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By Cuba specialist Anna

You know you're in Cuba the second you leave Havana's airport and jump into a taxi heading for the old town. Rusting streetlamps flicker, battered American vintage cars and Soviet-era Ladas rumble past.

Propaganda statements are splashed across billboards (there's no advertising here). Locals stand around on street corners chatting in loud, passionate voices. And, most of all, there's music — strains of salsa and son rhythms seem to float on the hot Caribbean air at almost any time of the day or night. Music, like rum and images of Che Guevara, is pretty much inescapable in Cuba.

When I lived here, over eight years ago, Cubans weren't permitted to own mobile phones, enter hotels, or take part in any sort of private enterprise. Now, in the cities, you'll see families running restaurants from their own homes or selling coffee from stands outside their door — some of the 15 self-employed options open to citizens. Cuba is changing — but slowly.

The colonial city of Trinidad
The colonial city of Trinidad

I'd like to issue a bit of a warning at this point. Cuba's patchy infrastructure is sagging under the weight of an increased influx of foreign visitors, keen to witness this uncommercial communist relic of a nation before it's overtaken by Western influence.

So, if you're the kind of person who likes their travels to be logistically flawless, Cuba isn't for you. Despite every effort, taxis may not turn up. Shops aren't well stocked and it's impossible to buy a wide range of produce (a rationing system is in place for Cuban citizens). Queuing is part of everyday life. Accommodation options are limited, often restricted to homestays, and are sometimes basic.

But if you can be relaxed about service and punctuality, and are curious about Cuba's culture and countryside (from green, plantation-dotted valleys to mountainous national parks), read on.

Explore old Havana on foot and by classic car

Havana's old town
Havana's old town

Havana's old town, with its crumbling neoclassical architecture, reveals itself to be more and more dilapidated the closer you look. Here, the buildings speak of faded grandeur: think pastel façades of townhouses, some bright; others with peeling paint. Flags and washing flap over wrought iron balconies.

The best way to take it all in is simply to wander the cobbled pedestrian zones of the old town. Stop and watch impromptu salsa dancing in squares, or listen to live music from one of the many bars-come-restaurants that serve traditional, hearty Cuban dishes of rice, beans and stewed meats.

Hemingway fans can visit his preferred former watering holes, the Floridita and the Bodeguita del Medio. The walls are covered with the autographs of famous former patrons. Both are crowded joints but still serve the expertly made mojitos and daiquiris he loved.

Twenty minutes by car to the east of Havana sits Cojaimar. This tiny fishing village, where Hemingway would catch marlin, is thought to be the inspiration for the novella The Old Man and the Sea.

Malecón in Havana
Malecón in Havana

I think one of the best ways to experience Havana is to go down to the Malecón, the sea wall that runs along the seafront, bordering the old town and some of its less frequented districts. This is where Habaneros (residents of Havana) come to relax, sitting on the wall and strolling along the esplanade beside it. Looking out over the estuary, you'll see El Morro, a 16th-century fortress that guarded the entrance to Havana Bay. It fires a canon at 9pm every night.

I spent a great evening by the Malecón, drinking rum and nattering with friends while watching the sunset. Rum, I soon learned, is free-flowing, locally made and always shared in Cuba. Cubans sip it neat, but I prefer to mix it with a bottle of TuKola (Cuba's own brand of coke).

While the old town is compact, Havana is a sprawling city. To see more of it, I suggest taking a tour in a classic American car like a Cadillac. You'll have your own driver (Cubans are precious about their cars due to the scarcity of repair parts.)

Try to include a visit to the Plaza de la Revolución as part of your tour. The beating heart of political Cuba, this huge concrete square is where Fidel Castro made many a famous address. A statue of a pensive-looking José Martí, a political theorist and national hero, sits at the foot of an immense ridged concrete tower, a memorial to him. Steel outline drawings of Che Guevara and Camilo Cienfuegos, another father of the revolution, watch over it all.

Take a walk through the Viñales Valley

Viñales Valley with its limestone hills
Viñales Valley with its limestone hills

Roughly a two-hour drive from Havana, this flat, verdant valley is a rolling patchwork of palm trees and leafy tobacco crops, broken up by domed clumps of vegetation-thick mogotes, limestone hills.

You can get to know the landscape and, with it, rural Cuba by taking a four to five hour walking tour through the valley. En route, you'll stop off at tobacco plantations and drying houses, where farmers will offer to sell you their homemade cigars.

The pace of life is very different here from Havana. You'll see tobacco farmers' modest shacks, oxen working the fields, and local people riding to work on horseback. Few own cars here.

I recommend following up a visit to the Viñales Valley with a tour of a cigar factory, to see the process of cigar manufacture from beginning to end. Even without any interest in tobacco, I found the rules and traditions surrounding cigar making at the Pinar del Rio factory fascinating. Those rolling cigars would listen to a lector, someone reading aloud to them from Cuban history books, newspapers, or communist-approved texts, often paid for by the workers themselves.

Visit Las Terrazas in the Sierra del Rosario

Orchids in Las Terrazas
Orchids in Las Terrazas

One and a half hours by car from the capital, this place is worth visiting for its beauty and relative seclusion from the rest of Cuba. There's great hiking in the Sierra del Rosario, a mountain range laden in tropical forest and perennial orchids, with hidden waterfalls.

Las Terrazas is a small, close-knit but friendly farming community. It's famous nationally for being the home of Polo Montañez, a popular Cuban folk musician who died in an accident in 2002. I really like his music (think a Cuban version of Bob Dylan) and visited the house where he lived, meeting his brother and learning about his life among the farmyards and fields.

Trinidad and Santa Clara's music and history

Monument to Che Guevara, Santa Clara
Monument to Che Guevara, Santa Clara

If you only visit one other place in Cuba outside Havana, make it Trinidad, three and a half hours away from the capital by car.

A sleepy colonial city of uneven cobbled streets, baroque churches and elegant mansions that sprung up when it was the heart of the 17th-century sugar trade, Trinidad is a lovely place to wander around. It's also well situated for a day trip to Santa Clara, a pivotal place in Cuban history, where the final battle of the revolution took place in 1958. It was here that Guevara and his revolutionary forces famously used a bulldozer to derail a government train.

The train was carrying ammunition and fresh troops to the enemy. Derailing and capturing it cut off vital supplies from General Batista, and so proved a turning point for the rebels.

The train is still on display, and the town later became the location of Che Guevara's mausoleum. Now, his face looks out from murals, and a bronze statue of him brandishing a rifle looms over the place where he's buried.

Mandolin player in Trinidad
Mandolin player in Trinidad

Back in Trinidad, come evening the streets fill with music. There's no need to book to see a certain performance — just follow what you hear. One of the best places in Trinidad to experience authentic Cuban music and dancing is Casa de la Música.

Located up a flight of steps on a rooftop, this venue hosts bands that play home-grown salsa, son (an older, Afro-Cuban style) and the more poppy reggae-ton, but also merengue and cha cha cha. Trumpet players are the stars of the show, but you can expect ten-piece bands with shakers, pianos, acoustic guitars and drums. Whenever music is playing, you'll see Cubans spontaneously getting up to dance salsa — expect, too, to be asked to partner them.

You can have private salsa lessons in Trinidad as well as Havana. I've also found that most Cubans you meet in bars are warm and enthusiastic about sharing their national dance with you, and will show you the basic steps. Although you can sit back and marvel at the speed and skill of locals who have been learning salsa from childhood, it's customary for everyone to join in, no matter their age or level. It makes for a joyous, celebratory atmosphere in bars whenever music is playing.

Hike in Topes de Collantes National Park

Topes de Collantes
Topes de Collantes

Trinidad is conveniently close to Topes de Collantes, a national park spanned by the Sierra del Escambray mountain range.

When I lived in Cuba, I loved hiking the different trails here. As you tramp the forest and mountain paths, you may pass tiny smallholdings, grottos and waterfalls, where you can stop and swim in their fresh, clear pools.

Keep an eye out for butterfly lilies, Cuba's national flower. You can explore the vine-strewn tropical forest rich in mosses, ferns and wild banana trees on foot, or take a tour of the mountains in an old Russian jeep.

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Start thinking about your experience. These itineraries are simply suggestions for how you could enjoy some of the same experiences as our specialists. They’re just for inspiration, because your trip will be created around your particular tastes.