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Sailing Behind Assateague

So you want to enjoy a few hours on the water and experience sailing without the uncertainty of what the Atlantic Ocean serves up? This experience is for you... Several times during the summer, the tides and currents behind Assateague Island afford the most pleasant sailing imaginable: a quick trip south, with a strong current heading 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/friends take in the scenic views from a choice seat on the trampoline or on Alyosha's spacious deck.

If you like the idea of sailing, but maybe not the actual seas and boat movement, try this trip out. It is fantastic!

Trips on Alyosha depart promptly at the scheduled time from the berth alongside of Pier 23 restaurant/bar in Ocean City Harbor. (Actual address is 12817 Harbor Road Ocean City, 21842) 

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, (mainly lightning) 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. Feel free to bring any food or drinks you would like onboard. Pier 23 will be featuring special “sailaway snacks” for Alyosha customers- plan to order your food there about 20 minutes prior to departure.

In terms of seating and spacing: There is plenty of room for everyone! Trampolines built for lounging and, new in 2022, cushioned seating for an additional 6 people!

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

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.

There is a 4 person minimum for this trip to go out. If your party is less than 4, please go ahead and book the trip and know that you will receive a full refund if the trip does not go forward!

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?

You can make this trip a Private Charter -- a trip that is exclusvely for you and your group.

By booking all 12 seats on this trip, you'll get a discount and be able to set the itinerary: whether we go sailing, cruising along Assateague, or anchor for a bit and go swimming!


Any Children? (under 12 years old)