Join Frannie, Solomon, and Captain Steve for a chill, Jamaican-themed tour behind Assateague Island with food and beverages included! We will provide the boat, the scenery, the food and the soundtrack: You bring the sense of adventure!

Alyosha will stay behind Assateague Island for the entirety of this two hour tour but we will hopefully put the sails up and kill the engines to enhance the party vibe! This trip is only for adults over 21 years old. Plenty of other options for kids on Alyosha.

The spread of food- provided by local favorites One Love Cafe- will include the option of a Chicken or Tuna salad sandwich with Caribbean Slaw chips and a pickle all served on toasted Brioche bun.

And Solomon promises to put everyone in the right mood with his Jamaican- inspired playlist!

This trip will depart promptly at the stated departure time from the pier alongside of PIER 23 in West Ocean City Harbor. (Actual address: 12817 Harbor Road, Ocean City, 21842)

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.

Alyosha has plenty of water bottles for guests. There is plenty of room onboard to store coolers, food and drink.

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!)