U.S. Sailboat Show 2014, photo by Fine Art America.

As long as the weather is good — knock on wooden sailboat hull! — then this weekend will be a busy one in downtown Annapolis for the annual Spring Sailboat Show at City Dock. Hundreds of seasoned and future sailors gather in Annapolis every spring to see the boats and the exhibits clustered by the water, and to take in all the live entertainment, food, drinks and lively atmosphere that Annapolis boat shows are known for.

Visitors are welcome to climb aboard the sailboats that are in the water and on land, to check out the exhibits and even partake in a sailing lesson. This year, there are classes and four daily seminars offered to everyone from experienced sailors to beginners; The First Sail Workshop allows first-time sailors to learn the basics and experience the joy of sailing in a 45-minute classroom session, immediately followed by 90 minutes on the water, while Cruisers University offers a wide range of curriculum for every area of expertise. 

Late April often sees some of the first perfect boating weekends of the season, and 2019 has been no exception. Get your sailboat out of storage, or acquire one at this weekend’s Sailboat Show, and launch an adventure on the water.

Spring Sailboat Show Features

With so much going on at Annapolis boat shows, it’s important to come prepared to make the most out of your time there. Find an overview of the 2019 show below, or take a look at the official show guide for a more in-depth description of what’s being offered. 

Sailboats and exhibitors. First and foremost, the most important part of the Spring Sailboat Show is the sailboats themselves, including catamarans, monohulls, family cruisers, daysailers and blue water sailboats, on the water and on land. Most sailboats at the show are available for immediate sale (and then, of course, immediate sail). There are also exhibitors on the floating docks and on land offering every kind of sailboat-related product and service under the sun. Exhibits include those for navigational equipment, high-tech electronics, inflatables, boating accessories, clothing and gear, plus boating clubs, charter companies, insurance firms, and lending institutions.

Sailing lessons and seminars. No sailing experience? No problem! Beginners can take part in a two-and-a-half hour First Sail Workshop taught by expert sailors. Additionally, free boating seminars presented by Chesapeake Bay Magazine will be offered daily. Sailors of every experience level are welcome to enroll in Cruisers University, which will offer over 50 programs that cover topics like cruising destinations, boat systems, navigation, procedures and more. 

Wine and beer tastings. Sample wine and beer in the Entertainment Plaza, courtesy of DOPS, Inc. Free tastings will include wine from Ammunition Wine Company, Pasqua Winery, Chatham Imports, Hammeken Cellars and a vast array of other wineries. 

Entertainment and prizes. Visitors will also find live musicians performing in the Entertainment Plaza every day. Performers include Matt Jacobs, Sean Hetrick, Shawn Owen, The Ginger Cats, Kristi Allen and Charles Kavoosi. Watch the 5th Annual Annapolis Junior Keelboat Regatta, where high school sailing teams compete for the traveling cup, and enter to win all kinds of prizes donated by sponsors and exhibitors. 

Spring Sailboat Show Details

Hours. Friday, April 26 and Saturday, April 27 10 a.m.-6 p.m. Sunday, April 28 10 a.m.-5 p.m.

Admission. Adult one-day admission: $12. Adult two-day admission: $19. Children 12 and under are free.

Parking. Parking is limited during the Boat Shows, especially on the street and in the downtown garages, so it’s best to have your plan ready before you leave the house. Cars will not be permitted to park at City Dock beginning at midnight on April 22, and Dock Street and Prince George Street from Craig Street to the water will be closed to vehicles and used for show setup.

Attendees can park at the Navy-Marine Corps Memorial Stadium and take a free shuttle downtown, or park at any one of the regular city garages including Noah Hillman, Knighton, Gotts Court or Park Place, and take the Circulator shuttle. 

Handy Tips

  • Some boats require you take your shoes off before stepping on-board; wear shoes that can be easily slipped on and off. 
  • Bring cash. Some vendors may not accept credit, and lines will move faster when patrons pay in cash. 
  • Pets are not allowed, and strollers are strongly discouraged. 
  • Download the map and know where you’re going!