My back hurts, I can feel each muscle in my legs and arms. I have paint imbedded into vast portions of my hands, and at least five new bruises. Each night I crawl down three feet into a bunk where all my earthly (with me) possessions surround me, scuttling from clothes to books to towel on my knees, hunched over. For the past three days it’s been an endless stream of cleaning, sanding, painting, moving stuff from one place to another, carrying and hauling, with the occasional break for bullshitting. I’m exhausted, too tired to sleep more than five hours a night, really.
I couldn’t be happier.

The Topsail Schooner Wolf, sailing to Cuba as part of the Conch Republic Cup
Later today, somewhere between 5 and 6 this evening, I will sail away from Key West, along with 11 other people, aboard the Topsail Schooner Wolf, a two-masted, 74-foot schooner, as part of the inaugural Conch Republic Cup. At last count, some 59 boats and around 400 people are making the run from Key West to Varadero, Cuba. Three days later, we’ll race from Varadero to Havana, Cuba. Three days after that we will race back to Key West.
This isn’t the first time for the Key West to Cuba race – but it’s the first LEGAL one, made possible by Obama working to “normalize” relations with Cuba since he announced the changes in December, 2014. The result: a field of boats, large to small, all trekking to Key West to participate in this historic event, which could also easily be one of the largest contingents of US citizens to converge along Cuba’s coast since prohibition.
(Fun fact: During the US’ alcohol prohibition from 1920 to 1933, the Key West to Cuba trip via boat was a popular method to get to a legal rum source. Havana is only 90 miles off the US’ southernmost island’s point.)
This race is a goodwill mission- an ambassadorship of sorts, and at the rate the US keeps announcing new allowances in trade and financial regulations, I wouldn’t be surprised if we get to see one of the last visions of a Cuba un-touched by the American way.
Making this race even MORE special for me (as if sailing a trip aboard my favorite ship and visiting Cuba wasn’t enough), is that my husband Jay is along for this trip, our Greenhorn crew. I’ve spent nearly four of the past 13 months down here in Key West crewing on Wolf again, and Jay has only been with me for five days of those. I now get to show him the ship I so love. He’s already been pulled into working on hatches, cleaning all sorts of things – the stuff of the lowly deckhand.
In many respects this is our last hurrah. Jay and I are approved foster parents, and we will start taking “placements” (aka, foster kids) into our home when we return. I won’t be able to just head south for a few weeks to go sailing, and there’s no international travel looming on the horizon since you can’t take foster kids abroad. Change is afoot. Good change, a new adventure. I can’t think of any better way of saying goodbye to our kid-less couple hood than jumping aboard a pirate-inspired schooner for a sail and a visit to a place most Americans have never gone.
You can track our progress here.
Meanwhile, wish us fair winds and following seas. Cuba has no real internet access, so we will see you on the flip side, full of sea tales, Cuban travel tips and just a few more high jinx up our sleeves.