Skip to main content
In The Area

Sailing In Annapolis

Make the most of your stay at Historic Inns of Annapolis by embarking on a sailing adventure. It's a short stroll to the city dock, where you can catch a water taxi to reach the nearby sailing and powerboat schools. There, skilled instructors will ensure that your maritime learning experience is both enjoyable and exciting.
Sailing in Annapolis, Maryland
Distance from hotel: 0.72 mile

Other Water Activities

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


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.


Whether you're already an experienced sailor 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 offer sailing packages for visitors. A few options include Schooner Woodwind cruises for sunsets or brunch, Watermark Cruises that leave from the Annapolis Dock, and Arabella which offers evening excursions along the water.