Command & Crew the boat that sailed the world!

Ever wonder what it is like to actually try to maneuver a 50' sailboat in a tight harbor? Want to experience the thrill of manning the helm, raising the sails and setting a course for adventure? Or how about this: Unable to sit still and would rather be doing something because that's how you're wired to relax? Then we have the perfect trip for you!

Revamped in 2024, Customers Loved This Hands On Experience:

This is a hands on sailing adventure that will have you and all other customers completely handle EVERY aspect of a 4 hour sailing adventure! You will be expected to review a brief guide to staying safe on Alyosha beforehand, and there will be a 10-15 minute orientation at the beginning of this trip to ensure everyone stays safe! Then, you can expect to be put to work at the helm, on the sails, or in a variety of other capacities! Captain Steve's perfect vision of this trip is to use his voice (and kind, patient demeanor) to direct everyone to successfully navigate Alyosha through a sailing ocean experience! (If the weather does not cooperate, we will cancel and refund this trip, there is not enough hands on sailing to be had behind Assateague Island...)

Captain Steve Butz has over 35 years of sailing experience and recently completed a circumnavigation on Alyosha. He has logged over 50,000 nautical miles on the boat. You and your fellow guests will be in good hands.

No question is off limits as Steve is happy to pursue whatever topics interest sailors looking to boost their knowledge or stoke the interest of newbys to the sport. This trip- which is a longer experience at 4+ hours- is for those wanting more than just a ride in the Atlantic Ocean. You will leave with a deeper appreciation of the sport of sailing and the physics behind it.

Please note: If you just want to get out there and sail, and this is the most convenient time for you, by all means please book the trip! We have many “Hands On” sailors who actually prefer to just chill out and relax and let others do the work. Also, we have many couples choosing this trip where only one member really wants the "hands on" part! That is fine: This trip is exactly as engaging as you want it to be.

We only allow 6 people on this trip to ensure everyone is able to get some "hands on" experience.

(We prefer no youth under 13 years old for this experience)

Logstics:

Trips on Alyosha depart promptly at their scheduled time from the downtown marina called "Olde Towne Marina" in downtown Ocean City. (Actual address is 307 Dorchester Road, Ocean City 21842)

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.

Hands On Sailing day trips will generally last close to 4, full hours- it is one of our longest experiences. 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. We do make an effort on the Hands On Sailing trips to try to get all of the sails working.

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. 

What to expect:

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 is plenty of 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.

Specific Hands On Sailing Expectations

People choosing this "Hands On" sailing experience are expected to be in good physical shape and be willing to sign a fitness waiver before participating. Participants will be given a chance to "re-confirm" their desire for a "Hands On" experience at the onset of the trip. It is no problem at all if participants decide, based on the conditions, to participate a bit less than they had planned. Additionally, we understand that some participants are choosing the "Hands On" experience to accompany a friend- again, no worries at all if this is the case.

(We prefer no youth under 13 years old for this experience)

Safety is paramount on this trip. Any customer looking to participate should review our orientation guide (which will be reiterated at the start of the trip).

Hands on Sailing Extra Credit: Sailing gloves. If you have them, bring them. We do have a few extra pairs onboard as well. Not required.

What else to bring:

Alyosha has plenty of bottled water for customers. Feel free to bring any food or drinks you would like onboard. There is plenty of room for everyone.

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!)