When it comes to St. Maarten, a lot has been written and documented about the Dutch side of the island, around Princess Juliana Airport and Maho Beach, famous for being an aerial playground of sorts. I dove in myself last year, standing behind an A340 as it took off, and it was one of my Holy Shit Moments of 2012.

Also on the Dutch side, Philipsburg is mostly talked about in conjunction with the cruise ship industry (which, by the way, is under fire as you probably know — we’ll talk more about it during Breakfast Table Conversation tomorrow). And, truth be told, not much happens in Philipsburg outside of the nine to five port hours. Although the promenade is beautiful, the entire town is centered around duty-free shopping and quick lunches before heading back to the ship.

That said, there’s something I rarely see mentioned about Philipsburg in travel coverage, and that is the incredibly vivid and beautiful bright-blue water — arguably the most classic display of Caribbean water on the island (seriously, it’s bold, see photos). Called Great Bay, it’s a nice spot for water activities due to it’s large side and relatively calm waters. On Saturday, I took the mountain/ocean drive combo (more to come on island driving) across the south side of the island from Maho to Philipsburg for an afternoon aboard a 12-metre sailboat. But it wasn’t necessarily to relax — it was to race.

Twenty-some people are split between two former America’s Cup 12-metre vessels and pinned against one another in a five-leg race that takes about 45 minutes to complete. Without getting into too much explanation involving math formulas, the 12-metre is an international class of boats that ensures fair competition while allowing for creativity in design. The boats are multi-million in cost, but I hitched a ride for under a hundred (about $75). I was assigned to be a primary grinder, which meant that I had one of the more active positions and was responsible for trimming and easing the jib sails when tacking (turning) and changing course.

While there are crew positions for people who don’t want to get too involved (as well as plenty of beer on board for when cruising downwind), I would recommend the excursion for those who are interested in sailing and getting their hands dirty. It’s not exactly intense, but it also isn’t a joy ride — the point of it all is to finish first.

The captain and two other main crew members instructed us on when to do what — there wasn’t much thinking involved — but we were completely responsible for our tasks, which were directly connected to the performance of the ship. And this was no small vessel. It varies boat to boat, but on average, a 12-metre sailboat is about 70 feet long with a mast length of 86 feet, and they weigh about 35 tons. What’s awesome about the weight is that of the 35 tons, almost 30 of them are in the keel, or the hydrodynamic beam on the underside of the boat that generates lift and prevents it from flipping over. What this means is that it’s almost impossible to flip, even if you were to tip the mast down into the water (everyone might go overboard, but the boat would right itself!).

I could gush about it all day. It reminds me of my sailing days when I lived in Santa Barbara on my trusty old rig I called Lolita. She was a good girl, and you can’t beat a warm breeze out on the water — see photo above/below. Check around wherever you live for similar opportunities (I know they do something similar in San Diego, for example). For more information on sailing in St. Maarten, visit the 12-metre regatta website.

By the way, it was a tight race, and we won by a hair, crossing the finish line only seconds before our competition. I’m still celebrating.

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