Forty-one Years of Bareboat Chartering in the Caribbean

On Christmas Day 1969, after we’d opened presents, with wrapping paper still strewn across the floor, my father made an announcement: “Our big present this year is a trip to the Virgin Islands.”  I was ecstatic.
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On Christmas Day 1969, after we’d opened presents, with wrapping paper still strewn across the floor, my father made an announcement: “Our big present this year is a trip to the Virgin Islands.”  I was ecstatic.

On Christmas Day 1969, after we’d opened presents, with wrapping paper still strewn across the floor, my father made an announcement: “Our big present this year is a trip to the Virgin Islands.” 

I was ecstatic. For some reason this 13-year-old kid from the Windy City had fallen in love with the idea of sailing and snorkeling in the azure waters of the Caribbean. 

Our first trip was ambitious. My dad determined we would sail from Red Hook Bay on St. Thomas up to North Sound in Virgin Gorda and back, all in a week, on a Cal 34. The accommodations were Spartan. Our dinghy didn’t come with an outboard. Refrigeration came in the form of a huge block of ice. And air-conditioning? Forget it! We opened our hatches and hoped the tropical breezes might keep the cramped space below passably cool. I loved it. 

To this day, I remember what became a milestone experience in my teenage life. We were sailing through the cut between Great Thatch, Little Thatch and Frenchman’s Cay on the way to the Bight. With my left hand on the luff of the genoa and my right on the pulpit rail, I reveled in the mountainous islands jutting above shimmering seas into cloud-scudded turquoise skies. 


This was the world as it ought to be!

When that first trip was over, I realized my father had given me a great gift. 

Not only did I fly back to Chicago with a new skill, but our first adventure provided us with common ground that would prove essential during my tumultuous teen years. From then on, sailing was our thing, something we could be good at together, something we could talk about and reminisce over. Each Christmas, my present to him had something to do with sailing. 

The following year I joined the junior sailing club in Winnetka, Illinois. My skills grew sharper in the cool waters of Lake Michigan. 

From 1970 to 2011 we took just shy of 20 trips together. My mom always came, and other family members joined us as well. Mom’s enormous capacity for hospitality made these trips extra enjoyable. She was the emotional glue that held us together when dehydration and too much sun made us all crabby. 

Dad’s gift was his genius for planning creative vacations, especially when it came to sailing trips. 


As I grew into my 30s and early 40s, he’d phone me in the spring of each year. The calls went something like this: “Let’s join the Moorings flotilla out of Tortola next year. It would give us opportunity to do some racing,” or, “You like fly-fishing. Let’s plan a trip to Belize. We’ll sail. We might even get a guide and go bonefishing.” 

In 1994, we introduced my four kids to sailing in the Abacos. In 2000, my dad suggested we charter two boats from the Moorings in Grenada. My family and I sailed a Beneteau 413 while my mom and dad sailed a Moorings 463 with my sisters and their husbands. Sailing in tandem, we stayed in touch with walkie-talkies.

In 2002 we chartered in Belize, our most challenging trip yet as we carefully threaded our way through coral reefs and had to count islands to determine precisely where we were. 

On July 1, 2011 various members of our family converged at the Moorings base in Tortola for what my dad had suggested earlier might be his last charter. Our Moorings 4600 was fully provisioned, and the air conditioning made the cabin wonderfully cool. 

Tacking up the Sir Francis Drake Channel, my father and I sat at the helm of our big cat. We reminisced over our 40 years of sailing together. We recalled losing our diesel engine near Johnson Reef. We remembered our keel bumping in the shallow waters of Leinster Bay at 0300 as our anchor dragged. We celebrated the time we were the grand winners of a flotilla race from Gorda Sound to Anegada. (We talked about that one for a while!) 

The great thing about sailing, especially as father and son, is that you’re not solving the problems of the world. You’re not talking shop. You’re just sailing. You’re wonderfully and simply engaged in the present. 

Forty-one years after that first trip, sailing is still the common ground that binds us. And I’ve carried on the tradition with my kids: we often talk of distant harbors and wind and waves. Dad’s legacy lives on.

Photos courtesy of Rod MacIlvaine



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