Sail twice a year a couple of months each, at the Caribbean or at the Mediterranean?

[Preluding]

Grew up sailing small boats as a child. As an adult I had severeal boats in Argentina and one at the Caribbean. Never I have lost the love to sail. Now, I'm looking for a boat to live part time abroad. Some cruising and open ocean sailing is on my desire.
My experience sailing was mainly from the Rio de la Plata and the South Atlantic. Sorry for my English!!
As a child I grew up learning sailing with optimist, then as an adult I had several sailboats at the south atlantic. Some very old and then almost new. ( Not to big 34 feet)
And years ago while I had my own boat at the Rio de la Plata and an ownership of a Hunter 40.5 at BVI I was sailing two weeks at the Caribbean and the whole year at the South Atlantic.
Unfortunately at a race to Punta del Este with a heavy storm I felt of the boat because a knock of the boom when I tried to shorten the major sail. Luckily I reached the boat swimming , water so cold in winter!!!. Because of that shock I sold the boats, 15 years ago, and promised not sailing anymore.
Now that I'm partially retired but my love for sailing continues. So I thought like as a project to sail in calm waters more warm three or four months a year. I have to decide between the Caribbean or the Mediterranean Sea.
I think that also I have to hire a skipper for practice!!

[dlymn]

Many people who sail in theMed will tell you that it's a great place to motor. That's because they're sailing to destinations with a budget on time. You can bet the wind will be in your face often when you do that. Some of the winds, the Mistral, the Meltemi can blow long and hard. I f you choose to sail in the Med, and it truly is a beautiful place to tour, then choose a patch such as the Ionian or Aegean and sail where the wind takes you. You will always find a port nearby.
Generally, marine services in Greece are basic compared with the rest of the EU but that's part of the charm. Schengen restricts you to 3 months every 6. If you. Buy a boat with VAT pai, you might avoid the foreign boat rules. Come on over,start a new life.