Book Your Experience

Private Charters

Book Alyosha for your next event or group outing! Private charters for up to 12 people are available on request. This specific offering- usually on Saturday afternoons, is our longest available private charter outings for groups of up to 12 people. The time will run at least 1pm to 4pm and could run as long as 4:45pm depending on whether your group wants to go sailing, enjoy the nature and serenity of the bays behind Assateague Island or just set up an afternoon party on the water!

Trips on Alyosha depart promptly at the scheduled time for your Private Charter  from the berth alongside of Pier 23 Bar & Restaurant in Ocean City Harbor. (The actual address is 12817 Harbor Road, Ocean City, Maryland 21842.

Whether we go out on the Atlantic Ocean for a sail or whether we stay behind Assateague Island for a swim is entirely up to you and your group.

What to expect:

If your Private Charter decides to sail: Keep in mind that this experience is real open ocean sailing! Typically June, July and August on the Atlantic Coast features gentle, rolling swells as a "seabreeze" builds throughout the day. But not everyday is "typical."

Alyosha is a big, stable sailing catamaran, and she sails flat. But there is plenty of motion in ocean sailing and if you are prone to seasickness then you should plan to take some preventative medicine BEFORE we leave the dock. (Once you get sick, it is too late!) We recommend "Bonine" or "Dramamine".

This trip is, of course, weather dependent. If the captain feels that there is any risk given the conditions of a particular day, including a forecast that doesn't look promising, then the trip will be cancelled. You will receive a full refund in the event of any cancellation.

What to bring:

Alyosha has plenty of bottled water for customers. Unless you are specifically choosing the "catered" option, feel free to bring any food or drinks you would like onboard. There is plenty of room for everyone.

There are restrooms ("heads") aboard Alyosha for use by customers. Keep in mind that the toilets on a sailboat are a little bit bit more sensitive than land based toilets...

Protection from the elements: Although Alyosha has a roomy salon area and cabins that our guests may use, the real action is outside, on deck! Therefore, we highly recommend plenty of sunscreen and sunglasses.

Alyosha is big, wide and the absolute perfect activity for families and friends looking to do something different while vacationing in Ocean City, Maryland.

Aligned with the goal of ensuring all Sail Alyosha customers have a great experience, we will only run trips that are deemed safe by our Captains. Generally, the weather on the coast of the Ocean City area is very pleasant but sometimes storms and thunderstorms do occur.

In the event that your trip is cancelled, you will receive a full refund. Sometimes, the weather conditions, particularly high winds causing choppy seas, will allow us to run a safe trip that is a bit unpleasant.

Our captains will always strive to let people know when conditions will be less than ideal and if conditions warrant a possible refund you may choose to not take the trip. (But sometimes those rough passages make for the best experiences!)


How Many Seats?


Any Children? (under 12 years old)