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Sailing in Annapolis

You're in the sailing capital of America! Take advantage and learn how to sail while staying with us at Historic Inns of Annapolis. You can walk to city dock to pick up the water taxi to take you over to the schools, and the professionals at our sailing and powerboat schools make learning the maritime basics easy and fun.


Watermark Cruises

Schooner Woodwind Sailing Cruises

Annapolis Sailing School

Sailtime Annapolis Sailing Academy

J World Annapolis

Cruise Annapolis

Other Water Activities

  • Charters & Rentals
  • Boat Shows
  • Tours & Sightseeing
  • Kayaking & Paddleboard
  • Marinas
  • Fishing & Crabbing

Get on the Water

When it comes to bountiful aquatic resources, we've got a lot to brag about. Anne Arundel County's rivers, streams and coves form over 533 miles of shoreline. We claim the Chesapeake Bay, the nation's largest estuary, as our very own playground. Glimpses of sparkling water can be had even from the middle of downtown Historic Annapolis. It's no wonder countless people come to play on the water here.

Sailing & Water Activities

Whether you're already an experienced sailer or kayaker, a day-tripping motor boater or a beginner who yearns to spend some time on the Chesapeake Bay or the winding streams, creeks, and rivers that flow to this crown jewel of the Mid-Atlantic, we can provide the information you need.


  • How Big is Chesapeake Bay?

    This enormous body of water spans over 200 miles between Maryland and Virginia.
  • Where can I go Sailing on the Bay?

    There are several marinas easily accessible to visitors where ships launch into Chesapeake Bay and there are several companies that offers sailing packages for visitors. A few options include Schooner Woodwind cruises for sunsets or brunch, Watermark Cruises that leaves from the Annapolis Dock, and Arabella which offers evening excursions along the water.

Helpful Links


Driving Direction to Sailing in Annapolis
or Historic Inns of Annapolis
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