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 $105/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 12. 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.  

Sunset 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.

Consider having dinner at the brand new "Oyster and Scales" restaurant opened by the same owners that brought Ocean City the Spain Wine Bar!!!

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, (mainly lightning) 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.

In terms of seating and spacing: There is plenty of room for everyone! Trampolines 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. And in the Spring and Fall: Layers, many layers!

There is a 4 person minimum for this trip to go out. If your party is less than 4, please go ahead and book the trip and know that you will receive a full refund if the trip does not go forward!

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!)