Sail the Sea on the Pintita

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. You are welcome to bring your own snacks and drinks aboard. Hourly option shown is based on 7-12 guests. See more rates below. Rates: Passengers 2 Hours 3 Hours 4 Hours 1-6 guests $750 $1000 $1250 7-12 guests $1500 $1750 $2000 13-20 guests $2000 $2250 $2500 Rates do not include 20% Crew Gratuity, 11% Admission & Amusement Tax and Dockage fees. These will be added to the charter base price. Delivery fees and catering, if applicable will also be added. Holiday rates apply on holidays.