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During the 2025 Annapolis Sailing Schools BVI Flotilla, there was an event that left everyone both in stitches and in awe. The illustrious Rick Nelson, owner of the Annapolis Sailing School, decided to take matters (and scrub brush) into his own hands to clean the hull of our trusty catamaran. This might have contributed to our fast and smooth sail from Virgin Gorda to Anegada; it was clear that the Admiral's hull cleaning had indeed made all the difference:)

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.

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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

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 #hellyhansen #annapolis #sailing #annapolissailingschool #sailingregatta

At the Annapolis Sailing School, we have "Seriously Fun" Seriously, because we teach you how to be a competent sailor Fun, because we do it in a safe and enjoyable environment find out more about what we offer on our website: https://www.annapolissailing.com/

Brian Harrison shot this time-lapse video of the floating docks being installed. The Annapolis Sailing School is gearing up for a "Seriously Fun" 2023 Sailing Season. Be sure to thank the staff for all the hard work in getting everything ready.

This video was made with Clipchamp

Our March 27, 2022 edition of our Cooking and Provisioning Class. The members wanted to learn how to use up leftovers on their passages. We taught them frittatas and fried rice, along with basic provisioning principles, sanitation and knife skills.

KeelBoat Members participated in the 7th season of North Sail U Performance Race Week at St Thomas Sailing Center in the U.S. Virgin Islands. They honed their skills during 5 days of racing instruction including a combination of on-the-water training and races, and shoreside seminars. They will be bringing those skills to the KeelBoat Clubs Monday Night Races. #BillGladstone #annapolissailing #annapolissailingschool #keelboatclub #northsails #sailboatlife

In this video we interview, Jessica and Nick, members of the Keelboat Club, discuss their recent project of converting their sailboat "Pazuzu" to electric power. They share their experience and insights on the benefits and challenges of making the switch, as well as their thoughts on the future of sailing with electric boats. They also talk about their involvement in KeelBoat Club Monday Night Racing and their competitive spirit, as well as their passion for sailing and the sense of community in the club. Overall, the interview provides an inside look into the world of electric sailing and the benefits of being an Annapolis Sailing School KeelBoat member and Its close-knit sailing community. Intro: 0:19 KeelBoat Membership: 0:42 Club Racing: 1:50 Converting to electric: 3:14 Challenges: 4:13 Components Decision: 5:36 Batteries and Charging:: 6:58 Sailing on electric power: 8:46 Parting Wisdom: 10:09 Electric Yacht: https://electricyacht.com #sailingelectric #electricsailboat #annpolisracing #keelboat #annapolissailing #sailboat Music: Artlist, Taste of Freedom, Steven Baddall Video Clips: Ian Morrison -Director KeelBoat Club Video Editing: John@71h2o.com

This Annapolis KeelBoat Club video shows examples of several boats on a light wind night making the leeward rounding and the mistake and advantages of the various boats while rounding the mark. Narrated by Maille Lyons and Jamey Dumas Drone Footage provided by : Brian Harrison #annapolisailing, #keelboatclub, #keelboat #annapolissailingschool, #Rainbow24 #racingrainbow24, #mondaynightracing #sailingCommunity

In this Annapolis KeelBoat Club video you will see three examples of strategies to start a race: Reach in reach out strategy Port Tack Approach through the fleet Port Attack of the Start Narrated by Maille Lyons and Jamey Dumas Drone Footage provided by : Brian Harrison #annapolisailing, #keelboatclub, #keelboat #annapolissailingschool, #Rainbow24 #racingrainbow24, #mondaynightracing #sailingCommunity

This Annapolis Sailing School Keelboat Club Video demonstrates how tactically it's often better to go wide and tight if you cannot establish an inside overlap at the zone at a Leeward mark. Narrated by Maille Lyons and Jamey Dumas Drone Footage provided by: Brian Harrison #annapolisailing, #keelboatclub, #keelboat #annapolissailingschool, #Rainbow24 #racingrainbow24, #mondaynightracing #sailingCommunity

This Annapolis KeelBoat Club Video demonstrates how several boats use different choices to round a windward mark. Narrated by Maille Lyons and Jamey Dumas Drone Footage provided by: Brian Harrison #annapolisailing, #keelboatclub, #keelboat #annapolissailingschool, #Rainbow24 #racingrainbow24, #mondaynightracing #sailingCommunity