Since we bought Rocinante in 2013, the goal had always been to sail to the Caribbean. 8 years later, we (I mean me) were finally ready to make the trip. The next step was to ensure that our faithful steed Rocinante was ready after taking a Chesapeake vacation.

We worked on the boat throughout the summer but it always seems to come down to the last minute to get the final details right.

Meanwhile, as we planned our weather window, our incredible crew flew in. Chris was Tim’s original instructor from his ASA class in the San Juan Islands in 2010. The class was a 40th birthday present that started this entire adventure. After 11 years, we have become great friends and Chris, who now owns his own sailing school in Grenada, took a 3-week break to help us sail Rocinante to the USVI.

Our second crewmate was our long-time friend Gretchen from Jackson Hole. It can rain; it can be 30 degrees and windy; it can be 15 foot standing seas; it just doesn’t matter, Gretchen is smiling. Always ready for adventure, Gretchen is an amazing crewmate.

Up until we left the dock at Stingray Point Boatworks, we worked on the boat. From the tip of the mast to the aft stateroom toity, Rocinante was getting ready for the trip.

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We headed to Hampton at the mouth of the Chesapeake Bay. From there we would wait for a weather window to leave. When we discovered that we’d be in town for Thanksgiving, the amazing Hartz family invited us to Thanksgiving.

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2am on Sunday the weather window opened and we headed out into the open ocean! The first goal was to cross the Gulf Stream as quickly as we could. We sailed south to Cape Hatteras and then the first casualty of the trip died. The Autopilot.

As good sailors know, always have a backup. Once we decided that we’d continue on, even without the autopilot, the hand steering began. For 36 hours Chris and Tim took turns hand steering through the Gulf Stream. It was a chilly, windy, wavy journey with very little sleep. We paired up for watches ensuring that someone (almost always the guys) were at the wheel, while we made our way through the most challenging part of the trip.

The seas were big and confused after a series of storms, but the blue skies made it easier. At least during the day…

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We even got a visitor. Huey hung with us for about 2 days, 400 miles from land, taking breaks on deck, falling off the solar panels a few times and managing to poop everywhere.

Once we passed through the Gulf Stream, Chris and Tim went to work on the Monitor wind vane. The Monitor is an amazing tool. Setting the vane to the angle of the wind, you can steer long distances with only slight adjustments. Once set up, with lower winds, we were all able to go back to separate watches and we all got a lot more sleep.

The winds reduced and the waves eased and we were even able to have our second Thanksgiving dinner! 3 weeks prior to departure, I made 10 dinners and vacuum sealed them up. Since we thought we’d be sailing for Thanksgiving, I roasted a turkey, made green bean casserole and froze it solid. Thanksgiving “leftovers” were a great treat, complete with cranberry jelly!

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As things got warmer, the seas calmed even more and we even had to run the motor a bit. Occasional squalls and the subsequent rainbows kept us entertained, as well as viewings of downloaded episodes of Yellowstone.

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After 9 days, we crossed the Tropic of Cancer! It was a warm beautiful calm day, so we all dove in for a swim and a shot of Rum!

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After days of blue skies and rainbows we arrived into St. Thomas. We celebrated until 4 am (our usual watch schedule! 🙂