ll receive a full refund.
There is a 4-person minimum for all ocean sailing trips. Don’t let that discourage you—book the trip if you want to sail. We almost always hit the minimum, and if we don’t, we’ll find another time and date that works for you.
What to Bring
This is a 3-hour sail, so come prepared. Alyosha has plenty of bottled water, but feel free to bring any food or drinks you’d like onboard—yes, even a small cooler if you prefer. There’s plenty of room for everyone.
Sunscreen and sunglasses are a must—the real action is outside on deck. Alyosha has a roomy salon area and cabins if you need a break from the sun. Restrooms (“heads”) are aboard for customer use—just keep in mind the toilets on a sailboat are a little more sensitive than the ones on land.
A: Yes, Ocean Sailing Advanced is designed for return sailors who’ve already been out on Alyosha and know they love the experience. If you haven’t sailed with us yet, we recommend starting with our 2-hour Ocean Sailing trip—it’s open to everyone with no prior booking required. Once you’ve experienced ocean sailing on Alyosha, you’ll be ready to book the Advanced trip and enjoy three hours on the water instead of two.
Ocean Sailing Advanced gives you 50% more time on the water—three hours instead of two. This means more time under sail, the opportunity to push further offshore when conditions allow, and a chance to truly settle into the Atlantic Ocean experience. It’s for sailors who’ve done the 2-hour trip and left wanting more. The boat, the crew, and the quality of the experience are exactly the same—you just get a bigger dose of what made you fall in love with sailing the first time around.
When Atlantic conditions are good, this trip heads offshore for three hours of open ocean sailing. However, if the ocean is too rough on the day of your trip, Captain Steve may keep the sail inside the inlet for a tour along Assateague Island instead. Either way, you’ll get three hours on the water aboard Alyosha. If conditions require cancellation entirely, you’ll receive a full refund—no questions asked. This is real ocean sailing, so the weather always has the final say.
Getting Here
Trips depart promptly at the scheduled time from our slip at Olde Towne Marina (307 Dorchester Street, Ocean City, 21842). Plan to arrive about 5 minutes before departure—there’s no formal check-in. But please know: if we have other guests and you’re late, we will still leave on time. It’s not fair to punctual guests to make them wait. Parking can be a challenge, so arrive early and maybe have a drink at the restaurant next to the marina.