Author Archive | Captain Jennifer

J-Boats racing in very, very light air taken from our sunset sail on the Schooner Woodwind

Chillaxing on a Light Day

Today, we had a private charter book us for a 3 hour cruise. No… not the Gilligan’s theme song.  They were 5 minutes late, so no need to sing. Anyway, they all were teachers in a private school and wanted to relax before the first day of school on Monday. Relax they did. With very […]

Blue Herons in their nests up Chase Creek, on the Severn River

This Cruise was for the Birds

Another light air day on the Schooner Woodwind II. The first cruise had wind, and the others had enough to sail up wind but motor downwind. All through the day we saw tons of birds. And lucky for us, we had Don, our bird enthusiast, aboard as crew. We saw cormorants flying in V-shaped formations […]

Schooner "Adventure" sailing towards Schooner Woodwind II in Annapolis

When Schooners Meet

Today was a great, very light day. The wind started out very light on our first cruise with just 5 people. It was overcast and cool, and as much as we tried to sail, there was not enough wind. We took them up Back Creek. They really enjoyed it. We had a family from England […]

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

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

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 […]

Wine in the Wind, Woodwind in a glass!

Wine in the Wind

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 […]

Schooner Woodwind sailing fast in Annapolis

Great wind for 2 sails

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 […]

Beautiful sunset over the Annapolis City Skyline

Teachers, Clouds, Buy Boats & More

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 […]

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 […]


Intimate Details

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

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

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