Step 3: Get a small boat and "sail the hell out of it"

After deciding on ASA certifications, and signing contracts with Island Dreamer Sailing School, my next step was clear.  While researching how we would learn to sail, one piece of advice was common among all the skippers I had spoken with.  Without exception, everyone recommended finding a small sailboat, or sailing dinghy, and "sail the hell out of it".  Our ASA training would be followed up and supplemented with sailing our own small sailboat.

The idea behind sailing a small boat is that each and every move the skipper and crew makes, along with each slight change in wind or waves, makes an immediate and drastic perceived effect on the boat.  This differs from large, heavy, keel based sailing yachts where actions with wind, sheet, and wheel are not as easily recognized.  It was explained to me, that by gaining lots of experience on a small sailboat, I would learn to have a much better "feel" for the boat I was sailing and what effect my actions had upon it, therefore making me a better sailor.

Me, first time sailing a Laser (Virgin Gorda Sound, BVI)

Deciding to buy a small sailboat was far easier than the actual act of making the purchase.  There seemed to be endless options.  At first I thought about really small dinghies such as the Laser and the Sunfish.  I had a little experience sailing a Laser in the Caribbean.  It was a lot of fun, but it didn't really appeal to Sharon after she watched me repeatedly get catapulted into the water, thus doing more swimming than sailing.  Lasers, Sunfish, and the sort, are agile rides but they share the downfall of being a very wet ride and being more or less intended for one person.  These options were out.

Next I started looking at what seemed to be the next size up in dinghy sailboats.  These boats were generally in the 14-18 foot range and many models are sloop rigged (a main sail and a head sail) which is great as it is ultimately the type of rigging encountered on yachts we would consider living on.  These boats have virtually no ballast (the skipper and crew make up the ballast), and employ either a dagger board, or more commonly a swinging centerboard.  Another plus, is that they are "trailer sailors", meaning they are carried on a small boat trailer, are easily/quickly rigged and launched, and can be readily stored in one's yard right on the trailer.  These types of boats seemed like a good fit, but the majority of options I found were geared towards racing, and "one design" race classes (Thistles, Catalina 14.5, Mutineer, etc).  The problem for me with race boats, is that they generally have very low sides (freeboard), are extremely twitchy, require hiking (crew hanging off the high side of the boat) and end up giving a very wet ride with a high chance of capsize.

Getting acquainted with "Rhumb Line" on Bantam Lake

An important part of my selection would be keeping Sharon interested - meaning dry and comfortable and relaxed.  Wet, twitchy, capsizing boats were not part of what she was willing to explore - and owning a boat she wouldn't sail was pointless.  I needed a boat with a design and features aimed at leisurely recreational sailing, while still allowing for spirited sailing in stronger weather.  Larger trailer-sailors in the 20-22 foot range were available but presented a few other problems (Catalinas, Potters, etc).  Firstly, they take up more room while stored on the trailer.  Second, they take a long time to rig before sailing.  Lastly, many of these boats are more meant to be launched and retrieved once a year, and left on a mooring during the sailing season.  This was not an option for me.

Our American 14.6 "Rhumb Line", at Bantam Lake boat ramp

With my criteria set, I was having a hard time finding options.  Each winter, I attend the Hartford boat show to check out all the latest in power-boating.  Unexpectedly, there were two small sailboat vendors in attendance - Catalina, and American Sail.  I was immediately drawn to a couple of American Sail models - the American 14.6, and the American 18.  These boats stood out with features geared not towards racing, but towards an relaxing day on the water.  They were straight forward beamy (wide), sloop rigged with quality Harken blocks and hardware, and were made from hand laid fiberglass right here in the good ol' US-of-A at a family owned and operated company.  These boats featured a no-hiking design with a hard chine hull, overhead boom height (no ducking on tacks and jibes), forward storage compartments in the bow, high backed comfortable seating, motor mounts, swim ladders, and even a place for coolers.  The owner, Dave Stanton, quickly had me enamored with these boats which he sells in nicely setup packages.

After a continued month of researching and looking for other options, I couldn't find a better boat to suit our personal wants and needs for the sailing we wanted to do.  I ordered my American 14.6 optioned with a Plexiglas door for the bow storage, a motor mount, Honda 2.3 outboard, trailer, multi-colored main sail, and cover.  While most use boats like this without a motor, it was a requirement for me.  My sailing grounds would be Long Island Sound, and the launches available to me require motoring out of channels upwards of a mile before being allowed to raise sails.  On delivery, I outfitted my American with a Danforth anchor and 100 feet of rope rode, a handheld Garmin GPS, waterproof charts, lines, and a few bumpers.  After our ASA training, we would be ready to "sail the hell out of it".

At the helm on Bantam Lake

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

Welcome

After years of hearing the buzz-word "blog" and always assuming I would have nothing to do with it, a friend suggested I might use one to document my travels and the new adventures of which my wife and I are about to partake. After much reflection and contemplation of our current life, we recently began to turn our dream of making a life in the Caribbean into something more of a plan. 

Happy Hour, Saba Rock, Virgin Gorda

While we still view our endeavor as a bit far-fetched, we are taking it more seriously and starting to take steps towards moving aboard a sailboat in the Virgin Islands. Here in this blog, I will go back in time a bit with our travels through the islands, from our first visit to our current journey of learning to confidently skipper sailing yachts. 

At the helm of "Antiquity"

Everyone needs to start somewhere. We are on step 1 in what I am sure are more than a million steps. We may not succeed in our goal. We know that. However, we also know that if we never try, it will be guaranteed that we fail.


"Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." - Mark Twain