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History
History
History

There are more 18th-century brick homes in Annapolis than any other city in the nation, making a trip to Annapolis a true walk down memory lane.

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BUSINESSES (10)

National Sailing Hall of Fame
Attractions

The National Sailing Hall of Fame is a not-for-profit educational institution dedicated to preserving America's sailing legacy....

Sail the Pintita
Boating

The 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...

Sail the Pintita
Tours

The 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 ...

Sailing Lessons with Cruise Annapolis
Boating

Learn 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
Boating

Specializing in personalized hands-on instruction, our courses are taught by top level sailors aboard late model performance sailboats. Limi...

Classic Sail Charters
Boating

Classic 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
Boating

Sail 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 & Paddleboarding

The 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
Boating

America'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
Tours

Sail 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)

Tuesday Beer Tasting Sunset Sail

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 sample...

Tuesday Beer Tasting Sunset Sail

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 sample...

Tuesday Beer Tasting Sunset Sail

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 sample...

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 h...

Thursday Acoustic Music Sunset Sail

Sit back and relax as Don Shapelle & Don Sennett entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annap...

Tuesday Beer Tasting Sunset Sail

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 sample...

Tuesday Beer Tasting Sunset Sail

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 sample...

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 h...

July Wine In The Wind Sail

Join us for a two-hour sail around the Bay to celebrate Bastille Day by sampling wonderful wines from France - A representative will int...

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