top of page

Sailing Charters aboard the 'PINTITA' out of Annapolis & Baltimore

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

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 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.















Plan to join us for the U.S. Navy Blue Angels in Annapolis during Commissioning Week in May, 2024

See our Charters page from the menu above

Call us now to book your getaway:


The ‘PINTITA’ is perfect for:


Bachelor & Bachelorette Parties

Engagement Proposals



Alumni Events


Company Events

Team Building

We offer many charters to meet your needs.


The 'PINTITA' Sailboat is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passing showers! She is designed to make your outing as entertaining and comfortable as possible.

Come sail the Chesapeake Bay.


Join us in Annapolis & Baltimore.  We hold a current USCG Certificate of Inspection for Private charters, meaning that she is inspected in her construction, equipment, and maintenance to rigorous federal standards.

bottom of page