The Keelboat Club members take to the water, dividing into British and French forces for a lighthearted reenactment of one of history’s most famous naval battles. The cannons may be imaginary, but the sailing is real! (when there is wind) Ammunition? Croissants and English muffins, of course. Fortunately, no ships were harmed, no Admiralty inquiries were launched, and history was only slightly rewritten. Seriously Fun, friendly rivalry, and a healthy dose of nautical nonsense at the Annapolis Sailing School! #AnnapolisSailingSchool #BattleOfTrafalgar #KeelboatClub #Sailing #Annapolis #SailingFun #NavalHistory

Ian Morrison, Director of the KeelBoat Club, walked the crew through a light-wind roll tack—a sailing maneuver that uses body weight and the rudder to smoothly turn the boat through the wind, then pump it back up to speed without losing momentum. This video was shot onboard the School's Tartan Caraluna 245, during the Hospice Cup 2026. Annapolis Sailing School's Race Instruction Course. #HospiceCup2026 #AnnapolisSailingSchool #SailingAnnapolis #HospiceCup #annapolismd #NaptownSailing #chesapeakebayretriever #DowntownAnnapolis #VisitAnnapolis

Watch the ultimate seasonal transformation! This breathtaking timelapse captures the Annapolis Sailing School as it shifts from a completely frozen winter bay into a bustling, sun-drenched summer sailing paradise. See the ice melt away, the docks come alive, and the sailboats return to the beautiful waters of the Chesapeake Bay. Whether you love sailing, changing seasons, or the beauty of Annapolis, this video is for you! If you enjoyed watching this transformation, please hit the Like button and Subscribe for more beautiful Annapolis content! ocated in the sailing capital of America, the Annapolis Sailing School has been helping people learn to navigate the waters since 1959. 🔗 Connect With Us: Website: https://www.annapolissailing.com/ Instagram: https://www.instagram.com/annapolissailingschool/ Facebook:https://www.facebook.com/annapolissailingschool/ #annapolismd #Sailing #Timelapse #ChesapeakeBay #AnnapolisSailingSchool #WinterToSummer #BoatLife #sailorlife #learntosail #chesapeake #

Learning when and how to reef is the difference between a beautiful day on the water and an overwhelming, exhausting experience. By reducing the size of your mainsail, you balance the boat, reduce the severe angle of heel, and eliminate heavy weather helm. This keeps the crew comfortable and ensures your vessel handles smoothly, even when the breeze pipes up unexpectedly. Here at the Annapolis Sailing School, our expert instructors teach you the practical steps of slab/jiffy reefing right on the water. Whether you are taking a Basic Keelboat Course or brushing up on coastal cruising, learning to tame your sails is a staple of our curriculum. Ready to get hands-on experience mastering the wind? Visit the Annapolis Sailing School website to view our Course Schedule and book your next sailing adventure in Annapolis, MD. Click the link to book your course. https://www.annapolissailing.com/?gad_source=1&gad_campaignid=1608757816&gbraid=0AAAAAC6ccGEB-2n-93lD83GHGCNKeDnVE&gclid=CjwKCAjw6rfSBhAqEiwA_yocphQKzhCuEL21N8BsI-BnlMlxIcW1FuyHaaKMZYgmUYepTXj7AOTT9xoCKRwQAvD_BwE

On October 19th we reenacted the Battle of Trafalgar. The fleet manager wouldn't let us cross the T, but we had a good time shooting water cannons, tossing croissants and english muffins and finally limes. In our battle a couple of English boats ended up between the French allied boats and got limed to death, leading to a French victory!

Jonah walks a class through tying a Bowline.

This is about the middle of the deep freeze of 2026. The ice formation eventually froze all of Back Creek and most of the way across the Severn River. On the Eastern Shore they even broke out their ice boats. The USCG brought in icebreakers so the Baltimore Harbor pilots could get out to the tankers they needed to guide in. Thank you to Brian Harrison for this amazing drone footage. You can see more of his work here: https://vimeo.com/user167830425

The Annapolis Sailing School in the Eastport Yacht Club Light Parade. Happy Holidays to all the sailors. This could be you in 2026!

It's hard to see wind puffs from the rail. In this video we use a drone to make it easier to see the puffs.

The Annapolis Sailing School's keelboat team was ready to learn the fundamentals of racing on the school's Tartan Caraluna in the 2023 Annapolis Helly Hansen regatta. Expectations were met under the stewardship of instructor Jonah Lane and the guidance of Keelboat member Jamey Dumas, The School's slogan of "Seriously Fun" was in play on both days of sailing, Crew : Megan Hartwick Matt Sheridan John McConnell

During our 65th Employee Anniversary, we had wonderful speakers talk about their experience and history of the Annapolis Sailing School. Video filmed by Brian Harrison.

Mike Hull reviews the 2025 BVI Flotilla details and also answers some FAQ's from our guests.

Once a month during the summer we open up our dinghies to our KeelBoat Club and the public. Come out and join us every July, August and September.

A great perspective of sailing the Annapolis Sailing Schools Tartan Caraluna 245 during the Wednesday Night Annapolis Yacht Club race; captured by Jamey Dumas. Watch as the crew maneuvers the Caraluna 245, under the watchful eye of John Sweeney, Crew members: Maille Lyons Jamey Dumas Donna Aulds John McConnell Subscribe to Jamey Dumas's YouTube channel, @jamey-dumas, to stay updated on more Keelboat Club Racing Videos Tags: Sailing, Sailboat, Competitive Sailing, Annapolis, Annapolis Yacht Club, Annapolis Sailing School, Tartan Caraluna 245, Wednesday Night Race, Chesapeake Bay, Sailors, Jamey Dumas, Videography, Adventure Regenerate response

Ceremony to rename and christen the Annapolis Sailing Schools Rainbow Fleet by keelboat members 2023