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Family Friendly

Regardless of when you visit or how old your family members are, everyone's certain to have a a great time.

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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 ketch Pintita is licensed for groups up to 20 and is one of the most economic vessels available.  She can heat or air condition...

Sail the Pintita
Boating

The sailing ketch Pintita is licensed for groups up to 20 and is one of the most economic vessels available.  She can heat or air condition...

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
Music Venue

Sail away on a 74-foot wooden, schooner with terrific local musicians performing while under full sail on the Chesapeake Bay. Schooner Wood...

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, ...

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 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...

EVENTS (10)

Beer Tasting Sunset Sail

Sample beer from Heavy Seas Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket ...

History Monday Sunset Sail

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. The Life of Frederick Douglass with William Ridgley. Fred...

Local Music Sunset Sail

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail to enjoy music performed by Crab Alley Lite...

History Monday Sunset Sail

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. During our 25th Anniversary Celebration Week, we invite yo...

Local Music Sunset Sail

Enjoy music performed by Mike & Kelly Lange during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind. Mike and Kelly Lange a...

Father's Day Brunch Sail

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. The sailing cruise in...

Local Music Sunset Sail

Enjoy music performed by Deanna Dove during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind.  Deanna Dove is best known as th...

History Monday Sunset Sail

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. The Key to Annapolis History, by Jeff Holland.  The Key t...

Local Music Sunset Sail

Enjoy music performed by Kyle Offidani during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind. Born and raised in the bay area...

History Monday Sunset Sail

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. Legends and Lore of the Annapolis Waterfront by Dave Gende...

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