From Ocean City, Maryland To Beaches Around The World!
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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 customer 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!
The 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.
There is still time to become eligible – we still have Fall sailing trips – a great time to go! Our Fall Schedule
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. (and 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.
What’s Next and What’s Coming
This winter, we are going to return to fabulous St. John’s in the US Virgin Islands, and rekindle our commitment to offering short term charters! We are investing in fitting out the boat with more luxurious accoutrements that will raise our game a bit without raising our prices. We still have many weeks available, especially in January and February, for those looking to give this a try!
Currently on tap: Open “Houses” on September 20th and October 12th. If you have been sailing with us and want to learn more about what a Sail Alyosha Vacation Adventure might look like, come and join us on these mornings (previous booking on Alyosha is required AND please indicate how many people are coming through our booking software- the event is FREE)
On the Horizon: We have not completely decided yet, but we are leaning towards exploring the British Virgin Islands in the winter of 2027… We already have several groups vying for positioning for this trip and we will of course give all of our current SAVA customers first dibs on our 2027 schedule when it is announced (in June, 2026)
Open House Options
A great way to learn more about the boat, the captains, and how the ‘cruising life’ works, sign up today!
September Open House
September Open House
The event is free but you will have to book to let us know you’re coming. (The event is also only open to those who have sailed on Alyosha previously. And yes, there will be Taharka Brothers Ice Cream and heavily discounted Sail Alyosha Merchandise available! Use the button below to book.
October Open House
October Open House
The event is free but you will have to book to let us know you’re coming. (The event is also only open to those who have sailed on Alyosha previously. And yes, there will be Taharka Brothers Ice Cream and heavily discounted Sail Alyosha Merchandise available! Use the button below to book.
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 newsletters – click on the link below to sign up for our newsletter.
Check out past SAVA newsletters
Ready To Sign Up
Not ready for a multiday trip? We’ve got space!
If you ask most seasoned sailors when is the best time to go sailing. most the time you get the same answer….Fall. Why, the winds are steady, the days are still warm, and the nights are cool. It is a sailor’s paradise. We are running trips through October, click on the link to see availability.
