Annapolis Sailing School

Annapolis Sailing School Annapolis Sailing School was founded in 1959 and remains committed to teaching sailing the Annapolis Way - seriously fun and relaxing.

We have options for people of every age (youth and adult) and skill level (novice sailor to advanced certified cruiser)!

08/31/2026

For our members the coaching is a bit more helpful. Everyone is having a good time though!

08/31/2026

The mantra on our docks is simple: Reef early, reef often.
Reducing your sail area before the wind overpowers you keeps the boat balanced, protects your gear, and keeps everyone comfortable in the cockpit. Stop wrestling your boat in a blow and start managing the wind with total confidence.
Ready to level up your seamanship and master skills like underway reefing? Check out our courses and book your next on-water session via the link in our bio!

08/29/2026

Whether you’re sailing right here on the Chesapeake Bay or heading out into open water, knowing how to heave to is one of the most valuable seamanship skills you can master. By intentional alignment of your sails and rudder, you essentially lock the boat in a controlled, gentle drift. Come learn how at the Annapolis Sailing School. Click on the link in our bio for class schedules.

08/26/2026

Every boat in our classic Rainbow 24 fleet is named after a unique wind or cloud. Meet Eyvindr. Watch. We celebrate the winds and skies that guide us out on the Chesapeake Bay. Have you ever sailed on Eyvindr, or do you have a favorite name from our fleet? Let us know in the comments. Learn more about our boats and programs by visiting the Annapolis Sailing School. Click on our link in the Bio for class schedules.
Annapolis Sailing School, always seriously fun.
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08/24/2026

We race through October! Come out and join us. The KeelBoat Club at the Annapolis Sailing School

08/22/2026

Shake out that reef and catch a breeze! Time for full power and a full sail. Come master your skills at the Annapolis Sailing School. Tap on the link in our bio.

08/21/2026

Learn how to safely shorten your sails and stay in control when the breeze picks up with a hands-on lesson at the Annapolis Sailing School. Click on the link in our bio for class schedules. sailing

08/20/2026

Master high-wind sailing with the Annapolis Sailing School as you learn to safely reef the mainsail on a classic Rainbow 24 sailboat. Reduce sail area, balance your helm, and gain ultimate on-the-water confidence when the breeze picks up on the Chesapeake Bay

08/17/2026

A little rain never hurt anybody!

08/07/2026

At Annapolis Sailing School, we turn docking dread into complete confidence. Our patient instructors teach you how to read the wind, manage the current, and control your boat at slow speeds. No yelling, no panic—just proven techniques in a supportive environment. Click the link in our Bio for Classes

Address

7001 Bembe Beach Road
Annapolis, MD
21403

Opening Hours

Monday 9am - 4:30pm
Tuesday 9am - 4:30pm
Wednesday 9am - 4:30pm
Thursday 9am - 4:30pm
Friday 9am - 4:30pm

Telephone

+14102677205

Website

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