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

Oh what a beautiful Sunset

Sailing into Annapolis for Sunset

Two blogs today for me! Our sunset sail was really nice. We had a family celebration of the marriage of Mr. and Mrs. Bull. They brought aboard a tiny 3 month old, who was quite adorable (and a life-jacket). She wouldn’t give up the wheel. We had a great sunset with Woodwind sailing past the … Read more

The Best Charter Guests EVER

Cliff sailing the Woodwind to Cantler's Crab House

This may sound like a challenge to all of the other private charter groups  that have sailed on the boat, and all the ones that are upcoming, but it is not a challenge. It is a reflection of how nice people can be to their fellow employees, our crew and waitstaff at the restaurant they … Read more

Wine and the Wind

Drew Baker talks about Old Westminster Wine

We had two cruises today and they were total opposites of each other. The first cruise was a girl scout cruise of mostly teen aged girls. They learned about sailing, navigation and the Chesapeake Bay ecosystem. Each girl would go to all three stations where the crew would engage them in fun discussions and show … Read more

Pictures tell 1000 words

Woodwind Sailing under the Bay Bridge

Beautiful day of sailing! The day started with a successful team-building program for a local company in the morning. They learned how to sail around buoys and navigate safely in the Bay, while using great communication. On our second sail, we took out another private charter for a regional office outing. The wind picked up … Read more

Magical, Musical Cruise

Another pretty sunset over Annapolis

Pretty lucky weather we are having here in Maryland. We have had cool, dry conditions for the past 3-4 days and it has been gorgeous. We started the day with a private charter that had enough breeze to get under the Bay Bridge and back… well sort of. The wind died and changed direction a … Read more

Seeing over the Steering Wheel

Sailing the Woodwind again. Holding up picture of when she was little and sailed

For Woodwind, we only had two sails today. A 3:00 and a sunset sail at 5:30. Both were public cruises. On the first sail there was a nice size birthday party, and on the sunset sail we had a Air Force retirement party of about 20 people. If course there were other guests aboard, these … Read more

20 Years Ago…

Claudia having fun sailing

It is so amazing to me that my family started Woodwind twenty years ago. Every so often I am reminded of how long ago it was, although sometimes it seems like yesterday. Read on and you’ll see where I am going with this. Thursday’s sails were incredible. The first sail, now at 12:30, we sailed … Read more

Spectacular Saturday

Mark shows his son Nate how to sail the Schooner Woodwind. A new crew-member in the making.

Winds 10-15 knots from the North East, temps in the high 70s, a couple of clouds in the sky and tons of boats on the Chesapeake were the ingredients of a spectacular Saturday. The first sail started with an exuberant bachelorette  party for Colby with 11 of her friends. Other folks shared this cool sail … Read more

The Perfect Photo Cruise

Photo by Charlotte Faracai of the Thursday Night J Boat Races

Today we had the perfect night for learning how to take amazing photos on the water. Roger Miller hosted a Photography Workshop aboard the Woodwind. It was fun, as the captain, watching a group of 25 people rotate around to catch the perfect picture. I also had fun trying to place the boat in the … Read more

Schooner Woodwind
410-263-7837