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Our
flotilla of 7 boats parade through a narrow passage heading for Jost Van
Dyke - One of many British Virgin Islands
I first visited the Caribbean in about 1998 on a cruise with Kathy, ex-wife #2. I still remember getting off the cruise ship in Grand Cayman and boarding a water taxi. I stared at the aqua-blue water in disbelief, kind of like when you see the Grand Canyon live for the first time. Pictures just don't do it justice. We traveled by land taxi to a local beach and did a little snorkeling. The fish were not that plentiful, but swimming in that warm tropical water was spectacular.The one thing I took away from that trip was a thought: it would be great to spend some time on this island paradise.
Here is a overview of the Caribbean Sea:
I returned to Grand Cayman with Chelsea, Chris, and Brett in 2007 when a friend of a friend offered his timeshare for a week. This vacation was everything I had hoped it would be (read about it here). I could not wait to return to anywhere in the Caribbean on just about any kind of trip.
So when I retired in June 2015, June and I began to think about a fitting way to celebrate the occasion. I thought of the ultimate vacation: Sailing in the Caribbean. I had talked to a friend and heard stories of people who chartered sailboats there. I have done plenty of sailing over the past 25 or so years, mostly on my own 17 foot trimaran. And I have been out on the bay with a friend on his 30-something foot yacht. But I have never been in a position to skipper a large yacht. Who, I thought, would even consider renting their $200K - $300K yacht to someone like me? I know I wouldn't! And if by some unbelievable chance, someone WOULD charter their boat to me, who in their right mind would consider coming along on this suicide mission? June made it VERY clear that she most definitely would NOT. So I figured this was a longer-term proposition, and one thing I now had, was plenty of time.
I started reading about the various sailing certification programs, most of which take several months and thousands of dollars. But in the end, they will not trust you to take their boats out alone. Further in my research, I stumbled upon Latitude 38, the online magazine for sailing in the SF Bay Area. In their classified adds, I found 'Captains looking for Crew'. Maybe I qualify as 'crew'? I found one captain, Suzanne, who was willing to take damn near anyone, really. So I connected with her and, over the following months, spent several afternoons on her gorgeous 45' Jeaneau sailboat, crewing and learning the ropes - literally.
I also continued to look at potential sailboat charters in the Caribbean. One lucky mouse-click took me to a unique opportunity: the Sunsail Flotilla. After reading a bit and then making a 10-minute phone call to Sunsail, they asked several probing questions about my sailing qualifications. The support person assured me that they WOULD indeed allow someone with my limited yacht-sailing skills to rent one of their yachts for a week. Basically with the Flotilla option, they send you out with 6 or so other flotilla boats and a lead boat that is manned with a few expert sailors. Every evening, the flotilla skippers would meet as a group with the lead captain who would identify the next day destination island / harbor and potential stops one may want to take along the way. They would also be in close contact by radio and cell phone in case there were problems. I sent the above link to June to see if she would consider it. She was IN!!
So we checked out their smallest and cheapest boat for a week anytime in January, the high season for sailing in BVI, their most popular destination. The cost would be roughly $4000 for a 38 ft. Jeanneau with three cabins and two heads. Now if we could only persuade one or two more couples to come along to share expenses. I had already asked two of my friends who have extensive sailing experience and neither were available. So we began to ask friends who might have the means and availability, and we were coming up empty. Then June thought of her brother Steve and his girlfriend Sherlyn, a fun couple who we have traveled with to Mexico several times. As it turns out, this kind of sailing adventure was on Sherlyn's 'bucket-list'. They we IN! Let the planning begin!
June looked at their online itinerary and investigated potential
side-trips. Steve, who has basically no sailing experience, joined me for
an afternoon on Suzanne's boat. We all agreed that a good arrangement
would be to have Steve at the helm (steering wheel) and I would work the
lines. We made our payments, bought plane tickets to St. Thomas, bought
ferry tickets and other travel arrangements. We were at the point of no
backing out. Little did we all know then that Sunsail would soon regret
their decision to rent to us.
Next: Getting There