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BUSINESSES (10)
National Sailing Hall of Fame
AttractionsThe National Sailing Hall of Fame is a not-for-profit educational institution dedicated to preserving America's sailing legacy....
Sail the Pintita
ToursThe sailing vessel Pintita is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passing ...
Sail the Pintita
BoatingThe sailing vessel Pintita is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passin...
Sailing Lessons with Cruise Annapolis
BoatingLearn to sail on the boat you ultimately want to own. Catamaran sailing schools are our specialty. Go out at any time, for any length of tim...
J World Performance Sailing School
BoatingSpecializing in personalized hands-on instruction, our courses are taught by top level sailors aboard late model performance sailboats. Limi...
Classic Sail Charters
BoatingClassic Sail Charters offers Chesapeake Bay sailing adventures for small private parties (up to 6) on Licentia, a beautiful 2008 Catalina 42...
Annapolis Sailing Cruises: Schooner Woodwind
BoatingSail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event ...
Annapolis Sailing School
Kayaking & PaddleboardingThe Annapolis Sailing School now has Stand-up paddle boarding and Kayaking off Bembe Beach for our Keel Boat Club members. This is one of th...
Annapolis Sailing School
BoatingAmerica's oldest and Annapolis' largest sailing school. Learn to sail the "Annapolis Way" with classes for kids and adults of all skills lev...
Annapolis Sailing Cruises: Schooner Woodwind
ToursSail the Chesapeake on one of two, 74-foot wooden, schooners that offer a real Chesapeake Bay sailing experience for 2-hour public cruises, ...
EVENTS (10)
Thursday Acoustic Music Sunset Sail
Sit back and relax as Deanna Dove entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hot...
Monday Chesapeake Bay History Sunset Sail
Enjoy learning about Annapolis with Jeff Holland. When you set sail from downtown Annapolis, you see the gorgeous historic skyline that ha...
Thursday Acoustic Music Sunset Sail
Sit back and relax as Roadside Show entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront H...
Monday Chesapeake Bay History Sunset Sail
Enjoy learning about Annapolis with Kevin Brooks. When you set sail from downtown Annapolis, you see the gorgeous historic skyline that h...
Thursday Acoustic Music Sunset Sail
Sit back and relax as Roadside Show entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront H...
Fall Sailing on the Chesapeake Bay Begins!
Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. For the month of October, weekday cruises req...
Fall Sailing on the Chesapeake Bay
Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. For the month of October, weekday cruises req...
Monday Chesapeake Bay History Sunset Sail
Enjoy learning about Annapolis with Michael John William. When you set sail from downtown Annapolis, you see the gorgeous historic skyli...
Thursday Acoustic Music Sunset Sail
Sit back and relax as the Eastport Oyster Boys entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis...
Daily Sailing on the Chesapeake Bay
Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5...