We spent most of the winter in Florida doing all the stuff you have to do to an almost 30-year old boat to get it ready for cruising.
We added solar panels, revamped the electrical system, installed a new roller furler, replaced rigging, got a storm jib, added a water catchment system (works great!), and tweaked a million little stowage issues.
That last item is very important before you head offshore. Dishes have to be wedged in so they don't rattle, cans stowed so they don't roll, bottles stored so they won't break, spare parts stowed so they are out of the way but you can find them when needed. It takes a lot of time and effort, but it is a never ending task. Each offshore voyage indicates new flaws in your system, but gradually you get things so you can leave harbor with a few moments spent on final stowage.
The final gear problem was our self-steering system. Our old autopilot was perpetually failing so we bit the bullet and installed an Auto-Helm windvane steering unit. Once that was in place we felt we could at least have self steering when under sail, though I also purchased a small tillerpilot that could be hooked to the windvane for steering under power--at least that was the theory.
We left Marathon, Florida, had a nice sail across the Gulf Stream to near Cuba in a light northeast wind, passed through the Yucatan Channel, then began a long slog across the Gulf of Honduras in flukey southeast winds with a strong adverse current. Conditions were exactly like the pilot charts predicted, but the reality of beating into a hot, humid wind and current, day after sweaty day, was tough.
Finally, we decided to stop at remote Swan Island, which provided a couple of days of respite from the relentless headwinds. We met one other sailor there, a singlehander, and we were the only two boats to visit in a month. It is nice to know there are still places so remote in the Caribbean.
On to Providencia Island we motored, in light winds and seas. Providencia is part of Colombia. It has 1200-foot high peaks that loom over a beautiful and protected anchorage. The people are friendly and the port captain welcoming. We finally felt like we had arrived in a Caribbean paradise.