Have you considered crewed yacht charters? They are very popular in the Caribbean and anywhere where you've got strings of islands dotted in the ocean.

I can see the advantages of living at sea and stopping wherever you like. Some yachts are nicer than my house. They have got everything and are floating palaces more like mini cruise ships than standard boats.

And they are big, too. I always thought yachts were average sized till I saw one up close and it was massive. I would have liked to see inside, but instead I had to look at pictures.