From Ocean City, Maryland To Beaches Around The World!

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Sail Alyosha sailing route from Ocean City to the U.S. Virgin Islands.

The Back Story...

Alyosha has been a conduit for many big adventures for Captain Steve and his wife, Lisa, and their family… from initial small journeys in the Chesapeake Bay and along the Eastern Seaboard to a 3 year Circumnavigation, Steve and his family have visited incredible places and met amazing people and it is Alyosha that has been a consistent thread in these adventures…

Two years ago, Steve and his brothers (Dave and Jim) decided to offer Alyosha for weekly charters in the US Virgin Islands. We weren’t sure how it would be received, but the feedback from our customers was overwhelmingly positive. St. John’s proved to be the real star of the show: A beautiful island that can easily support a week’s worth of exploration!

The really cool thing, however, were the connections formed by customers experiencing this kind of sailing vacation for the first time. Seeing their joy- and enjoying their company- was eye-opening.

Now, with all three kids in college, and with a capable captain recruited to do some of the charters, Steve and Lisa are launching Sail Alyosha Vacation Adventures. We are hoping to form somewhat of a club, or affinity group, of people who are looking for a bit more adventure out of their vacations. And it starts this year! 

Details Of Sail Alyosha Vacation Adventures

What are we offering And How To Become Eligible

Sail Alyosha Vacation Adventures (SAVA) is your chance to live aboard a 50’ sailing catamaran in a remote corner of the earth and sample the “cruising” lifestyle… SAVA can come in many different flavors, including simple, meet the boat at a location and spend time cruising a locale, or more intense “passage-making” trips- where you will join us sailing across vast oceans!

 

Everything starts with your first booking on Alyosha in Ocean City, MD SAVA reservations can ONLY be made by people who have sailed with us in Ocean City, Maryland, where Alyosha is chartered everyday between May and October. Our reasoning is simple: we want to meet people first, and have them get to know us a bit, and the boat a bit, before committing to a longer sail. If you are interested in spending time aboard Alyosha on an exciting ocean passage or relaxing in tropical islands, first come and meet us (and check out the boat!) in Ocean City, Maryland.

So if you are interested in learning more, and you haven’t joined us before, check out Our Summer Schedule

"It was absolutely perfect! It was a perfect mix of beach, water activities (and I tried them all!), sailing, eating on the boat, fine dining and beach bars. We couldn’t have orchestrated a better vacation. I really don’t know how you top it - it was a such special experience for all 6 of us. “Perfection” is the best way to describe the trip. We’ve taken a lot of vacations to very nice places, but this truly was the best trip Brian and I have ever been on. Thank you for the experience and sharing your love of sailing with us."
- Jennifer Zimmerman

Captains Corner: Who are we?

Currently, all Sail Alyosha Vacation Adventures will be helmed by either the vessel owners (Captain Steve and Captain Lisa) or Captain Kyle Foster. (we are working on qualifying a few more captains to join this team) Kyle has been operating out of the US Virgin Islands for the past 5 years and has deep experience running short term charters on vessels both smaller and larger than Alyosha. We are beyond excited to have him join us this year!

This past winter, we returned to fabulous St. John’s in the US Virgin Islands, and Captain Steve, Captain Kyle and some adventurous passengers are soon to be heading back to the US and Ocean City, Maryland.

Currently on tap: Right now, Captain Kyle and Captain Steve have hammered out an incredible Fall 26/Winter and Spring 27 schedule. Before we post any availability, we need to circle back with all of our previous SAVA customers- those who have spent time exploring the USVI with us- to make sure they get a first crack at the schedule.

On the Horizon: From now until May 15th, we will be taking reservations from previous SAVA customers. Starting May 15th, we will reach out to any and all who have sailed on Alyosha and open up our bookings. Finally, on August 1st, if necessary, we will take bookings from anyone.

"The boat was amazing! Captain was amazing! Thank you for providing an amazing experience! Please let us know when/where the next adventure will be!"
- Austin Powell

More Information About SAVA

We do our best to communicate as much information as we can. The best way for you to keep up with the information we are putting out now is through our app – click on the link below to download the Sail Alyosha app.

"This was truly a magical vacation and completely exceeded all expectations. Would do it again in a heartbeat!"
- Angela Deaven

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