When I was younger my parents took me and my sister on vacation to the Cayman Islands. While sheltered from a lot of the culture and people of the island (because I was a kid on a family vacation), one memory that really sticks out is swimming with stingrays. While staying on Grand Cayman (not sure what city), we took a boat out to this shallow area in the Carribbean that was just swarming with stingrays! We were given snorkels and fins and a bit of raw squid and set free to swim with these amazing creatures.
There were so many that it was hard to avoid stepping on them and rubbing up against them when you were in the water. The best way I can describe how they felt was sand paper covered in petroleum jelly. As they came down to take the squid from our hands (biting down with no teeth but pretty strong jaws!) I marveled at how close you could get to their huge "wings" and pointy little stinger tails. Now I'm not sure what types of rays these were but knowing how Steve Irwin died I would probably be a bit more hesitant to jump right in with these gentle giants these days- but the experience was sure one to remember!
Other highlights/ memories from the trip:
Snorkeling right by the beach and seeing hundreds of the most vibrant fish!
My poor sister got bit by a yellow snapper and had her finger all cut up.
Colorful beach houses
(Picture from: http://www.expatify.com/cayman-islands/monday-escape-grand-cayman-cayman-islands.html)