Sailboat Sailing on Water Near Island

My husband, Simon, and I spent over ten years dreaming about the type of boat we’d get and what we wanted to do with it.

Our plan was to win the lottery, buy a new Oyster 56’ or Oyster 62’ Yacht (type of sailboat made in England) and sail around the world.

In preparation for our lottery win, we’d read sailing magazines, go to boat shows, attend private Oyster boat showings, and once a year we’d even charter a sailboat and spend a week of bliss sailing the Mediterranean or Caribbean.

Sailing around the British Virgin Islands

Sunset from Sopers Hole, Tortola, British Virgin Islands, Caribbean

We’d often say, ‘when we have our Oyster built we’ll make sure to have this or that feature…’

At night, in bed, we’d visualize taking our boat out of the marina and sailing it into the sunset heading for 360 degrees of beautiful blue ocean. We wanted the sun-soaked-salt-laced wind in our hair, the sound of the hull slicing through the waves, the feeling of freedom at our disposal.

And then one day it dawned on us that we might not win the lottery.

I said to Simon, ‘imagine if you hit 90 and I’m 80 and we didn’t live our dream?’

We held on so tightly to the concept that we had to win the lottery that we failed to consider other options. We failed to consider buying a used boat. We failed to think about perhaps buying a boat, other than an Oyster 56’ / Oyster 62’, to practice with until our lottery win arrived. (yes – I admit that we were still banking on a lottery payout at this point…)

Out of frustration, I told my husband, ‘we need to either shit or get off the pot.’ I was tired of dreaming…I wanted to make my sailing dreams a reality.

We decided to research some low cost but quality used sailboats. Until asking that question, we only ever focused on buying the $1.5 million yacht with our future lottery winnings. I wondered if it was possible for a ‘normal’ couple to find an affordable boat so that we could at least start to practice for our around the world trip. (I put ‘normal’ in quotes because from what I’ve been told, we’re anything but normal – hahahaha).

One thing led to another and after researching quality older boats, Simon went on Ebay and found a 1980’s 35’ Moody sailboat priced to be sold. The boat was located in Scotland and at the time we were living in England. Simon flew up to Scotland, rented a car and inspected the boat prior to having a professional survey conducted.

Things flowed, a final price was negotiated and plans were made to move the boat from Scotland down to the south coast of England.

A month later, Simon flew back to Scotland, picked up a professional skipper and sailed the boat down. The duo got stormbound in Ireland and had to leave the boat there for a few weeks but eventually they got her to a marina in Port Solent near Portsmouth, England. Looking back, sailing Selene down to England was one of the highlights of my husband’s life. It was scary but also exhilarating.

Apparently, the boat started to fill with water when they left Scotland. Simon puked because he thought, ‘Oh no, I’ve bought a boat that’s about to sink.’ When the leak was found it was from the fresh water tank. A hose clamp simply came lose and the problem was quickly remedied.

When our new boat, Selene, came into the marina I felt a mixture of nerves and excitement.

Our frustration didn’t lead to getting the boat of our dreams but it did lead to getting a boat.

Interestingly, I quickly realized that it’s not the boat that makes the dream come true, although that can be part of it… What’s important is what you do with the boat that really matters.

At first I discovered the transition from being WAY outside my comfort zone to feeling comfortable with boat handling and sailing skills (rising to a challenge and succeeding) to be monumentally fulfilling. I was a grown woman – I didn’t want to go out and learn something new. What if I failed? What if I messed up? Expanding my comfort zone actually made me come alive.

And then there are the countless sunsets my family and I enjoyed while sitting in the cockpit looking out into the sea. There are the memories of week-long trips from one seaside town to another.

There’s the time that I told Simon we’d be able to go west even though we’d have to sail against the tide. Simon disagreed that we’d be able to make progress. For over four hours we stayed in the exact same spot despite having 20 knots of wind sailing us at over 5 knots. Note: Don’t mess with the tides around the UK!

It’s also the stories about learning how to cope in emergency situations – we took on lots of water once and were effectively sinking…we also had our engine cut out (ran over a lose fishing net) in the middle of a massively busy shipping and small craft lane. During both emergencies we handled the situation well and grew in confidence.

Our first boat, Selene, provided us with so many magical moments and learning experiences.

Another memory that will never fade is when I took a friend of mine, and his 12-year-old daughter, out for sail. There happened to be a famous race going on – it’s where loads of sailboats race around the Isle of White, a small island off the south coast of England. Well…I thought it would be cool to sail near the island to watch the race. Low and behold, as the boats came around the island I was right in the middle of the race path.

We quickly got out of the path but it was as if we were all alone one minute and the next we were surrounded by large and small sailboats. It was my first taste of racing and part of me enjoyed the commotion!

After we safely navigated away from the race, my friend and I were complacently lazing about in the cockpit feeling proud that we took the boat out and avoided a potential disaster with the racers. And then out of nowhere this massive gust of wind filled our sails, we both jumped up to fight the steering wheel and lost – the boat rounded up!

Our hubris got us in trouble.

From there on out, we stood attentive and made sure both hands were on the wheel. I’m sure that any onlookers would have loved to have seen our reactions. We looked so calm and confident. I suppose we were trying to feel what it’s like to be ‘real’ sailors.

Anyway, that gust of wind got us on our toes faster than a lightening bolt!

Selene also provided us with an opportunity to truly determine what was necessary for our future boat and what we definitely didn’t want. A good example of this includes Simon being 6’2” – he couldn’t standup straight anywhere in the boat. After gaining a bad back and a crick in his neck during long stays on Selene, we made a mental note that our next boat had to be high enough for him to stand!

Less than three years later we obtained our Oyster 56’

No…we didn’t win the lottery. And, no…we didn’t get a new Oyster. We managed to buy a priced to sell used Oyster. After discovering that the boat wasn’t the be all and end all we decided we could settle for an older boat. And considering how much new boats devalue after you drive them out of the marina, I’m not sure I’d ever buy a new one!

Furthermore, we gave up on waiting for our lottery win.

We loved sailing Selene so much that we decided to sell our house, our car, our possessions and buy the best boat we could afford. The plan was to sail around the world.

So far, we’ve circumnavigated the Mediterranean, crossed the Atlantic Ocean, sailed up the Caribbean and are now on the east coast of America. It might take use 5 years or 20 years to get around the world, but so far, so good.

We found a way to purchase our dream boat, we’re living our dream of sailing around the world and slowly, we’re figuring out how to make the money necessary to keep going.

I truly believe that the Universe supports you when you decided to get off the pot rather than sitting on it. It hasn’t been easy for us but for some reason after five years of giving our dream a go, we’re still going!

Morals of the story

  • The boat is a big issue and it’s important to get one you like but it’s not the whole package. Also, don’t make the dream boat your first step towards living the sailing dream.
  • Don’t be a dreamer, consider what you can do now to be a do-er. You don’t want to hit the age of 80 and look back thinking, ‘Maaannnnnn, I didn’t even attempt to live my dream.’
  • Don’t rely on the lottery…I think your chances of getting struck by lightening are higher. Furthermore, it can keep you stuck.


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