Hey! Me too! My sister has a place in the neighborhood past hawk cay. We stayed at the resort... it was meh... Kids had a blast on a fishing trip pulling out fish like crazy. Ate in marathon a couple times. Sat by the dock at her house as the sun went down. Peaceful place but kinda expensive.
You can get all those in the places you mentioned. That's pretty generic. Here are my feelings about each place: Key West. As others have said it is okay for a couple of days, after that it's kind of like Vegas and the scene just gets old. No real beach. quite a few activities, Tortola, jet skis, sunset on the pier... Other keys are also really nice so you could make a vacation out of it if you move around a bit. Puerto Rico. Beautiful main town which is a one full day experience, beaches are not great, big resorts have plenty of golfing. Of the three this would be my last choice. Now if you use it as a way point to get to Vieques (small island off the coast) then that's a different matter. Check it out for sure. Cost no object, go to St John. Best island in the USVI. Find a good VRBO and rent a jeep for a week. Plenty to do on island. It can get spendy especially in high season. Wife and I have been here probably 10 times or more. If this is your choice then let me know and I can recommend lots of stuff to do. Beaches are amazing and so long as you plan right can be mostly deserted. Hiking ranges from a stroll to pretty strenuous. There are some good snorkling spots and plenty of off island trips. Visit the Baths and Jost Van Dyke where you can get an amazing drink on the beach at the Soggy Dollar. There is a reason my wife an I keep going back here. It's so nice.
We've spent about 18 months total vacationing in the Keys. If you fish, dive or spearfish then it's pretty cool. As a destination it lacks a lot. Full of super sketchy tourist town types and deadbeats on one side and wealthy elitists on the other. Restaurants are in KW are numerous and good to great but it's full of goons. Middle Keys are more laid back. Working class. Upper Keys are a little too close to Miami and all douches there. A couple of high end resorts and a lot of overpriced hotels. We always do VRBO or Airbnb.
I like the keys, as a Floridian, but it's stupid expensive, crowded, and more crowded. So many options, Staniel Cay Bahamas, Cuba, DR, Caye caulker, Belize, corn islands, Nicaragua, any thing Panama, Both Mexican coasts
