Sail the boat that sailed the world! 

A longer bit of sailing for customers who have sailed with us before, and know they will love the sailing action on Alyosha! (If you have not sailed with us before, please stick to the 2 hour experiences offered throughout the week- or the sunset cruise offered nightly) This experience is only available to those who have a prior booking with us. We know you, you know us, and you are ready for 3 hours of sailing!

Join Captain Steve Butz and prepare yourself for a very different Ocean City attraction! This is not the Sea Rocket! Sailing on the Atlantic Ocean is sometimes very exciting and often very relaxing, depending on the conditions. Don’t worry, you will have a great time either way…

The adventure will begin promptly at the scheduled start time and Alyosha will head out for an unforgettable sail on the Atlantic Ocean. The fun really begins when the diesel engines cut off and the boat moves along effortlessly under only sail power. Yes, this trip is about sailing! Pods of dolphins often playfully swim right off the bow of the boat, making a once in a lifetime natural experience! There is plenty of room aboard Alyosha for you to spread out and enjoy yourself- we encourage guests to utilize the wide trampolines in front of the boat for lounging.

There is always a four person minimum for all Ocean Sailing trips. Don’t let this discourage you! Book the trip if you want to sail and if we don’t get enough people- we almost always do- we will find another time/date for you.

Birthdays, Anniversaries and Special Events:

Let us know if you are celebrating something with your cruise: We now have anniversary, birthday and special event flags- complete with a nautical number set- that we hope you will consider raising during the sail.

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 expect:

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.

Alyosha is a big, stable sailing catamaran, and she sails flat. As noted in the trip description, the Captain will decide whether to stay inside the inlet for a tour along Assateague Island if the Atlantic Ocean is too rough.

What to bring:

Alyosha has plenty of bottled water for customers. Feel free to bring any food or drinks you would like onboard- yes, even a small cooler if you prefer... 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.

Ocean Sailing is something that can be a once in a lifetime experience and even a gateway into the sport of sailing. Join us and experience an incredible way to see "the other side" of Ocean City. 

There is a 4 person minimum for afternoon sails. Don’t let this discourage you! Book the trip if you want to sail and if we don’t get enough people- we almost always do- we will find another time/date for you.

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!)