A Brand New 2024 Offering:

Have you sailed with us before and been left wanting more? Can't commit to the 6 hour "Big Blue" trips on Sundays but still need a sailing fix that is bigger and better than our standard, almost three hour tour? Try our newest offering: Ocean Sailing "Advanced"

On Tuesdays, Fridays and Saturdays we will embark on a longer, over 4 hour sail out on the Atlantic Ocean! This trip is primarily offered to thosse who have sailed with us before, and who just can't get enough of Alyosha, sailing, or our friendly crew!

Watch OC fade into the horizon as the crystal clear Atlantic Ocean waters surround the boat. 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.

Birthdays, Anniversaries and Special Events:

One of the great surprises of our first year of operations was how many people decided to celebrate their anniversaries and/or birthdays with us! (We have had weddings, first dates, and proposals as well...) 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.

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.

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) 

Plan to arrive about 5-10 minutes before your departure time, there is not really any "check in" necessary... but please know that if we have other guests and you are late- we will still leave on time. It just is not fair to those guests that are punctual to make them wait for late arriving folks. Sorry in advance!

Ocean Sailing "Advanced" trips will generally last over 4 hours- so plan accordingly! We will go through the OC Inlet (often the roughest part of the entire journey) and then let the wind dictate the triangular shape we will sail. 

Keep in mind that this experience is real open ocean sailing! The Captain and Crew have yet to be able to control the wind and seas...although there is no lack of effort on that account! 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 could be 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. (If you get sick, it is too late!) We recommend "Bonine" or "Dramamine". If you are on the fence after reading this: Please take a look at our “Seasickness Guide!”

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. Feel free to bring any food or drinks you would like onboard. There is an excellent smoothie/coffee spot across from our boarding location called One Love Smoothie Cafe.

In terms of seating and spacing: There is plenty of room for everyone! Trampolines are built for lounging and 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.

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!)