The dream of retiring to a Caribbean island with powder-white sands, clear blue waters and tranquil island life is, for many people, just a fantasy. There’s the expense to worry about, and then you have to find the island that’s right for you.
But what if I told you that you could retire to them all and spend your time island-hopping without worrying about property taxes or utility bills? And that you could do it for just $1,000 a month?
That’s what my wife Julie and I did in 1994. And I’ll tell you a secret… You don’t need to be a lifelong sailor or know anything about boats to spend your retirement sailing around the Caribbean.
You just need to want to live the dream that Jimmy Buffett sings about. Let me explain… In 1990 my wife and I took a Caribbean cruise on a liner. When it docked in St Thomas, in the U.S. Virgin Islands, we were looking for something different to do.
On a whim, we signed up for a four-hour shore excursion on a 36-foot sailboat. My wife and I had never been on a sailboat before and we asked the boat owner plenty of dumb questions. But by the time we sailed back into port we knew we had to live like this.
As our cruise ship left St Thomas that evening, I looked back at the sailboats bobbing in Charlotte Amalie harbor. And I promised myself that in five years I would be down there with them on my own sailboat.
At the time I was a successful commercial real estate broker in Houston, Texas. I faced the same obstacles to sailboat cruising that you probably do now. I knew nothing about sailing or anything nautical. But that wasn’t going to stop me.
Over the next four years we prepared, taking the baby-steps approach to sailboat life. I read everything I could get my hands on about sailing and cruising. We started taking sailing lessons in Kemah, Texas, 90 miles from our home. We took sailboat vacations in the British Virgin Islands with a captain and cook… And after three such trips, we started taking these trips by ourselves.
In January 1994, we chartered a 35-foot sailboat for three straight weeks in the British Virgin Islands. We found out that we really could do this! When we returned to the U.S., we started shopping for a boat.
That summer we purchased a 35-foot Island Packet and named her Shadowtime. We spent most weekends on the boat, docked in Kemah, getting ready to sail to the Virgin Islands in November. Was I an experienced sailor by then? No way. Looking back, I’m still amazed at how little knowledge I had. But we had our dream.
For the first trip I took two friends; one who had a little sailing experience and one who was a golfing friend and knew less than I did about sailing. After 18 days at sea and stops in Key West, Florida, and Marsh Harbour in the Bahamas, we dropped anchor in Jost Van Dyke, in the British Virgin Islands.
The passage hadn’t been a smooth one. We made some real bonehead mistakes, but we learned something new every day—nautical on-the-job training. I flew home for Christmas, my wife quit her job, and in January 1995 we started living on our sailboat for six to nine months a year.
For the next eight years, we had an absolute ball. We spent 90% of our time swinging on the hook at some of the most beautiful anchorages on Earth. 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.
Our boat Shadowtime didn’t leave the Caribbean until we sold her in 2002. We sold her for $118,000, exactly what we paid to buy her eight years previously. And we just found out that she is for sale again, for the same price. Proof that if you get the right boat it will maintain its value.
Do you have to pay this much money to enjoy sailboat cruising? Not at all. 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. We met one young German fellow who had circumnavigated the world twice by himself in his 24-foot boat. He was selling it for $10,000. If a $10,000 boat can take someone safely around the world twice, the same boat will certainly keep you safe cruising in the warm waters of the Caribbean.
We were reluctant to sell the boat and I really miss the stressfree lifestyle. When we put the boat up for sale we never thought anyone would meet our price, but they did, and with aging parents it was time to stay closer to home. It’s so inexpensive. You eat most meals onboard and anchoring is free. Once we were on the boat in the Caribbean, we spent around $1,000 a month.
Getting around the islands was easy. We copied the locals and took the bus. Sometimes a regular bus, but most of the time 14-passenger vans, which are called maxi-taxis. How much? In Venezuela, the local bus cost seven cents. In the U.S. Virgin Islands a maxi-taxi was one dollar.
It seemed we always knew someone when we sailed into a new anchorage. Sailboat cruisers stick together; you quickly fi nd out what is going on ashore and where to buy staples. You can share a cab with a few other sailors to take island tours and go to the weekly farmers’ market. You stay in touch in harbor on the VHF radio. You can talk all over the Caribbean with a single-side band radio, which you do not need a license to operate.
Our annual schedule went something like this: Return to the boat from the U.S. October to November. Spend four daysgetting the boat ready to splash, then start island-hopping up the Windwards and Leewards (in the Lesser Antilles).
The longest passage is 90 miles and navigation is simple: All these Caribbean islands (except Anguilla and Anegada) are mountainous, so you can see where you are going. Go from Trinidad to the Virgin Islands and return to Trinidad by May. We did this three times. One winter we stayed in Trinidad (you really must experience Carnival at least once) and Venezuela.
Today when we tell people that we retired to a sailboat the questions they have are predictable. Usually they concern personal safety, including piracy, getting mail and health care questions.
First on piracy. We never heard of any sailboats being hijacked. As far as being safe ashore, using the same common sense we would use in the U.S., we never had a problem in eight years. When we knew our schedule, we would have our mail forwarded to an island post office along the way, which worked fi ne.
As far as health care is concerned, we found local doctors and dentists were excellent, and that the only difference between them and U.S. doctors was the price.
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. 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.
Editor’s Note: Read more about Gary and Julie’s sailboat retirement on their website.
No Experience Required
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 a person.
Take sailboat vacations. This is called crewed chartering, where you can sail the boat under the watchful eye of the captain. The boat comes with a cook, too. A week-long vacation on a 50-foot boat, costs from $8,000 to $9,000 for up to eight people and covers most meals. Volunteer as crew. Once you have a little experience you can offer your services in return for food and on-the-job training aboard someone else’s boat.
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 prime winter months. For a 50-footer (big enough for four couples) $4,000 in the summer, $6,500 in the prime winter months. Winter is the best time for sailing as you avoid the summer rains and hurricanes.
Editor’s Note: Read more expat profiles here.