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

Crabs, Beer, & Sailboat Racing (that’s what Annapolis does)

Sailing to a Crabfeast at Cantler's Crab House on the Schooner Woodwind

Quoting a line from Wedding Crashers to make it appropriate here… but it’s so true! We sailed to a crab-feast, the guests had plenty of beer, and then 2 Maryland Breweries battled it out on the racecourse to see who would take home the Brewer’s Cup. All in a day’s work. The day started with … Read more

Wine in the Wind

Wine in the Wind, Woodwind in a glass!

Today was all about wine. “Wine in the Wind” is the name of our wine tasting cruises aboard the Schooner Woodwind. The region for this month’s tasting was Down Under Wines, New Zealand and Australia. Howard Dinkel from Bacchus Distributing was aboard to educate us about wines from this region and to explain about the … Read more

Great wind for 2 sails

Schooner Woodwind sailing fast in Annapolis

We had a terrific day today with 2 great, windy cruises. We hit over 10 knots. The guests aboard both of our cruises really appreciated that we really sailed. And sailed fast. The boat was healing nicely over and everyone felt the excitement of a wonderful sail. We had a lot of sailors aboard and … Read more

Teachers, Clouds, Buy Boats & More

Beautiful sunset over the Annapolis City Skyline

Our first cruise of the day, 11:00 sail, we had a light breeze from the North that allowed us to sail at around 5 knots of boat speed, out into the middle of the Bay, into the shipping channel and back. We saw a bunch of anchored ships. One named “Genius” (funny name for a … Read more

Wood-windy!

Sailing up the Severn River on the sunset sail as its raining

What a day!  Amazing wind for the middle of summer. You have to love the days, as a captain, when you need to warn people where the “splash zone” is. On the first sail, we had 20-25 knot winds and sailed under the bridge in what felt like record time. On the way back to … Read more

Intimate Details

The Harbor at dusk with all of the lights and moored boats

Enjoying everything local dinner cruise to celebrate our 9th wedding anniversary. This is how we ended our evening. What a view! Photo by Stephanie Sutton of Eldersburg, Maryland

Moonlight and Romance

2012_07_29-9th-Anniversary-Dinner-Sail

After a lovely evening with my wife celebrating our 9 years of marriage on the Everything Local dinner cruise , we sailed into Annapolis to this lovely view. Photo by Kevin Sutton of Eldersburg, Maryland

Room at the Bay Bridge

Woodwind sailing under the Chesapeake Bay Bridge while a car carrier crosses under too!

Our first sail was with 11 people. The wind was beautiful and the clouds reminded me of the Caribbean. We sailed out with great wind for the first half of the trip and then the wind dropped down just as we headed into the Severn. One of the comment cards read, “Amazing trip… I want … Read more

takin a day off so dad can sail

Sailing aboard the Woodwind II for a dinner cruise

Captain Ken wanted to sail so Jennifer got to enjoy time with the passengers. Photo by dave pierce of centreville, va This photo was entered into our photo contest, but I think it deserves it’s own blog. (I published 2 of his photo contest entries already.) Dave and his wife came from Virginia to go … Read more

Best Sunsets lately!

Great photo as Woodwind II passes us at sunset in Annapolis

Our first sail was a private charter for a pretty full boat. The partners of the company were taking out their summer interns to say thank you. The bottles of bubbly were a favorite amongst the crowd. We had some very interested folks who loved sailing the boat and talking with me about navigation. We … Read more

Schooner Woodwind
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