Private Charters on Alyosha

There is no better way to bring families and friends together than hanging out on a 50’ Catamaran and enjoying either the natural beauty of Assateague Island or the excitement of sailing in the Atlantic Ocean.

On Alyosha, Captain Steve and his crew will work tirelessly to make sure your entire group is taken care of and the boat is the perfect platform for these kinds of adventures!

Alyosha can accommodate groups as large as 12 people- for private charters larger than this, consider the OC Bay Hopper.

There are two ways to schedule private charters on Sail Alyosha…

  1. ONLINE: Any “Ocean Sailing,” “Assateague Sunset,” or “Sunset Cruise” can be made private by booking all 12 spots on the boat- you will immediately receive a 10% discount and the boat is all yours for that time period. (if you want more time, fully book two slots and we will discount 15%- you must call for this duration of an event…) As a private charter you can dictate the itinerary, whether we go sailing, cruising along Assateague, or anchor for a bit and go swimming!
  2. THROUGH PHONE/EMAIL: On Saturdays and Sundays (and other mornings…),  Alyosha is available to be booked for private charters as long as there are no currently booked trips. The rate for the boat is $600/hour with a minimum booking of 3 hours.  Looking for family outing that is a little more “budget friendly?” Choose any weekday or Saturday morning and we will build a special outing just for your group- cost is $450/hour with a 2 hour minimum. (Trips can start as early as 9am…)  BUT PLEASE BE PATIENT, BECAUSE WE ARE RUNNING PRETTY HARD AS SOON AS THE SEASON STARTS AND IT WILL TAKE US TIME TO GET BACK TO YOU!!!


Remember: When you book a private charter, the boat is yours for that period of time… You can bring your own food and drinks with plenty of table space to set up a fantastic spread. Alyosha has a cold box, refrigerator and room for big coolers if that is not enough! There are two bathrooms available on board as well.

Private Charters can be sailing adventures, or casual parties cruising in the Sinepuxent Bay along Assateague Island… and if you book enough time we can do a combo adventure.

(If you are looking to swim, we recommend booking at least 3 hours to allow for us to anchor, etc…)