I’ve always been fascinated by the small island country that’s swimming distance from Key West. Tropical weather, warm water, beautiful women, cigars, Hemingway, and boat drinks — what’s not to like? And, to be honest, I’ve wanted to go for a while. I’ve wanted to visit before the massive invasion of pasty white baby-boomer Midwest-American chubbers ruined the perfect picture of Havana I had built up in my head. Plus, as any warm-blooded male is wont to do, I had visions of rescuing some beautiful mixed Russian-Cuban girl with green eyes and a sexy accent. I would steal her away from the grips of Cuba’s failed blend of communist-run socialism and bring her back to the city — proof to all my guy friends that dating foreign women is actually the key to happiness for American men. If it works for Trump, then hell, I was game to give it a try. I was also keen to check out Hemingway’s Finca Vigia and a few of his old Havana haunts. So I packed a small bag, grabbed my passport, and off I went in search of adventure, desperately needing a break from Manhattan’s serial dating scene.

My Game Plan

Fly down on a Sunday, spend three days and be back Wednesday for a business meeting I couldn’t miss. I didn’t want to hire a U.S.-based tour agency, as I figured it would elevate my profile and be a huge waste of money. It’s a decision I’m glad I made. I booked the Hotel Saratoga, which is centrally located, only a short walk to old Havana, and recommended by a friend.

Getting There Safely — And Without Getting Screwed Over

As a former Navy SEAL sniper turned media CEO who’s worked with a variety of three-letter intelligence agencies, I have friends who could make Jason Bourne shit his pants. Point being, I know a bit about personal protection and blending in to your travel environment.


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