We made it to St. Thomas! Alyosha is ready to make more memories for all down in the USVI… Check out our Winter Schedule where we will be offering sailing day trips in addition to our many 5 day, 5 night offerings…
We made it to St. Thomas! Alyosha is ready to make more memories for all down in the USVI… Check out our Winter Schedule where we will be offering sailing day trips in addition to our many 5 day, 5 night offerings…
Glide up and down Ocean City’s beautiful Atlantic coastline or back in the coastal bay area behind Assateague Island on Alyosha. The real fun starts when the engines turn off and the only thing powering the boat is the wind.
Will you and your friends or family be in the US Virgin Islands this winter? Alyosha will! And we stand ready to take your group (up to 6 people) out on an adventure exploring all of the best bays and cays. We have all the gear for swimming and snorkeling and will build you a day out sailing you won’t ever forget!
A magical sunset cruise coupled with dinner reservations at Oyster and Scales– an upscale seafood establishment brought to you by the same people who delivered Spain Wine Bar. We don’t think there is any better way to spend time as a couple than this… we will have some complimentary champagne and our “Anniversary” flag at the ready!
For 6 years, we have been building a schedule that incorporates the many things we offer on Alyosha: coastal cruising, peaceful sailing behind Assateague island, and even real, offshore cruising. In 2026 you can specify exactly what your group of 4 or more people is looking for and we will tailor something for you!
Private Charters on Alyosha are the absolute gold standard for a group outing in OC. How can we make them better? How about we add in a reservation at Oyster and Scales for your group before or after your trip and include parking or a private pier pickup and drop off so you can avoid driving altogether? All of these options and more will be available in 2026!
See another side of Ocean City from the Atlantic Ocean. Experience the pure joy of sailing fast on a 50’ catamaran! The incredible views, marine life on display, engaged captain/crew, and serene movement on the water without engines make these unforgettable experiences…
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
Sit back (or lay back on the spacious trampolines!) and take in OC’s West Harbor, and the coastal bays adjacent to Assateague Island. We can’t always conjure up those magical Assateague ponies but we can ensure your family/friends and/or significant other will have an incredible platform to experience the beauty of Ocean City. Feel free to bring snacks and beverages of your choosing…
Coming in 2026… A Private Charter builder for customers looking to book the whole boat for their group. We probably won’t have this until mid-April so if you have a date you would like to reserve now make sure to let us know.