San Juan PR or Montego Bay?

T

The Bloak

100+ Posts
Wife was going to surprise me for my upcoming 30th birthday, but I made her give up the secret.

We have never been to either and right now I'm torn 50/50.

Any pros/cons to offer up about either place? We are planning to go in early December and will be there for roughly a week.
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A lot depends on where you are going to stay at each place and what types of activities you enjoy. If you like history, San Juan would probably be a better fit. If you want to lounge in the Caribbean sun on a white sand beach, go to Jamaica.

More info is required.
 
We want a little of both- some R&R but also want nightlife and we certainly plan to get out and explore the respective country.

Pro of Jamaica is we are looking at Sandals (so its an all inclusive) but we would likely spend a majority of the time on the resort.

Pros of San Juan is we found a pretty good deal at the Ritz-Carlton and there are casinos.....not a bad way to ring in the birthday.

I'm leaning towards Puerto Rico because most I have talked to who have been to Jamaica say they wouldn't go back.
 
Ya won't find Jamaica at Sandal's mon! By your comments, you are not really into any native experience. Just go and do the American thing. You will be happier that way...
 
You assume I'm not into a "native experience"- actually quite the opposite.

Went to Costa Rica last year and rented a car and drove all over the country....certainly could have sat at a resort but I like to explore and see what a country has to offer.

I have heard old San Juan, with the history, is pretty incredible. I have also heard, from many people, you really don't want to go 'out and about' in Jamaica.

Funny you say the 'American thing', what exactly is that? I grew up overseas so I'm not sure what the typical 'American thing' is.
 
Bloak - the wife and I are leaving the day after RRS for San Juan for our 1yr anniv. Don't have a lot of info right now, but will get what I can from the wife and post it.

Neither the wife or I have been to PR before, so for anyone that has, please post your thoughts.
 
The correct answer is Negril, Jamaica. Fly into Montego Bay and get to Negril. It' my favorite place to vacation.
 
I've been around the Caribbean a bit and you've picked two of most different destinations (though I've admittedly never been to Jamaica). I've heard that it can be difficult dealing with the locals, though stories can always get distorted and blown out of proportion. Bottom line, if you're on vacation, you want to have fun, or at least a pleasant time, and not be hasseled for money or whatever every time you turn around.

I spent a week at the Ritz in San Juan (Isla Verde/Carolina to be more exact) in April; my wife's family is from Guaynabo. Frankly, you'd be much happier on a lot of other islands. PR has a population of 4 million people, so in a lot of ways it will remind you of South Florida (congestion and people) and the beaches aren't really that nice. Old San Juan is quaint and all but will get old after four or five hours.

By contrast, you can get to Paradise Island in Nassau, New Providence Island, Bahamas with about the same level of effort and the beaches are dramatically better. And you can gamble at Atlantis.

St. Martin has some fantastic beaches, too. Baie Longue and Grand Case are beautiful. If you want to get exotic you can take a cheap ferry to Anguilla, which might have the best beaches in the Caribbean or a not so cheap ferry to the not so cheap island of St. Barths (but it is, without a doubt, heaven on earth).
 
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