Find A Sailing School

New sailors or those returning to sailing may want to seek instruction or coaching at a sailing school or club. Many such organizations exist on the Chesapeake Bay and its tributaries. They offer certifications for beginners, returning sailors hoping to brush up on seamanship skills, cruisers seeking bareboat chartering or navigation experience, and racers wanting to hone their skills. The following is a sampling of schools and clubs that offer sailing instruction on the Chesapeake. For a more complete list of schools offering certifications outside this region, visit US Sailing or American Sailing Association.  

A new sailor receives hands-on instruction about dock lines. Photo courtesy of J World Annapolis.

Chesapeake Bay Sailing Schools: 

Annapolis Sailing School:

American Sailing:

Annapolis Naval Sailing Association:

Blue Water Sailing School:

Brendan Sailing: 

Captain In You Sailing Schools, Inc.:

DC Sail:

Downtown Sailing Center: 

Eastport Yacht Club:

First Sail:

J/World Annapolis:

Rock Hall Yacht Club Sailing School:

The Sailing Academy:


Sail Solomons:

Severn Sailing Association:

U.S. Sailing:

West River Sailing Club:

Youth Sailing Virginia: