Sailing the Caribbean off St. Martin

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Friday I booked a day trip with Random Wind to sail out of Simpson Bay. It was a beautiful, sunny day. We sailed east towards Phillipsburg along the southern coast, stopped to allow snorkeling and eat lunch, then sailed back towards Mullet Bay and moored to allow folks to take advantage of a trapeze swing out into the ocean and have snacks, then finally returned to moor back at Simpson Bay. Diane and Trevor picked up passengers from the boat dock behind Skip Jack’s, and after climbing aboard the sailboat from the dinghy, enjoyed an all day sailing adventure.


The Random Wind is a ketch that was originally built in South Africa, but has been in St. Martin for about 20 years. Diane & her husband bought the business in 2007; she still runs it even though she and her husband have separated. The captain is Trevor, originally from Great Britain, but sailed all over. They do a great tag team in sailing the ship and catering to their guests. Diane made a delicious, healthy lunch, lots of snacks, open bar/any beverage you could desire throughout the day. Trevor captained the ship, and supervised the trapeze swing… the pre-teen and teen girls were a hoot, swinging out over the ocean, dropping in, swimming back to the ladder, climbing back aboard and waiting for their turn to drop in the drink again!


I wasn’t interested in aquatic gymnastics… I just enjoyed the sail. Although one person in our group of 14 ended up experiencing some seasickness, I thoroughly enjoy the rolling of a sailing ship. There’s something so calming about looking out at the ocean or back to land, and being lulled by the motion of an ocean vessel. The turquoise water close to shore that the Caribbean is famous for is so stunning, and St. Martin sports mountain peaks that rise fairly precipitously up from sea level. For those who like to marvel at big ships, we also saw cruise ships and huge yachts… But I always find the natural landscape provides the most fascinating views.


When I go back to St. Martin (already planning on it!), I’ll want to sail on the Random Wind again. My only regret for the whole day was not putting enough sunscreen on top of my feet… I got a little sunburn!


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