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Excellent advice offered here! The only things I would add would be:
1) Take a look at when you are at port for each island. For me that is a big factor. For example, you want to be in St. Thomas during the day for shopping and excursions and Jamaica would be fun to experience the night life. So, make sure you are in ports during times where you get to truly enjoy the island and where the time isn't so short you feel pressured to run around.
2) You don't have to book the nicest cabin on the ship. When you get there, they most likely will upgrade you with a little charm.
3) I love Radisson Diamond Cruises because they usually keep you in port for 2 days in each stop.
4) WindJammer can be a blast if you want something totally original and laid back. (I have never been but have heard good things from my friends)
5) Booze is expensive on board. Personally, I don't mind paying a premium for something but the costs can get big. Its fun to buy booze on the islands and bring it on board and mix drinks in your room and walk around the ship. Makes me feel like a kid again.
6) Yes there can be rough seas, coming back from the Bahamas or Cape Hatteras can make the boat rock, but......it reminds you that you are on a ship and not terra firma any more.
&) Most commonly asked questions for a cruise line......does the crew live on board and what time is the midnight buffett!
Happy Sailing!
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