I believe the best way to approach the Caribbean is with frozen fingers and toes. To do this, your takeoff point needs to be somewhere cold, like New England. This way, when you land in Puerto Rico or Tortola or St. Thomas, you have maximum contrast. Today all the elements were working in our favor for this system to work; 3:30 a.m. wakeup in Maine, 22 degrees, drive to Portland, bus to Boston. I'm traveling with guide Heather, a frequent travel companion. She wants to get to the Caribbean so bad that she doubles the speed limit on a deserted highway, gets pulled over, quickly talks the cop out of writing her a ticket, then peels out down the road again. Snowstorm at Logan Airport. De-iced on the runway by the war of the worlds looking spray guns. Quick nap and bam we're in Puerto Rico eating empanedas in sticky heat and humidity. I love entering Caribbean time. It suits me. Add 10 minutes to everything. maybe more.  No hurry.

Our final flight is a quick 30 minute jump to Tortola, with amazing cloud formations along the way. I tick off the islands as we pass over them, The Spanish Virgins, the US Virgins, then above the Drake Channel toward the airport on Beef Island. As I do every trip down here, I scan the water below for choppiness, swells, and look for new swimming spots. Pilot Danielle, a familiar face to us now, deftly skirts some clouds. I used to get nervous at this point, worrying about the trip, if the clients would be happy, if the boat would sink (unlikely), if it would rain for days.  I'm not as worried anymore about these things. Most are out of my control, anyway. I prepare as best I can for the things that I CAN control. I make lists. I outline little talks I like to give aboard the yacht. I chill out.





Boston to Puerto Rico on Jet Blue, Puerto Rico to Tortola on Air Sunshine with our favorite pilot, Danielle.

There's a random $10 fee collected at Tortola's airport by a pleasant woman who describes it as an entry fee. Sometimes she collects it, other times she doesn't.  The government needs a few bucks to make ends meet for the month, they send her to the airport with a basket. It's Caribbean quaint, really.


A walking Caribbean Christmas Tree on Main St. A festival stilt walker taking a break.

Our charter yacht Promenade owners Kerry and Bazza meet us at the airport and whisk us through the East End; ramshackle stores, chickens in the street, low slung churches, some neon signs. It's bustling on a Saturday night, as is Road Town, where a Christmas street fair is underway. We dinghy out to the Promenade, a 65-foot trimaran sailing yacht. It's so familiar, I love this boat. Guide Dave Barra is already here. We head out for dinner, where guide Heather is reacquainted with guest Patty, they are friends from waaay back. Guest Mark also joins us. Chicken roti, rum punch, zzzzzzzzz.

- Hopper