We were in Bermuda and Puerto Rico this year and I'd suggest Bermuda. It is truly just droppingly gorgeous, in my opinion. Loved PR also though, so I might look around for hotels and see what feels like the best fit.

Bermuda or Cayman checks all of your boxes except hiking. But in Cayman you can walk the beach for so long it feels like quite a hike.

St John is perfect

Anonymous wrote:Puerto Rico

No no no.

The PR Ritz looks amazing (!!) but I don't think it is in the budget for this particular trip. The PR Wyndham looks like a great option and close to a lot of off-site activities as well. Love the idea of both beach and rain forest time. That one is very promising. Thank you.

From what you’ve said OP I think you’d like PR better than Bermuda (although I’ve been to PR more recently than Bermuda).

You might look at the Wyndham— it is a big resort but it has a lovely beach and it’s conveniently located to a bunch of things like El Yunque, biobay kayaking, Luquillo beach.

Or you could look for something closer to Old San Juan— it’s only maybe 40 mins between them.

If you can afford it Dorado Beach Ritz Carlton. Get a room with the little pool.

Get a rental car. My boyfriend drove all over the island. He really liked the rain forest.

I was surprised at how much hustle and bustle Puerto Rico has. It definitely is not economically depressed.

Almost all of our servers were former military or are currently in the reserves. Maybe everyone enlists to get the free college and travel a bit.

Key West, take a trip out to Dry Tortugas.