The boats are worth the trip. So is the Bay they’re sailing on.
Make your plans, bring the crew, and spend the weekend where your Chesapeake sailing life begins.
October 15–18, 2026
City Dock, Annapolis, MD
City Dock, Annapolis, MD
Your Chesapeake getaway is closer than you think.
Just over two hours from Philadelphia, downtown Annapolis becomes the center of the sailing world every October — the world’s largest in-water sailboat show, docked and ready to board.
Your Chesapeake Lifestyle Begins Here
Annapolis isn’t just a boat show.
From the broad northern rivers to the open southern reaches, and historic Annapolis to the quiet anchorages of the Eastern Shore, the Bay delivers variety without distance.
Bustling waterfront towns. Working harbors. Wide horizons where the only sound is wind in the rigging. You can log real miles under sail or lazy cruise all afternoon and call it perfect.
What makes the Chesapeake truly unique is how easy it is to make it your own. Many sailors choose to keep their boats on the Bay, returning on weekends to sail, anchor out, and unplug. No once-a-year planning. Just a standing invitation to sail.
With steady winds, protected waters, and miles of shoreline, the Bay rewards both first-time sailors and seasoned passagemakers. Sailing here isn’t just recreation, it’s rhythm. It’s freedom you can return to again and again.
And, the Annapolis Sailboat Show is where your Chesapeake Bay lifestyle begins.
On the Water
Featured Boats
-
Aquila 45
-
Tartan 34
-
Voyage 510
Find Your Second Home
Owning a sailboat on the Chesapeake isn’t complicated. It’s practical. At the Annapolis Sailboat Show, you can step aboard everything from comfortable daysailers to capable cruisers and performance designs, compare layouts, and envision your weekends under sail.
Connect with dealers, marinas, and service providers who make it easy to keep your boat in the water, maintained, and ready when you are.
With the right support close to home, spending more time under sail on the Bay becomes a simple part of the weekend.
Explore:
- New monohulls and catamarans
- Cruising and performance sailboats
Come Shop. Or, Just Come Look.
Never sailed before? Perfect. Already shopping for your next cruising boat? Also perfect.
The Annapolis Sailboat Show welcomes both — walk the docks, step aboard everything from daysailers to bluewater cruisers, and decide for yourself. No pressure to buy. Just an unmatched chance to see it all in one place.
Gear and Services
Everything to outfit the boat you already own, or the one you’re about to buy.
- Marine electronics and navigation systems
- Sails and rigging
- Anchoring and safety equipment
- Apparel and accessories
- Charter companies and sailing destinations
- Marinas, marine services and sailing organizations
More Than Boats
Build Confidence
The Annapolis Sailboat Show features the First Sail Workshop for beginners, and free daily seminars led by experts.
Go Farther
Cruisers University delivers a curriculum that addresses a complete range of cruising topics for all levels and experience.
A Simpler Way to Sail
Owning a sailboat is just one way to enjoy the Chesapeake. Boat clubs offer an easy path to time on the water without the responsibilities of ownership, with access to well-maintained fleets and the flexibility to sail when it fits your schedule.
At the Annapolis Sailboat Show, meet regional boat clubs, learn how membership works, and see if it fits your sailing goals. Many clubs also offer training, helping new sailors build skills while getting regular time on the water.
Plan Your Visit
Getting Here
Annapolis is just over two hours from Philadelphia via I-95 and Route 50 — an easy day trip or an even better overnight.
Tickets
General Admission, October 16-18 – $32
Preview Day, October 15 – $55
Children 7–15 – $10
Children 6 and under – Free
Military Personnel Day – $22 Sunday, October 18 only (must show ID at gate)
Dates and Hours
Thursday, October 15 – 10:00am to 6:30pm
Friday, October 16 – 10:00am to 6:30pm
Saturday, October 17 – 10:00am to 6:30pm
Sunday, October 18 – 10:00am to 5:00pm
Location
City Dock, Annapolis, MD
Box Office located on
Compromise St., exit bus at 2nd stop.