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.

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.

What to expect:

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.

Alyosha is a big, stable sailing catamaran, and she sails flat. As noted in the trip description, the Captain will decide whether to stay inside the inlet for a tour along Assateague Island if the Atlantic Ocean is too rough.

What to bring:

Alyosha has plenty of bottled water for customers. Feel free to bring any food or drinks you would like onboard- yes, even a small cooler if you prefer... There is plenty of room for everyone.

There are restrooms ("heads") aboard Alyosha for use by customers. Keep in mind that the toilets on a sailboat are a little bit bit more sensitive than land based toilets...

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. 

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!)