© TheRealDestinations 2018
In a relentlessly modern world, Havana is something special. The historic center is practically a time capsule to another era. A product of decades-long misguided Cold War-era policy that somehow didn't end with the Cold War. The Cuban people persevered, adapted, and the result are the iconic vintage cars roaming Havana's streets. The same goes for the incredibly well preserved neighborhoods of Old Havana.
But all of this is changing, fast. Imported cars from Europe and Asia are making their way here, rendering many of the non-resorted vintage cars obsolete. Tourism is growing, helped by recent relaxing in travel from the US and direct flights. Recent backtracking from the new administration notwithstanding, you better get here and see it before it's all changed—and probably a lot less interesting.
[The interior of a lovingly restored '57 Fairlane.]
United MileagePlus: [Direct: United]
American AAdvantage: [Direct: American]
Delta Skymiles (good luck…): [Direct: Delta]
JetBlue TrueBlue: [Direct: JetBlue]
Southwest RapidRewards: [Direct: Southwest Airlines]
The Good:
One of the most unique places you'll ever visit. Caught in a Cold War time trap, right when Fidel's revolution swept into Havana, the surroundings of Old Havana—not to mention much of Havana in general—has scarcely changed since the early 1960s.
The cars! Gorgeous, restored and no-so restored vehicles from the 50s still running on streets that have barely changed since then.
Prices are incredibly cheap. Stay at Airbnb. Use your CUCs and enjoy a massive difference in purchasing power in a country where even the educated upper middle class makes significantly less due to Cuba's economic isolation.
The music! The vibrant Cuban culture can be seen everywhere in this city.
The Bad:
Get ready to travel from another era. No, you probably won't be using travelers checks here. But don't think your US cards will function thanks to ongoing US sanctions. Cash only, better make sure you bring enough.
Continuing the theme of a different time, no internet! Well, no residential or cellular internet. You better find a Wi-Fi hotspot and some way from the locals to log in to a very slow connection. It's digital detox in a destination. But, that also means no live google maps, no Uber, no messaging.
Getting around can be a challenge. Taxi's aren't always plentiful outside the major tourist hotspots, since the locals can scarcely afford them. At night, the streets can be eerily dark, as you adjust to the surprising lack of street lighting that you unconsciously expect in urban environments.
Private vintage car tours are both incredibly fun and surprisingly affordable given what you're getting. In another words, a must-do here. © TheRealDestinations 2016
the Summary:
This is a place you need to visit ASAP. New travel restrictions notwithstanding, this will take some moderately advance travel planning. Bring enough cash to last the whole trip. No internet, no smartphones, no cards. Just incredible surroundings, welcoming, polite people, and some of the richest culture in Latin America.
While some blocks directly off the squares of the historical center are newly renovated, it does not take a long walk, even in the old city, to find streets still as they've been for decades. But you never feel unsafe in these streets, where children play and neighbors of all ages hang out to socialize.
This place, and the people who live there, will challenge your assumptions of what makes people happy in relation the society they live in. Is it just a certain level of affluence? Or perhaps absolute material wealth is less important than relative wealth to those around you, as long as critical needs like healthcare, safety, food, shelter and education are met.
© YC 2016
Live music is everywhere in this city, where the arts are vibrant.
© YC 2016
Pro Tip: Ask around where to buy a WiFi card like the locals instead of getting gouged at select tourist hotels. Figure roughly $1 for an hour of sweet, sweet internet after a few days of going cold turkey.
At the time I visited at the end of 2016, internet in Cuba was still restricted to a handful of hotels and public parks. You have this otherworldly sight of crowds hanging out in city parks, staring at the soft blue glow of their smartphones. The modern world is coming to Cuba, and things will be different. That much is inevitable.
The changes that are sweeping over Havana will lead to predictable shifts. The beat-up vintage cars will gradually disappear, replaced by generic imported subcompacts. The decayed—some say authentically gritty—streets of Old Havana will be fully renovated and gentrified. Havana will be another tourist destination, trading on the glories of its past.
But for now, experience a vibrant city, shaped by the accidental forces of geopolitics, in transition. While there's time.
© YC 2016
When to Visit
While the winter months bring cold and darkness, Havana will be warmer than Miami. Perfect time to go. Summer's will be hot, and air conditioning is not something you can take for granted there.
Language Barrier
Finding English speakers outside the tourist hotspots will be a challenge. Brush up on your rudimentary Spanish.
Price Level
~70% cheaper than home.
Getting There
~$300 Roundtrip or 35K miles on Star Alliance, Oneworld, or Skyteam carriers.
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© YC 2016