Especially good for families with small children...

Are you interested in a quiet, scenic tour aboard the comfort of a 50' catamaran (with 2 restrooms!)??? 

This tour- offered only in the mornings- is especially nice during the "shoulder seasons" when the migratory birds of Assateague make their appearance. 

This 2 hour trip is not about sailing, it is about enjoying the views on Sinepuxent Bay and Assateague. Of course we will also be scouting the shore lines for ponies as well.

The flat, calm waters behind Assateague will allow you to enjoy any kind of spread, food-wise, that you bring out. And please feel free to bring any beverages you would like, including alcohol. (We know its a morning trip, but no judgement here- you are on vacation!)

No worries about seasickness whatsoever!

Trips on Alyosha depart promptly at the scheduled time from our brand new location at the "Olde Towne Marina" (address 307 Dorchester Street). Check in with our staff at our shed or come directly down to the boat at the end of the dock. (You can't miss Alyosha, we are the only sailing vessel around.) If you don't see the boat, please don't worry! We are probably off on another adventure and will return just before the scheduled departure time. Parking can be limited, so arrive early and consider having a drink at the new restaurant right next to our location.

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 four person minimum for this trip. So if you are a couple looking for a "boat ride" this could be (depending on other bookings) your best chance to get a private ride.

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!)