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: annapolissailing.com

American Sailing Association: asa.com

Annapolis Naval Sailing Association: ansa.org

Blue Water Sailing School: bwss.com

Brendan Sailing: brendansailing.org 

Captain In You Sailing Schools, Inc.: captaininyou.com

DC Sail: dcsail.org

Discover Sailing: discoversailing.com

Downtown Sailing Center: downtownsailing.org 

Eastport Yacht Club: eastportyc.org

First Sail: firstsail.org

J/World Annapolis: jworldannapolis.com

Rock Hall Yacht Club Sailing School: rhycsailingschool.org

The Sailing Academy: thesailingacademy.com

Sailtime: sailtime.com/annapolis

Sail Solomons: sailsi.com

Severn Sailing Association: severnsailing.org

U.S. Sailing: ussailing.org

West River Sailing Club: learn2sailwrsc.com

Youth Sailing Virginia: youthsailingva.org