Anytime friends or family visit us in Annapolis we try to fit in as much of Naptown as possible. Any new visitor is likely to get a trip to the Crypt of John Paul Jones and the Naval Academy Museum followed by a crab cake lunch. Or maybe it will be a stroll along Ego Alley followed by bay oysters washed down with our favorite local brew. Our dog loving friends and family can expect a visit to Paws Pet Boutique, then a double scoop from Annapolis Ice Cream Company, followed by a Maryland beer at 1747 Pub.

I recommend all of those things to anyone visiting Annapolis for the first time, but you honestly can’t experience the “Sailing Capitol of the World” unless you leave the shores of this fair city. Now Casey and I are mildly competent sailors; I crewed my share of boats in Guam and have taken a small boat or two out onto the Chesapeake. However, no one else in our family can tell a cleat from a clew, and if I told them to grab the sheet they would start hanging from the sails. In a situation like that a man needs a beer, and since that wouldn’t be an option while captaining a boat you can count me out. Luckily The Schooner Woodwind has been there for us over the years with their Tuesday night sunset cruise and beer tasting.

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The Woodwind and Woodwind II are 72 foot schooners that set sail daily from behind the Annapolis Marriott Waterfront Hotel. Every Tuesday the sunset cruise includes a sampling of local beers along with a brewery rep that’s there to talk about the beers and answer any questions. June featured Flying Dog, and July is all about Heavy Seas.

If you’re looking for something extra special then check out the upcoming Maryland’s Brewer’s Cup race between Heavy Seas and Flying Dog. Supporters will board their brewery’s boat for an evening of racing and brews as Heavy Seas defends their title. Will you be joining me on the pirate ship, or will you be a scurvy (Flying) Dog?

You can get tickets for all of the Schooner Woodwind cruises at their website.