Blog 1: Off to a Flying Start
Our first few hours after weighing anchor from Charlestown were anything but easy sailing. After thorough training ashore, we set off but flukey winds off the land, shifting waves, squalls, and a maze of fishing pots kept the crew on their toes.
But this is what offshore sailing is all about—problem-solving, teamwork, and getting comfortable with the unpredictable.
Within hours, the team had gybed, reefed, set up the pole, taken it down again, and experienced their first night watches under a rising moon. As the stars came out, the wind steadied, and the sea state calmed, we settled into a rhythm, making a solid 7-8 knots through the night.
With the first light of dawn, we gybed once more, poled out the headsail, and adjusted for the best wind angle. The on-watch team, guided by First Mate Manu, shook out a reef in the main and switched to the powerful Yankee 1. Now, with full sail, we cruised under the Caribbean sun—next stop, Jamaica.
Blog 2: Celestial Nights and Fast Miles
Night two brought calm seas, gentle swells, and a star-studded sky—ideal conditions for our watch leaders to grab their sextants at first light for a morning star fix. As the sun climbed higher, so did the wind, settling into a steady Force 4 from the east.
With full sail up, we picked up speed, making a sharp 8-9 knots across the Caribbean Sea. Clearing Puerto Rico, we pushed south of the Dominican Republic, less than 600 nautical miles from Jamaica. The crew rotated through their watches, keeping us on course and fully immersed in the rhythm of life offshore.
Blog 3: Racing the Squalls
With forecasts predicting up to 27 knots overnight, the crew prepped early—reefing down before dark and enjoying a well-earned fajita feast while the conditions allowed. Throughout the night, our radar watch tracked approaching squalls, adjusting course ever so slightly to avoid the heaviest of the rain and wind.
The biggest squall—four miles wide—passed just to the north, sparing us from any drama. As soon as the moon rose and the radar screen cleared, we shook out a reef and found ourselves back at a steady 7-8 knots. By morning, the wind shifted just enough to let us move the headsail across and settle into a dreamy broad reach.
This afternoon, we’ll pass the western tip of the Dominican Republic, cross into Haitian waters, and sail through the Jamaica Channel—officially marking the halfway point of our Caribbean 1000 journey.
Blog 4: Land in Sight!
As dawn broke on Monday, the smell of fresh coffee, French toast, and bacon filled the boat—one of those simple offshore sailing moments that never gets old. With the sun high and a poled-out Yankee 2 keeping us moving, our watch leaders took their morning sights.
The first glimpse of land since Nevis came into view—Haiti! With the Jamaica Channel ahead, traffic picked up, adding a new challenge. Tankers steamed toward Kingston, cruise ships made their way east, and our watch teams worked together, using AIS, radar, and the trusty hand-bearing compass to keep a sharp lookout.
As the sun set behind the distant coastline, the crew devoured Thai green curry and prepared for another stunning night under the Caribbean sky.
Blog 5: The Final Push to Jamaica
The last full day at sea, and it was a beauty. A pitch-black night gave way to a golden sunrise peeking through wispy clouds. With dying winds predicted, we hoisted our biggest sail—Wanda, the Yankee 1—to squeeze out every knot.
A-watch, with Greg (who should have been sleeping), made quick work of the sail change, and we soon found ourselves heading west along Jamaica’s northern coast. The final gybe of the passage set us up on a perfect 270° course toward Montego Bay, cruising at 9 knots.
Just as we started settling in, the Caribbean reminded us who’s boss. The wind made an abrupt 180° shift—going from a dead run to a punchy 18 knots on the nose. For the first time in a week, we were close-hauled! Unfortunately, it didn’t last, as the forecast promised light winds ahead. Two hours later, with only 73 miles to go and a breath of 4 knots pushing us along, it was time to fire up the engine for the final stretch.
As the sun dipped below the horizon, thoughts turned to landfall. A well-earned pina colada, a hot shower, and a full night’s sleep await. But for now, we soak up the last few miles, knowing this incredible offshore passage – the Caribbean 1000 – will stay with us forever.
