Cuba has five distinct regions: Havana and Western Cuba, West Central Cuba, Central Cuba, East Central Cuba, and Eastern Cuba. Once you know this, navigating your way around the country and its amazing cities becomes a hell of a lot easier.
Each city has its own unique, distinctive features that make it worth visiting but, as with any country, there are always some that should be higher on your list than others – especially if you’re not visiting for very long. From the white sand beaches and cobbled streets, there’s a lot that Cuba has to offer, which is why we’ve rounded up the best of the best town and cities that you absolutely cannot miss.
Havana & Western Cuba
Everyone’s heard of Havana, and the likelihood is, if you’re travelling there it’s going to be your first stop. And it should be because it’s great, just make sure you don’t get stuck here because there is so much more of Cuba to see and experience. Having said that, if you want a lot of history, a lot of culture, and a great nightlife all in one handy place, then Havana is the place to go. Soak up the colonial architecture, test out a few too many daiquiris, and then learn all about the revolution in the Museo de la Revolucion.
Pinar del Río
Pinar del Rio has to be on your Cuba bucket list, even though it’s pretty small and works better as a little run through on your way somewhere else. It’s barely inhabited, but its national park protects a unique dry-forest ecosystem that is not to be missed – literally a once in a lifetime opportunity. Plus, nearby Maria la Gorda is known for the amazing scuba diving options.
One of the most picturesque places in Cuba, this is where the tobacco fields that grow the famous Cuban cigars can be found. You have to time it right, because if you go when it’s too hot you won’t be able to enjoy all of the fantastic hiking opportunities, but even so, there’s plenty to do. Take a wander towards the town’s baseball stadium, and visit the ranch of Raul Reyes, who sells everything from coffee to pineapples to tobacco. Plus, he’s eco-friendly and fills plastic bottles with coffee beans – making these single-use plastic items suddenly sustainable and reusable.
Old Town Havana
Sure, you can include it with Havana, but Old Town has so much more about it that it deserves to be included in our round-up as a destination in its own right. Here, the streets are narrow, and the town is almost as old as Columbus. Completely squeezed in by the harbour on one side and the strongly fortified walls meant to keep out pirates on the other, this city had to adapt to the ever-increasing population size in a town that physically could not expand. As a result, you get hidden away cafes and bars, people dancing on the street, and a real, authentic Cuban atmosphere.
This small, relaxed, unhurried town is surrounded by Sierra de las Casas to the west and Sierra de Caballos to the east, so it’s easily forgotten off people’s Cuba travel lists. It’s also right on the shore of Rio las Casas, the little island’s only large river, making it a great spot for a bit of sailing, kayaking, swimming and more. It might be small, but the museums and entertainment are worthy of a shortstop along with visit.
Central Western Cuba
This is Cuba’s big resort. I’m talking mega. This is where the tourists go, and if it helps to contextualise it, it’s often compared with Cancun in Mexico. Told you it was big. The beach resort has more than 60 hotels along an 8-mile strip of white sand, and more often the tour operators will offer excursions to nearby Matanzas and even Havana – making it a really good base if you’re not in Cuba for very long. If you want to avoid the tourists though, head to the beaches in the centre of the city, where they’re more beautiful and way less crowded.
Often forgotten about for the way more popular Havana or Varadero, it’s only a short distance from both of these but it offers so much more. It lacks in tourists, which is a plus, and although it’s a little run down this just lends the city a charming and relaxed feel to it. Thanks to its hidden away qualities as well, the Casa Particulares are a lot cheaper than you’ll find in the big tourist trap cities.
Known to some as the Paris of the South, Cienfuegos is split into two parts: the first centred around the main town square with its wide streets, while the second is Punta Gorda, a long thin strip of land that stretches out into the bay. The city is absolutely full of parks and art galleries, and the architecture is so great it was awarded UNESCO World Heritage status in 2005.
Famous for being the location for the last battle of Che Guevara’s revolution, Santa Clara has that typical rebellious spirit you would associate with the Cuban revolution, and its locals fit this stereotype to a T. Seriously, they’re mostly young students, into art, culture, music, and everything else.
Trinidad de Cuba
Trinidad is one of the oldest towns in Cuba, and you can really sense that when you visit. The colonial town hasn’t really changed at all since it was built – funnily enough, in colonial times – and you can still wander down streets lined with houses of all different colours and take a ride in a horse-drawn carriage – not as an extravagant experience, juts as a way to get around town. It’s one of the best places in Cuba for photo opportunities, and there’s live music dotted all over town to listen to and enjoy with an ice-cold mojito in hand.
One of the best places in Cuba if you want to stay in a casa particular, but not necessarily the best place to visit if you’re looking for crystal clear blue waters and golden sand beaches. It does, however, have the cheapest diving options in the country, and it’s basically completely devoid of tourists, which works great if you want to get off the grid and enjoy your own company for a bit.
Founded in 1514, Sancti Spiritus really is an old colonial town. Very similar to Trinidad, Sancti Spiritus has the one added bonus of being sans tourists, wherein lies much of its charm. It’s one of those little towns where you get all of the culture of the big cities, while also being able to enjoy a cold drink or a stay in a casa with virtually no issues.
Famous for its old shipping port and the best crab in Cuba, Caibarien is a hidden gem on the country’s Atlantic coast. Most of the buildings are now just shadows of their former grandeur, but their history can still be seen through the cracks, and it has the same colonial splendour of many of the more well-known cities – just without the tourist prices.
Camaguey is Cuba’s labyrinth city. Literally, it was built like a labyrinth in the hope of confusing possibly enemies and invaders, to the point that even most of the maps are just useless. The country’s third-largest city, if you can find your way around the tangled streets and cobbled plazas, you’ll find hidden gems: historical museums, boutique hotels, fantastic scuba diving options, small alleys and more.
An old port city, Nuevitas lies on a peninsula jutting into Nuevitas Bay. If it sounds familiar, that’s because it’s hella famous: it’s the very same place that Christopher Columbus sailed into land in 1492. Pretty funky claim to fame if you ask me. It’s now a blossoming little city, with an industry based in sugar cane, molasses, coffee and fruits. Plus, you’ll be pleased to hear the pirate raids have all but disappeared.
A little bit hard to get to, Morón is nevertheless not a town to be forgotten about. Founded in 1543, it’s known locally as the City of the Cockerel thanks to a “cocky” bullying official who was around in the colonial era. The architecture is fantastic, as you would expect from a colonial town, and there are some amazing Casa Particulares to stay in, lending your trip a truly authentic Cuban feel.
East Central Cuba
This little town is exactly that – little. There are not masses of things to do here, but it is worth at least a one night stay on your way to Playa La Boca, or any of the off the beaten track beaches along Cuba’s eastern coast. Popular with the locals, make sure you include a trip to the Refugio de Fauna Silvestre Monte Caganiguán-Ojo de Agua, one of the best places to spot Cuban crocodiles and flamingos.
Holguin is authentically Cuban, and I mean that in every sense of the term. There’s a magic and mystery here that can be found in the vintage Chevys that line the streets or the plazas filled with local Cuban schoolchildren, or the religious solemnity of the annual procession climbing Loma de la Cruz. The town barely focusses on tourism, and instead, you find eager to please Casa Particulares, cheap but amazing food, and great beer that’s brewed in the city.
Another massive resort, Guardalavaca is a great place if you want to enjoy some of the best beaches in Cuba, interspersed with mojito breaks and a bit of kiteboarding or scuba diving. The area is picture-perfect, literally, and it has a little bit more Cuban authenticity than Varadero – hence its popularity.
One of the best things about Bayamo is the historic centre, which played a crucial role in the Cuban War of Independence. You won’t be able to go anywhere in the city without hearing or seeing something to do with this history, so if you’re a history buff this is the place for you. The city also happens to be a great gateway to Sierra Maestra and the town of Manzanillo which was a base for supplying Fidel Castro’s Rebel Army from 1956 to 1968.
Santiago de Cuba
The second-largest city in Cuba, Santiago is absolutely chockfull of culture, history, art, and everything you would associate a typical Cuban city to be. The architecture is distinct to this city, and it was here that Fidel Castro launched his revolution with an attack on the Cuartel Moncada – where you can still visit a set of military barracks. Plus, Santiago is literally the birthplace of pretty much all of the island’s music, which you can experience in full at the Casa de la Trova.
One of the most famous areas of Cuba, thanks to the U.S. Naval Base nearby, Guantanamo is only a 90-minute drive from Santiago but is still bypassed by most travellers. The colonial city is fantastic for anyone looking to experience regional music and dance in the streets, and it is the birthplace of changui, an early 19th-century style of Cuban music that first emerged among slave workers in sugar cane factories. If that’s not your vibe, try the mountains just outside of town and have a look at the life-size stone animals at Zoologico de Piedra, created by a self-taught Cuban sculptor in the 1970s.
The oldest city in Cuba, Baracoa was founded in 1511 in the midst of tall, leafy mountains. It’s the rainiest city in Cuba as well, and you can easily tell given the lush rainforest that surrounds it, providing excellent hiking spots in places like Parque Nacional Alejandro de Humboldt. There’s also a cacao farm, and the city is a centre for chocolate production – so definitely make sure you try some homegrown chocolate while you’re there.
There you have it, everything you need to know to make sure you don’t miss any of the fantastic cities and towns that Cuba has to offer. These are the places you need to see if you want to ride in a classic Cuban car, or smoke a cigar, drink a daiquiri, or learn more about the revolution. You can thank us later.