Annapolis Sailing School

10/16/2026

10/12/2026

Beautiful Fall Weather for our Monday Night Races. Come out and join us!

10/05/2026

A beautiful fall evening to race up the Severn River.

10/05/2026

Sailing after dusk turns into darkness is always a challenge, but it didn't faze our five adventurous sailors who took our nighttime sailing class! Motoring Summer School our Jeanneau 41, out into the Severn River in the pouring rain before raising the sails, sailors identified other boats on the water, brushed up on the rules of the road, and learned how to be safe and handle nighttime emergencies under the skillful instruction of KBC director Ian.

10/02/2026

Nine months of the Annapolis Sailing School in two minutes. Still plenty of time to sail this year. Click on the link in our Bio for Class Schedules.

09/28/2026

We’re racing through the end of October!

09/26/2026

You can’t win if you don’t race.
Click on the link in our bio for Keelboat Club membership.

09/22/2026

09/17/2026

"At the Annapolis Sailing School, we believe the magic of the Chesapeake Bay belongs to everyone. We are immensely proud of our leadership team, Owner Rick Nelson and KidShip Director Michaela Turner, who recently received an official Executive Citation for their roles as founding partners of the 2-CM Dreams youth program. Driven by a shared mission to provide equitable water access, Rick and Michaela have transformed our historic KidShip fleet into a space of empowerment, safety, and confidence-building for local youth. This citation honors their dedication to charting a more inclusive course for the future of Annapolis sailing."

09/14/2026

Joining the Annapolis Sailing School's Keelboat Club gives you on-water sailing access, exclusive clubhouse amenities, and private waterfront beach privileges on the Chesapeake Bay. Click the link in our Bio for membership and access.