For me, it is Negril Jamaica. I love the sandy beach, the western facing sunsets, the people and the music, etc...
I usually stay on the south end of the beach where there are smaller hotels and resorts instead of staying on the north end of the beach where there are the larger all inclusive resorts.
Negril is a gret destination. I also like Playa del Carmen in Mexico, but I think I favor that destination mainly because I know of a small hotel with a rooftop room that I have stayed in. My wife and I went to Playa del Carmen without a hotel reservation and looked at about four hotels before we found the rooftop room with a private balcony we spent a lot of time on.
I've been thinking about going to the beach area south of Cancun.
Playa del Carmen was one place I was looking into.
Any chance you want to share your secret rooftop hotel name and location?
Sounds like you found a good spot.
Sorry Willie, I honestly don't remember what the hotel was called. I think it had Dolphin in the name, but I'm not sure. It was on the main tourist road one block up from the beach. It has a swimsuit/surf shop on the first floor.
If you go to Playa del Carmen, I highly recommend going without a reservation and looking at rooms before you decide where to stay. It can be a little hectic and time consuming, but it really paid off for us as we found the rooftop room and had a great week.
For me, I think my top warm weather destination is Maui.
I spent a couple of weeks on Maui a few years ago and really enjoyed it.
I liked both the beaches on the west side of the island and also the lush vegetation and waterfalls on the east side fo the island. The ride on the road to Hana was worth the trip itself since it had so many things to see with crazy twists and turns and beautiful views. There is a state park just a few miles east of Hana that has cabins you can rent (in advance) and a black sand beach.