2024 Sailing Season is coming! See you April 13, 2024!

History Mondays are Winding down

William as John Sands on History Monday

  Only one more History Monday to go for the season.  Tonight we had William from Historic Annapolis out with us and everyone thouroughly enjoyed his portrayal of John Sands. Thank you William. Besides William’s wonderful performance we also had wonderful sailing. The breezes were blowing between 12-15 knots and the boat was roaring along. … Read more

Saturday’s Sails….B&B Sunrise

Sunrise In Annapolis Aboard Schooner Woodwind

We had a great day of sailing today. The winds were steady in the 12 to 15 knot range and we had a 4.5 hour  charter. We sailed down to Thomas Point Light and then most of the way to Bloody Point Light then all the way back up the bay to home. What a … Read more

Saturday’s Sails….B&B Sunrise

Sunrise In Annapolis Aboard Schooner Woodwind

We had a great day of sailing today. The winds were steady in the 12 to 15 knot range and we had a 4.5 hour  charter. We sailed down to Thomas Point Light and then most of the way to Bloody Point Light then all the way back up the bay to home. What a … Read more

Another Great Day of Sailing…..

Jim and Michele at the Wheel of Schooner Woodwind

And the wind came up for the end of the week just great. We had 3 excellent sails today. On our 1st sail we had a couple that actually grew up with one of the brother s that owns the company in Albany,NY. where the Woodwinds were built. Michele and Jim had a great time … Read more

It’s Schooner Season

Schooner Woodwind and Martha White meet in Annapolis

I hope this fall sailing pattern is setting in. We have had some  glorious sailing days in the past 5 days. Today was no different, we had winds just topping 10 knots and beautiful blue, crisp skies. The first trip filled up quick for a mid-week lunch-time cruise. A local association treated their employees to … Read more

Sandbagger? “What are you talking about?”

Skipjack on the Bay

We had an unusual combination of circumstances to make today’s cruise special and hopefully this will result in a unique blog.  The most important part of the blog is that one of our guests, Luc Lapointe, is an excellent photographer and was kind enough to share his talent with us.  Thank you Luc. I have a … Read more

Can You Say Fall Sailing….WOW

Sunset Anniversary Sailabration

We had the most incredible day of sailing yesterday. Everyone who came out with us was treated to one of the better days of sailing we’ve had in a long time. The temperatures felt like a nice fall day. Cool, crisp and really clear. The visibility was fantastic up and down the bay all day. … Read more

International Sailors

Peace from Japan aboard the Schooner Woodwind

Yesterday, an awesome cold front moved across the Chesapeake.  The temperature dropped 25 degrees in 30 minutes!  This brought some very mild and comfortable conditions today.  The air had the crisp smell and feel of the autumn season. Aboard the boat today we had a girl from Tokyo!  She was a former exchange student visiting … Read more

Wedding, Winds & Wetness

Wedding aboard the Schooner Woodwind II

What a day! The day started out with the wedding of Stephanie Mafrici and Frank Cook. This couple sailed with me earlier in the season to see about having their wedding aboard. By the time we got back to shore the wedding was planned.   They wanted the ceremony to be on the Woodwind, while … Read more

FAST Sailing, Some science, Lots of excitement

Woodwind sailing cruises Marriott Waterfront Hotel, Chesapeake

The wind was blowing 18 to 25 knots from the South.  This is a windy day with a little bit of chop to produce spray enough to occasionally douse the guests forward.  With the sun and warm temperatures, the spray is refreshing.  We are flying through the water and at one point hit 11 plus … Read more

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