You can’t miss the beautiful, 74-foot schooner docked outside of Pusser’s, taking locals and visitors out on the Bay from Tax Day through Halloween. As they get ready to put in for a new season, kicking off their 16th season on April 13, here’s a little more about Captain Jennifer Kaye, one of the owner-captains of the family-run business, Schooner Woodwind Annapolis Sailing Cruises.

Get to Know Captain Jennifer of Schooner Woodwind

Where are you originally from and long have you lived in Annapolis?

J: I am originally from Wallingford, CT and have lived in Annapolis for 26 years, since October of 1992. I came here to start the Woodwind business with my family. We had signed a contract with the folks at the Annapolis Waterfront Hotel to have a 74-foot schooner on the docks for the 1993 season, so I was sent down early to promote and meet people and create a rapport with the people of Annapolis.

Funny story, I knew I was in the right spot when I went to breakfast at the old Eastport Deli (now the Eastport Kitchen) and one table next to me was talking about the big breeze over the weekend and how they ripped their spinnaker, and another table was talking about their engine having some water mixed in with their fuel, and the furthest table was acting out race rules from a race over the weekend. I knew I was in love with Annapolis from that moment on. We started sailing around June 3, 1993.

How did you get into sailing? 

J: When my parents were married, they wanted to learn a sport that they both didn't know. They were school teachers so they chose sailing. When I was born, they continued their sailing and took me along, supposedly putting me in a below hammock on their 17-footer. As time went on, the family boat grew to 21 feet, then a 25-foot sailboat, and then finally a 31-footer. That last one we really sailed, on month-long summer adventures from Connecticut to Maine. We actively raced that boat as well, on most summer weekends and Wednesday nights. When I got old enough, I became a sailing instructor at our local sailing club.

What is your favorite thing about your job? 

J: I love introducing people to the magic of sailing. To me, there is no better moment than when you turn the engine off and it's so quiet, and the boat still moves forward with no noise other than the small bow wave it is creating. Then we start talking about Maryland craft beer, conservation of the Chesapeake, or how an osprey catches a fish. I love sharing things that I love with other people.

What is your favorite thing about living/working in Annapolis? 

J: Where to start… I love being so close to the water. The history also speaks to me, especially how involved our forefathers of our country - who lived here and partied here - made HUGE decisions about the future of our country, right here.

What are your favorite things to do/eat/experience in Annapolis?

J: To do? anything on the water. I kayak, paddleboard, walk or drive to see sunsets or sunrises on the water, and I just like to sit on or by the water. I also love to increase my knowledge of the history of the area, finding new hidden gems. For dining, I love seafood, and Sailor Oyster Bar has a lot of it, from their oysters to their crudo. And then there's Vin 909 Winecafe for pizza and a salad - I can't force myself to order anything else, it's that good. For experiences, that would be the local music scene. I love watching Michael McHenry jam out on his guitar.

What are your favorite places to experience nature in Annapolis off the water? 

J: Off the water, is there such a thing? OK, let me think... I like Quiet Waters Park, especially where it's the hilliest in the forest and the trail winds around. I drive up to Bay Ridge Road to watch the full moon rise over Kent Island a lot. (Beautiful spot, but yes, still on the water.)  I also love the Nature Trail on Greenbury Point, where the old radio towers are -- but because it's near the water.

With Boat Maryland Week coming up, now is the perfect time to get on the water. If you want to know more about Schooner Woodwind Sailing Cruises, or all of the other ways you can celebrate the deep-rooted maritime history in Annapolis, check out Visit Annapolis and plan your water-adventure today!


Images courtesy of Schooner Woodwind Annapolis Sailing Cruises