Sail the Pintita

Make your next getaway a sailing adventure on the Chesapeake Bay!

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Are you planning a birthday or anniversary celebration, planning a proposal, getting married or renewing your vows, or just want to enjoy the Annapolis or Baltimore skyline with a cold beverage while sailing?  Help raise and trim the sails, navigate, man the helm or simply take in the experience and sights while relaxing with a cold beverage. Come see what the allure of sailing is all about. The professional Captain and Crew of the ‘PINTITA’ can help make your next adventure a memorable one. 

​We are currently booking private sailing charters on this classic 43′ Endeavour Ketch, designed and built in the era when sailboats were built for easy motion and seaworthiness, for up to 20 passengers!

We ask that you continue to support your local businesses and this Veteran owned small business needs your support and patronage.  Please book your private sailing charter soon for your next friends, family, and or corporate outings.  We are looking forward to harnessing the wind and creating memories with you.