A Navy SEAL's Guide to Cuba

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 — something most passengers on my Delta flight 442 to Havana could’ve used massive help with.

The most difficult things about Cuban travel are money, cell coverage, and Wi-Fi — things I’ll get to in a sec. The first issue is getting a flight. These days you can book a direct flight to Cuba online, and you can pick up your Cuba travel visa and State Department declaration form at the airport — that’s it, very easy. But there are still scams: the Cuban visa is $50 dollars at the airport. The guy next to me in line bought his for $80 online and wasn’t happy I told him I was getting mine for $30 less.

Fast forward three hours later, and I was in warm tropical weather. Walking off the plane, the third-world smell hit me with familiarity that brought a smile to my face. I don’t care if you’re in Mexico, Afghanistan, Iraq, or Cuba, the smell is roughly the same, a byproduct of inadequate sewer, trash, and other basic services we take for granted in America. Clearing customs was easy, now off to my hotel.

I did my homework and knew that a cab to the Saratoga should cost $25 U.S. They’ll take U.S. money most everywhere (including cabs), and start at $40 but hold firm. Also, don’t get suckered waiting to change money at the airport, the line is massive and hours long and you’ll get a fair rate and no line at any nice Havana hotel. So in my moderate-to-fair Spanish I negotiated my cab rate and was off.

From the main terminal, it takes about 20 minutes to get downtown. The first thing I noticed, as all Americans do, were the amazing vintage cars, a symbol of old American auto dominance long past. I haven’t owned a car in years — just airplanes — but watching those vehicles made me want to go on an eBay auto bidding binge.

The hotel was nice but not worth the $400 a night I paid. (Note: prepay with a credit card. I did this and it limits your cash exposure.) After checking in, I headed up to the roof deck to watch the sunset and grabbed some photos to feed my Instagram monster (@BrandonTwebb). I then grabbed dinner at a local restaurant down the street, which came recommended by the doorman. (Note: Tip the door guys well and they’ll negotiate cabs and find you just about anything you need at a fair price, including cigars.) The seafood in Havana is fresh and amazing, I had grilled lobster and two beers for under $20.

A SEAL in Castroland

One thing I learned in the SEALs is that the secret to any great planning is simplicity. It’s amazing how many people don’t get that.

Day one, I’d take a driving tour through the city and out to Hemingway’s old house, then spend the other two days walking the dusty streets of Havana to get a feel for the local vibe and enjoy some of Havana’s nicer restaurants, cold beer — and no real man will pass up a good Cuban cigar. The other parts of Cuba I’d save for next time.

Up early the first day, I grabbed an easy workout, because I’m rehabbing a dislocated shoulder from my Alps ski trip a few weeks back, when the boys and I were filming Big Mountain Heroes for my company. Down to the lobby for a quick cup of joe, and I was off to link up with my guide, the proud owner of a 1957 Ford convertible. This guy looked like some Havana playboy, and I almost burped up my coffee when I overheard one of the nearby American Millennial girls actually say, “I bet that guy gets a lot of pussy.”

My only regret on the tour was not asking for a good English speaker. There’s plenty, and I got by on decent Spanish but felt I would have learned more about the city if my guide spoke English. A guide should cost you no more than $100 per day in Havana and only a quarter of that outside the capital. That day we toured the Cristo De La Habana, Hemingway’s house, Che Guevara’s museum, and Hemingway’s favorite seaside bar, where I smoked a cigar and had a Cuban rum. I couldn’t help but notice that all over the city there were tributes to Castro and Che. One thing for sure, Cubans appreciate a good rebellion, and there were clear displays of Cuba’s successful American resistance everywhere. Get past that, and the people of Cuba are incredibly friendly.

The last two days I walked the entire city on foot including the old town. Incredible architecture, and highlights for me were the outdoor car mechanics garage next to the boxing gym. People were friendly and I started to think that this would actually be a great place to bring a girl, not find one.

My favorite restaurants were Ivan Justos, O’reilly 304, and La Guarida. Amazing places to eat but expensive, even by American standards. In old town, there’s some amazing bars that offer great cigars, rum, cold Cristal (the local Cuban beer), and live music. I enjoyed live music, cold beer, and cigars every night, and it felt like I was in an old movie with the 1950s cars passing by. I also imagine Cuba would be a great place to have a bachelor party, but I’d definitely hire a full-time local to babysit the group, drive, and negotiate rates. The money you’ll save will be worth the rate of a local guide.

Overall, and despite the usual tourist-trap crap you’re going to encounter most places, I had an amazing trip and managed to stay out of trouble. Friendly people and beautiful women everywhere but, alas, I did not find my elusive green-eyed half-Russian girl sadly. Also, poverty is everywhere, and clearly Communism has failed Cuba, and Havana is living proof that it’s good in theory only. I’m just glad trade with the U.S. is opening up and injecting some capital into their depressed economy. Change is definitely coming — construction was blowing up all over town — so get down there while you can and see Havana as it will never be seen again.

What You Should Know About Cuba

Wi-Fi is available at most good hotels, but some charge for it and it’s always spotty. There’s No major cell carrier. Get a T-Mobile global card or buy a local SIM. I used Cuba Cell via my T-Mobile global plan. There are no U.S. credit cards accepted or ATMs anywhere, and this is a massive pain in the dick. It also ups your risk profile by making you a walking cash machine, which as they say in Cuba, “es no Bueno,” especially when the average wage is roughly $500 U.S. a month. Note, there are two systems of currency in Cuba however, your American dollars will be converted to CUC (Convertible Cuban Peso) nearly 1-1, the other form for currency is the Cuban peso, which is issued to Cubans to spend money on basic-needs stuff. Both forms of money cannot be exchanged on the foreign markets, so spend it wisely and don’t change a huge amount all at once. I changed money once a day at the hotel.

When traveling to poor third-world countries, get a local guide and earn his trust, he’ll show you the ropes, and keep you out of trouble. It also automatically takes the “let’s screw the American tourist” off the table anywhere you’ll go. Dress down. This doesn’t mean you have to dress like a dirt bag, just wear earth tone colors, mimic local dress standards (Google is your friend here), and wear older shoes, sandals, or boots. I like nice watches, and always wear a black Panerai when going third world, because a Rolex stands out like dog’s nuts, and most people can’t spot a low-key black Panerai unless they’re watch guys like me. There’s a departure tax to leave the country (U.S. $25, cash only), so don’t blow all your paper money on cigars and rum to take home.

About the Author: Brandon Webb is a former Navy SEAL sniper, bestselling author, the CEO of Hurricane Media, and an avid adventure traveler.