This is probably not your conventional location, but you might want to consider Cuba.
I know, I know, we are not allowed to go there. Not really. I went there last summer with (family trip) and had an amazing time.
I spent a couple of days in Nassau and then took a flight to Havana (real Russian air plane, with Russian signs and everything!).
Havana was everything they said it was an them some! Coming from Bahamas, the biggest difference I felt was that there was no American music! Don’t get me wrong, I have nothing against Hip-Hop, but to hear live Cuban music in almost all restaurants that we went too, was an excellent experience.
After spending 4 days in Havana, we went to this ultra exclusive, tourist only, island strip called Varadero. Its a 2 hr drive and you can rent or take a bus. Beautiful, all inclusive resorts. From huge buffet tables to exclusive steak dinners. Everything is included in the price, even the drinks.
Getting package tours from Canada is very popular, so you might want to consider that option as well.
As I said, a bit unconventional, but definitely worth the little trouble you have to go through.
Enjoy!