Instruction on Your Sailboat

The Options Are Limitless for Custom Instruction on Your Boat:
  • All Your Boat classes are expertly customized to your boat, your background, and your goals.
  • Learn to operate and sail your boat - start from the beginning.
  • Adapt your prior sailing and/or cruising skills to your new boat.
  • Advance your skills and extend your horizons.
  • Earn internationally recognized certifications.
  • Choose a specific skill set you want to grow.
Earn Internationally Recognized Certifications on Your Boat
  • Basic Keelboat
  • Basic Cruising
  • Bareboat Cruising
  • Coastal Passagemaking

Core Sailing & Cruising Classes

Start here for your best comprehensive sailing & cruising training

Cruising Sailboat Foundations

You're excited to get your new boat out and sail into the sunset.  But hold-on!  Can you get out of the marina in one piece?  This class gives you the foundation for operating your new toy safely - preventing the most common causes of damage.

  • Three full days on your boat, at your marina
  • Cruising Sailboat Systems
  • Close quarters Maneuvering
  • Top-end docking skills & strategies
  • Tuition includes up to 4 students on the boat
  • Contact us to schedule your class

Sailing Essentials:  Your Boat!

These are the core sailing skills and knowledge for safe, confident, effective sailing of any kind.  Whether your heading for the race course or sailing around the world - it all starts here.

  • Four full days on your boat, in your sailing turf
  • Earn your Internationally recognized, US Sailing Basic Keelboat Certification
  • Customized to your boat, your rig, your background and your goals
  • Tuition covers all materials & Certifications for up to 4 students
  • Contact us to schedule your class!


  • Cruising Sailboat Foundations (unless you own a daysailer)
  • Navigation Essentials strongly recommended

San Juan Immersion Cruising - Your Boat
  • A five day training expedition exploring the San Juan Islands and/or Puget Sound
  • A deep dive into the essential skills to keep your boat and crew safe, day and night, under sail and under power, anywhere in the San Juans and Puget Sound.
  • Earn your internationally recognized US Sailing Basic Cruising Certification
  • Tuition includes up to 4 students on the boat
  • Contact us to schedule your custom cruising class


  • Cruising Sailboat Foundations
  • Sailing Essentials
  • Navigation Essentials
  • Or equivalent training/experience

Advanced Cruising: Inside Passage and Beyond!
  • Prepare for extended cruising, and the challenges of the Inside Passage and Alaska
  • Earn the coveted US Sailing Bareboat Cruising Certification
  • Qualify to charter cruise anywhere in the world
  • Cross the border and enjoy seven days of immersion training in the Canadian Gulf Islands
  • Includes Night Operations training and Endorsement
  • Tuition covers up to 4 students on the boat
  • Contact us to schedule your custom class


  • Cruising Sailboat Foundations
  • Sailing Essentials/Basic Keelboat Certificate
  • San Juan Immersion/Basic Cruising Certificate
  • Navigation Essentials & Coastal Navigation
  • Or equivalent training & experience

Coastal Passage Making

Preparing to head offshore?  This class provides critical training for long, exposed passages, whether crossing into Alaska, exploring the west side of Vancouver Island, heading to Mexico, or embarking on a circumnavigation, don't leave shore without this.

  • Cruising Sailboat preparations for more exposed and longer passages
  • Overnight passages - preparations and practical training
  • Advanced seamanship for heavy weather conditions
  • Advanced navigation, including radar, electronics, and paper plotting & logging
  • Safety & emergency preparedness for remote locations
  • Seven out to sea. training in the Strait of Juan de Fuca and nearby Pacific coast options
  • Tuition inclusive for up to 4 students on the boat
  • Contact us to schedule your class


  • All on-water classes through Bareboat Cruising, or equivalent
  • Sufficient experience to prepare you for the rigors of this class
  • Coastal Navigation Certification

Custom Instruction on Your Boat

The Options Are Limitless, and designed around your boat, your background and your goals
➤  Adapt your prior sailing/cruising skills to your new boat
➤  Advance your skills and extend your horizons
➤  Earn internationally recognized certifications
➤  Choose a specific skill set you want to grow
➤  Contact us to schedule your customized class
Your Custom Program:
  • Begins with a look at your background skills and experience
  • We build the curriculum to reach your goals
  • We work with beginners through licensed captains
  • Challenge certification option for skilled & experienced mariners
  • Play & Learn option encourages organic learning experience while enjoying sailing & cruising with a highly skilled & licensed Captain/Instructor on the Salish Sea


Phyllis Woolwine

Phyllis Woolwine, AKA Captain Wooly, is a US Coast Guard licensed Captain, US Sailing Certified Keelboat Instructor, and National Board Certified Teacher.  She has spent her life on the sea, sailing all parts of the Inside Passage.  Captain Wooly is also a career professional educator. For over 30 years - both on and off the water - she has taught all types and ages of learners, in the classroom, on the sea, in the wilderness, in universities, high schools and private settings.  

Mark Hersh

Mark has been pursuing sailing on all sizes of boats for most of the decades of his life.  As part of Shearwater University, he has refined both his skills and instructional abilities to serve every kind of student on every kind of boat.  Your knowledge of your boat's systems, your ability to maneuver, dock and sail your boat will grow rapidly in the time you spend with him.