Chesapeake Sailing Schools: What Is New for 2024?

Time for sailing school lessons and courses to brush-up on skills

Springtime marks “back-to-sailing-school time” on the Chesapeake and the beginning of a six-month season of opportunities for adults to learn to sail or hone their sailing skills. Here are three common questions about choosing the right sailing school for you, followed by news from regional schools.  

sailing school boats
Why do you want to start sailing? Is it to experience the wind in your hair, the sun on your face, and waves gently rocking the boat? Or is it because you’re an outdoorsy type who likes water and trying new sports? Photo: FJs racing out of DC Sail

How do I choose between different programs? 

We hear this question from new sailors a lot, and there’s no right or wrong answer. We recommend first taking a look at the schools that advertise in SpinSheet. If they are investing their ad dollars in these pages, they support their local sailing magazine and are committed to the Chesapeake sailing community. They want your business! 

Next, you need to ask yourself why you want to learn to sail. Is it to experience the wind in your hair, the sun on your face, and waves gently rocking the boat? Or is it because you’re an outdoorsy type who likes water and trying new sports? Have you always dreamed about learning to sail and chartering a sailboat in the islands? Do you have a long-term vision that includes owning a boat? 

These are all legitimate reasons to get started. If sailing is an experience you’d like to try, you may do that at any sailing school, big or small, or club or community sailing program. If you find a school that feels right, sign up. If you have big dreams and long-term goals, consider a school that offers American Sailing Association or US Sailing certifications and more advanced programs and a progression of learning opportunities as you advance your skills.

How can I keep practicing my sailing skills after my class? 

Sailing is an experiential sport, so it’s important to take a lesson, practice what you learned, and do it again. That’s why it’s important to have future access to boats, whether that’s a club, a rental boat option, or a boat to borrow, or even a friend with a boat. Some schools, such as Annapolis Sailing School, J/World Annapolis, or Sail Solomons have a club membership option with boat access. 

Others, such as the Annapolis Naval Sailing Association, offer learn-to-sail programs and group or club sails on their boats. SailTime offers sailing classes as well as part-ownership of boats and a welcoming community of sailors. These are all great ways to get on the water without owning your own boat (yet). 

SailTime members
SailTime Annapolis members Misti and Mike successfully completed their SailTime training last spring. Photo courtesy of SailTime Annapolis/Facebook

What if I’d rather take a brush-up course than a learn-to-sail course?

Any good sailing school will talk to you about where you are in your sailing journey and what their recommendations are for starting up again. Most good sailing schools have a private instruction option, so you could spend a day or two with an instructor on their boat (or your own) without starting at ground zero. For more ideas on learning to sail, visit Start Sailing Now

sailing school boats
Annapolis Sailing School celebrates its 65th anniversary this year.

Calling all current and past employees of the Annapolis Sailing School! 

As Annapolis Sailing School and Boat Rentals gears up to celebrate its 65th anniversary, they’re embarking on a journey down memory lane and need your help to make it truly special. The staff invites you to reconnect and share your stories. Whether you were office staff, a dock hand, a sailing instructor, or learned as a student yourself, your stories hold the key to Annapolis Sailing School history.

Hunter Sugg writes, “We’d love to know when you sailed with us, if you made any friends, and if you still sail! If you have a tale to tell, please share your stories on land or sea, photos, and memories by emailing [email protected]. Let’s come together to celebrate 65 years of the Annapolis Sailing School.”

DC Sail’s new Thursday evening races 

DC Sail will offer additional racing opportunities for its members in the 2024 season. The popular Thursday evening race series will expand from 16 weeks to 20 weeks.

The Adult Racing Series began on Thursday, April 18 and will continue through September 12, which is the week of the Cantina Cup Regatta (Saturday, September 14). Registration for the Adult Racing Series will cost $320 for the entire season, with a breakdown price of just $16 per evening. There will be an option to purchase the entire season or exclusively the first or second half of the series for $160 each. 

Note that with the racing season starting earlier, there is a chance for colder weather mandating drysuits/wetsuits while on the water. Hopefully the spring will bring reliable warm weather, sunny skies, and solid wind on these April and May weeknights. Find more at dcsail.org/racing

Not an experienced FJ sailor? DC Sail hosts an Intro to FJs Course once a month in June, July, and August. Find more at dcsail.org/lessons-introtofjs.

sailing instructors
Tom and Beth Ackerman of Sail Solomons

New instructors, catamaran, and courses in Solomons

Sail Solomons recently welcomed three new instructors to their staff: live-aboard cruiser Captains Tom and Beth Ackerman and Captain Mark Gyorgy.

Tom and Beth have been living full time aboard their Irwin 43 Ancora Qui currently in Solomons Island, instructing and captaining with Sail Solomons. Both are USCG captains, and ASA certified instructors. Tom is a lifelong sailor, and Beth started sailing when they met. After a career as physical therapists, they began the cruising lifestyle in the summer of 2022. They plan to spend summers on the Chesapeake and winters someplace warm. 

Mark Gyorgy has enjoyed 20 successful years racing locally aboard his Tartan Pride P270 Wicked Good and with the local Buccaneer fleet. Learning to sail in his home state of Maine at the age of nine, Mark was a career Navy helicopter pilot and defense worker. He is also a USCG captain and ASA instructor.   

New to the Sail Solomons fleet starting April 1 is the 2023 Seawind 1260, Second Sight. She will be available for instruction, Bareboat Cruising (ASA 104), Catamaran Endorsement (ASA 114), and Advanced Coastal Cruising (ASA 106) as well as being available for charter. Her first event with Sail Solomons was a passage from Key West to Solomons the first week of April.

New class offerings for Sail Solomons include: Basic Keelboat II (ASA 102), Dinghy Endorsement (ASA 116), and Catamaran Endorsement (ASA 114). Learn more at sailsi.com.

sailing corporate team building
Sailing with your work friends at J/World Annapolis. What a great way to foster team building. 

Escape the conference room and embark on a sailing adventure

Experience an unforgettable team bonding activity with J/World Annapolis and Chesapeake Boating Club’s Corporate Team Building Program. They also provide venue space for different occasions like parties and meetings. Additionally, check out the newly opened retail store Tomorrow’s Dawn for beautifully handcrafted jewelry. Learn more at jworldannapolis.