2024 Sailing Season is coming! See you April 13, 2024!

Spring Sailboat Show April 22-24

Help Sail or Relax
Raise the sails!

“Woodwind” sails from temporary docks during the Spring Sailboat Show April 22-24.

What is the Spring Boat Show?
It is a collection of sailboats and vendors who are selling their boats, products, classes and more. There are boats of all sizes and they are open for you to go aboard.  Many of the vendors have great deals on outdoor clothing, footwear, sunglasses and more. More Info

Tickets can be bought online (see below), at our normal dock office location, by phone or directly from the booth at the Sailboat Show.
For daytime cruises, you must have a ticket into the show, so all sailing cruise tickets include discounted  Boat Show admission. Enjoy the show before or after your cruise.

Each trip is unique. All cruises depart from the Spring Sailboat Show and pass by the United States Naval Academy and then into the Chesapeake Bay. Spring sailing usually brings nice breezes for perfect sailing weather.

2-Hour Cruises: Friday, Saturday & Sunday

Let our captain and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.  Our cash bar is stocked with wine and beer, including a nice selection of local micro-brews. Adults $50, Seniors $48, Children under 12 $27. Includes discounted admission into Boat Show (which is necessary) soft drink, snack and tax.

1. Pick your Day


Saturday, April 23:
3:00-5:00 SOLD OUT
Buy Tickets Now
5:30-7:30 Sailor’s Delight Cocktail Cruise


Sunday, April 24:
Buy Tickets Now

2: Enjoy your Boat Show experience

  • Wear soft soled shoes and layered clothing.
  • Arrive early (show opens at 11:00) and check in at Dock Office to get your sailing boarding ticket and Boat Show admission ticket. With that ticket, you can go on most of the boats that are exhibiting to take a closer look. (They may even ask you to take your shoes off.) This is also a great place to get good deals on raincoats, sunglasses, portable coolers, books, calendars and so much more.

 3: Allow plenty of time for traffic and parking!

This is a big event in the city of Annapolis. Some parking lots are not used for parking due to the Boat Show.

Click here for parking and shuttle information!

4: Check in at least a half hour before cruise

  • Come to Dock Office at 80 Compromise Street to Check In.
  • Walk through Pusser’s Restaurant to the Dock.
  • You will get your Boat Show admission ticket and Boarding Pass for cruise
Schooner Woodwind