Passage Making On Alyosha! Mobjack Bay to Ocean City, Maryland (Atlantic Ocean Overnight!!!)

Trip Summary

Spend an incredible overnight in May with Captain Steve and crew as Alyosha leaves the Chesapeake Bay enroute to Ocean City, Maryland. This trip- part 2 of 2 trips to get Alyosha from Baltimore to Ocean City for the start of the season- will involve crossing the southern end of the Chesapeake Bay, passing through the Chesapeake Bay Bridge Tunnel and moving into the Atlantic Ocean! We will then turn north, and sail along the Chincoteague/Assateague coastline. This trip will involve an overnight in the Atlantic Ocean, with all the unpredictability that might entail. We are intentionally planning to leave Friday and arrive in Ocean City saturday but will change to a saturday departure (and sunday arrival) based on the weather forecast- so if you are considering this trip, please stay flexible for those three days!

Given the amount of ocean sailing involved here, the key to this trip will be FLEXIBILITY! Alyosha will be launched back into the water from Zimmerman’s Mathews Marina on Friday by noon and we will plan our departure on the best possible weather window for the ocean passage. This might mean waiting overnight until Saturday morning or even later on Saturday evening. So book this trip for the incredible experience that an overnight at sea affords, but not for schedule certainty!


Food and drink is included in this trip, including lunch on Friday and Saturday, snacks throughout the trip, breakfast on Saturday and dinner on Friday evening. Because of the nature of this particular trip (mostly ocean sailing!) the dinner will be something compatible with “being underway…” Steve will work with all of those who sign up for this trip to ensure all dietary concerns are taken into consideration;

Please note that this is a 130 nautical mile passage, with about 100 nm taking place in the Atlantic Ocean. And we will be sailing through the entire evening/overnight to make Ocean City the following day. Passengers will not stand watch and will get the full experience of an overnight at sea!

Guests should bring whatever they want to help "pass the time." Sailing and cruising is fun, relaxing, and sometimes boring! Feel free to bring a book or podcast or table game- anything you want that will help you enjoy this passage.

May weather is fairly unpredictable- it is as likely to be shockingly warm and muggy as it is to be cold and chilly. So watch the weather forecast as the trip approaches and plan accordingly. In the spring, it will definitely be a bit colder on the water than at home.

Passengers will need to arrange their own transportation back home after we arrive in Ocean City. (Depending on the arrival time, there may not be an opportunity to stay a second night on Alyosha once in Ocean City, plan on departing when the boat arrives.

Transportation from Baltimore down to Alyosha's departing location (near Cardinale, Virginia) will be available but could be limited. We will share all passenger information to facilitate planning. Further details on this trip (updated as the departure date nears) will be available online through a google sheet shared with all passengers.

  • Unfortunately, there are no scheduled trips for this type of Experience.
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