Splash zone: Looking at the Malecón from Hotel Nacional

I’ve wanted to go to Cuba for years. So when my good friend Ankit mentioned he was planning a trip, I assumed he was inviting me and immediately booked non-refundable tickets before he could clarify that it was a family vacation.

I wrote some notes in my knock-off Moleskine but they read like a series of captions from a teenage girl’s Instagram account so I threw them out along with my dreams of ever being hired by National Geographic (an example: Everyone is as warm and welcoming as the weather. The pace of life is a few steps slower. The food is infamous for being bland, but your eyes can feast on the vibrant scenery instead.).

The photos came out (slightly) better than the writing. Scroll down for some pretty pictures, highlights, and recommendations.


Wander Around Old Havana

Check out the street art. Admire the colorful buildings and classic cars. Try to talk to people in Spanish. Skip lunch and opt for churros and ice cream instead.

Unlike Europe or Asia, friendly people aren’t necessarily trying to scam you. Cubans are actually just friendly. There’s no internet, so people have to talk to other people. A welcome change from life in San Francisco.

Five different strangers approached us to say how much they love Indian people. It was confusing until we found out that every Friday is Bollywood movie night national TV. It makes sense when you remember that American movies and music were illegal until recently and that India consistently produces the best entertainment.

Egg-scuse me, could you crack a window? It’s boiling in here.
Spoiler alert: the “Vegetarian Offer” is always just bread, cheese, and cabbage.
I only played indoor soccer as a kid, otherwise I would have totally schooled him.
Find you someone who looks at you the way she’s looking at those churros.

History and the revolution

Was your exposure to Cuban history a short paragraph about the Cuban Missile Crisis and a grainy picture of Fidel Castro in a Houghton-Mifflin textbook? Same here.

Fix that with a day tour. Our guide, Amanda from Havana Journeys, was knowledgeable and also candid about everyday life.

As tourism expands, many have left white-collar jobs which pay $25 to $60 a month to make more than that in a day working in hospitality. Your taxi driver might have been an engineer and your bartender might have been a dentist.

“Vas bien, Fidel” (“You’re dong fine, Fidel”) — Camilo Cienfuegos
“Hasta la victoria Siempre” (“Toward victory, forever”) — Che Guevara

Hemingway’s hangouts

Confession: I’ve never actually read any of Hemingway’s books. But seeing his favorite spots is still entertaining.

Sign your name on the wall at La Bodeguita de Medio (pack your Sharpie). Have a (disappointing) daiquiri at La Floridita. Enjoy a Bucanero (or three) in a quiet garden courtyard and brainstorm titles for your memoir.

Then, as you watch the sun set over the city from Hotel Ambos Mundos, it’s easy to see how he was inspired (drunk) enough to write so well.

Music, Dancing, Art

Live music is hard to escape in Cuba. You’ll hear it coming from cafes, restaurants, bars, plazas and parks. Even a live music hating Grinch like myself found it hard not to love.

Fabrica de Arte is a must-see and a night out in itself. It’s a multi-story art gallery, live music venue, theater and bar. Sip some rum and ponder the art. Watch a play in Spanish and argue about what you think happened afterward. Rock out to an energetic fusion of Spanish and American music (we saw Toques del Rio).

Other highlights include: live Jazz at La Zorra y el Cuervo and salsa dancers at Sarao.


“Wait, you guys, why are we going to a tobacco farm? Oh… cigars!” — me (taking way too long to put two and two together)

A day trip from Havana takes you out to the countryside where the tobacco for those famous Cuban cigars is grown.

Enjoy a fresh, hand-rolled cigar dipped in honey. Buy way too many to take home with visions of smoking them in your bathrobe while reading the paper in your study. Immediately regret it after remembering your tiny apartment in San Francisco doesn’t have a study or a humidor.

The best meal you’ll have in Cuba is at El Paraiso. It’s an organic farm with the freshest ingredients all grown on site. Don’t forget to wash it down with their “stress reliever” cocktail.

“Ciga-cigar right from Cuba-Cuba. I just bite it. It’s for the look I don’t light it.” — Will Smith, Gettin’ Jiggy Wit It
Swipe right for an increased risk of lung cancer, heart disease, and emphysema.
America’s Next Top Backpack Model
Location scouting for SRK’s next blockbuster.
Farm fresh food and they let you pour as much rum as you want into your cocktail.


A 3 hour scenic drive to the east takes you to the beautiful beaches of Varadero.

Skip the all-inclusive resorts and snorkel in the coral reef at Bacunayagua. Dive into an underground lake at Saturno Cave. Jog on the pristine beaches and debate whether you can actually see the Florida keys if you squint really hard.


Visa: It’s illegal for Americans to travel to Cuba without one of 12 valid reasons. For those of us that aren’t journalists or humanitarians, “People-to-people educational exchanges” or “Support of the Cuban people” are the most applicable.

“People-to-people educational exchanges” requires that you have a fully documented itinerary. Remember to print everything out before you go.

JetBlue flies to Havana and you can get a Visa at the Fort Lauderdale Airport for $50.

Stay: Use AirBnb instead of hotels. A decadent home-made breakfast will typically be available for a small additional charge.

Morning run before eating my body weight in fruta bomba.
Our host Orlando shared his (potent) homemade whiskey and entertaining stories with us.

Money: Get Euros in the US before going since there is a 10% fee for changing US Dollars. The airport will give you the best rates for exchange but count your money out before handing it to the clerk so they don’t palm any bills.

Getting around: Taxis are easy to hail and entertaining to bargain with. $5-$10 CUCs should get you pretty much anywhere.

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