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Seeing the Caribbean in your own sailboat

Boomer sails the Caribbean. Could that be you? Azure blue water, warm weather and boomer adventure sure sound appealing to Alan and me. Well, Gary Pierce has been there and done that. Today, he tells us all about it:

Charlotte Amalie

View of Charlotte Amalie

Hello boomers! My wife and I have always enjoyed Caribbean cruises, and I bet you do as well. When visiting one of these idyllic islands have you ever had the thought, “Gosh, I wonder what it would be like to live here?”

We were on a Caribbean cruise in 1990 just leaving Charlotte Amalie, St. Thomas United States Virgin Islands, and as I like to do when the boat is pulling out of harbor, I went up to the sundeck with a cold Heineken in hand—the Heineken always helps when you are looking for the elusive green flash. I declared to myself, “In five years I am going to be down in that harbor on one of those many sailboats toasting the cruise ships as they leave.”

I was wrong; I cheated a year and did it in four years.

Boomer sails the Caribbean

Up until the cruise excursion on a 36-foot sailboat that we had taken that day with two other couples from the boat, I had never stepped foot on a sailboat. Nor had my bride of then 15 now 37 years. Therefore, to make this dream a reality we had some catching up to do.

The steps that we took to get ready for this sailboat adventure included: reading everything I could get my hands on about sailboat cruising, taking sailing lessons and booking crewed, then bareboat charters, mostly in the British Virgin Islands. We finally purchased our boat in May of 1994.

In December of 1994, with two other friends, I sailed our 35-foot Island Packet, Shadowtime, from the Galveston, Texas area to Jost Van Dyke in the British Virgin Islands—22 days, 18 days at sea. When I returned to Houston, my wife and I quit our jobs—she (42) was a secretary and I (49) had my own commercial real estate business.

This began an eight-year journey of sailing from the Virgin Islands stopping at almost all of the islands in the Windwards and Leewards. Our southern boundary was Trinidad and Venezuela We did this circuit almost every year, hauling the boat out of the water in Trinidad during hurricane season and returning to the states where we RV’d during the summer months.

Those eight years were the most enjoyable of our 37 years of marriage. The Jimmy Buffett song “Changes in latitudes, changes in attitudes” is right.” The island lifestyle is laid-back, unhurried and just plain fun. No one is in a hurry, everything really is “No problem Mon.” It may be a problem for you if you expect things to be done as quickly as they are in the U.S. Eventually things are done and as we quickly found out, at a much cheaper cost, at least boat-wise, than if they were done the United States.

Look at the benefits of living on a sailboat and cruising the Caribbean—breathing fresh air 24 hours a day, feeling your blood pressure and pulse rate lower as you get on island time plus anchoring is absolutely free.

Caribbean Beach

Beautiful Caribbean Beach

One of our perverse pleasures in the islands would be to anchor off a resort that charged $500 a night and up for a waterfront view that we had for free. During the day, we would lower the dinghy (that is our inflatable rubber boat to you landlubbers), go ashore and enjoy the resorts amenities. The looks of awe and wonder from the resort guests as we admitted, “Yes that is our boat,” always made us laugh. They were returning to next week’s two-hour commutes and their jobs. Our immediate plans would be to meet up with someone in Antigua the following month—maybe 100 miles away.

Sailboat cruising means that you are stopped 98% of the time. We never left a safe, comfortable harbor for another island unless the sea conditions were calm and the wind direction favorable.

So what about about pirates, theft and personal safety? In our eight years, we never experienced an uncomfortable situation nor did any of our cruising buddies. Healthcare? It was great and at a fraction of U.S. prices.

So baby boomers, if we could do this with no previous experience you can too.

In closing, it really is “No problem Mon.”

Boomer sails the Caribbean resources:

All photos courtesy Gary Pierce.

Have you thrown your boomer cares out the window to sail the seas? Join the conversation at the My Itchy Travel Feet page on Facebook or send us an email to ask a question or share your experience.

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