I would contact a travel agent (you don’t pay unless you book the trip) and look into Sandal Resorts or maybe an island hopping cruise. I lived in Puerto Rico for a while and the cruise ships docked there twice a week in San Juan.
I’m not sure of the age restrictions on Sandals, if it’s 16 and over or 18…
Breezes, their sister company accepts teens…
I’m leaving for San Juan in 10 days!!

We’re spending a week there, then off on a Back to Back Cruise… We really enjoy our time in SJ… this will be our 4th visit…
Someone suggested St Lucia, while it is a beautiful Island it is also VERY impoverished, if this makes you uncomfortable and would spoil the vacation not for you… Many that stay in the all inclusives are somewhat hidden away from this…
On saying that a lot of these Islands have their All Inclusive resorts… which become what I call more of a ‘compound Holiday’
Jamaica, although the ocean and sites were great, if you ventured off by yourself you were hassled a lot!!
If you want one the Caribbean Islands … St Maartin is prob my Fav, St Thomas, St Kitts and Antigua also have nice beaches…
I love Bonaire, Barbados, Tortolla, and Virgin Gorda…
If you are looking for a Fun ‘All inclusive’ time then you really can’t go wrong as another poster has suggested with Caribbean side of Mexico … My preference is The Mayan Riviera… around Playa Del Carmen. We’ve had great vacations here, but you have to be careful on which resort for the better beaches… Dominican Republic also offers some great all inclusives…
I had friends who took the family on a cruise, the kids (late teens) initially didn’t want to go but they loved it… Consider that, as there is always plenty going on to suit all tastes…
If you have any Questions feel free to IM me…
I’ve been to Most of the main Islands and a lot of the less touristy ones such as Dominica and Tobago…
Have Fun