Step 2: Choosing a sailing school

"Island Dreamer", a 41 foot Morgan Out Island, our platform for ASA 103, 104 certifications

"Kermit", a 20 foot Balboa we used for ASA 101 certification

When Sharon and became serious about learning to sail - for us formal education was the only option.  I personally don't know anyone locally that sails, and I also wanted a skilled instructor that would adhere to some sort of structured program, versus some guy saying "pull that line over there and crank this thing-a-ma-jiggy" in between chugs of beer.  I do know one captain that is not officially an instructor, but someone whom I would fully trust to teach me.  However, his west coast location, and the fact that we would have no official proof of my instruction, eliminated him as a possibility.  When considering a life aboard, I wanted to know we had educated ourselves correctly, and not cut any corners.  After all, one day our lives might depend on it.

Sharon reviewing ASA course books aboard "Island Dreamer"

After doing much research, I also decided that we should obtain some sort of standardized certification.  While no specific license is required to sail (non-commercially), US Sailing and American Sailing Association are two widely known and accepted standards.  By showing these levels of certification, it is official proof of the training one has accomplished for their sailing resume - be it for bareboat chartering (renting and skippering a yacht yourself), or for possible employment.  Deciding that education standards were a must helped to narrow down the type of schools we would consider.

Tim at the helm of "Island Dreamer" under Capt. Margie's command

The American Sailing Association and US Sailing both have similar levels of certification, starting with the basics of keelboat sailing, progressing up to and beyond bareboat chartering.  My goal was to achieve proficiency to a level in which we would feel comfortable enough in our skills to safely live aboard a 40-50 foot sailing vessel.  With this goal in mind, it was decided that we should aim for Basic Keelboat, Basic Coastal Cruising, and Bareboat Charter certifications.

Sailing "Island Dreamer" through a narrow mangrove channel

Google search quickly found a local school on the Connecticut's southwest coastline of Long Island Sound, offering US Sailing courses.  On one hand, the benefit of a local school would be the ability to schedule at least a portion of the schooling on weekends, thus saving vacation time.  On the other hand, a local school is also a downfall.  We don't like Connecticut, nor do we feel we fit in here - so why would we ever feel comfortable with a Connecticut school or a class setting here?  Also, education of any flavor is generally expensive, and this school was no exception.  The final nail in the coffin for the local school, was the complete unresponsiveness from the owner when I asked for additional information.  His nonchalant and seemingly non-caring attitude towards me as a possible client quickly helped me eliminate his school as an adequate solution.

Sharon at the helm of "Island Dreamer"

The next best option to local training, was to find a school somewhere in an enjoyable area, where we could pursue our education as somewhat of a working vacation.  I found lots of options in the Virgin Islands, as well as Florida.  But one school really stood out.  Touting the advantages of private, "couples to couples" instruction (a husband/wife instructor couple teaching a husband/wife student couple), as well as a no-yelling policy, Island Dreamer Sailing School grabbed my attention.  Located in Miami, and offering certification while sailing in the Florida Keys was also a very appealing benefit.  While Sharon was still unsure, I was quickly beginning to think this was the right school for us.  Even with the added cost of airfare, this school was still less expensive than the local option we had explored, and offered a much more private and tailored program considering there would be no other students.

I placed a call to Harold Ochstein, the owner of the school, and also an instructor.  Harold immediately convinced me that he truly understood our needs, and our reasons for seeking knowledge towards a new life adventure.  This was not a used car salesman making a sale, this was a guy that had been in my position, and had gone through the things we were facing.  Cementing our choice, Sharon also placed a call to Harold herself.  Harold's calm, reassuring nature soon put all of her concerns at ease.  With our decision made, and acknowledgement of the work ahead of us, dates were decided and contracts were signed.

Capt. Harold Ochstein grilling a great meal aboard "Island Dreamer"

It was real now.  Funds were committed.  Much like college, once a few thousand dollars vacates your checking account, it all gets a little more serious.  An even more valuable commodity, vacation time, was also entered in work calendars.  More precious than gold to us, we would have one full week less to spend at our vacation home to ease the stresses of living in Connecticut.

Promptly after booking with Island Dreamer Sailing School, our course materials arrived in the mail.  With a matter of months until our week aboard Island Dreamer with Captains Harold and Margie, we had three course books and a lot of material to cover.  Each of the three levels of certification we were pursuing would require passing a written test, and also demonstrating our skills via a practical assessment aboard.  It was immediately apparent that if we were to be successful, we would need to cover all the course materials before our week of training aboard Island Dreamer, thus allowing us to focus fully on all the physical sailing skills.  Our lunch hours and evenings would be filled with regular reading and study sessions.  Our week aboard was approaching.

ASA Course Materials