Ocean City Sailing Adventures on a 50-Foot Catamaran
From peaceful bay cruises to Atlantic Ocean sailing
Everything's Better on the Water
Date nights. Proposals. Family reunions. Bachelor parties. Birthdays that matter. Or just a Tuesday when you need to get away from it all. Whatever brings you out here, sailing on a 50-foot catamaran off the Maryland coast makes it unforgettable. We’ve got trips for every occasion—and a few for no occasion at all.
Celebrations & Milestones











Proposals, Weddings, Anniversaries, Birthdays, Bachelor/Bachelorette Parties
Some moments only happen once. Make yours unforgettable aboard a 50-foot catamaran with the Maryland coast as your backdrop. We’ve hosted proposals, weddings, anniversary celebrations, and bachelor parties—and we’re ready to make your milestone just as special.
Family Adventures








Family Outings and Get Togethers, Calm Waters, Wildlife Spotting….even Yoga!
Bring the whole crew—kids, grandparents, the works. Our Assateague trips stay in flat, calm bay waters with zero seasickness risk, two restrooms onboard, and plenty of room to spread out. Watch for wild ponies, settle into the trampolines, and actually r-e-l-a-x.
Ocean Sailing Adventures








Ocean Sailing, Atlantic Offshore, Hands-On Learning, The Big Blue
Tap into your inner sailor. This is real sailing. Engines off, sails up, Atlantic Ocean stretching out in every direction. Whether you’re looking for a 2-hour introduction or a 6-hour offshore expedition, you’ll leave understanding why we’ve sailed Alyosha 50,000 nautical miles—and why we keep going.
Private Charters
Private Charters allow you to book the entire book for whatever the occasion! Reach out to us with your idea and we will make it work. New feature for 2026… A Private Charter builder for customers looking to book the whole boat for their group.
Smooth Sailing Trips
Alyosha’s a 50-foot catamaran. We can take her into calm bay waters where families spread out on the trampolines and watch for wild ponies. Or we can go off the coast of the blue Atlantic for a beautiful sunset. Or even a combination of both! Either way, it will be calm, spacious, and just what you are looking for.
Sunset Cruises and Moonlight Cruise






Evening Sails, Calm Waters, Date Night Favorites
Watch the sun sink into the marsh or sail under a full moon on the Atlantic. These evening cruises are our most popular date night experiences—and the ones Captain Steve looks forward to most. Gentle conditions, no seasickness risk, and the Maryland coast at its most beautiful.
Assateague Island Bay Trips






Calm Waters, Wildlife Spotting, Zero Seasickness
Flat, protected waters behind Assateague Island. Wild ponies on the shoreline. Ospreys overhead. These trips skip the Atlantic entirely and stay in Sinepuxent Bay—perfect for families with kids, anyone nervous about seasickness, or mornings when you just want peaceful water and room to breathe.
Why Sail Alyosha?
This isn’t a tour boat. Alyosha’s a 50-foot St. Francis catamaran that Captain Steve sailed around the globe—Pacific, Indian, Atlantic. Over 50,000 nautical miles logged. She’s stable, spacious, built for open ocean, and the only sailing catamaran operating out of Ocean City. You’re in good hands.
Sail Alyosha Vacation Adventures



Introducing Sail Alyosha Vacation Adventures, your chance to explore the world’s best waters aboard a 50’ luxury catamaran. Experience the laid-back cruising lifestyle with adventures ranging from ocean sailing to leisurely island hopping. Our first journey sets sail in the US Virgin Islands this November—an unforgettable escape from the winter cold
Frequently Asked Questions
If you are considering any of the Assateague Trips, Sunset Cruise, or Moonlight Cruise then no worries- you will not have an issue.
We have run hundreds of trips touring along the West OC Commercial Harbor and in the Sinepuxent Bay inland of Assateague Island and we have not had anyone get sick. Some of the trips might go into the ocean along the coast, if it is calm enough – the captain makes the call, but again no seasickness. The fact of the matter is that Alyosha is a 50’ Catamaran and the small waves that could possibly kick up on the inland waterway don’t move the boat at all. Waves from passing vessels may temporarily rock the boat but the motion quickly subsides….
Out on the Atlantic Ocean… that’s a different story. And so the below advice is offered to anyone booked or considering booking an Ocean Sailing Adventure.
Depending on the conditions, sailing Alyosha out on the Atlantic Ocean can be anything from a chill ride to an absolute thrill ride- largely dependent on the winds and waves. In 2022, we are going to add a “conditions” update to our website- including automatic messaging- to try and prepare people on what to expect on their particular trip. (and if it is too rough out there, we just don’t go out!)
With the idea that knowledge is power, we offer several “Do’s and Dont’s” related to seasickness on Alyosha:
- Do take anti-motion sickness drugs about 30 minutes before your trip on Alyosha if you are susceptible to motion sickness (and you have checked with your physician);
- Don’t use Alyosha as a “testing ground” to see if your already-prone-to-motion-sickness child will get seasick- odds are they probably will…
- Do know that there are plenty of places to sit on the deck of Alyosha during the entire experience- all outside and in fresh air! Clear visibility of the horizon and a fresh breeze are immensely helpful in preventing seasickness;
- Don’t make Alyosha your “second day after a night of partying” event! We saw this happen quite a few times over the years…. A nice hangover will substantially increase your odds of feeling nausea out on the ocean- trust us on this!
- Do trust your gut about whether you are going to be susceptible to motion sickness- if you “think” you are susceptible, then you likely are- take the drugs!
- Don’t worry if you end up getting sick. It happens to the best sailors. Captain Steve and his crew will help you get through it.
- Do know that we have yet to find a motion sickness drug that is really effective after someone starts feeling sick- see #1 above;
- Don’t think that the captain and crew are going to be upset if someone does get sick- nope, not even a little… We just can’t stand the idea of people (who are prone to seasickness) paying for agony.
We are very invested in making sure everyone has a quality experience on Alyosha- and we know what a large role weather can play in the overall experience! The following policy is offered as a guide for how we handle refunds and communication about the weather:
- If the trip does not run because of unsafe conditions, then you will be fully refunded. We don’t try to keep your money as an exchange for a future trip, we just refund. Unsafe conditions are lightning, thunderstorms and extremely high winds/waves for trips planned out on the ocean. (We can run our assateague experiences on Alyosha just fine with high winds/waves.)
- Quite often, there will be the “chance of a thunderstorm” during the summer months. We don’t cancel trips because of the chance of a thunderstorm (we would run about ½ of our trips!!!). If we have strong certainty that the weather may impact your trip, then you will hear from us via email/text the morning of the trip. Usually, we don’t consider a weather cancellation until we are within 1 hour of the trip departure time and can see weather coming on the radar. We will make sure you hear from us then. (Many of our favorite trips have happened just after storms have gone through!)
- If you are on a Sunset cruise and you don’t have a great sunset, we are sorry. But we don’t refund.
- If you have logistics issues that keep you from attending the trip, you may be refunded if you both give us plenty of warning (ie 2-3 days) and if we are able to resell the seat. This sometimes happens. We won’t refund at all for day before or day of cancellations. Our recommendation: If you have doubt about whether everyone can make it for the trip, etc… then do not book it!
- Very rarely, we run a trip which is safe but where the weather really impacts the experience in a negative way (heavy fog, a trip cut short by a thunderstorm, etc…). We try to make accommodations for this by offering heavily discounted tickets for you next experience and/or working something out with OC Bay Hopper.
Final thoughts:
Please don’t call about the chance of a thunderstorm 2 or 3 days before your trip. Everything we can tell you is right up there in #2, above!
We really do want everyone to have a great time on Alyosha and we largely succeed- check the reviews!!!
In an effort to set expectations for your sailing adventure on Alyosha, Captain Steve is committed to setting a quick little “take” on the weather and sea conditions that will impact trips on Sail Alyosha. Keep in mind that after doing this for three years, there are a couple of things that can be taken for granted:
- Prevailing summer conditions are for a south to southwest breeze that builds throughout the day but diminishes as the sun sets. These conditions exist for about 50% of the summer season;
- The more east in the breeze, and the longer we have a southeast breeze, the bigger the seas will build;
- The most unpredictable conditions usually come with a strong north/ northeast breeze. We have had fantastic sails in these conditions, but have also had some larger waves/rougher seas;
- West wind= calmer seas. Even big west winds are welcome! The shoreline blocks the development of the seas and so Alyosha moves fast but with much less motion.
There is absolutely no smoking on board our vessels during normal operation. We also do not permit vaping or the use of other nicotine products onboard.
Please don’t ask, because we hate to say no (but we will).
Customers are able to bring their own food, snacks, and alcoholic beverages onboard for consumption during a trip on Alyosha.
Alyosha has a refrigerator and cold box available but there is plenty of room for your coolers if you’d like to bring something on ice.
The captain of Alyosha shall ensure that no one under 21 years of age is consuming alcohol and also that customers consume alcoholic beverages responsibly.
The captain of Alyosha shall have full power to ask a customer to stop drinking alcoholic beverages for any reason.
Remember, not all sailing adventures are conducive to a full meal onboard. It is much easier to enjoy a catered meal or your own food on our “Chill” trips.
If you’re nervous about seasickness or have young kids, try the Assateague Island Sunset Cruise or Assateague Trips. All stay in flat, calm bay waters or only go in the ocean when it is calm. If you want to try ocean sailing, Start with our 2-hour Ocean Sailing trip—no prior booking required, no experience needed. It’s the perfect introduction to what Alyosha can do.
Not at all. Most of our trips are passenger experiences—you sit back, relax, and let Captain Steve and the crew handle everything. The only exception is our Hands On Sailing trip, which is designed for people who want to learn by doing. But even that’s provides options to participate at various levels.
All Ocean City trips depart from Olde Towne Marina at 307 Dorchester Street in downtown Ocean City, Maryland. Alyosha’s docked at the end of the pier—you can’t miss her, she’s the only sailing catamaran around. Parking can be tight, so plan to arrive a few minutes early. If you don’t see the boat at the dock, we’re probably out on another trip and will return just before your departure time.
View our schedule and book online at book.sailalyosha.com. You’ll see available trips, times, and pricing. Most trips have a 4-person minimum to run, but don’t let that stop you from booking—we almost always hit the minimum, and if we don’t, you’ll receive a full refund. Questions? Call us at 410-376-5454 or email hello@sailalyosha.com.
Our Schedule
Getting to Our Ocean City Sailing Trips and Charters
Trips depart promptly at the scheduled time from Olde Towne Marina (307 Dorchester Street, Ocean City, MD 21842), right next to Oyster & Scales in downtown OC. Parking can be limited, so plan to arrive a few minutes early. You can’t miss Alyosha—we’re the only sailing vessel around.
