Upcoming Events
  • Oct. 4-9: Great Chesapeake Bay Schooner Race
  • Oct. 13-17: United States Sailboat Show @ Annapolis City Dock
  • Saturday, Oct. 22: KBC Potluck
  • Sunday, Oct. 23: Last Day of Classes and Rentals
  • Sunday, Oct. 30: KBC End of Season Regatta
Stay Informed!
Want live updates on weather and wind conditions at Annapolis Sailing School? Check out our weather station on Weather Underground by clicking here.

Joke of the Day
Why did the captain refuse to believe there were no ghosts in the crow's nest?
There wasn't a shroud of evidence!

Follow Us On Social Media!
To see more of what's happening at the sailing school on a daily basis, be sure to follow our accounts. 

Want to show us your sailing photos? Send them to to get featured on our social media.

 KeelBoat Club
Looking to sail more often, boost your skills, and join a fun social sailing community? Learn more about our KeelBoat Club here.

Ahoy sailor!

Happy October! Fall came in right on time in Annapolis last week with cooler temperatures and beautiful breezes. While remnants of Hurricane Ian started off this month with heavy wind and rain, we’re looking forward to sunny skies as we head into the last month of the season!

Aside from this month’s beautiful weather, we’re also looking forward to the United States Sailboat Show coming back to Annapolis later this month! The Fall boat show is one of the largest shows of its kind, and we’re excited to be back repping the Sailing School and showing our Caraluna 245 by Tartan. If you’re coming to the show, be sure to stop by and say Hi to us on Dock S!

Don’t miss out on the last few weeks of sailing too! We’re open for rentals until Oct. 23. 

Ready to get out on the water? Come rent with us or check out our open course offerings. 

Questions? Bookings? Give us a call.

See you on the water!

Fair winds,

Annapolis Sailing School
(410) 267-7205

What's Happening at Annapolis Sailing School

Nothing but smooth sailing on the Severn! Our ASA 101 students are loving the cooler breezes that come with fall sailing in Annapolis.
Spinnaker flying is a team effort! Our Beyond Basic students had beautiful weather as they learned to fly the kite on our Caraluna 245 by Tartan.
We might be biased, but there’s no better place to view beautiful early fall sunsets than from our docks along Back Creek and on Bembe Beach.
Look at that intense focus! Navigating into our marina and docking our 37-foot Beneteau is always one of the most challenging skills to learn in ASA 103.
Seafarers Regatta Wins!
What a weekend! On Saturday, Sept. 24, KeelBoat Club members and Sailing School staff competed in the inaugural  Seafarers Regatta. Despite light winds making the one-leg race challenging, all of our sailors performed well — earning two trophies for high finishes!

Skippered by our ASA 101 instructor Jonah and crewed by other Sailing School staff members, our Farr 230 “Farrfetched” finished second! Our two Caraluna 245s, skippered and crewed by KeelBoat Club members, finished third and fourth. Racing was followed by an awards ceremony and after party hosted by the Seafarers Yacht Club.

Congratulations to all who sailed in the regatta! We’re thrilled to see our sailors learning and practicing advanced racing tactics. We’d also like to thank the Seafarers Yacht Club for hosting such a wonderful event, we can’t wait for the next one!

Check out the video below!
KeelBoat Club member Brian Harrison shot this awesome drone video of our Caraluna 245s racing in the Seafarers Regatta!
Come See Us At The Boat Show!

Heads up, sailors: the boat show is back in town from Oct. 13 through Oct. 17!
We'll have Annapolis Sailing School staff and instructors on site every day to answer questions about our ASA classes, KeelBoat Club and more! We'll also have one of our Caraluna 245s by Tartan at our booth. Come find us on Dock S, just behind Tent A. To see the show guide and maps, click here. We can't wait to see you!

Pumpkin Boats for Fall?
Nothing says getting ready for fall quite like...boating by pumpkin? In late August, a 60-year-old Nebraska man set out on the Missouri River to make history: earning the Guinness World Records title for longest journey by pumpkin boat. Check out the details of his 38-mile journey by clicking here.
Crew Quarters
Learn about cool local places, events and more from our staff.

The start of October means it's officially #spookyseason, and Annapolis loves its haunted history. We've got the perfect October activity for all of our ghost story-loving sailors: a haunted pub crawl in downtown Annapolis! You'll visit three to four bars downtown and listen to ghost stories from an experienced tour. Several Annapolis Sailing School staff members went on a tour last fall, and we highly recommend it if you're looking for a fun evening activity in town (after sailing)!
To learn more, click

Fall also marks the start of oyster harvest season in Maryland! If you're looking for a recommendation, our KeelBoat Club Director Ian (who's also a chef) has you covered. Ian suggests checking out Wild Country Seafood in Eastport - the oyster po boy is fantastic!

Contribution Corner:
The Great Chesapeake Bay Schooner Race

What could be better than racing to save the Bay? The Great Chesapeake Bay Schooner Race is a nonprofit organization dedicated to promoting education and public awareness of the Chesapeake Bay’s maritime heritage and encouraging the preservation and improvement of the Bay's natural resources. This year marks the 33rd annual race down the Bay from Baltimore to Norfolk, and it's open to all schooner-rigged vessels. Proceeds from the race support nonprofit organizations in the two areas where the race starts and finishes.

Annapolis Sailing School has a special link to one of the sailors in the race: ASA instructor evaluator Duncan Hood! Duncan has certified over a dozen of our instructors over the last several years. Duncan will be captaining on his 56-foot schooner Adventurer, which has competed in over 20 races.

To learn more about the Great Chesapeake Bay Schooner Race or to donate to its mission, click here

Rigging Refresher
It may be nearing the end of the season, but if you've forgotten how to rig a Rainbow, we've still got you covered. Watch our rigging video for a quick refresher! And if you have an ASA 101 class coming up this month, the video is a great way to get ahead beforehand.
Want to rep Annapolis Sailing School wherever you go? We've got you covered.  Click here to check out our merch.
Rep the sailing school with one of our car magnets! Stop by the sailing school to pick yours up for FREE.
Interested in sailing with us? Have a question? Email us.
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Annapolis Sailing School
7001 Bembe Beach Rd.
Annapolis, MD 21403

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