On to the Caribbean

Fellow delivery crew member (and CW staffer) David Gillespie shares the experience of his first blue-water passage to the Caribbean after leaving George Town, Bahamas.

Dave G

Yours truly—happy to be sailing.

After the leisurely pace of the last four days, it was time to pick up the tempo and make a real push for the islands. Captain Jesse had all hands on deck for an early departure. Given that I was up in the wee hours of the morning (0530) to dinghy our reluctant-to-leave crew member Jen into catch a taxi (she only had a week to spare- Read her story in Pt. 1- Cruising in Fast Forward), they let me sleep in until just after the anchor was secure in the bow roller and we were under way.

The sun was low in the sky as we headed for an east-end exit at 0800. Heading directly into the sun, the glare off the water made spotting coral heads much more difficult. Eye fatigue set in quickly as we strained to scan the horizon for hazards. Jesse decided to take the first exit possible to clear the reef to give us a break. It was a bit dicey but we finally had cleared into deeper water.

After a collective deep breath to relax, we suddenly noticed something dramatic had changed, the windex was no longer pointed straight forward—we could at long last actually sail this fine vessel and guess who just happened to be behind the wheel. Yep, Dave G (me). Up went the sails and we doused the engine. Ah yes, the quiet hum of the hulls skimming through the water. With a freshening breeze in the 17- to 20- knot range, we were soon scooting along at 10 knots. Still in the lee of Long Island, the sea was flat and Jesse leaned over to point out this would probably be the best sailing we’d have. I took that to heart and spent the next four hours trying to sort out a straight line so the old autopilot didn’t bench me.


Our fine young chef Jacob whipped up some sweet breakfast sandwiches. What a glorious day in the making. By noon we had our new watch schedules which would run 24/7 until we made landfall. This is what I had come to experience, a true blue-water run. Although I live in Colorado, I still manage to get four days of sailing in each week but really had an itch to see what offshore passages are all about.

We settled into our daily routines. James and Amanda would take a daily noon sextant reading and then huddle over the table for hours working out the math until the evening reading. Jesse was on a reading spree and burned through six or seven books, pausing only to make yet another snack of some sort—usually involving bacon or butter. Jacob would make his way to the stove to create yet another masterpiece for lunch or dinner. Afterward we would tag-team the dishes. All told each meal took a good two hours or so out of our day. In between eating and watches there is yet another glorious sunset (no green flash though) followed by the full moon rising on the opposite horizon.

By the second day Jacob and I were struggling to pass the time. To say Jacob’s cell phone is a source of all things entertainment related would be an understatement. Besides housing the Smithsonian of music collections, it also recorded trip highlights via camera and carries a fine assortment of games. Soon we were locked in an epic battle of backgammon, which I hadn’t played since college. A bit weary from my night watches, it took me awhile to remember how it’s played as well as figure out why the screen kept going dark right in the middle of my most excellent strategery (An SNL Bush Jr. reference).


Not meaning to sound impatient, Jacob kindly suggested we could start with something simpler like… checkers. Ouch, am I that brain dead? Really? My ego was glad he didn’t dumb it down to Go Fish. In the end, my age advantage prevailed, and I summoned the crew to witness my final move to seal a victory—YES! On day three Jacob had unpacked all the miscellaneous junk stuffed into the forward hull to dig out a huge stash of board games. He would gain redemption with back-to-back victories in Trivial Pursuit.

Another source of entertainment was the daily ukulele tunes. Both Amanda and Jacob had committed to learning the instrument with the goal of playing at least one song the rest of us could recognize. Jacob, of course, actually had sheet music on his phone and managed to sort out some Bob Marley tune. Tiny Tim would be proud to see the instrument is enjoying resurgence in the sailing community.

And so the days passed, and soon we were within striking distance of St. Thomas. Jesse ditched our original destination of Puerto Rico as we needed to make up some time. As the midnight hour struck we inched our way into a somewhat sheltered cove on the northwest end of St. Thomas. With the wind out of the south we could get away with a few hours sleep on this normally unsuitable side of the island.


We awoke Sunday to the serenity of waves lapping up on the beach. No engines or rocking, just the glory of the green hills of St. Thomas. As we enjoyed a morning coffee, I couldn’t help feeling a bit of a let down knowing that within a day or so this fine collection of a crew would be scattered over the Caribbean. Based on the horror stories each told over the course of the last 10 days about other deliveries, I knew this one would be a standout.

The one thing Captain Jesse had gone out of his way to make a point of is that crew compatibility was the number-one attribute he looked for in assembling a team. We certainly had that. Everyone was eager to pitch in, on time for watches, and we laughed our a**es off.

Well played sir.


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