Not all boat buying regions are equal
I would agree on the Caribbean. We left North America (we are Canadian and bought our boat in the US) with the intention of going to the Eastern Caribbean for the winter and Europe this summer but were dissuaded by the many Europeans we met who complained about the coast of cruising in Europe.. The Western Med is particularly bad - apparently there is no where to anchor in Mediterranean Spain and docks are 40 to 60 euros a night - way out of our budget.
Another consideration is where it is best to get a boat. Prices are much better In fact, many Europeans (and Canadians) go to the US to buy because the selection is great and costs now excellent. If you bought a boat on the east coast of the US it would be too much of a rush to go the Eastern Caribbean (via the Thorny Path) and back in one season. Better to take your time and spend the summer in Grenada. If a hurricane is coming it is not too hard to nip south to Trinidad or Venezuela if you have to (unlikely to happen but possible). If you go offshore to the Virgin Islands from the US it can be done in one year but you would want to really get your boat sorted out first - it is 1500 nm from the Chesapeake in November so not to be taken lightly.
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.