Our Instructors

Kat grew up in Brewster, MA, where she spent summers out on Pleasant Bay. She started sailing at the age of eight at Namequoit Sailing Association, eventually becoming an instructor and later the junior sailing Program Coordinator. After countless hours on the water, she still couldn’t stay away – she joined Arey’s Pond as a launch driver and now also manages purchasing, supports marketing, and runs the sailing school’s private lessons and rentals. She holds a degree in Environmental Policy with a minor in Linguistics from Middlebury College and cares deeply about making both sailing and education more accessible. Outside of work, she helps high school students with their college applications and enjoys spending time outdoors, collecting way too many houseplants, and any kind of adventure. She has a Launch Tender’s License, US Sailing Level 1 and CPR/First Aid certifications, and is an NWS-trained SKYWARN volunteer.

A native of Brewster, Jamie was raised on the beaches of the Outer Cape with stories of whalers, surfmen and shipwrecks. He learned to drive a boat before he could drive a car and quickly fell in love with life on the water. A career working in the outdoors as a filmmaker and educator would take him to the Norwegian Arctic, the Falkland Islands, and eventually to his second home of New Zealand, where he taught traditional sailing and bushcraft at the Outward Bound School. A former New Zealand Coast Guard rescue crewman, Jamie holds advanced First Aid certifications and a love for sharing adventures out on the water.

John is from Northampton, Massachusetts, and grew up sailing and racing dinghies during the summertime here in Orleans. During the school year, he is a student-athlete at Bates College, where he studies geoscience and chemistry and competes for the varsity men’s rowing team. John has taught sailing for more than three years and joined the Arey’s Pond team in 2024. He is excited to return for another great season sailing on Pleasant Bay!

Wim (sounds like “Vim”) grew up in The Netherlands where he began sailing as a teenager, and he has loved sailing ever since. While in college, he and a group of friends built a sailing school in Holland that is still operating today. Wim first came to the US to teach sailing at Stanford University in California. Wim’s travels on the water have included sails from The Netherlands to islands in the Caribbean, from San Francisco to the Gulf of California in Mexico, and from Nova Scotia to the Bahamas. Wim enjoys sharing his love of sailing with the beautiful Arey’s Pond community.