What better way to celebrate the warm weather in Annapolis than hoping aboard one of two, beautiful 74-foot schooners – Schooner Woodwind and Woodwind II – for a fun sailing experience in Annapolis!

I had the pleasure of joining Captain Jennifer Kaye of Annapolis Sailing Cruises for their Wednesday Night Racing where the Woodwind and Woodwind II take to the Chesapeake for some friendly competition. This race happens in conjunction with the Annapolis Yacht Club Race every Wednesday night from May to August. Passengers along for the ride have the opportunity to act as a “guest crew” and participate in sailing the massive wooden vessels. Of course, I had to participate!

Schooner Woodwind is proud to be celebrating their 25th anniversary this year. To commemorate such a monumental milestone, they have created a week-long list of events for frequent sailors, guests, and friends to enjoy at the start of June. The events are meant to highlight the past, present, and future of the Woodwind. Plus, as you will see in the video above, they even had a special Maryland craft beer made by Hysteria Brewing Company for the special occasion, named Seas the Bay.


Check out the special 25th anniversary cruises and purchase your tickets here.

FUN FACT: Woodwind II was used in the movie “The Wedding Crashers!”