Private Lessons
$55 Per Person Per Hour
Private Lessons are completely customizable to your skill level and goals. A minimum of two hours is required for booking. We can also train on your personal boat.
First Sail Experience
$50 Per Person for 2 Hours (One time per student)
Learning to sail can be a big commitment and, while most people love it, it isn’t for everyone. This course is designed to give you the opportunity to try a lesson with Captain Matt at a reduced rate and see if sailing lessons are for you!
As a US Sailing initiative the First Sail Experience is a two-hour lesson offered to anyone through a growing list of First Sail Locations, comprised of community sailing centers, sailing schools and yacht clubs around the country.
This unique opportunity offers beginners an introduction to sailing in a casual setting and is designed to provide a memorable experience that will motivate newcomers to continue sailing.
Participants will get out on the water with an instructor in a sailboat provided by the First Sail Location. The First Sail Experience features basic hands-on learning on board a sailboat that will cover topics such as: how a sail works; parts of a sailboat; points of sail; and important safety guidelines.
Learn to Sail
$500 per person
This 32 hour course covers the basic theory and practice of sailing a keelboat. Based on the US Sailing standards, our course is 32 hours long, typically run over 4 days with a maximum student to instructor ratio of 3:1.
This course is designed to give you the basic skills required to start your sailing journey!
Topics covered include:
How to be safe on the boat
Parts of the boat
Points of Sail, proper sail trim, and how to “read” your sails
How to helm (steer) the boat and the essential crew positions
“Rules of the Road”
Essential Knots
Person in the Water Recovery
Docking
And much more!
Fall 2026 dates:
Weekend Sessions:
Weekends Fall 1: August 8, 9, 15, 16.
Weekends Fall 2: September 18, 19, 20, 21.
Weekends Fall 3: October 17, 18, 24, 25.
Weekday Sessions:
Weekdays Fall 1: September 8, 9, 10, 11.
Weekdays Fall 2: October 13, 14, 15, 16.
Weekdays Fall 3: October 20, 21, 22, 23.
All of the above sessions run from 9am to 5pm with lunch being eaten during classroom sessions or while sailing.
Spinnaker Workshop
$50 per person
This is a 2 hour workshop focused on the basics of setting, trimming, and dousing a symmetrical spinnaker with a spinnaker pole. This workshop is designed for new(ish) Wednesday night crew looking to learn how to fly a spinnaker in a non-race environment or for beginner/intermediate sailors who want some experience flying “the chute.”
Prerequisite: Basic sailing experience strongly encouraged.
Topics covered include:
Rigging the spinnaker
Setting the spinnaker pole
Hoisting the sail
Trimming a symmetrical spinnaker
Jibing a symmetrical spinnaker
Take downs (dousing the spinnaker)
*Multiple workshops will be offered and techniques used may vary on the night based on conditions. 2 hours is not enough to cover all of the techniques needed for spinnaker work, but will give participants a great foundation to work from.
Current Dates offered:
Thursday May 21, 2026 5:30-7:30pm.
Tuesday June 9, 2026 5:30-7:30pm.
Tuesday June 16, 2026 5:30-7:30pm.
Cancelation Policy: Cancelation requests for refund will be charged a $10 processing fee. No processing fees will be charged for a transfer to another course. No refunds or transfers will be granted within two weeks for the first class of a course or of a private lesson.
Cancelation Due to Weather or by Kilroy Sail Training: While we try to avoid canceling lessons, there are times that it is necessary due to weather or other unforeseen circumstances. If a class is canceled by Kilroy Sail Training a credit will be issued or a make-up day may be scheduled if available.