Annapolis Sailboat Show 2025: October 9-12

Come to the Annapolis Sailboat Show October 9-12 (Thursday-Sunday, no Monday!) where sailors and would-be sailors can experience fun, friends, new boats and products, and educational seminars on-and-off the water. This is an Annapolis experience like no other, and it’s not to be missed!

Annapolis Sailboat Show
The Annapolis Sailboat Show runs October 9-12 at City Dock in Annapolis. Photo by Larry French

SpinSheet's guide to the show:

Nestled (or jammed?) into the heart of Annapolis, you will find well over a hundred gleaming, brand-new boats, 500-plus exhibitors offering almost anything and everything a sailor could desire, more than a dozen premiering boats, and seminars designed to take your sailing to the next level. As Annapolis Boat Shows states, “This is where sailing legends gather and new ones are born,” meaning whether you are looking to move up to a larger vessel or simply curious about learning to sail, this is the place for you. SpinSheet has suggestions for families, new sailors, those looking for charter vacations, and even advice for seasoned sailors.

Be sure to stop by the SpinSheet booth at its new location, Land Space 22, near the Dock Street entrance. Our staffers love to meet our readers, and you can get a free, temporary SpinSheet tattoo to sport throughout the show. On Friday, October 10 at 5 p.m., swing by the booth to join the casual celebration we’re hosting to mark the magazine’s 30th anniversary.

You’ll notice this year that the show layout is slightly different due to changes to the City Dock area to transform it into a more resilient and inviting public space. The plan calls for the existing asphalt area to become an elevated active park with resiliency features throughout the park and promenade. Construction has begun, and the old Annapolis Harbormaster’s office has already been demolished. Its new location is 4 Dock Street, Suite 100. 

There’s no better place to spend a fall weekend than historic downtown Annapolis, especially when it’s filled with enthusiastic sailors. We can’t wait to see you there. For more details, visit annapolisboatshows.com.

Annapolis Sailboat Show attendees on the docks

Chart your course: tips for navigating the show:

Parking: Show-goers are encouraged to park at the Navy-Marine Corps Memorial Stadium (550 Taylor Avenue) and take one of the free shuttles that run between the parking lot and the show gates, beginning one hour prior to show opening and going continuously through one hour after show closing. Online, pre-sale stadium parking is sold at a discounted rate of $23 per day. Online pre-sale closes at 10 p.m. on the evening prior to the day you plan to attend. After that, you may purchase parking onsite at the Stadium Gate 5 entry for $30, credit card only. Parking can be reserved at parkmobile.io. Oversized vehicle parking costs $45, paid for at the stadium. Parking will also be available on October 11-12 at Eastport Elementary School, 420 Fifth Street, Annapolis. Reserve your space at spothero.com. Additional parking is available in the parking garages in downtown Annapolis. Be sure to plan ahead as parking garages downtown fill up fast.

What To Wear: There’s no such thing as bad weather, only bad clothing, so dress for success. October in Annapolis can be sunny and warm or crisp and cool. Think layers, such as a short-sleeved shirt, warm mid-layer, and rain-repellent outer layer. You’ll be on your feet most of the day, so wear comfortable shoes that are easily slipped on and off (for boarding boats). Be sure to bring a hat to protect your head from sun or rain.

Bring This, Not That: You are welcome and encouraged to bring backpacks, reusable water bottles (refill stations will be located inside the show), snacks, notepads, boat cards, pictures of boat projects, children of all ages, and your boating buddies. Loaner lifejackets are available for kids and are especially encouraged while on the docks and boats. Strollers are not permitted but may be brought inside the show gate to the “stroller park.” Pets are not allowed unless they are certified service animals. Printed tickets aren’t necessary—all tickets can be scanned from your phone.

Getting Around:

On the water, we love the water taxis, and there is a stop inside the show, nestled between the Annapolis Waterfront Hotel Chart Your Course: Tips for Navigating the Show and Spa Creek Bridge. You can also call (410) 263-0033 or hail “water taxi” on VHF radio channel 68. Prices are $4 to $9 per person, depending on the destination (minimums apply in Back Creek and Upper Spa Creek). For cashless payment, download the Where in Annapolis app and click on the water taxi icon. For a route map with rates, visit watermarkjourney.com. Water taxis run Monday through Friday from 10 a.m. to 10 p.m., and Saturday and Sunday from 9 a.m. to 10 p.m.

On land, it’s easy to walk to restaurants, bars, shopping, and more. If you need a lift, try the Annapolis Free Downtown Shuttle, which connects parking with local restaurants and businesses. Find a full list of stops, hours of operation, and a route map at annapolisparking.com/ free-downtown-shuttle or download the mobile app. Another option is the City’s free electric trolleys, which run every 10 minutes and connect the Gotts, Whitmore, and Calvert Street parking garages to shops and restaurants along Maryland Avenue and State Circle Saturdays and Sundays from 11 a.m. to 5:30 p.m., except during inclement weather.

When you go

Dates: October 9-12
Where: Annapolis City Dock
Times: Thursday through Saturday 10 a.m. to 6:30 p.m.; Sunday 10 a.m. to 5 p.m.
Tickets: Attendees are encouraged to purchase tickets ahead of time. The show’s box office will be located on Dock Street, exit bus at second stop. Thursday, Preview Day $55; youth ages seven to 15, $10; children six years and younger enter for free. General Admission Friday–Sunday Adults, $32; children aged seven to 15 years, $10; children aged six years and under are free. Two-Day Combo Tickets Preview Day Combo Ticket (Thursday plus one other day), $82; Friday-Sunday Two-Day Combo Ticket, $59. Military Personnel Day Sunday only. Must present valid ID at gate, $22. Offered to Active Duty, Veterans, Retired, and Spouses. VIP Experience Show admission and access to the VIP lounge with food and full bar, $251.75.  Purchase tickets.