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

Islands and ADKs

When my wife and I met, there was no way we would have ever known we would one day be contemplating a complete change in direction after well rooting ourselves with houses, careers, etc.  Some things happen simply by chance, while others are a product of one's surrounding environment.

Sharon and Rebel snowshoeing

The very first time I took my future wife to my hometown in the Adirondacks, we stepped out of my Dodge pickup into -22F temperatures and a windchill with a punch like Mike Tyson.  Friends soon arrived at my doorstep to take us out for a night on the "town".  We took her to some local watering holes of dubious distinction - "The Skunk's Nest", "The Wayside" - only the classiest joints for me...  The fact that she didn't want to leave by the next morning was a sign that she was a keeper.  The following day the excitement of showing her my beloved lake nearly got us in serious trouble.  In hyper anticipation of sharing my hometown, I soon found myself navigating my truck in the knee deep snow of un-plowed seasonal roads.  I had so anxiously headed out of the house that I had failed to properly prepare with boots, heavy coats and gloves - winter weather attire.  When my truck spun and ground itself down deeply into the snow I realized we were now sitting on the frame which was robbing precious traction, and we were far down a narrow one-way road.  We were still early on in our relationship so I worked hard to hide my initial panic.  After assuring her all was fine and "normal" I managed to execute a virtual 135-point turn, squeaking out enough traction here and there to get us out.  Awkward situation averted...  Soon thereafter it was summer again and we returned to the Adirondacks, and again to the lake.  The effect the area had on her was immediate and exactly what I had hoped for - she was smitten with the area I called 'home' just as much as I was.  I couldn't have hoped for more.

Crown Princess at the Bonaire pier

Years would pass and we found ourselves on our honeymoon.  Sharon was determined to show me a place that meant as much to her as my precious Adirondacks meant to me.  We booked a cruise with an eastern Caribbean itinerary.  I had seen the crystal blue waters of the Caribbean in pictures and on TV, always wondering if they were truly as turquoise as the pictures showed.  I also had an affinity for steel drums and reggae music, both of which I was hoping to experience while on this honeymoon cruise.  Words can not express the profound impact of seeing and experiencing these things in person for the first time.  Even though we were on a cruise and were viewing a very cleansed and diluted version, there was definitely something here.  As I was thrilled that Sharon had fallen in love with the Adirondacks, she was equally pleased that I was starting my own affair with the islands.

Aboard S/V Kuralu sailing back to Tortola

Over the next years we began to cruise every year.  We quickly found though, that we were not like the large majority of fellow cruise ship passengers.  While most were perfectly happy to quickly consume what the cruise line dished on a platter - we found that we were venturing further and further from the ship seeking adventure and a more "real" view of the islands we visited.  We booked our cruises a year in advance, chosen by itinerary.  We spent the year prior reading and researching, finding new places to explore.  More times than not, we went sailing and snorkeling away from the ship.  After each cruise it was a given that our favorite part of the entire vacation was away from the ship, usually on a sailboat.  This slow progression is how we were swayed away from cruise ships, and towards private sailing vacations.  While the cruise ships were a great way to explore a massive portion of the Caribbean islands in a short number of years, we were now narrowing our pursuit of adventure.  We wanted to go places on our own schedule, as we saw fit.  We wanted to go where cruise ships simply could not.  We wanted to reduce the passenger count from 3000 down to 2.

Fast forward almost 10 years.  It's time for a new life.  Our love of the Adirondack mountains, and of the Caribbean islands has not faded.  If anything, it has grown with us and matured from a lofty dream to a fledgling set of plans.  The parallels between the Adirondacks and the islands are uncanny.  The areas are rugged, as are the people.  Life in either place is hard.  Climates are challenging.  Weather can be brutal although opposite.  In the Adirondacks the winter can beat people and things into submission, while in the islands the heat and the dreaded hurricane season can weather even the heartiest of souls.  Populations are low.  Communities are tight-knit.  Tourism is the dollar king.  The list goes on and on.  I even dare to ask one to find a beach in the Caribbean without an Adirondack chair gracing its warm white sands.  And those local watering holes where I first took Sharon - "The Skunk's Nest", "The Wayside"?...  They are really nothing more than cold weather cousins of "Foxy's Tamarind Bar" and "Woody's Seafood Saloon".  As we embark on a journey towards a new life in the Caribbean, all we are really doing is adding heat to an Adirondack life we love.

Sharon at the Trunk Bay overlook, St. John USVI

The Drinking Man's Guide.....

We all dream of spending time at the quintessential palm lined white sand beach, surrounded by crystal blue waters.  After a day sailing, exploring, hiking, or whatever strikes your fancy - what better way to relax than by checking out the local watering hole.  This my friends, is something I excel at.  I would dare say I'm down right talented at sniffing out new tropical temptations.

Like any other subject, to become proficient one must study.  This requires sufficient resources.  In the British Virgin Islands, luckily these resources are easy to find.  There is no better guide for a little bar-ology than "The Drinking Man's Guide to the BVI" by Julian Putley.  This guide covers all the island haunts that even the most surly pirate would be proud of.

The book contains simple maps with numbered locations and legends showing each corresponding bar name.  Each numbered location corresponds to that bar's page in the book.  The  write up for each bar contains a catchy poem, a nice description, and usually a drink recipe or two for specialty drinks served there.  With a little bit of planning, and an understanding of how to get around in the Virgins, one can easily fit a good number of these bars into a week long visit.

One of our "more used" pages 

So...  What's better than a book that guides you through the best drinking in the BVIs?  This book has a kicker.  In the last pages of the book, each bar has a drink special and a place for a bartender to sign off.  Free drinks?  I ask you - what is better than free island drinks?  Through the years, Sharon and I have put quite a dent in our sign-offs.  We even ask bartenders to sign each year even though we have already enjoyed the free drink.  This book is a great memento
(sometimes you need these after a good night of rum) of your liquid exploration.

Autograph of Micheal "Beans", a great island character and popular musician

Sailing back to my senses

When I began the process of learning to sail, I was taken aback by what seemed like an infinite variety of things happening - all of which must be tracked and managed at the same time to safely and effectively sail.  I have never been a quick thinker.  I analyze, evaluate, and attempt to make an informed decision.  This is probably why I was never great at sports.  The best players think quickly, and simply react to the environment of which they are immersed in at that moment.

As I began to understand the pure physics of sailing, the next task was to actually perform the physical task of doing it.  It wasn't easy, it was awkward.  I was trying to analyze the direction and speed of the wind, the angle of my sails, and the direction I needed to push or pull the tiller.  I was a mess.  I mostly knew "what" I needed to do, but my brain was busy analyzing things that had already happened while my body was awkwardly trying to handle the things that were currently happening.  I was one step behind my situation at all times.

For me this was a terrifying and telling moment.  Flashbacks of myself as an uncoordinated teen on a highschool basketball team flashed through my head.  Maybe I would just never "get it".  That thought of failure was almost paralyzing to me.  I really wanted this. Sailing wasn't something I intended for myself as just a hobby - this was intended to be a start of a new life.  An escape plan.

Living in Connecticut for almost 10 years now has not been fun.  I have come to realize my senses have been dulled, nearly erased.  I feel less compassion.  I notice less of the world around me.  Often it takes me up to two hours each way to get to and from work, and then I don't remember the trip.   Sometimes I have found that I have driven somewhere, only to realize I don't know where I am or how I got there.  I don't stop, nor do I have time to stop and "smell the roses" as they say.  Urban environments are like ant colonies.  People move like ants, in endless lines on the ground.  They crowd into tiny places like ants to an ant hill.  They seemingly have no regard for one another.  But somehow like an ant colony, it somehow works.  At least it works for some.  Urban living is not for me.  For me, Connecticut is torture.  I'm merely a nameless ant trying to not get run over by the millions of other ants with pure disregard.  I feel nothing, I see nothing. I simply move day to day while life passes me by.

So in my moments of panic while learning to sail, feeling that I might not ever "get it" - I kept going.  I told myself that if other people do it, it must be possible.  Soon, I found that my brain wasn't analyzing the sails and the wind and the waves and the tiller.  It was starting to all work together as my brain went against its nature of over thinking my situation.  Like learning to ride a bike, my body and my knowledge of sailing began to take over.  It was an immensely freeing moment.  I am not entirely sure of the exact point in time when it happened.  The important part is that it did.

Then came the side effect.  I began to sense again.  I began to notice the environment around me, something that had been long forgotten.  Without my brain going into analysis-paralysis, I noticed the wind direction and speed.  I notice the sights, sounds, and smells around me.  I see the water, the waves, the trees on the shoreline.  I don't think about the sheets, the tiller direction or the wind or the concert in which they must all work together.  It just happens now.  This may seem like such a minuscule thing to many, but imagine being robbed of these things.  These simple things are part of "normal" life, one that I will someday be glad to get back.  For now, I'll go sailing.

Coming soon to my "Sailing" page

S/V Island Dreamer, the boat we sailed and lived aboard while earning our ASA certifications

Sailing...  Now there's something I never pictured myself doing while growing up in the Adirondack mountains of New York.  On this page, I'll be documenting how we started sailing, the boats we have experienced, the memories we have made, and our progression from non-sailors, to hopefully confident skippers. 

From being passengers on a day charter, to exploring the Virgin Islands and Florida Keys on private charters, to our preparation to bareboat, be our own skippers, and eventually live aboard our own sailing yacht - it will all be here.

Sharon and I and Capts. Harold & Margie Ochstein after completing our ASA 104 Bareboat certification

At the helm of S/V Island Dreamer in the Florida Keys

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