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Sailing School

Have you ever wanted to learn to sail, advance your skills, get blue water experience, or learn about cruising a boat to remote locations? If so, join me for a week or more aboard the Guiding Light as I show you the basics of sailing and cruising.

I have two options for you. The first is chartering the whole boat for a week with friends and/or family for $6000 plus expenses and telling me you want to put an emphasis on learning to sail. The second option I call my “cruising experience” charter, where you charter a cabin for $3000 per week, plus expenses, for a minimum of two weeks as we cruise around and explore the world. The latter is the better option, in my opinion, because this gives you more time aboard in an actual cruising environment to gain valuable experience.

Speaking of experience, I often get questions about certifications. While I am an ASA instructor I am not affiliated with an ASA school, so I can not give out certifications. This is actually not a big deal since all the certification really does is tell bareboat rental companies where your knowledge level is and you can do this just as easily by showing your experience aboard the Guiding Light on your sailing resume. Plus, I think you will get way more knowledge and experience aboard the Guiding Light on a “cruising experience” charter than you will in a certification class offered at the minimum time allowed. I do find it telling that many of the people I have had aboard to learn have since either successfully chartered a bareboat or have bought their own boat and are now cruising.

The other benefit you will get while aboard the Guiding Light, besides lots of learning and experience, is plenty of time to snorkel reefs, visit beaches, hike, see waterfalls, etc. Basically getting all the benefits of a vacation while learning to sail and cruise.  Let’s call it a LEARNCATION!!! Check out the calendar for my availability to see when and where you can come aboard and start learning.

Driving the boat
Unzipping the bag
Brian learning to sail
Driving and instructing


“We were two couples from Colorado with a goal of learning how to sail a catamaran so that one day we might become full time cruisers. Shane’s program of hands-on ASA instruction fit our goals perfectly.  And what better place to do it than the BVI’s.

Shane’s teaching method of “I’ll show you once, and you do it after that”, but still there with a guiding hand, was great.  Motoring, picking up a mooring, anchoring, plotting a course, and then finally raising the sails.  By day 4, we were running the boat and having a great time.  When approaching other boats, Shane would quiz us often about who has the right-of-way, and ask us why.  All of this was wonderful practical learning experience that you can’t get from a book.

The guys wanted to know practically everything about the boat and Shane was very patient and answered all of their questions.  They opened every access panel, discussed all the systems and components, checked and filled the engine oil, and ended up with an excellent understanding of a catamaran.

We also had plenty of time snorkeling, relaxing, and having fun.  We’ve never quite had such a vacation where we completely lost track of day and time.  What a life!

Thanks so much for an awesome week Shane!  We hope to be anchoring beside you on our own boats someday soon.” – Melissa & Chris

I am an American Sailing Association (ASA) certified instructor in Basic Keelboat (101), Basic Coastal Cruising (103), Bareboat Cruising (104), Coastal Navigation (105), and Cruising Catamaran (114).

I taught in Denver for four years at Victoria Sailing School on their J22s, where I learned I have a talent as an instructor.  Then in 2009 I bought my boat and promptly sailed it from the BVI to Houston, TX on a 16 day passage. After that I sailed the boat along the Gulf and East Coast of the USA all the way up to Nantucket and back to the Florida Keys. 2011 saw me sailing through the entire Bahamas island chain before starting my chartering business and sailing school in the Virgin Islands in 2012. Since then I have extensively sailed the Leeward and Windward Islands of the Caribbean. All of this has given me valuable sailing and cruising experience, which I love sharing.

So why don’t you charter the Guiding Light and come down for some sailing instruction (and, more importantly, experience) just like lots of other people have already done? Until that time please enjoy the videos and blogs I have made to help aspiring sailors out.


Enjoy the following sailing school videos and don’t forget to check out the sailing school blogs below. If there is a sailing subject you would like me to write about or make a video for, please let me know.


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