The Annapolis Spring Sailboat Show is back — April 24–26, 2026 — and if you're making the trip to City Dock, you already know: this isn't just a boat show. It's a full-on Annapolis experience. Salt air, rigging lines, and the kind of crowd that actually knows the difference between a jib and a genoa.
So what do you wear? We've got you covered — literally.
Dress for the Dock (and the Weather)
April in Annapolis means one thing: layers. Mornings on the water can be crisp, afternoons warm up fast, and the breeze off the Chesapeake Bay doesn't ask permission. The move is a comfortable, garment-dyed tee as your base — something that looks good whether you're walking the docks or grabbing a crab cake on Ego Alley.
The Annapolis Sailboat Show Packing List
- A go-to coastal tee — soft, broken-in, and ready for a full day on your feet
- A lightweight layer — a hoodie or sweatshirt for the morning and evening chill
- A great hat — sun protection and style, all in one
- Comfortable shoes — you'll walk more than you think
- A tote bag — for show programs, snacks, and whatever you pick up along the way
Rep Annapolis While You're There
There's no better place to wear your Annapolis pride than the Spring Sailboat Show. Our Annapolis tees and coastal Maryland apparel are made for exactly this kind of day — comfortable enough to wear from opening bell to sunset, and designed to feel like home.
Whether you're a seasoned sailor, a curious landlubber, or just someone who loves a good Annapolis spring weekend, the Sailboat Show is one of those events that reminds you why this town is special.
See you on the docks.