I spent much longer than I should have deliberating over where I should go in Cuba. It's a really big country, and with limited time at our disposal, we had to make some trade-offs. I felt pretty good about our travel plans as we were leaving for the trip, but it was only once we were on-the-ground in Cuba that the actual best places to travel presented themselves. This list is basically an amalgamation of common sentiments that I heard from travelers that I crossed paths with during my time in Cuba...
1. Havana
This is an obvious one. Havana is the first (and sometimes only) stop on pretty much everybody's Cuba trip. It's the capital city of Cuba and the largest city in all of the Caribbean region. Havana is one of the most interesting and unique cities that you will ever have the pleasure of visiting. Every inch of this city is alive with history and culture, and even as the city continues its slow decay, the Cuban identity holds firm, colorful and proud. You should definitely visit Havana if you can.
2. Valle de Viñales
Surely you're familiar with Cuba's legendary cigars. Well, this is where they come from! Viñales is perhaps the most popular travel destination in Cuba, second only to Havana. Because of its distinct prehistoric-esque landscape, Viñales is actually a protected national park in Cuba. It's an easy 2 and a half hour drive west from Havana, and there are plenty of accommodations available for travelers once you get into town. In Viñales, you can expect lots of cigars, horseback riding, and caves.
3. Trinidad
Trinidad has solidly clinched the #3 spot on the list of places to go within Cuba. Nearly everybody that I crossed paths with in Cuba was either on their way to Trinidad or had just come from Trinidad. It just didn't fit into my time frame so, unfortunately, I never got around to coming here. But that is a regret for me. You can expect this place to be touristy but very beautiful. It's actually a UNESCO World Heritage Site, so that should give it some additional street cred.
4. Santiago De Cuba
Santiago de Cuba is Cuba's second largest city after Havana. In the remote southern stretches of Cuba, it's really not close to much, and it's a commitment to get here. Flying might actually be your best option. This is another place that I never actually visited myself, but those that I know who have managed to come here have universally given it great reviews. It's supposed to be a very cool part of the country. Also, the Cuban revolution began over here (not in Havana), so there is some cool history.
5. Pico Turquino
This one is a bit of a curveball. At 1,974 m (6,476 ft) high, Pico Turquino is the highest mountain in Cuba. Surrounded by its own national park, it's located in the heart of the Sierra Maestra mountain range in the far-south of the country. It's actually not far from Santiago de Cuba. This part of the country is remote, rugged, and steeped in political history. This is one that doesn't show up on many guidebooks—I certainly haven't been here—but I wanted to give you a few off-the-beaten-path suggestions.
6. Varadero
Just a few hours' drive east of Havana, Varadero is 10(ish) mile long peninsula protruding out towards Florida. The sand it clean and almost white. The water teal blue just like in the post cards. There's very little trash anywhere. It's a tropical paradise. Maybe it's not the most culturally relevant destination, but if you don't mind being surrounded by resorts and tourists, it could make for a beautiful few days at the beach. It's not Cuba's only beach, but it might be the longest and most well-developed.
7. Matanzas
This last one isn't going to show up on many touristy lists about places to go in Cuba, but I'm putting it on mine. This was one of my favorite places that I went in Cuba. It's a sea-side city situated on Cuba's northern coast between Havana and Varadero. Before coming here I was told that it was a small, inconsequential city, but make no mistake: Matanzas is bustling. It's also a center for Cuban music and art—with a little Spanish, you should be able to plug in pretty fast! Oh, and it's stupid cheap. You'll save money here.
