Sail Alyosha

08/08/2025

Beautiful skies and unforgettable sunsets are waiting. Book your sailing trip now and enjoy the view from the water!

08/08/2025

Alyosha now (finally) has a running restaurant next door! Oysters and Scales is open, so you can grab a bite before your cruise or stop in after you’re back on shore. Perfect way to round out your sailing day!

08/08/2025

Alyosha now (finally) has a running restaurant next door! Oysters and Scales is open, so you can grab a bite before your cruise or stop in after you’re back on shore. Perfect way to round out your sailing day!

08/04/2025

DOLPHIN ALERT! Spotted some playful fins cruising alongside Alyosha 🐬✨

We have some southeast winds today, a more “normal” pattern of weather for this time a year. Hoping to get that spinnaker flying if possible! Not many spots available so book soon if you’re keen to go sailing! (That 3:15pm afternoon sail should be a great one but for Alyosha veterans only)

07/27/2025

A relaxing day on the water and a fun, unique experience you won’t find anywhere else in Ocean City! Sailing on Alyosha is calm, beautiful, and just the right mix of different. Book now!

07/26/2025

Alyosha is looking good out on the water! There’s no better way to wrap up your summer than with a sailing trip. Come aboard and join us for a sail!

07/24/2025

Captain Lisa taking a good look at yesterday's sunset! There is nothing like a good sunset on the water...

07/17/2025

If you're looking for something different to do in Ocean City, sailing on Alyosha is a good place to start. Laid-back vibes, great views, and a nice way to spend time on the water with friends or family! You can try Ocean Sailing or a peaceful cruise behind Assateague Island!

07/14/2025

Considering a winter escape to the Virgin Islands? We’re excited to introduce Captain Kyle Foster, who will be at the helm for Alyosha’s winter sailing adventures in the Caribbean. This week, Kyle will be joining us on select sails to meet guests, answer questions, and give you a preview of what to expect aboard Alyosha this winter.

You can meet Captain Kyle on the following sails:
🌅 Tuesday on the Sunset Cruise
🕛 Thursday at 12 PM
⛵ Saturday at 10 AM or 12 PM

If you’re curious about booking a winter charter, this is the perfect opportunity to step aboard and learn more!

07/11/2025

Date Night is back on Alyosha and it's way better than dinner and a movie. Ocean breeze, golden skies, your favorite person, and a boat. What more do you need!?

07/06/2025

A sailing trip on Alyosha provides a different perspective of Ocean City, combining time on the water with the chance to unwind and take in natural beauty. Come enjoy with your friends and family!

The only way to beat the heat is to get out on the Ocean, where the temps are much more reasonable! We have openings today and tomorrow for Ocean Sailing!

07/03/2025

Having fun on the water 😎