Captain’s Blog

How could it. Sailing on the Schooner Woodwind and Flying dog Beer. Every Tuesday for the month of August is Flying Dog Beer tasting night on the Schooner Woodwind. Tonights line-up included their Woody Creek White, Old Scratch Amber lager and Snake Dog IPA. Ben Wiser from the Flying Dog Brewery was on hand to … Read more

Monday started out with a forecast of rain, no wind and not too many passengers signed up. But that all changed! It didn’t rain all day, the wind picked up and blew 10 knots most of the day and everyone figured this out and came sailing with us. Our 1st sail of the day took … Read more

Easterlies can either bring rain and nasty weather or dry light air  (sometimes almost no wind) sailing.  Saturday was neither.  The wind was light, but strong enough to provide us with nice sailing and comfortably cool temperature.  It also allowed us to head toward Thomas Point Lighthouse.  On the first three trips we were able … Read more

Breeze on! We had a wonderful 1st sail with only 4 people all the way down to Thomas Point Lighthouse and back. The wind was blowing 15-18 knots from the NW and it made it an easy sail . Everyone got involved in raising the sails and steering the boat. The crowds were light, I … Read more

History Monday is always a lot of fun. And this Monday proved to be the same. New fact: Did you know Chesapeake is Algonquin for “shellfish bay” ? The winds were very light to start the day off, but picked up a little as the day wore on and we were able to ghost around … Read more

Saturday was a great day to be on the water. Actually I don’t think I’ve ever found a day that isn’t better once you get out on a boat. Wind or not. And that’s the way it was today. We did a lot of motoring but saw a lot of great areas and had some … Read more

Thursday was a great day for sailing. The temperature was down and the winds were up . We sailed under the Bay Bridges 3 out of 4 of our trips. We had some great folks out today as well. On our 1st trip of the day Joe came out with his grandfather and helped me … Read more

Most people think the perfect day is blue skies and bright sunshine.  While that is great for business, please take it from me, come sailing with us on a cloudy but windy day and there is magic.  Ask these happy people.   Not only did our guests have a dramatic sky, but also, with less … Read more

This was a pleasant day on the Bay.  As you can see by the photos, everyone is relaxed and enjoying the moment. Frequent sailor Jay and his grandson, Drew, joined us and they brought Drew’s cousin Andrew.  Drew took the helm.  Very nice to see how well Drew was able to handle Woodwind II with … Read more