Islands that are less touristy, more adventurous, but with a good nightlife?

Planning a trip to somewhere in the Caribbean for around 9-10 days in late November. There will be 3 of us, myself (M31), my girlfriend (F31) and a good friend (M31) and all fairly well traveled. While not applicable to a lot of the islands, we all speak spanish to varying degrees. We aren’t doing the resort thing, will be staying at airbnb or hotel. Trying to decide on an island (or two if it is easy to travel between) for our trip.

We’re looking for, in no particular order:

• Hiking
• Biodiversity
• Mix of culture/city/town and remote areas
• snorkeling/diving
• fishing
• surfing
• other exciting/adrenaline junkie activities (?)
• night life
• drug friendly

So far, we’ve considered:

• Grenada
• St. Lucia
• Jamaica (some concerns here regarding safety, especially with one woman in the group)
• Puerto Rico.

I’ve been building a spreadsheet to try and rank islands, but everyone online has a different opinion so I thought some more specific feedback might help point us in the right direction. So, what islands should be on our list?