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)!

07/21/2026

Mastering the wind on the Chesapeake Bay is the ultimate summer thrill! Join Annapolis Sailing School at Bembe Beach to learn sail trim, tacking, and reading the breeze. Whether you are a total beginner or ready for ASA certifications, let the wind take you to your next adventure.
Click on our Bio for courses and schedules.
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07/20/2026

Monday Night Races, the best way to practice your skills . On the water coaching and film analysis. Get better at sailing today!

07/17/2026

Ready to spend the night under the stars? Our ASA courses break down everything you need to know about anchoring out in the Chesapeake Bay. Learning to anchor safely opens up a whole new world of cruising, from peaceful hidden coves to overnight weekend adventures.
Whether you are a beginner or just need a refresher, we have you covered. Click the link in our bio to read the full guide and book you

07/13/2026

This could be you ! Learn to sail today!

07/12/2026

Did you know you can spot bottlenose dolphins right here in the Chesapeake Bay? It is true! These playful marine mammals love visiting our waters during the warm summer months. When you learn to sail with us, you are not just learning a new skill. You are getting a front-row seat to the incredible wildlife that calls the Bay home. There is nothing quite like the magic of hearing a dolphin exhale or watching a fin break the glassy water right beside your boat! Ready to share the water with these amazing creatures?
Click the link in our Bio to book a Trysail or class now.

07/03/2026

The Caribbean is calling.

Join Annapolis Sailing School's February 2027 British Virgin Islands Flotilla and experience turquoise anchorages, unforgettable sunsets, world-class snorkeling, beach bars, and a new island almost every day.

Whether it's your first Caribbean charter or your tenth, our flotilla combines the freedom of sailing your own yacht with the confidence of our experienced captains and a welcoming community.

Ready to trade winter for warm trade winds? Click on our Bio to sign up or ask questions!

🌴 February 2027
⛵ British Virgin Islands
📍 Limited boats available

07/01/2026

Summer is slipping through our fingers, so decide to do something epic before it ends! 🌊 Learning to read the wind and master the tiller is the ultimate reset button. Have you ever tried sailing? Let me know in the comments! 👇 ⛵️🌬️⚓️
Review Basic Courses to see if you want to complete your ASA 101 certification. Learn about the Private Instruction options to get 1-on-1 time on the water. Check out the TrySails program for quick, weekend introductory sessions. Click on our Bio for course listings and Try Sail reservations. Boats, friends, and unforgettable journeys.

06/28/2026

Want to tie a Flying Bowline faster than you can yell "cast off"? ⛵️💨The "Flying Bowline" (or tugboat bowline) is a must-know trick that creates a secure loop in just seconds. Practice your lines before your next TrySail class or Beyond Basic Sailor session on the Chesapeake Bay! Visit our link in the Bio!

06/26/2026

Decoding the sky is the ultimate sailing hack, that’s mother nature’s way of talking to sailors. Stay tuned to the sky and let the wind do the talking. Learn about the weather and so much more at The Annapolis Sailing School, click our bio for classes and events.

06/25/2026

Fast, locked, and ready for docktails. The flying cleat hitch strikes again at the Annapolis Sailing School! Secure your boat in a single fluid motion with the flying cleat hitch! Perfect for showing off at the Bembe Beach dock after a day on the Chesapeake, this satisfying trick—frequently practiced at the Annapolis Sailing School—keeps your line locked tight under load. Sign up in our Bio for classes and lessons.

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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