We’ve been lucky to paddle in some amazing destinations and meet some fantastic people along the way. Every year we invite some friends & fellow coaches to join us at Osprey to offer some specialized courses.

John Carmody

With the exception of a few misguided years a while ago, John has lived on the ocean his entire life. He has been in and around most every type of boat, tending towards the wind and human powered types. Almost 20 years ago, the sea kayak became his vessel of choice, and he has enjoyed adapting his “Big Boat” skills to kayaks.

John’s love of the traditions of the sea is infectious as he passes his seamanship and navigation skills on to his students. As a Coach, his understanding of the human body and biomechanics, gives him unique insights into what will make his students more efficient, safer from injuries and better able to enjoy these centuries old craft in more exposed environments.

John has led trips throughout Maine, the Canadian Maritimes, and the British Isles. He regularly instructs at Kayak Symposiums throughout the US.

John is a BCU Level 5 Sea Coach, ACA Advanced Open Water Instructor, ACA Level 4 Surf Instructor, BCU 4Star Sea Assessor,
Wilderness First Responder, & Registered Maine Sea Kayak Guide.

contact [email protected]

Joshua Hall

Josh is the Outdoor Recreation Program Manager for the Charleston County Park & Recreation Commission and the Program Chairman for the East Coast Paddlesports & Outdoor Festival. He holds ACA certifications as a Level 5 Advanced Whitewater Kayaking Instructor and Level 5 ITE Coastal Kayak Instructor. He was the country’s first Level 2 Essentials of SUP ITE, and has taught L-2 SUP certification classes throughout the United States.


Omer Singer

Omer is the co-owner of Terra Santa Kayak Expeditions. He lives in Israel, but he received his kayak instructor training & certification in Wales. Omer has lead many kayaking trips around the world, and has a vast knowledge of sea and river kayaking, but he is truly a surf and whitewater kayaker at heart. He is a BCU level 4 coach and guides our Greek Isles Adventure.

Click here for Omer’s website.

Cheri Perry & Turner Wilson

Cheri and Turner are sole partners in Kayak Ways llc, a venture based on the notion that the traditional kayaking skills and tools of the Inuit seal catchers offer valuable lessons for the modern day recreational kayaker.

A paddler for 18 years, Cheri has taught Greenland-style kayaking for three years at several national kayaking symposia. She competed in the Greenland National Kayaking Championships in both 2004 and 2005, in events ranging from rolling to individual and relay races, winning 12 gold medals. She has won several rolling competitions in the United States and is widely regarded as one of the best Greenland-style kayak rollers in the world. Cheri and her incredible aptitude for rolling were featured in the action sea kayaking video “This is the Sea 3”

Turner Wilson has taught Greenland-style kayaking for 5 years, at several national kayaking symposia. Turner competed in the Greenland National Kayaking Championships in July of 2005, in events ranging from rolling to individual and relay races, winning 6 gold medals. He has demonstrated Greenlandic kayaking techniques from Maine to New Zealand, and has served as a judge at many rolling competitions. He has presented several talks relating to Greenlandic kayak technique and Greenlandic culture, as well as skin on frame kayak construction to participants of events across the country and beyond.

Click here for Cheri and Turner’s website.

Rob Fisher

Rob has been a part of the Osprey family from the very beginning. He is a south coast local who knows all the best paddling spots. His natural athleticism, local knowledge and easy-going personality make him an exceptional instructor. Rob is not only a talented sea and surf kayaker, but also an excellent prone board & SUP surfer. Rob is now a full time Flight Instructor at Bridgewater State University but we try to get him out on the water anytime we can.


  • ACA Level 4  Coastal Kayak Instructor
  • ACA Level 3 Surf Kayak Instructor


Kaitlyn Fowle

An outdoor professional, Kaitlyn has instructed & guided kayaking adventures from Florida to Maine. We were lucky that Kaitlyn likes to play in the rocks and surf because that is what drew her to Westport & Osprey. She is an avid Stand Up Paddler and cruises the river and rips it up in the surf. Whether sitting down or standing up , Kaitlyn is a top notch instructor whose enthusiasm will get you fired up on any paddling adventure. She is currently the assistant director of Maine Bound Adventure Center at the University of Maine.


  • ACA Level 4 Coastal Kayak Instructor
  • ACA Level 3 SUP Instructor
  • Maine EMT


Jessica Davis

We were introduced to Jess through Saint Micheal’s College Outdoor Program, where she was not only a student, but a whitewater kayak instructor and program assistant. She has a wealth of experience working in the outdoors, from teambuilding and adventure skills training to guiding and instructing both whitewater and seakayaking adventures. Her keen eye can quickly assess your learning style and adapt to present information to you with the best approach for success. Jess has a dry & quick wit that matches her high energy & drive and keeps her lessons and tours fun & exciting.


  • ACA Level 4 Whitewater Kayak Instructor
  • BCU 3 Star
  • WFR


David Lee

We met David when he was a student on an instructor training program. We immediately knew he would become part of our team. David is truly the nicest person we know. He has an easy going way about him and a fantastic sense of humor that make every trip a great experience.


  • ACA Level 3 Coastal Kayak Instructor
  • CT EMT
  • RN


Bob Baldridge

Bob has been with Osprey Sea Kayak from the beginning as both friend and guide. He is an accomplished outdoorsman, who enjoys fly fishing, whitewater canoeing, and of course sea kayaking. Bob has spent most of his life exploring the south coast and Westport shorelines. He has been involved with many kayak clubs and organizations, and we treasure his knowledge. His perspective and patient style have helped many new paddlers to increase their knowledge and fall further in love with the sport.

Bob loves his new board


Osprey Sea Kayak Adventures
489 Old County Rd.
Westport, MA 02790

American Canoe Association, Canoe and Kayak Recreation

Our Instructors are American Canoe Association (ACA) certified, British Canoe Union (BCU) coaching certified, or both

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