Destinations

It quickly became a running joke. “How come we never went snorkeling here before?” my wife, Shelly, would ask. “What a great beach. Why didn’t we go swimming like this the last time we were here?”The answer in each case was exactly the same: we’d been sailing, beating our way up and around St. John, reaching through the trades, reveling in the sheer joy of our boat speed. Not until the sun

Thus begins a time of hunger, but the trade-off is compelling: 10 days of sacrifice for the serious fun of sailing in a legendary Caribbean event with a group of dialed-in high-school sailors and the boat’s skilled and gracious owner, Mike Williams.The 37th annual St. Thomas Rolex International Regatta sees 66 boats racing in seven classes to compete for four Rolex timepieces. Walking into

Thus begins a time of hunger, but the trade-off is compelling: 10 days of sacrifice for the serious fun of sailing in a legendary Caribbean event with a group of dialed-in high-school sailors and the boat’s skilled and gracious owner, Mike Williams.The 37th annual St. Thomas Rolex International Regatta sees 66 boats racing in seven classes to compete for four Rolex timepieces. Walking into

Racing a charter boat is very different from campaigning your Sonar or Etchells or, as in our helmsman Charlie Garrard’s case, your J/105. Some bareboats are pretty tired, and sails can have a short lifespan in boisterous Caribbean conditions. Some of the bigger, heavier boats are cumbersome and slow to tack and trying to sail them well can be a frustrating exercise. Local knowledge of winds and

Racing a charter boat is very different from campaigning your Sonar or Etchells or, as in our helmsman Charlie Garrard’s case, your J/105. Some bareboats are pretty tired, and sails can have a short lifespan in boisterous Caribbean conditions. Some of the bigger, heavier boats are cumbersome and slow to tack and trying to sail them well can be a frustrating exercise. Local knowledge of winds and

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.”