Annapolis Spring Sailboat Show 2026: Sailing Excellence in the Heart of the Chesapeake

The Annapolis Spring Sailboat Show 2026 (commonly referred to as ASSS) stands as a cornerstone event for the maritime community on the East Coast. Returning to the historic City Dock in Annapolis from Friday, April 24 to Sunday, April 26, 2026, this premier show offers an unparalleled opportunity to explore the latest in sailing innovation and brokerage opportunities.

Organized by the esteemed Annapolis Boat Shows, Inc., the event is set against the picturesque backdrop of a city deeply rooted in naval tradition. Whether you are a seasoned offshore sailor or a novice looking to catch the wind for the first time, this show provides the perfect platform to immerse yourself in the nautical lifestyle.

A Fleet for Every Sailor

The 2026 show will feature an impressive lineup of vessels, including:

• Multihulls: Explore the latest spacious catamarans and high-performance trimarans.

• Monohulls: From sleek racing yachts to stable family cruisers and nimble daysailers.

• Brokerage Boats: A dedicated section for those looking for pre-owned vessels with proven blue-water pedigrees.

In addition to the vessels on the water, the docks will buzz with activity from boat clubs and charter companies. For those looking to plan their next global exhibition schedule beyond the maritime world, you can find comprehensive listings of upcoming events at Trade Fair Bazaar, a leading resource for industry trade shows.

World-Class Education: Cruisers University

One of the most significant highlights of the Annapolis Spring Sailboat Show 2026 is its dedication to maritime education. The world-renowned Cruisers University will be in full swing, offering over 70 seminars tailored to all experience levels.

Featured Training Opportunities:

• Offshore Emergency Medicine: A vital course for those planning long-range passages.

• Beginner’s Sailing Workshop: A gentle, hands-on introduction to the basics of wind and water.

• Diesel Maintenance & Electronics: Technical sessions designed to give owners the confidence to handle onsite repairs.

The Maritime Marketplace

Beyond the boats themselves, the show is a sprawling marketplace for nautical gear and services. Exhibitors from across the globe showcase cutting-edge maritime technology, including:

• Electronics: Advanced GPS, sonar, and satellite communication systems.

• Maritime Fashion: High-performance foul weather gear and coastal lifestyle apparel.

• Services: Onsite experts specializing in marine insurance, financing, and custom boat building.

For more information on regional maritime activities, see our Internal Guide to Chesapeake Bay Boating or check out our 2026 Boat Show Calendar.

Why Visit Annapolis in April?

Visiting the City Dock in April offers more than just a trade fair; it is a gateway to the unique ambiance of “America’s Sailing Capital.” The venue’s prime waterfront location provides easy access to the city’s historic district, boutique shops, and world-class seafood restaurants.

The Annapolis Spring Sailboat Show 2026 is a celebration of the region’s heritage and a driver of future maritime trends. Mark your calendars for April 24–26 to join thousands of sailing enthusiasts in shaping the future of the Chesapeake’s sailing scene.