Approximately a week ago today, Jason and I took off from Chaguaramas on the 43 ft. race-modified Beneteau Wayward. We left under cover of night, both to time our arrival with early morning sun and to minimize the beat upwind as winds in Trinidad tend to subside at night.

The preferred course from Trinidad to Tobago dictates that you hug the uninhabited and mountainous north shore of Trinidad for 40 miles or so until you reach Toco at the northeast end of the island, then turn left and head approximately 20 miles north until you reach Store Bay, a beautiful, palm-lined shore in Tobago.

It’s fairly simple really, so long as you stay close enough to the shore in Trinidad that you don’t run into the 3+ kt current that runs westward off the north coast, and you don’t go so close to shore that you run over a fisherman in his pirogue in the dark. Only catch is that this course takes you directly upwind for about 3/4 of the journey, and if you want to get there quickly, overcome the lack of wind, and outdo the current, you’re gonna be motoring my friend. Good thing diesel is only $0.69 a gallon for the locals down here.

Once you make the turn to Tobago, which happened just after first light for us, it’s sails up and you’re off. Sight Tobago’s mountains in the distance and you’re there — just make sure to avoid the very shallow reef surrounding Pigeon Point. It is responsible for the calm turqouise waters of the lagoon by the anchorage, but it won’t to your bottom any favors if you run aground.

On Wayward, we agreed to two 2-hour watches with two people on each. Jerome, the owner, felt this was the safest way to keep Wayward in one piece and assure that the watchkeepers stayed awake, especially since we’d never been on the boat before. We didn’t disagree. So Jason and Fred headed to bed and Jerome and I took first watch, til 2 a.m.

The night sky from a sailboat is a beautiful thing to behold, and it kept me entertained for awhile, but despite even Jerome’s admirable conversational skills, my eyelids were failing me after an hour. I didn’t want to look like a wussy on my first overnight passage, so I pushed on through, but I can’t say it was easy. I gave in and woke Jason at around 1:50.

When I awoke four hours later, Jason and Fred had directed the boat closer to shore to avoid the oncoming current and improve on our arrival time. Jerome and I took over until daybreak, and made the left turn to Tobago just after sunrise. Thinking everyone probably needed it, I went downstairs to make some coffee before we woke the guys to set the sails. BIG MISTAKE. It turns out that, in 2 meter seas, no matter how big the boat seems, my stomach can not handle rocking and rolling below. I never recovered, and after the sails were hoisted and the other shift went below, I laid in the cockpit with my eyes closed until we pulled into the reef-protected, palm-covered shores of Tobago. Turns out I have some training to do before we get into big seas and solo shifts. Yuck.