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

Promotions & Deals

Schooner Woodwind Frequent Sailor Card

Frequent Sailor Card

Come sailing with us 5 times and your sixth sail is FREE plus a free “Crew” T-shirt- just like our crew wear!  At the end of your sail, the crew will hand out these “Frequent Sailor Cards”. The crew will stamp your card with the date of each sail. They do not expire!  If you cannot wait for your free t-shirt, check out our Ship’s Store for a wide selection of tees, sweatshirts and hats.  Please remember to bring your card everytime!

The FREE sail is a public, 2-hour cruise.

Redeeming your full frequent sailor card: You must book your ticket OVER THE PHONE. Our online ticket system cannot be used for this type of redemption.

Schooner Woodwind Koozie

Schooner Woodwind Koozies

We know you like to keep your beer cold but your hand warm when sailing on the Woodwind. That is why we made Koozies available on your sail. But this isn’t just any koozie… on the bottom, they say “Fill ‘Er Up”. And that’s what we will do.

For $3, you can buy a Koozie aboard the Woodwinds, and keep your beer cold. When you sail with us every time after this cruise AND remember your koozie, we will fill your koozie with your first beer or wine of your choice for free. This is free beer or wine for life aboard the Schooner Woodwind when you remember your koozie! (Well, your first beer or wine on each cruise.)

Schooner Woodwind Photo Contest

Do you have the winning photo?

Photo Contest

We love photos! Enter your favorite photos into our online photo contest! All eligible photos are taken either from Woodwind or Woodwind II. We love shots of passengers having fun aboard as well as action shots of the boats cruising the Bay. You can upload your photos directly to our website for entry into the contest. All rules are on our photo contest page. The Grand Prize winner will receive a $200 Gift Certificate for use during the following year.  Deadline is December 15.

Facebook Notifications of Specials

Facebook is the easiest platform for us to get in touch with our friends, fans, and all the people who love the Woodwind. Please “Like” our page, Annapolis Sailing Cruises: Schooner Woodwind. We post information like:

  • Reduced rates on certain cruises
  • Facebook only specials
  • First notice of new cruises added to our line-up of specialty cruises and events
  • Ticket updates (when we are getting low on tickets for our specialty cruises)
  • Awesome pictures from sailing on the Chesapeake
  • Play-by-Play Wednesday Night Racing Recaps

Email List

Sign up for our monthly email mailing list. We send you updates about what is new, what is upcoming, and other specials. Sign up here

Schooner Woodwind