Bareboat chartering--general newb questions

[JPS27]

Looking for some experienced opinions of those who have done bareboat charters.



I would like to accelerate my dream of sailing beyond my 'backyard', specifically areas south of me like the keys and areas in the Caribbean. I have a 36 foot Pearson. Sail in the Chesapeake (15 years experience). Have made a run down the coast from New England to VA when I bought the current boat recently. So I have experience and sail mostly solo.



At the present time I don't have the time to prep the boat etc and make a trip south on my boat. But, a charter situation would work. My wife is interested in the charter idea and has shown more interest in learning how to crew on our boat...to the extent that she has taken ASA 101 and will take 103 soon (works best when I'm not the instructor).


What questions should I be asking charter companies? Which companies? Should I stick to US and its territories? What are the red flags and scams to look out for? What else? Thanks.