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Sailing Cruises: October 5-9 from the U.S. Sailboat Show

Help Sail or Relax

Raise the sails!

“Woodwind” sails up to four times daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 5th – 9th from Dock “F2”.

Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket. 

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, footwear, sunglasses and more. More Info

Sailing Tickets can be bought online (see below) or directly from the booth in the Sailboat Show.
For all cruises, you must have a ticket into the show, so all sailing cruise tickets include discounted  Boat Show admission. Already bought your ticket for Boat Show? We will give you a discount by entering in your boat show ticket number below.

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)

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 craft beers, sparkling wine, soda, water and bagged snacks (like pretzels and potato chips)

1. Pick your Day

Thursday, October 5, VIP Day:

1:30-3:00
4:00-5:30
Adult Cruise + Discounted Admission Ticket for Boat Show: $57
Child Cruise (under 12) + Discounted Admission Ticket for Boat Show: $47
Buy Tickets Now for Thursday
Already have your Boat Show Admission Tickets? Click here and we will sell you “Sail Only” tickets as long as you provide your Boat Show Ticket Number.

Friday, October 6:

11:00-12:30
1:30-3:00
4:00-5:30
5:45-7:15 (Sunset Sail)
Adult Cruise + Discounted Admission Ticket for Boat Show: $45
Child Cruise (7-11) + Discounted Admission Ticket for Boat Show: $31
Child under 7 (no Boat Show Ticket needed): $25

Buy Tickets Now for Friday
Already have your Boat Show Admission Tickets? Click here and we will sell you “Sail Only” tickets as long as you provide your Boat Show Ticket Number.

Saturday, October 7:

11:00-12:30
1:30-3:00
4:00-5:30
5:45-7:15 (Sunset Sail)
Adult  Cruise + Discounted Admission Ticket for Boat Show: $45
Child Cruise (7-11) + Discounted Admission Ticket for Boat Show: $31
Child under 7 (no Boat Show Ticket needed): $25

Buy Tickets Now for Saturday
Already have your Boat Show Admission Tickets? Click here and we will sell you “Sail Only” tickets as long as you provide your Boat Show Ticket Number.

Sunday, October 8:

11:00-12:30
1:30-3:00
4:00-5:30
5:45-7:15 (Sunset Sail)
Adult Cruise + Discounted Admission Ticket for Boat Show: $45
Child Cruise (7-11) + Discounted Admission Ticket for Boat Show: $31
Child under 7 (no Boat Show Ticket needed): $25

Buy Tickets Now for Sunday
Already have your Boat Show Admission Tickets? Click here and we will sell you “Sail Only” tickets as long as you provide your Boat Show Ticket Number.

Monday, October 9:

WE HAVE CANCELLED SAILING CRUISES FOR TODAY DUE TO FORECASTED WEATHER INCLUDING HIGHER WINDS.

11:00-12:30
1:30-3:00
Adult Cruise + Discounted Admission Ticket for Boat Show: $45
Child Cruise (7-11) + Discounted Admission Ticket for Boat Show: $31
Child under 7 (no Boat Show Ticket needed): $25

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. (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.
  • List of Vendors can be found by clicking here.

 3: Allow plenty of time for traffic and parking! (Seriously)

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: Enter at any gate with your Discounted Admission Ticket

Annapolis Sailboat Show Map

Oct. 5-9 Boat Show Map Printable Version

  • 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.
  • You will get your Discounted Boat Show Admission Ticket separately from the confirmation of your sailing ticket. Admission Tickets will be sent under a different email no later than 8 am the day of your cruise.
  • For sailing on the Woodwind, go to “F2” Dock, we are near where you would get a Water taxi to the Brokerage Show.
  • We board 10-15 minutes prior to sail.
  • No telephone purchases during the Boat Show.
  • Cash or Credit Card only.

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