The plan...

The initial plan...subject to change at a moments notice!

Quite a bit of thought and research was done around what we wanted to do and hence what we wanted. As we are both relatively inexperienced with cruising, we wanted to ensure that we started off in a location that was not only fantastic for sailing, but also not too challenging so as to allow us to learn safely and comfortably. Hence us deciding that the Caribbean would be an ideal place. Many of the islands / anchorages are day sails apart with the odd over night passage required. The climate is tropical, water gin clear and it is a beautiful place to sail. We did initially toy with the idea of buying a yacht in Europe / UK and sailing it locally and prepping it before then crossing the Atlantic, however a number of factors dissuaded us. The price of yachts in Europe are a lot higher than the US, sailing in the UK can be a bit chilly (even in summer) and doing a transatlantic crossing might scare the crew from ever setting foot on a yacht again. The game plan is to pick up a yacht in Florida and sail it down the leeward and windward isles and be out of the hurricane belt by July. A bit of a push seeing as the season has already begun and buying a yacht is not just a "jump on it and sail it away the next day" sort of activity! Generally a fair amount of time will need to be spent preparing a yacht for cruising.
There is also the risk or "analysis paralysis" - Sitting in a marina trying to buy every contingency piece of gear, waiting for the perfect weather, needing to do "just one last thing" etc
There is also the risk of being naive and heading out under equipped / prepared and running into issues.Getting the right balance is tricky and different for each individual.

So now we had a jump off location to start our adventure; our next step was to identify our requirements for a yacht!