Photo: Tim McKenzie/autoevolution
Roughly ten years ago, I decided that I wanted to relieve myself of what I had earlier perceived as worldly possessions, sell my business, and move onto my sailboat in South Florida. I was tired of living like everyone else and wanted to live the life of a modern-day pirate with only flip-flops, t-shirts, and shorts as a wardrobe.
All who I was acquainted with, either casually or professionally, knew that living afloat on my sailboat was my dream, but I would learn they never believed I would leave a seemingly comfortable life for an existence on the sea until I did!
I had always been at home, so to speak, aboard my boat, being close enough to the Intercoastal Waterway in South Florida that I could take off at any time, taking all my belongings with me. Whether it was a short 60-mile jaunt over to Bimini, a weekend trip down through Biscayne Bay and around to the Florida Keys, or a sojourn down to my playground in the Caribbean, it did not matter, I was on a permanent vacation and did not care what people thought.
The first couple of months, I would chronicle my travels on social media, namely Facebook, until I began to hear from people that I went to high school with back in the mid-80s. Some I knew, and others I did not. I later learned that I was unknowingly connected to a Facebook group started by my graduating class. To a person, they would express a great deal of envy and explain how it was their dream to live aboard a sailboat, just as I was doing. I would usually reply with encouraging words like
"Live your dream" or "Where there is a will, there is a way."
I did, however, reconnect with some old classmates that I hung around with, and we chatted quite often. One friend throughout my four-year stint in High School asked if he could come out to Florida and spend a couple of days aboard as it "had been his lifelong dream" as well.
I learned some valuable lessons during his stay, which lasted about three days. Upon his arrival, we went down to my favorite watering hole called the Elbow Room in Fort Lauderdale and tossed a couple back while I explained the rules I had about staying aboard my home and, just as importantly, the rules while we were underway.
This guy turned out to be the guy you invite to your Christmas party.... just once!
I do credit him for giving me a reason to form a litmus test for guests aboard, whether they were old friends or new. The test involved a series of “shakedown cruises” that began with short excursions up and down the Intercoastal and grew in length if warranted.
Over the course of the first year or so, I had many guests, and they all had a singular thing in common. While they all claimed to have wanted to live on a sailboat, none of them really understood what it took or why people do it. They were all in a hurry to do something; every time we were underway on a beautiful sunny day in light air making 4-5 knots (4-6 mph/7-9 kph), just cruising along without a care in the world, they would all ask, “Can we go any faster?” Ironically, they had no clue where we were going in the first place.
My point is that most of the people who dream about living aboard a sailboat are in a trance from books they have read or movies they have seen. There is an old saying about sailing not being about the destination but the journey. That could not be more true. In all my years of sailing, I have never, ever been in a hurry to get anywhere when aboard.
There is another saying that goes something like this: without a destination, no wind can take you there. Hogwash!
In addition, if boredom sets in when you are sailing, it is simply not for you, no matter what your dream is. Wake up and conjure up another.
One of the funniest situations I experienced was sailing out of Key West, Florida, back up to Fort Lauderdale. Because I did not have a shoal draft boat (limited depth boat below the waterline) and with the waters around the Keys being somewhat shallow, it takes about 3 days if I don't bar hop. One Saturday morning, I was leaving Key West Marina under motor and hoisted my sails as I turned to the East. After about an hour or so on a close reach into the wind, a woman appeared in my companionway. I had my first stowaway!
Apparently, the previous night she overheard me talking to some friends at Jimmy Buffet's Margaritaville on Duvall Street about sailing back to Fort Lauderdale in the morning. She explained that she did not want to ask for a lift back, so she followed me back to my boat, waited an hour after I turned the lights off, came aboard, and stowed away in the aft cabin.
I wasn't angry and thought it was rather cool that I had a stowaway. The funny part is, after about an hour, she asked if I could sail closer to shallow water where she could safely jump overboard and swim to waist-deep water and go ashore. The reason? We were going too slow, and she was bored.
Sailing alone is better!
I had always been at home, so to speak, aboard my boat, being close enough to the Intercoastal Waterway in South Florida that I could take off at any time, taking all my belongings with me. Whether it was a short 60-mile jaunt over to Bimini, a weekend trip down through Biscayne Bay and around to the Florida Keys, or a sojourn down to my playground in the Caribbean, it did not matter, I was on a permanent vacation and did not care what people thought.
The first couple of months, I would chronicle my travels on social media, namely Facebook, until I began to hear from people that I went to high school with back in the mid-80s. Some I knew, and others I did not. I later learned that I was unknowingly connected to a Facebook group started by my graduating class. To a person, they would express a great deal of envy and explain how it was their dream to live aboard a sailboat, just as I was doing. I would usually reply with encouraging words like
"Live your dream" or "Where there is a will, there is a way."
I did, however, reconnect with some old classmates that I hung around with, and we chatted quite often. One friend throughout my four-year stint in High School asked if he could come out to Florida and spend a couple of days aboard as it "had been his lifelong dream" as well.
I learned some valuable lessons during his stay, which lasted about three days. Upon his arrival, we went down to my favorite watering hole called the Elbow Room in Fort Lauderdale and tossed a couple back while I explained the rules I had about staying aboard my home and, just as importantly, the rules while we were underway.
This guy turned out to be the guy you invite to your Christmas party.... just once!
I do credit him for giving me a reason to form a litmus test for guests aboard, whether they were old friends or new. The test involved a series of “shakedown cruises” that began with short excursions up and down the Intercoastal and grew in length if warranted.
Over the course of the first year or so, I had many guests, and they all had a singular thing in common. While they all claimed to have wanted to live on a sailboat, none of them really understood what it took or why people do it. They were all in a hurry to do something; every time we were underway on a beautiful sunny day in light air making 4-5 knots (4-6 mph/7-9 kph), just cruising along without a care in the world, they would all ask, “Can we go any faster?” Ironically, they had no clue where we were going in the first place.
My point is that most of the people who dream about living aboard a sailboat are in a trance from books they have read or movies they have seen. There is an old saying about sailing not being about the destination but the journey. That could not be more true. In all my years of sailing, I have never, ever been in a hurry to get anywhere when aboard.
There is another saying that goes something like this: without a destination, no wind can take you there. Hogwash!
In addition, if boredom sets in when you are sailing, it is simply not for you, no matter what your dream is. Wake up and conjure up another.
One of the funniest situations I experienced was sailing out of Key West, Florida, back up to Fort Lauderdale. Because I did not have a shoal draft boat (limited depth boat below the waterline) and with the waters around the Keys being somewhat shallow, it takes about 3 days if I don't bar hop. One Saturday morning, I was leaving Key West Marina under motor and hoisted my sails as I turned to the East. After about an hour or so on a close reach into the wind, a woman appeared in my companionway. I had my first stowaway!
Apparently, the previous night she overheard me talking to some friends at Jimmy Buffet's Margaritaville on Duvall Street about sailing back to Fort Lauderdale in the morning. She explained that she did not want to ask for a lift back, so she followed me back to my boat, waited an hour after I turned the lights off, came aboard, and stowed away in the aft cabin.
I wasn't angry and thought it was rather cool that I had a stowaway. The funny part is, after about an hour, she asked if I could sail closer to shallow water where she could safely jump overboard and swim to waist-deep water and go ashore. The reason? We were going too slow, and she was bored.
Sailing alone is better!
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