So you wantta charter. Well to begin I strongly recommend the Caribbean
in winter and Med in Summer or even the north coast of France
and South coast of England
. Many charter boats in Carib make the semi annual trip across the pond you might consider that.
There is a large contingent of charter boats and broker network already in place. You should consider brochures and placement in local travel agency's currently near you and try to cut a special deal with them.
The Ben57 or the mood64 are perfect choices as would a classic boat of any type as these fit the Carib and European lifestyles and Boat choices. Definitely something with three cabins and by all means take the best cabin
for yourself (I know this sounds strange but your charter guests are going to be tired after full days of sailing and partying and there is plenty of room for them in where ever they sleep plus you can always give it up for a premium fee).
St Thomas is a good choice in Carib to start, you will learn a lot quickly and can always do daysails from the Criuse Ships as its set up for that.
does not have as many varied anchorages
and the Islands around are tough anchorages
Down Island to Bequia is another story as it has some great anchorages like Palm Island but is much rougher when going between Islands.
The Spanish Virgins do not have as many great Anchorages with the exception of Culebra
which can be a great place to take your time off in and its a half dayb sail downwind from St T.
After a while you'll probably want to base in the BVI so as to avoid the long trip to weather
to get to the best cruising grounds and the most requested trips.
is good in both St T and Bvi.
You will only need one person other than yourself and that is for cook position with sailing help during the short trips you'll take so a person to double as cook and hand, a girl is necessary as charter guests will feel more at home.
Good luck, it's an adventure, I spent 3 years charting from those destinations and loved every minute of it. Oh by the way the most important thing is you will need all the toys that yachting implies so stock well!