Meet the Crew

 Schooner Woodwind Captains

Great day for sailing on the Woodwind II. Of course I was smiling.


Sailing has been a vital part of Jen’s life since she was 5. Racing and cruising with her family filled her summers until she started teaching kids to sail. Her sophomore year in college, she sailed on a 125-ft schooner for credit in science, literature, and history. She now was addicted to schooner sailing. 3 years later, her family built the Woodwind. At 26, she became a captain.


Ken followed his passion and taught instrumental music for 25 years in Connecticut. When budget cuts ended the program he and his family commissioned to have Woodwind built and started the business 20 years ago. Ken considers himself very lucky indeed to follow 2 dreams. One about music the other about sailing. Now retired from the day to day captaining, he will certainly make an appearance again with us.

Schooner Woodwind Captain Mickey


Working as a Captain on the Schooner Woodwind is awesome. I figured out how to get paid for my favorite hobby(sailing). I started sailing when I was 6 years old right here on the bay. I am a very avid sailboat racer and when not working you can usually find me out racing. I lived/sailed in the Caribbean for 24 years, I returned to the Bay in 2008 and enjoy every day I am on the water!!


After 15 years looking for the perfect sailing job, he found it in the last place he looked. Isn’t that always the way? He couldn’t imagine living anywhere else.


Having always a love for being on the water, John started sailing about 14 years ago in Southern California and was hooked. His adventures have taken him from there to the waters on the east coast from Canada to the Bahamas and on the west coast from San Francisco to the Sea of Cortez in Mexico. Currently he looking forward to sailing on the Chesapeake Bay.


Andy learned to sail in a small day sailer on a lake in Pennsylvania. Eventually the lure of larger boats and better cruising grounds led him to discover Annapolis. After 25 years in a traditional desk job, a change was in order! He is now a certified sailing instructor and crews for us on Woodwind.

Schooner Woodwind Crew


This is Charlotte’s fifth season on the Woodwind. Since she started sailing seven years ago, it has taken her all around the Chesapeake as well as the Caribbean.


Growing up on the lower Chesapeake Bay Caitlyn fell in love with sailing and life on the water.  After three years of cruising on her own sailboat to the Keys, Bahamas and Puerto Rico she has found her way to Annapolis and back on the Bay where it all began.


Sailing has been tops on Peg’s list of fun since moving to Annapolis 18 years ago. She has had the opportunity to race and cruise on the Chesapeake with her family. Many days have been spent rafted up and nights anchored out with great friends, good food, and lots of laughter.


Sage has been working on schooners since 2014. She started on an educational sailboat in Long Island Sound, before moving to Boston to sail. She has also sailed in the Bahamas, up and down the east coast, Key West, and the Chesapeake Bay.


Chesapeake born and raised, Judy left Maryland to study Marine Sci, travel, and work at a craft brewery. She made her way back to Annapolis to pursue sailing, where she quickly singled out the two prettiest boats on the bay. This is Judy’s first season sailing with the Woodwind family and she promises the best Annapolis view can be found under sail on Woodwind watching the sister schooner pass by.


Sam grew up sailing on the Potomac River at Washington Sailing Marina. He loves visiting exotic places, automotive racing, playing music and animals. Sam just graduated from The Catholic University of America in Washington,DC where he was on the sailing team. Sam just moved to Annapolis and spends his free time exploring the city on his bicycle and meeting new people.


Pete grew up in the San Francisco Bay Area where he was fortunate enough to be a member of an oceangoing Sea Scout Program.  He operated both power and sail boats from Portland, Oregon, to San Diego. After graduating High School, Pete spent nearly 25 years in the US Navy / Navy Reserves attaining the rank of Master Chief Petty Officer and has over 3000 days of underway time.

Schooner Woodwind Sales & Support Staff

Beth, Schooner Woodwind Sales Manager


Beth is a natural born sales person. Her attention to detail serves her well in organizing private cruises and group events aboard Woodwind. Though she has not always been a sailor by nature, after several years sailing aboard the Schooner Woodwind she enjoys sitting back and enjoying a relaxing sail while Woodwind’s crew takes care of everything else.


Bill has lived in Maryland since 1992 and loves Chesapeake Bay and its tributaries. When not on the dock you will find him out on the water kiteboarding, sailing, or just cruising around the Severn River with his wife and two daughters.


I was born in Annapolis and raised in the surrounding area. The Chesapeake and her tributaries have entertained me as well as inspired delight throughout my life. I moved away once for 2 years, and could not wait to get back to the waters that fill and support my spirit! I love sharing my joy with others! Come see me at the Customer Service window on the dock by the Woodwind!


Originally from Hoboken NJ, I started out as an OB/GYN nurse then switched to my passion of setting up special events working for the Macy*s Parade & Special Events n NYC and freelance event planning, I know I can “Deliver” a memorable event for your group or private charter. My motto: Life is better with a tiara!


I am a life long sailor. I grew up as a “boat Kid” terrorizing the back waters of Lake Erie from my first motorized vehicle, an inflatable boat with an outboard. I grew up (so to speak) to become a professional boat captain and moved to Annapolis where I lived aboard my own 33 foot sailboat.  As an event sales associate for Schooner Woodwind, I get to share with our clients, my love for the sea.


Raised on the brackish shores of Annapolis, Miss Yumi has run away from home many a time but always comes back! She can’t seem to leave the best office window view in the world behind! When Miss Yumi is not holding down the WWIII fort, she’s teaching kids at Maryland Hall, working on ROGUERIES Jewelry or slinging oysters at Sailor Oyster Bar.


Donna is a sailor and loves family sailing! Here at home on the Magothy River, off the Chesapeake Bay, Donna and her friends sail her 24-foot Sovereign Sailboat. She has a 2017 sailing goal to complete her ASA 101, 103 and 104 Sailing Certifications. Her BIG Triolo family, for 24 years, love to charter two Catamaran Sailboats for Christmas vacations in the British Virgin Islands!


Fitz enjoys everything the great outdoors has to offer. Growing up on the Eastern Shore, he spends most of his free time hunting, fishing and crabbing. Fitz also grew up playing football and baseball which he still enjoys playing recreationally as well as watching his favorite teams on TV. Fitz loves spending time with his family, as well as his best friend Titan, his dog.

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