Barbados.
I went there a lot when we had family living there.
I believe you can fly Westjet, Calgary>Toronto>Barbados.
We have not been there for a few years, but when we went it was very safe. We were out and about at all hours of the night.
There are some resorts, but IIRC, no true All Inclusive like Mexico.
There are a lot of rental places on VRBO. Barbados, is kind of like a few islands in one. On the west the ocean is very calm and perfect for diving/snorkeling. On the east it is the opposite and there is surfing. The south is a mixture of the two. The north is no swimming.
All the beaches in Barbados are public. So even large resorts can't stop you from being on their beach. They can control your accessing their beach through their properties, but we never had any issues.
There are a few different things you can do, Rum Distillery Tours (
http://www.mountgayrum.com/ is the oldest rum distillery in the world). There are some pretty cools caves in the north of the island.