Trips and Experiences
This special event is for customers who have booked a trip in the past on Alyosha and sailed with us in Ocean City, Maryland. There is no "start time" for this event, just a period of time when Captain Steve will open up Alyosha and allow customers to check out the boat and envision themselves on an extended vacation on the boat!
We will bring out many of the "toys" available, have each of the four staterooms ready for show and spend time doing extensive Q & A with those customer who want to know more about what it looks like to spend time leisurely cruising the islands- or crossing oceans!- aboard Alyosha.
Alyosha will stay docked for the duration of the event, we won't go sailing or cruising... (we might have a special treat for visitors!) so this is the time to talk provisioning and get a sense of how much space is available for you when you cruise aboard for more than a day sail!
This event will last for three hours- you can come anytime but allow yourself at least 15 minutes onboard (ie Don't come with 5 minutes left in the event as we likely will be heading out after the event for a sail)
Ocean Sailing on a 50' Catamaran!
Come out an experience either the "chill" or "thrill" of Ocean Sailing (depending on the weather) on this nearly 2 hour adventure.
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. This experience is designed as an introduction into ocean sailing, and is appropriate for most children above age 4/5 and even for seniors who have fair mobility. There is sheltered seating in the spacious cockpit if enjoying the experience on the deck is too daunting!
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 have anniversary, birthday and special event flags- complete with a nautical number set- that we hope you will consider raising during the sail.
Take in a Sunset on a spacious, 50' sailing catamaran!
Newly revamped in 2025, our "Sunset Cruise on Alyosha" is one of our most popular trips and is the perfect cap to your adventurous day in OC - or the start of your date night! Cruise on Alyosha, a 50ft sailing Catamaran, out into either the Atlantic Ocean for a beautiful view of the sun setting on Ocean City or take in the fantastic scenery behind Assateague Island and watch the sun melt into the marshland. Either way, your pictures will be brilliant and you will have great time!
Each night, our captain will make the decision about whether the ocean or bay will make for the better voyage, keeping your comfort "top-of-mind." On the morning of your trip, you can check our website to see which way we are leaning (Ocean or Bay) weather-wise. Sunset cruises are an opportunity to unwind, and enjoy our natural surroundings. And whether your sunset is on the perfectly flat bay or a calm and gentle ocean, you are in for a treat! Additionally this year, the sunset cruise will be extended to offer a bit more time on Alyosha, generally ending with sunset and lasting 75-80 minutes.
Watch the sun set on Ocean City from the Atlantic Ocean as you glide along the coastline under sail. Lounge on the trampoline or enjoy any of the other excellent seating options that this 50' boat has available. This is a "must do" experience in Ocean City!
Note on Birthdays and Anniversaries:
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! (There were a few weddings and a proposal as well...) Let us know if you are celebrating something with your cruise: We now have anniversary and birthday flags- complete with a nautical number set- that we hope you will consider raising during the sail.
If the OC Bay Hopper can pull this off, why not try it on Alyosha! The 50' Catamaran that has literally sailed around the world makes for a fantastic viewing platform behind Assateague Island, with guest invited to sit on the upper levels of the boat- 10-12' above sea level, to enjoy Assateague Island's wonders.
Captain Steve can show you the Cormorants, Ospreys and his personal favorites: Great Blue Herons. But with a birding guide, there is so much more to observe.
You won't believe the variety of birds that inhabit the coastal bays right here in Ocean City! Many migratory species make their way here to nest and raise their young near the waters that surround Ocean City and Assateague Island. Possible Species may include: Royal Tern, Forster’s Tern, Common Tern, Black Skimmer, Brown Pelican, Piping Plover, Brown Pelican, Osprey, Snowy Egret, White Ibis, American Oystercatcher, Willet
The cost for the two-hour cruise is $85/person. Guests can register individually or in groups. We need a minimum of four participants to run a tour. Our maximum number of participants is 14. We are targeting a few select dates in the fall to pilot this trip.
We’ll investigate the bayside OC docks from M.R. Duck’s south to the inlet (there are often good birds hiding out there!), then we’ll cruise by the Assateague jetty. From there, we’ll explore the bayside of Assateague Island south towards Castaways campground, then back to the harbor. The cruise will feature a U.S. Coast Guard-licensed captain and a DBW Guide, so you will be in good hands.