My buddy Matt had not been on a (beach) vacation in a long time and was after the quintessential Caribbean vacation... so we decided to "do it up" and went to the first-worldiest of the Caribbean islands: Grand Cayman.
We stayed at the Marriott Beach Resort on Seven Mile Beach and had an absolute blast and went full tourist mode: went snorkeling, rode in a submarine, visited Stingray City, went out for a tour at a bioluminescent bay (which turned out to be amazingly cool), had some amazing food, saw some chickens... and I even got some diving in. So all in all a great trip!