“Woodwind” and “Woodwind II”, both classic, 74-foot staysail schooners will sail up to seven times daily on 90-minute cruises from Dock “F2” during the Sailboat Show October 10th – 14th, 2024.
If the boat looks familiar, one of the Woodwinds was used in the movie, “Wedding Crashers”.
What is the Sailboat 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, sailing accessories, and more. More Info
Sailing Tickets can be purchased online (see below) or directly from our booth inside the Sailboat Show.
For all cruises, you must have a ticket to the show. All sailing cruise tickets purchased online, in advance, offer the option to include discounted Boat Show admission. If you already have your ticket for the Boat Show, you will have the option to buy a “Sailing Only Ticket”
Combo-Ticket Deal (Advance purchase only!) Save up to a 40% discount on your ticket to the Boat Show by buying a 90-minute schooner cruise combined with your Sailboat Show Ticket.
What does the cruise include? All sailing tickets include a complimentary soda or bottled water. Our bar is stocked with wine and beer, including a nice selection of local craft beers, and sparkling wine. Raise the sails, steer the boat, or just sit back and relax!
The Cut-off for Advance Online Ticket Sales is 12 Hours Before the Cruise. (Tickets may be available at Dock F2 inside the Boat Show right up to the Cruise Time)
1: Buy Your Tickets
Thursday, October 10, Preview Day:
Possible Sailing Times:
(check the Buy Tickets page for current availability)
1:30-3:00
2:45-4:15
4:00-5:30
5:15-6:45
Sailing Cruise Ticket + Discounted Admission Ticket for Boat Show: $88.55
Already have your Boat Show Admission Tickets? $59.80
Friday, October 11 through Monday, October 14:
Possible Sailing Times:
(check the Buy Tickets page for current availability)
11:00-12:30
12:15-1:45
1:30-3:00
2:45-4:15
4:00-5:30
5:15-6:45
5:45-7:15 (Sunset Sail)
Sailing Cruise Ticket + Discounted Admission Ticket for Boat Show: $77.05
Already have your Boat Show Admission Tickets? $59.80
2: Plan for your Boat Show experience
- Come for the full day to enjoy the show, not just your cruise portion.
- Wear soft-soled shoes and layered clothing.
- With your discounted admission ticket, you can go on most of the boats that are exhibiting to take a closer look.
- List of Exhibitors & Vendors can be found by clicking here.
3: Allow plenty of time for traffic and parking!
This is a big event in the city of Annapolis. Parking is very limited! Our sailing cruises depart promptly. There are no refunds or exchanges if you are late and miss the boat.
Click here for parking and shuttle information!
4: Enter at any gate with your Discounted Admission Ticket
- Print out your Discounted Boat Show Admission Ticket OR have it available on your phone so the Gate Attendants can scan your ticket.
- The closest entrance to the Woodwind Sailing Cruises will be the gate to the right of the Annapolis Waterfront Hotel.
- Your Discounted Boat Show Admission Ticket will not be included with your sailing ticket confirmation. Boat Show Admission Tickets will be sent from a different email address no later than 8 am the day of your cruise. They will be sent out earlier if you buy your tickets before October 5.
- For sailing on the Woodwind, go to “F2” Dock, we are located at the end of the dock.
- We board 10-15 minutes prior to sailing.
- Credit Cards only
