Board 8 > Board 8, help me decide on my next vacation destination.

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CaptainOfCrush
09/01/17 10:46:42 AM
#1:


A few months ago, I made a topic asking you guys about Caribbean travel. Let me give a little background on that.

At my last job, I had an 8-month period where I traveled weekly. As such, I built up a ton of Southwest airlines points - enough that my vacation travel has been free for the last 18 months. Additionally, I earned the Companion Pass for my girlfriend, meaning that anywhere I fly, she flies with me for free (minus taxes and fees). I've taken pretty good advantage of this over the past year (Nashville, California multiple times, Punta Cana in the Dominican Republic, and most recently San Pedro in Belize). Her Companion Pass expires on 12/31/2017. I want to squeeze as much as I can out of it.

We're tentatively scheduled for Orlando/Disney in October (hopefully she can get the time off), but I want one last Caribbean vacation before the end of the year. The Caribbean is the furthest away Southwest flies, so it makes the most economical sense for me to travel there as often as I can. Here are the locations I'm weighing for a final December vacay:

Havana, Cuba
Montego Bay, Jamaica
Nassau, Bahamas
Grand Cayman Island
Turks and Caicos Islands


I'm looking more for an island getaway, but I'm still considering Havana because it's such a famous (and alluring) city for exploration. If anyone has been to any of these places, I'd love to hear your thoughts.

I remember a couple of Board 8ers recommended Belize last time, and it was an AWESOME vacation. I'd be thrilled if you can do it again. =)
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trdl23
09/01/17 11:38:26 AM
#2:


Havana before the current administration cuts off relations again.
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CaptainOfCrush
09/01/17 2:27:50 PM
#3:


A fair point that I hadn't considered.
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CaptainOfCrush
09/02/17 12:39:38 PM
#4:


Morning bumpo.
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TheKnightOfNee
09/02/17 12:46:05 PM
#5:


The only place that way I've been to was Punta Cana, so I don't know if I can give much of a recommendation for a new place! Those honestly all sound like potentially fun destinations.
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CaptainOfCrush
09/02/17 9:03:27 PM
#6:


How'd you enjoy Punta Cana? I loved it.
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ninkendo
09/02/17 9:04:57 PM
#7:


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kirbypikachuhat
09/03/17 10:06:26 AM
#8:


Montego bay or anywhere in Jamaica hands down.
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CaptainOfCrush
09/04/17 10:07:28 PM
#9:


Thank you and bumpo.
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CaptainOfCrush
09/06/17 12:01:26 PM
#10:


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