Preparing for my first charter

We first began discussing chartering a boat during our short courtship. Jeff mentioned a few charters he had been a part of, with Captain Jim ( in the British Virgin Islands, which sounded like a blast. Clear water, fresh island fruit, rum tasting…. perhaps one day Jeff will write about how he got thrown out of the BVI’s!

As I began researching charters, I looked through numerous websites comparing different yacht fleets and prices. It became very apparent that chartering is not a cheap vacation. Considering that we had just moved to a new state, lost one of our full-time salaries, bought a house, and got married over the course of the last few months, our finances were very tight.

My first choice would have been to charter in the Mediterranean. Spain has been on my must-see list for the past 10 years and I was dreaming big. Barcelona, with Gaudi’s Sagrada Familia and Museu Picasso, was calling me. But so too were our families, in Florida and Mississippi, who wanted to see us over the winter break.

I had all but given up looking for an affordable charter when friends of my in-laws recommended cruising off of the west coast of Florida near Ft. Myers, between Charlotte Harbor and Pine Island Sound. They said it was one of the top cruising grounds in the States. While I was still dreaming of tapas and tempranillo, I knew that Florida was more accessible and affordable (we could drive there rather than have to fly to our charter destination).

And then it happened. I revisited the Southwest Florida Yachts website and low and behold it was their birthday and they were giving the gifts. For folks wanting to charter with SWFY for more than 3 days they were willing to give free nights! Free nights! So we discussed, and procrastinated, and discussed, and waited a while longer. Then I told Jeff we should do it. I wanted the experience. I had been reading as much about sailing as I could. Jeff and I had been scouring YouTube for sailing videos. Jeff would tell me almost daily, that he was “ready to go.” We had started planning for our future of cruising and I had yet to spend a night at anchor!

The next day Jeff called and reserved Sojouner – an Island Packet 31. It was the last one in the fleet available for the days we requested. I was glad it was over 30’ as Helbent, Jeff’s old Catalina 22, was a bit small for my taste. We would sail from Burnt Store Marina on December 9th for 6 days/5 nights (2 of those days free with the birthday promotion!)

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