So where did the dream of sailing Ocean Angel to the Caribbean really begin? Was it 30 years ago when we bought our first dream boat; did it come to being with memories of our 2010 trip to the Bahamas or our trip to Central America? It’s hard to know because while we know every journey begins with its first step, just when you take that step is hard to say. 
We began talking about the trip while we were lying at anchor in Georgetown, Exuma Cays, in 2010. Our new alternative energy equipment was working as planned; the boat was running well; we’d undertaken extended voyages already. Could we afford the time and money it would require? Pieces of the puzzle began falling into place almost faster than we could control them. My work caseload was dwindling somewhat by design and somewhat by factors beyond my control. Cases we thought would never close came together all at once. It was beginning to look as if now was the perfect time. 
All our previous journeys paled in scope and distance compared to the one we now were contemplating. Our past adventures mostly consisted of daytime hops from one port to another; some very long days certainly, but nothing compared to some of the legs on this Caribbean journey. I had to strike a bargain with Joy , agreeing we would not head out on any given leg unless she was ready and comfortable with the weather forecast. This promise proved to be the single element in the passage planning that worked to our greatest advantage. Sailing nearly 2000 miles directly into the trade winds requires extensive planning, accurate weather forecasting skills, and sensible interpretation of all the elements that might affect any given leg of the trip. Not just the weather for the next day, but for the next three to six days would become vitally important. My skills in weather forecasting would become better with each additional move southwards.
We accumulated charts, cruising guides, weather books, reading materials, spare parts for the boat, provisions for six months, and more. Charts and guides can easily cost you thousands of dollars, or, you can look for almost new, but second hand materials and save many hundreds. Cruising Guides become out of date almost as soon as they are published; the globe doesn’t change all that much, so directions and true compass headings remain accurate. My first book purchase was Bruce van Sant’s “Gentlemen’s Guide to Passages South”, considered to be the authority for this trip, an absolute must-have. I found an older version for $1 at a yard sale, enough to whet our appetite and to teach us that we too, could make this trip if we followed his advice – never miss a sundowner, and never, ever, head out if the forecast called for more than 15 knots on the nose. A current version would come along later. We bought Steven Pavlidis’ Guides, the CYC charts of the Caribbean, and Scott’s Guides for the Virgin Islands, all for much less than new. On-line I found Frank Virgintino’s free “Cruising Guide to Hispaniola”. We pored over past provisioning lists to determine what worked, what didn’t, what we liked or didn’t like. We began shopping months ahead of our intended departure. We made a few upgrades to equipment, and in November, we drove to Melbourne, Florida, to attend the SSCA Gam – this time with specific goals in mind. We attended an in-depth medical seminar, a weather forecasting seminar, communications seminars, and sat in on a round table discussion with cruisers who’d made the trip before us. At the medical seminar, one attendee passed out, his eyes rolling up into his head. A potentially serious medical emergency was successfully resolved by the guest speaker. 
We talked with friends Jim and Janice Fauske, and Tom Rose who completed this journey to see what advice they might offer. Janice was concerned for Joy, worried that she would not be able to stand up to the rigors of this trip. But in the end, Joy won her over, convincing Janice that not only was she able, but she was excited to be underway