April Showers Bring the Annapolis Spring Sailboat Show

Like the croci, the Annapolis Spring Sailboat Show is a sign of good things to come for Chesapeake Sailors. Here’s how to get the most out of your day in Naptown.

Around Annapolis, April showers bring boat shows. And like the tulips and daffodils, the Annapolis Spring Sailboat Show is a tell-tale sign that the spring sailing season is officially underway. The show is for sailors: new or old, young or weathered; this is the boat show that launches a thousand ships.

There’s so much to do at the Spring Sailboat Show that we’ve made things easy for you, with a handy rundown that allows you to see all the action without missing a thing. So grab your foulies (just in case!), and get ready for a whirlwind of a weekend.

Before you hit the show, be aware that you do need a master’s degree in city planning to figure out where to park. The Spring Sailboat Show takes place down on City Dock, which is the city’s downtown open parking area. Luckily, you can reserve a space at the Hillman Garage, just half a block from the show, for a reasonable price. Those who enjoy a short walk can do as the locals do and park in the Eastport neighborhodd just across the bridge; it’s less than 10 minutes’ walk to the show gates, and on-street parking is free.

Now that you’re at the show, first up is First Sail. The American Sailing Association’s First Sail workshop is back again this year. The hands-on class teaches sailors (18 years and up) the basic fundamentals of sailing. With 45 minutes of classroom time and 90 minutes on the water in Beneteau First 22s, the class is an affordable way to get sailing with highly skilled, approachable instructors. The classes are priced at just $65 and include admission to the show, as well as a one-year BoatUS membership.

Photo by Ben Cushwa

If the First Sail workshop whets your appetite for more, it’s time to check out the many charter companies interested in working with you to get more time on the helm. And today’s charter companies don’t just offer exotic destinations; Chronic Sailing and Sail Solomons offer boats on the Chesapeake, from three hours to a couple of weeks. But also, maybe talk to someone about that Croatia trip you’ve been eyeing, since you’re down there and all.

This year’s docks are full of boats. At the time of writing, over 40 boats are set to crowd City Dock, from 11 to 60 feet. Catamarans and monohulls will be on offer, as well as the daysailers, bluewater beasts, and family cruisers that will launch your next adventure. The Spring Sailboat Show features both previously-loved brokerage boats as well as new, fully customizable options.

After you’ve looked at boats and caught some wind in your sails, make time for the many workshops, panels, and discussions happening on land. On Sunday, the Annapolis Sailing School is leading a series of panels on optimal crew participation, women’s sailing, and stepping into educational roles in sailing. Other great seminars include line handling, crewing tall ships, dock-and-dining, and much more.

Don’t forget the cockpit critters! Kids will enjoy checking out boats, interactive displays, and onsite activities for all three days.

This year, Cruiser’s University is offering two higher educational classes: Offshore Emergency Medicine and Master Diesel Maintenance. Unfortunately, at the time of writing, Offshore Emergency Medicine is sold out. Master Diesel Maintenance, however, offers three days of instruction (Wednesday through Friday) and includes entry to the show all weekend.

After your head is swimming in information and ideas, head to the No Wake Zone, a fun tent set aside for attendees to simply relax. With live music, a fancy outdoor lounge area, and even fancier cocktails, the No Wake Zone is an opportunity to enjoy the show without any agenda. On Saturday, there will even be a fashion show by Shanks Golf Apparel, who make 50+ UPF sportwear.

After you’ve luxuriated a bit, don’t forget to check out the 100+ on-land exhibitors and vendors. The spring show is a great place to catch deals on charters and get in line with your sailmaker. But there are also personalized gifts, techy new boat supplies, and every tool, book, boat shoe, and nautical charm you can think of. Annapolis is a sailing town with a shopping problem.

Finally, when you’re ready to leave the tents and docks and find a table and some appetizers, check out one of the many restaurants in downtown Annapolis. Latitude 38 and The Choptank Fish and Crabhouse are favorites for watching the Sailboat Show scene with white tablecloths, but Pusser’s keeps the party going with its painkillers, and just across the street you’ll find Annapolis mainstays Middleton Tavern and McGarvey’s. A new restaurant, Pearl, just opened and boasts a second-floor rum bar overlooking the seaport. We’re fans.

If you parked in Eastport, you’re in luck: the neighborhood is known as the sailors’ hangout, with Davis’ Pub, Forward Brewing, the Boatyard Bar & Grill, and the new Adam’s on Fourth (no website, just go) putting out some of the best after-racing food and drink in Naptown.

Whether you love to race your dinghy, or if you prefer to sail in the BVIs with a charter captain and chef aboard, the Spring Sailboat Show is the opportunity for sailors of every ilk to gather and celebrate the new season.