My wife and I honeymooned in Jamaica several years ago. We stayed at a small, traditional all inclusive resort in Ocho Rios, and except for an escorted outing to a local market and a snorkeling trip to Duns River Falls, we never left the grounds of the resort. I took an Omega and a Rolex, and I had no trouble at all. The resort also took care of our transportation to and from the airport in Montego Bay.
If I were going to a different kind of destination, with a little less supervision, I'd probably do what you're doing. I've also been to places in the Caribbean where I'd hesitate to wear any kind of watch at all.
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