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month stay on a caribbean island

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I have been on here for about six months and have gained much infro on the different Caribbean islands. I have been on three cruises and have visited many of the islands, st.thomas, St martin, Barbados, St Lucia, St Kitts, Cozumel. I will be retiring April 2015 and would like to spend the month of Jan 2015. I realize the cost of my adventure. I guess me question would be could I do this for $5000.

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