annapolis-sailing-school learning how to tie knots.
Check Availability

Annapolis Sailing Schools

Hitting the Water and Learning to Ride the Wind at Annapolis Sailing School and J World

As the country’s official sailing capital, our harbor is always bustling, with boats constantly coming and going. Sailing is part of our city’s cultural fabric, and there’s no better place to head out on a sailboat for the first time or brush up on your skills. At the Annapolis Sailing School and J World, both just across Spa Creek Bridge and less than 4 miles from our bed and breakfast in Annapolis, their expert staff and instructors have been guiding people out on the bay and teaching them to sail confidently for over 60 years. We have hosted several sailing students over the years, and our convenient location makes it easy to get from your room to the dock in just minutes. As sailing season officially kicks off in April, it’s the perfect time to realize that lifelong dream of getting out on a sailboat, with plenty of other opportunities to watch top-notch sailing races throughout the spring and summer months.

Annapolis Sailing School – Experienced Staff, Beginner-Friendly Boats, and Classes for All Ages

Annapolis Harbor, Maryland

With its often cost-prohibitive barrier to entry, sometimes arcane terminology, and specialized knowledge – there are famously thousands of unique sailing knots – sailing can seem daunting for those wanting to learn. With that in mind, the Annapolis Sailing School aims to make sailing approachable and affordable, even developing a specific beginner-friendly sailboat called the Rainbow 24. Their leadership has also always consisted of past instructors, keeping a lineage back to their earliest days in the late 1950s, expanding over the decades to include several levels of instruction. Their staff now consists of 16 people, all dockhands themselves and hands-on in their approach, bringing their intrinsic love of sailing to their classes. It’s one thing to watch YouTube videos or read sailing books, which are undoubtedly helpful entry points. Still, the Annapolis Sailing School method is to get out on the water as soon as possible, knowing that you must rig your sail, tie your knots, and feel the shifting winds to absorb and learn proper sailing methods firsthand.

Even if you’ve never stepped foot on a boat, their Rainbow 24 will have you feeling at ease. Its 24-foot main body hull is easy to navigate while being forgivable and impossible to capsize. Their two entry-level beginner classes, one three days and the other five days in length, will earn you ASA 101 certification, granting you official status as a trained skipper and sailor of a sloop-rigged keelboat. 

You’ll start by learning how to rig your boat and set up the main and jib sails, picking up important sail terminology like head, clew, and tack. Then it’s out onto the water for the more exciting stuff, like steering, chart reading, deciding right-of-way, and handling stormy conditions. Introductory Sailor courses open up for the 2024 season on April 1st, with 3-day sessions weekly, either on Mon-Wed or Fri-Sun. The Friday-Sunday sessions are the most popular and already booked into mid-April, so make your reservations soon if you’re aiming to get out on the water this summer.

Annapolis Sailing School also has a well-regarded kids’ summer program called KidShip, an excellent opportunity to get the whole family into sailing. The 2024 Lil’ Sailors five-day course still has open slots for ages 5-7, while the Jr. Sailing and Teen Sailing (8-16 years old) don’t have any openings. But if your child is 11-16 years old and has some sailing experience, their intermediate Hobie and advanced Quest sessions still have space. But those are bound to fill up quickly, too, so book as soon as possible. Our Murray Suite sleeps four – ideal for planning a family summer sailing getaway to Annapolis.

Keelboat Club – Perks of Getting Certified and Joining the Crew

In addition to crossing off a bucket list item of learning how to sail, one of the perks of getting certified through Annapolis Sailing School is that you’ll be able to join their Keelboat Club. With different levels and pricing, becoming a Keelboat Club member will grant you access to the casual Monday night racing regattas – a genuinely unique race setup where you’ll get expert coaching mid-race and video discussion afterward, an excellent way to improve – also an invitation to their annual 4th of July bash, and discounts on Rainbow 24 boat rentals. You’ll also get to head out with other KeelBoat members on “Blue Angels” Day, a breathtaking military jet aerial display over Annapolis Harbor during the US Naval Academy Commissioning week every May.

Once you get your sailing legs, the Annapolis Sailing School has several boat rental options that will allow you to expand your ocean-going adventures. Their Beneteau 37, Sabre 34, and Caraluna 245 bring more room and luxury – ample storage, a stand-up shower, and an oven/stove setup make overnight trips doable. If you get wanderlust, other more advanced classes like their cruising courses will guide you toward being able to take multi-day trips, hopping from island to island, harbor to harbor.

J World – Learning From the Best at Another Annapolis Sailing Institution

J World, another prestigious sailing school located just across the harbor in Eastport, offers more options for learning how to sail for the first time or broadening your skillset on the water. If you are curious about sailing but unsure how much time or money you want to commit, their 2-day weekend fundamentals class is an excellent introduction to sailing basics. You’ll probably catch the sailing bug, in which case you can add three more days to your initial fundamentals training and earn your keelboat basic certification, opening up the world of skippering a boat of your own. If you know straight away that you want to get certified, join their 5-day keelboat class, offered either Mon-Fri or over two successive weekends, a great option if you can’t take a week off work. 

All their training and instruction takes place aboard J-80 sailboats, 26 feet long and similar to the Rainbow 24 in maneuverability and ease of use for all ability levels. Winds are predictably around 10 knots on the Chesapeake Bay during the summer, and with the J-80’s evenly distributed weight, you’ll be cruising smoothly right from the start. J World also partners with Chesapeake Boating Club, so after you get certified, you can rent day-sailing boats from their fleet. With their sail club level 1 membership, you’ll have access to their six J-80s – the same boat style you learned on – an ideal way to jump right from your training to solo sailing.

If you already have some sailing chops, J World offers a two-day Performance Sailing class focusing on the finer intricacies and tricks for fully harnessing the capabilities of sail trim and tacking. For those looking to dip their feet into longer sailing outings, join their 5-day cruising course, when you live on-board with a captain on a bigger boat (30-40 feet) and learn the many details of anchoring, docking, planning weeklong outings on the ocean, and how to manage the complex workings of such a boat, such as plumbing, electrical systems, and galley maintenance.

Racing into Summer – Best of the Best Sailing Just Off Annapolis Harbor

There’s no better way to get inspired to sail than watching the best in action, and you’ll have ample opportunity in Annapolis. The Wednesday Night Racing series, organized by the Annapolis Yacht Club, features hundreds of sailboats racing along Spa Creek, a spectacle of skill and speed on the waters just off the City Dock. Stroll a few blocks from your Annapolis Inn room down to the water, where you’ll have spectacular front-row seats to the sailing competition every Wed evening, kicking off on April 24th and running through August 28th.

Sailing fervor around town hits a fever pitch this spring when the premier women’s sailing regatta, Santa Maria Cup, comes to Annapolis for four action-packed days of racing on April 23-26, 2024. All-women teams arrive from around the world with their most experienced skippers and crews—many of them Olympians and America’s Cup champions—and test their mettle in an ultra-competitive and highly entertaining format. See our recent blog about the Santa Maria Cup to learn more about the race and how to plan your visit to spectate.

Stay with us and discover the thrill of setting sail at Annapolis Sailing School!

learn rope hauling on the winch in annapolis sailing school