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Home > Baltimore > Baltimore Charters

Book your team of up to 12 people for an incredible afternoon or evening sailing Baltimore’s Patapsco River. This is the  perfect way to reward your team for a job well done or to gear up for another quarter of progress! Use our unique platform to plan for your next strategic initiative outside of the office. The setting cannot get any better- take in Baltimore from the Patapsco River and enjoy the feeling of quietly moving through the water under full sail. We are happy to cater the event for you or plan to bring your own food and beverages. There is plenty of space aboard Alyosha for lounging and/or meeting and both a men’s and women’s restroom!

What could possibly go better with sailing then enjoying some crabs with your friends and family before or afterwards? And did we mention that we always have some Taharka Brothers, Made in Baltimore ice cream aboard? Put together your group of up to 12  friends or family members and we will ensure they have a fantastic experience on the water sailing on the Patapsco River. Any Chesapeake Bay sailor will tell you that “shoulder season” sailing (September, October, November, April and May) is the best! There is plenty of room onboard for you to celebrate your special occasion- lounge up on the trampoline on enjoy the cozy confines of Alyosha’s beautiful interior. (Both a men’s and women’s restroom are available during the trip)

Would you like to give your special day a “victory lap” around Baltimore’s Inner Harbor? Interested in arriving at your waterfront wedding venue in absolute style? Sail Alyosha is now handling up to 12 people for special event cruises to enhance your waterfront event.

For examples of Weddings and other celebrations, visit our Baltimore Events page!

You can book your trip on Alyosha directly through our website! The calendar above lists the specific dates and times we’re currently offering charters.

Customers reviews

5/5
The whole experience was great, it was our first time on a sail boat. We loved the experience, cant wait to come back and hope to sail again. Thanks for making my birthday weekend great!!
Lisa B.
Sailed in Ocean City, MD
5/5
Steve and Ryan were extremely helpful and made the experience a great one. Steve had so much to share in terms of his sailing experiences and it was wonderful to listen to his many stories. They both were continually checking on all passengers aboard to ensure they were having the best possible experience. Every step of the way, Steve explained what to expect in terms of the water conditions. It made for a very smooth sail.
Patricia T.
Sailed in Ocean City, MD
5/5
It’ll exceed any of your expectations of what catamaran sailing could be like. Steve explains the experience through the entire trip, and makes you feel like you personally “matter”. It’s really something you CAN’T miss.
Dan M.
Sailed in Ocean City, MD