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These days, when I dream of finally getting to really experience Cuba, my thoughts generally center away from the classic American cars and historic sites of Havana in favor of more peaceful environs like these in La Boca.

Sailing Virgins, the sailing school born of the sexy, non-stop party at sea that is The Yacht Week, employs a chill method of instruction that's heavy on getting you up close and personal with the Caribbean's natural wonders, culture, nightlife, and irie vibes.

This trip to Negril was all about the wife; the things she wanted to do, eat, drink, etc. This meant a lot of relaxing, fine dining, and quality time together. If you're in the mood for all that, there's no place on the beach in Negril that better fits the bill than Sunset At The Palms.

Romance on the rocks? Sex life more fizzle than sizzle? Never fear! On my last visit to Haiti a few months ago I found a solution: Haitian Vodou Dolls.

The Magnificent Seven, a collection of ornate, historic mansions lining the famed Queens Park Savanah in Port-of-Spain, Trinidad, stand out among the Caribbean's finest examples of grand and distinctive architecture. Arguably the most distinctive of the bunch: Archbishop's Palace.

Like a lot of fathers, I have so many wishes and dreams for my kids — to appreciate their West Indian heritage, to value other's unique qualities, to relish travel, to feel like global citizens. But as a friend of mine was fond of saying "hope is not a strategy."

Recent news out of Venezuela has been decidedly bleak. Sadly, to me, Venezuela's Ron Diplomatico Mantuano jives with the headlines.

A few years ago, I was lucky enough to catch much of the beauty and fun to be had at the Black Point Regatta. One thing I missed, and now desperately want to experience is perhaps the most uncommon aspect of the event: the ugly. Specifically, the "world famous" Ugly Man Contest.

My latest travel hack is a bit unusual for our site, but seriously, this is why you should leave the Caribbean as early as possible.