The Caribbean -
To many cruisers, this is the Holy Grail of destinations. Few circumnavigators are able to get around without traversing this wonderland. While some geographers might not include the Bahamas in this area for the sake of convince I do. There are many jewels here and many just plain ol' stones. But, not everyone will agree which is which. In all the years cruising we've missed Hati.
When in our 30's and starting to dabble in this lifestyle we made the decision to miss places dreamed dangerous and places where the governments are not fond of Americans. Hati was what we thought of as a dangerous place.
So while Hati was missed, so was the group of island known as the Turks and Cacos. In the cruising community it is oft referred to as the "Thorny Path". Rightly so. Few boats are lost there that we know of; however there are not easy passages. One friend before the time of GPS loved to relay this story of them making what they hoped was a day passage. By night fall they could see the island but prudence kept them from attempting to make harbor in the dark. So they hove too and wait for daylight. The lights of the island disappeared and when they started out the next morning, his fix put them at a negative 7 miles for the 24 hours run. Yes they floated with the current all the way back and then some.
From Puerto Rico (PR) south traveling is easier. I am not saying easy, just easier. PR to the VI's is generally an upwind slog or a motor trip if you find the trades are flat one day. From British Virgins to Antigua it gets easier and there on down you will most likely find some time to have pleasant sails. Don't expect them all to be off wind sailing.
The islands often create their own wx. Mountains create a wind shadow so winds may be light or chaotic in the lee of the islands. As you reach each end the winds follow the land and curve around creating head winds and then tail winds. Between islands the wind increases from the smaller gap.
And as you get further S the island chain becomes N / S so often as not you will be on a reach.
For the most part the people are wonderful. As with any group of people there are bad apples and nepotism ranks high on the list. In the Bahamas one of the relatives of a politically connected was known to be a thief. In the VI's we saw a robbery, and called the Police to report it. The dinghy stolen was motoring in front of the police station. The police said they couldn't do anything about it. Two days later I understand the thief was caught and released because he was connected to one of the guardians of the peace. In Salt Whistle Bay there was a scam where cruisers would be invited ashore for dinner while another group would board their boat looking for cash. A cruising friend was robbed this way.
However, no matter what, the area is beautiful. Those events could easily happen in any city or country in the world. We thoroughly enjoyed our time in those islands. And one of them; after being half way around, the Bahamas, is still a favorite place. We spent the cyclone season in Trinidad doing boat projects and playing tourist. Our hub was Grenada where we shot off West, unfortunately skipping Venezuela. This phase of the life was spent in the ABC's, Columbia, and we settled in Panama for a couple of years. I put a page of Sunsets from the San Blas (Kuna Yala) together as well as a photo essay or our time there.
Entertainment
For cruisers in the Caribbean the entertainment many evenings are charters. After a few hours of training groups are set free with 40'-50' yachts. Every berth on the boat is filled with people wanting to maximize their vacation experience.
Years ago we anchored in Trellis Bay on Beef Island. Just before Sunset a charter boat full of party goers came in to anchor. The dropped the hook and backed down on the anchor. Then they powered up to the anchor and backed down again in a different direction. They repeated this several times covering all the points of the compass. I am sure they thought that was the best approach for a good nights sleep. Enjoy the shows.