If plying Caribbean waters in a gigantic cruise ship doesn't suit your fancy, perhaps something smaller would. Chartering your own yacht would give you ultimate freedom. Sure, it would set you back a pretty penny, but it would be one of the ultimate "once-in-a-lifetime trips."

And it might not be as bad as you think, especially if you can organize a group of friends to share the cost. According to my own informal survey, the basics (chef, guide, crew), costs are around $2,000 per person for a week-long voyage. That includes food, but not any shore based activities. The prices are as bad as I thought they'd be, all things considered. Of course, fewer shipmates, a bigger boat, and added luxuries can raise the price to around $8,000 to $10,000 per week pretty quickly.

Low season (Northern Hemisphere's summer) is deal time, though it is also hurricane season. If you're going to splurge on a chartered yacht, you might as well do so when the sun is guaranteed to be shining.

The Virgin Islands are a popular yachting spot, as is the route between St Barts and Antigua. But you might as well dust off the old atlas and get creative with your route. That's the whole reason to charter, isn't it?