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Best Carribean CRUISE destinations/itinerary
and why?

Brayden (5 1/2) born 12.28.06
Hailey (4 1/2) born 2.25.08
Taylor (8 Months) born 12.26.11

Re: Best Carribean CRUISE destinations/itinerary
i have faves based on my tastes. yours may not be the same.
what are you looking for specifically?
It would help to get some actual information from you. Are you traveling with kids? How long do you want to travel for? Do you have a preferred departure port? What kind of budget?
You might want to spend some time on cruisecritic.com and narrow down what you're actually wanting to do. This question is far too broad for people to be able to offer helpful advice, but I think you'll find if you come back with some more specific questions people here offer really great tips and advice.
Maybe "Best" isn't the right term here, how about "Fave"?
I've only been on one cruise, a Western Caribbean, and based on that, my fave destination so far would be Roatan, Honduras. It was beautiful, lush and tropical, gorgeous beaches, amazing snorkeling (huge reef there), and awesome people.
Well best would vary depending on the person.
My favorite Caribbean cruise itinerary is the one I went on last March to the Southern Caribbean. It was on the Carnival Victory out of San Juan, PR. We stopped at St. Thomas, USVI; Barbados; St. Lucia, St. Kitts & Nevis, and St. Maarten/St. Martin. I enjoyed it because we only had to deal with one sea day. I don't particularly like two sea days like our honeymoon cruise. I was bored to death after the first sea so I enjoyed having an island every day but one to explore. Plus in my opinion the Southern Caribbean has some of the best islands ever.
My favorite destination was St. Lucia though. I just fell in love with St. Lucia as soon as I stepped foot on the island. I had a great time sea kayaking to Pigeon Island.