The first time Gary Pierce and his wife Julie took a four-hour sailing cruise in the U.S. Virgin Islands, they knew they wanted to retire on a boat in the Caribbean. But could they do it with no experience and limited funds?
They lived 90 miles from the Gulf of Mexico – so learning wouldn’t be easy or convenient.
And they didn’t have a fortune to spend on buying a sailboat – or on heavy month-to-month expenses once they began “island-hopping” in the Caribbean.
The good news is, Gary and Julie discovered that learning how to sail, buying a sailboat, and cruising from island to island isn’t as difficult – or expensive – as they once believed.
In fact, they wound up spending eight full years sailing the Caribbean on their own boat, without any major problems, and spent only $1,000 a month to do it – all in first-class style.
In the May 2011 issue of International Living Magazine, Gary reveals what it’s like to cruise the Caribbean full-time. And he provides practical tips for anyone who, like he and his wife, has dreamed of retiring on a sailboat in the Caribbean, but always left that dream in the realm of fantasy.
“We spent 90% of our time swinging on the hook at some of the most beautiful anchorages on Earth,” Gary writes in the May 2011 issue. “And it’s so inexpensive. Once we were on the boat in the Caribbean, we spent around $1,000 a month.”
How did they live on $1,000 a month? Here are some of Gary’s money-saving tips.
“We copied the locals. In Venezuela, the local bus cost 7 cents. You can share a cab with a few other sailors to take island tours and go to the weekly farmer’s market. We found local doctors and dentists were excellent, and that the only difference between them and U.S. doctors was the price. You can eat most meals onboard and anchoring is free.”
What about the cost of buying a sailboat?
Well… although Gary paid $118,000 for his 36-foot boat, Shadowtime, he says it’s possible to own your own sailboat for much, much cheaper.
“We saw several 20- to 25-foot boats that had been sailed safely all the way from Europe. These boats can be purchased for $10,000 to $25,000.”
How do you gain the necessary experience to become a full-time sailboat captain? Here’s what he suggests.
“To get started, read everything you can get your hands on about sailing and cruising. Hang out at the docks and marinas and go day sailing. Someone offering day sails would probably charge $20-$30 per person.” Gary also suggests taking sailboat vacations to learn more. “This is called crewed chartering, where you can sail the boat under the watchful eye of the captain.”
Volunteering as crew is another way to gain valuable sailing experience. “Once you have a little experience,” Gary writes, “you can offer your services in return for food and on-the-job training aboard someone else’s boat.”
Finally, once you’ve mastered some skills, you can do what’s called bareboat chartering. In other words, you rent a boat and you’re the captain and cook! “A 32-foot boat for a week will cost $1,500 in the summer and $3,000 in the winter months.”
Even though Gary and Julie were careful with their funds, they discovered they could still enjoy a luxurious, exotic lifestyle.
“We especially enjoyed being anchored off fancy resorts that charged $500 a night. We paid zero and had a much better view, without noisy neighbors. During the day we would go ashore to these resorts, using our dinghy, and wander the grounds and enjoy the amenities for free.”
Gary’s a firm believer that anyone can retire on a sailboat in the Caribbean – regardless of experience or budget. “The biggest obstacle to people enjoying this dream is thinking that you have to acquire more nautical knowledge, a larger boat, or more money before you go cruising, “Gary writes.
“My advice? Take the boat that you have and go. The longer you wait, the more your current lifestyle will tell you that you cannot do this. You can. Listen to your dream if retiring to a sailboat is what you want.”