Annapolis Spring Sailboat Show Returns to City Dock April 24-26, Kicking Off Chesapeake Sailing Season
Date: April 21, 2026
For immediate release | April 21, 2026 | Annapolis, MD – The countdown to the sailing season is underway as the Annapolis Spring Sailboat Show returns to City Dock in historic downtown Annapolis, April 24-26, welcoming sailors, families, and sailing enthusiasts to the waterfront for three days of boats, education, and Chesapeake sailing culture.
Widely considered the start of Chesapeake sailing season, the Annapolis Spring Sailboat Show offers an unmatched opportunity to step aboard a wide range of new and pre-owned sailboats, meet trusted local experts, and prepare for the months ahead on the water.
From first-time sailors exploring their options to experienced cruisers planning their next upgrade, the show provides a rare chance to compare multiple sailboats in one place, right in the heart of America’s sailing capital.
The Perfect Place to Start the Season
The in-water display will feature more than 30 sailboats, representing the second largest annual in-water display of sailboats in the country. Visitors can step aboard an exciting mix of monohulls, catamarans, daysailers, and family cruisers to ask questions and explore different layouts and features side-by-side, an experience that’s difficult to replicate anywhere else.
Beyond the docks, the show offers a strong lineup of educational programming designed to support sailors at every stage. From introductory learning sessions and free daily seminars to more advanced instruction, the show provides practical knowledge that helps sailors get more out of their time on the water.
For those curious about sailing or ready to take the next step, the Annapolis Spring Sailboat Show offers a welcoming and hands-on place to begin.
Trusted Partners for the Long Run
One of the most valuable aspects of the Annapolis Spring Sailboat Show is the opportunity to meet Chesapeake Bay dealers and marine professionals face-to-face.
For many sailors, working with a local dealer is the beginning of a long-term relationship built on trust, knowledge, and support. These experts help sailors choose the right vessel, understand onboard systems, maintain their boats, and continue building confidence season after season.
Those relationships often start with simple dockside conversations, where questions are welcomed, expertise is shared, and the path to confident sailing becomes clearer.
A Full Waterfront Experience
While sailboats are the centerpiece, the show offers much more than boats. Visitors can explore sailing gear and services, connect with sailing clubs and charter companies, and enjoy the popular No Wake Zone, a gathering space featuring food, drinks, and harbor views. All of it unfolds against the backdrop of historic downtown Annapolis, adding to the atmosphere that makes the return to sailing season feel official.
With docks full of boats and the Chesapeake sailing community gathering once again, the Annapolis Spring Sailboat Show delivers the inspiration, resources, and connections sailors need to make the most of the season ahead. This annual tradition is made possible through the continued support of valued partners, including MTAM, Visit Annapolis & Anne Arundel County (VAAAC), Events DC, Cracker Barrel, and Renewal by Andersen.
The show runs Friday, April 24 from 10 a.m. to 6 p.m., Saturday, April 25 from 10 a.m. to 6 p.m., and Sunday, April 26 from 10 a.m. to 5 p.m.. Tickets are $20 ($15 for military), and children 15 and under are admitted free. For more information, visit AnnapolisBoatShows.com.
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Annapolis Boat Shows
Founded in 1970, Annapolis Boat Shows is the producer of the world’s first and largest in-water sailboat show and a leader in premier marine events. The company hosts four annual shows on the Chesapeake Bay — including the Annapolis Sailboat Show, Annapolis Powerboat Show, Bay Bridge Boat Show at Safe Harbor Narrows Point, and Annapolis Spring Sailboat Show — that draw tens of thousands of attendees and hundreds of exhibitors from around the world. Guided by its mission to foster a thriving boating community, Annapolis Boat Shows promotes accessibility, education, community, and sustainability while setting the standard for marine events worldwide.
Media Assets: High-resolution photos and logos are available here.
Media Contact
Ryan Gullang
ryan@annapolisboatshows.com
(410) 268 8828