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Home > Ocean City

Sail the Boat that Sailed the World!

Try something completely different and come sailing on our 50’ catamaran, Alyosha! We offer several trips each day, usually at 1pm, 4pm and sometimes a “Sunset Cruise” in the evening. Occasionally we depart as early as 10am! Alyosha can take up to 12 people and has a men’s and women’s restroom for your use throughout the trip.

All of our sailing adventures can be catered- we have partnered with OC’s best events company, Taste Events, to provide that option. (Catered trips are offered only with a minimum of a 6 person booking). Additionally, feel free to bring beverages of your choice aboard. There are plenty of options to keep things cold. Choose from one of the following sailing experiences:

Ocean Sailing!

See another side of Ocean City from the Atlantic Ocean. This 3 hour cruise will allow you to experience the pure joy of sailing fast on a 50’ catamaran! The incredible views, marine life on display, and fun captain and crew, will make this unforgettable.

Hands On Sailing

Interested in something more “hands on?” Assist the Captain and Crew of Alyosha and learn some of the basics of blue water sailing. Offered only at specific times during the week.

Sunset Cruise

Enjoy an evening on the ocean and watch the sun set on Ocean City from the water. These trips are typically shorter in duration (approx. 90 minutes) but still provide the thrill of sailing in a romantic setting.

Private Charters

Interested in a more intimate experience for just close friends and family? Alyosha is available for private charters at times when she is not scheduled to run trips. (You need to book the whole boat!)

See another side of Ocean City from the Atlantic Ocean. This 3 hour cruise will allow you to experience the pure joy of sailing fast on a 50’ catamaran! The incredible views, marine life on display, and fun captain and crew, will make this unforgettable.

 

Offered only during a full moon on 6 selective nights throughout the summer! This is a chance to sail the Atlantic under moon light as the sailors have been doing for centuries! You will not believe how different of an experience this can be. Trips last 2 hours later in the evening.

Offered only during a full moon on 6 selective nights throughout the summer! This is a chance to sail the Atlantic under moon light as the sailors have been doing for centuries! You will not believe how different of an experience this can be. Trips last 2 hours later in the evening.

Offered only during a full moon on 6 selective nights throughout the summer! This is a chance to sail the Atlantic under moon light as the sailors have been doing for centuries! You will not believe how different of an experience this can be. Trips last 2 hours later in the evening.

Throughout the summer there are occasionally events that can best seen from the water, including the Ocean City Air Show, 4th of July fireworks, and select music concerts. There is also a chance to accompany the Captain as Alyosha transits between Baltimore and Ocean City. 

Accordion Content

Catering Now Available!

We’ve partnered with Off the Hook Restaurant Group’s Taste Events to provide several options to compliment your sailing experience. Click below for more information on our catering options, how to order catering for your cruise, and more!

All Aboard!

Our trips from Ocean City originate from Mad Fish Bar & Grill in West Ocean City.