Does Size Matter?

I was sitting on the beach in Philipsburg, St. Maarten, in awe of the enormous cruise ships docked there, including the mammoth Oasis of the Seas. A couple sitting in beach chairs next to me asked which ship I was on. I laughed and said, “See that little charter sailboat out there, anchored in front of the cruise ship dock?” They nodded their heads in unison. “That’s the ship I’m on.” Now it was their turn to stare in awe.

As veteran charterers, my husband Herrick and I take for granted the fact that we can travel from island to island, port to port, stopping along the way, whenever and wherever we want. I learned from these cruise-ship passengers that they actually wished they could travel the way we do, pulling up anchor only when they were ready to move on to the next anchorage.

The couple complained that they could not stay longer in their favorite places, which struck me as ironic, given the way we’d changed our plans just a day earlier. We had originally planned to leave Philipsburg first thing, but then heard that the new Oasis of the Seas, the largest cruise ship in the world, was on its way. A beach vendor said all of the locals, including the schoolchildren, would be camped out on the beach awaiting its arrival. We didn’t want to miss such a momentous occasion, so we stayed the extra night. After all, we had no real schedule to keep.

As we continued our chat, I learned my cruise ship friends were not unusual, that many passengers wished they could have the freedom to follow the wind to the destination of their dreams. But since they had no sailing experience, they had to settle for the next best thing, which was seeing the Caribbean on a cruise ship.

They asked me about the inside of our sailboat, what accommodations we had, whether we had a bathroom and how we cooked our meals. For my part, although I’ve sailed my entire life, frequently in the Caribbean, I have never been on a cruise ship and have little idea what they are truly like. From the outside, cruise ships look amazing, although I still have trouble envisioning how anything that large can float. I imagine there are more amenities and more things to do than I can begin to fathom—albeit at the price of one’s freedom.

As the four of us talked, it occurred to me that in many ways these two forms of cruising aren’t that different. After all, we had all just spent the day on a picturesque white-sand beach in St. Maarten, gazing at the same aqua blue water and enjoying the same majestic sunset. Nonetheless, I also knew that as the sun dipped down, rather than standing at the balcony of a cruise ship with thousands of other passengers, Herrick and I would be experiencing it in privacy, nestled cozily in the cockpit of our charter boat.

The next morning, as we sailed alongside the Oasis and set a course away from Philipsburg, I took a moment to appreciate the enormity of the ship as it glistened in the Caribbean sun. I even felt a tinge of jealousy at the ease with which her passengers would spend the rest of their cruise, dining on gourmet food and watching top-notch entertainment.

But then, just as I was beginning to question our choice of vessel, the wind kicked up out of the east, we unfurled the sails and our charter boat began to heel as we fell into a comfortable groove. Sailing past the airport where the jets land over Maho Beach, I glanced at the charts and reflected gratefully on the many options that lay before us. Should we stop for the night in Marigot, the capital of the French side of St. Martin, or head for the island of Anguilla? Should we try to catch some fresh mahi-mahi for dinner, or dine in one of the many restaurants of Grand Case? Should we push our speed, or let the wind take us? Fortunately, all those decisions were ours to make.

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