Flag House Inn

Group of people on large sail boat coating through the water

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Things to do in Annapolis: Go Sailing / Race Night

Our guests frequently ask us for suggestions for things to do in Annapolis, and we’re pleased to provide a range of recommendations from Naval Academy tours to eating and drinking etc.  But there is so much more to do beyond the Naval Academy tour (which is really great, and no one else in town is closer to USNA than us)

During warm weather, nothing can beat getting out on the Bay.  There are a number of charter companies in the area, both for private charters and rentals (either you drive or with a skipper) or a group outing. This blog will focus on our favorite group outing:  America’s Cup night on the Schooner Woodwind (note – There is a another group outing with Watermark which is also great, they have a variety of tour both on land and sea.  Also Woodwind does other outings in addition to their Sunset Sail) 

The America’s Cup outing takes place only once a week on Wednesday night at 630p which coincides with Race Night by the local yacht clubs, there is frequently > 100 boats out on the water on Wednesday night.  We have gotten fantastic feedback from our guests and we tried it a few weeks ago when a friend was visiting. Woodwind has two boats so they race against each other in a semi-competitive way… A cash bar on board adds to the comfort

The wind was up so we were really moving.  Sadly because of the rain storms there was a lot of debris in the water so the yacht clubs had cancelled that week  

So when you come to stay with us, consider an outing on the Chesapeake Bay with Woodwind, Watermark or any of the other charter companies in town.  Very important, we are nearly full every weekend thru early November, so a one or two night midweek getaway with a boat outing could be a great way to wrap up your summer!  Book with us at www.flaghouseinn.com

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