And we’re sailing! Our season started in April.

Around Town

Annapolis, Maryland

One of the most popular regions of recent growth is the Chesapeake Bay area.

With its rich combination of historic charm and cosmopolitan culture, the cities and towns provide a small town atmosphere with easy access to major metropolitan areas. The centerpiece is Annapolis, which is nestled between Baltimore, Washington, and the outlying communities of the Chesapeake Bay.

The Atmosphere of Annapolis: Centuries of history carved into brick paved streets, Georgian brick mansions and clap-board row houses can be found in Annapolis. The town is a former United States capital and home of the U.S. Naval Academy. As the capital of Maryland since 1694, Annapolis continues to be a hub of political and social activities.

Considered the sailing capital of the U.S., Annapolis evokes an international yachting flavor. On any warm weekend afternoon, the Chesapeake is bustling with marine activity. Every Wednesday evening in the summer over 100 sailboats race into the harbor for their spectacular finish for everyone to see and you can even race with us on the Woodwind!

The Annapolis area also has a reputation for having wonderful restaurants and shopping opportunities. Numerous fine dining establishments line the city streets, offering a variety of cuisine. Internationally renowned boutiques are placed side-by-side with locally-owned stores and art galleries, providing a variety of merchandise bound to intrigue most shoppers.

Sailing on the Woodwind into Annapolis sunset
Photo by Jeff Norman

Annapolis Information

Annapolis Waterfront Hotel- The only hotel on the water in Annapolis and from where Woodwind cruises depart. A beautiful place to stay with views of the harbor and Bay.

Pusser’s Caribbean Grill Come and experience the sunshine at Pusser’s Caribbean Grille on Annapolis Harbor. This unique, waterfront restaurant offers a “taste of the Caribbean” at our exclusive dockside location. Located steps away from getting on & off the Schooner Woodwind and the Annapolis Waterfront Hotel. Best view in town!

Annapolis and Anne Arundel County Visitor’s Center- Links and information on all Annapolis businesses with a detailed calendar of events for the year.

Calendar of Events for the Annapolis Area  local events in the Annapolis Area.

Sailing Information

J-World Sailing in Annapolis- Sailing lessons for performance-oriented novices and other sailors. They specialize in learning-to-sail courses, cruising and racing classes.

Scarano Boat Building- The builder that designed and constructed Woodwind and Woodwind II.

Great Chesapeake Bay Schooner Race Get the history, facts and photos of this annual race down the Bay!

Annapolis Waterfront Hotel
Annapolis Waterfront Hotel
Pusser's Caribbean Grille
Pusser's Caribbean Grille
Schooner Woodwind