Interesting idea. I am planning to do the same thing. I spent 2010 - 2012 in the BVI and the last year in St Maarten and have done extensive research on the market. I am a former yacht broker and see an opportunity now given the current
boat market and the minor economic recovery taking place. The crewed motor yacht charter market has been in the dumps for the last 4-5 years but seems to be coming back slowly. Any boat over 90' ($100k and up) has been chartering very little if at all and there is a lack of charters available in the 70'-90' range under $40k. Unfortunately the boat market is starting to rebound and the inventory of cheap
70'-90' motor yachts for sale
is disappearing now. I know I have been following it and am ready to buy. I have spent a lot of time in both the BVI and St Maarten talking with the charter crews and learning
the markets. The BVI is a non starter for a number of reasons, and St Maarten presents a better base opportunity with the option of doing pickups in BVI. I have been to several of the charter brokerage shows in the Caribbean
and networked with a lot of the brokers that book the charters to get a feel for what I am planning and will probably be purchasing
a vessel and getting started in the next 6-12 months. Be careful of your planning, the margins are not as large as they seem at first glance and the logistics of owning and running a crewed yacht in this size range is much more difficult, and costly down here than you imagine. Also the need to offer something different than the 10-15 boats you will be competing with in this area is very important. There is a big difference between an owner with a 125' yacht that has their boat in a charter pool for tax reasons (no profit) and buying
a vessel to operate as a full time business (for profit). Good luck and maybe I'll see you on the docks down here.