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How should I go about planning and executing a boat trip in the tropics with my friends?

I want to get a few of my friends together (5-10) and rent/buy a motor boat to adventure around in the Caribbean with for a summer or so. I just would like some advice concerning the whole process. Your guys' How To Get A Free Yacht collection was very helpful and combining it with the idea of a roadtrip... well that's exactly what I want to do! Thanks much!

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Marsh5 years ago
Many of our friends rent vacation homes for weekends and the way we do it either by using evite.com and charge a fee to cover the costs, or we appoint a treasurer to collect the money and coordinate with the land owner. We're looking at renting a sailboat and sailing from port to port in Italy and the concept remains the same.