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Freeport
Port Rating: 
Great beach port. Straw Market at the dock is small but not bad. Junkanoo Beach is a short $14 round trip cab ride. Nice restaurant, good vendors (guy making fresh conch ceviche is a highlight), cheap $5 chairs and umbrellas ($5 for both, $3 for just the chair), and beach waiters. Crowded, but not OVERcrowded.
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Nassau
Port Rating: 
Lots of shopping right off the dock, but expensive and crowded. Paradise Island/Atlantis is SUPER expensive and probably better to avoid. A couple local forts which aren't bad to tour but nothing special. A lot of beaches to choose from, some free, some not. Lots of American chain eateries, so tough to find the more local fare. For all the press it gets, not a great port in my opinion. Also, you can avoid expensive cabs and just take local public transit. Less than $2 gets you just about anywhere.
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Key West
Port Rating: 
Lots of fun to be had. Quirky shops to look in, great bars, great restaurants, and some cool attractions. Highly recommend the Hemingway House! $13 to get in for the tour, and well worth it.
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