Schooner Woodwind Sailing Cruises

"My husband and I went on the mid-day sail at 1:30pm and it was great. In our case, the weather was perfect so there was minimal chop + a nice light breeze made for a great outting. The crew was welcoming and not overly enthusiastic which we preferred. If you have ever been on a Disney cruise or something similar, that "forced fun" and fake enthusiasm is awful. The crew of the Woodwind II were all genuinely enthusiastic and upbeat. Overall it was a pleasant day out on the bay. We learned a lot about the bay and connecting rivers, and meeting others on the boat was an added bonus. We will definitely sail with them again no doubt. (There is a restroom on board if you were panicking about your bladders capacity)"

"Absolutely wonderful experience. Captain Jen and her crew took us for the perfect 2 hour ride and even chased the sunset as it was cloudy until this stunning surprise (see pictures) over Annapolis. Pre-order beers or bubbly to enhance the experience. Be prepared to get a little sea spray and enjoy the ride!"

"We had a wonderful time aboard the Woodwind II. The captain and crew were all very friendly and welcoming. I had trouble finding the check-in location but when I walked to the dock, I was taken care of. We were out for a full 2 hours. Weather was beautiful (which they have no control over.). I would highly recommend this activity."

"We went to spend the day in Annapolis and popped by the information station. We inquired about cruises and this one caught our attention. I have done design work on the mansion featured in “Wedding Crashers”. When I heard the schooner was too, I thought serendipitously we must take this boat! We booked in the early afternoon, Tuesday August 1st. The weather was perfect to sail! An added bonus - There Are beer tastings on Tuesday!! Jen and her team were very attentive and made the trip enjoyable."

"Phenomenal sunset cruise with Capt. Andy and crew. He was personable and knowledgeable; sharing information about the harbor and the Chesapeake Bay. Saw several boat races going on and our captain explained what would be taking place with each of the boats. Great cocktails on board, too."