I recommend not trying to “do Cuba” in 2 weeks like many people do. This is not a place you want to rush. With such a rich culture, pulsating dance & music scene, unforgettable people, and diverse geography, my 6 weeks there felt like an injustice to the country.

That being said, I think that a month is a good, realistic time-frame to see the highlights. Due to the scarcity of internet within the country, it’s important to have a solid itinerary planned before you travel there. Lucky for you guys, I’ve done all the research and created this one month itinerary forCuba guaranteeing what’s sure to be a month that you never forget!

It’s no secret that diplomatic relations are improving between Cuba and the US, which no doubt has many positive implications. But in backpacker terms, that means go now before hordes of floral print-wearing, imodium-popping gringos descend on the streets of Cuba.

The authenticity of Cuba is sure to suffer, and I would suggest putting it at the top of your travel bucket list, no matter which region of the globe you’re currently devoted to.

One Month Itinerary for Cuba

But if we’re gonna do this, we gotta do it right. Ponle PLAY, mami..

Much better. Now, for that itinerary….


itinerary for cubaMore than likely you’ll be flying into the Cuban capital to start your trip, and there’s no better place to step through the Cuban time portal.

Suggested time: 4 days

What to do:

Stroll the Malecón

itinerary for cubaThe city sea wall which stretches on for 8 km is an emblematic symbol of Havana and Cuban street life. At any given hour of the day, you can find potentially hundreds of Cubans & tourists playing music, drinking rum, fishing, or simply just enjoying life.

Get lost in Habana Vieja

itinerary for cubaThis is the most beautiful section of Havana, and likewise the most touristy. By all means explore the many museums, churches, and bars that are highly concentrated here, but for me, the best thing to do is simply wander the streets and lose yourself in the aging decadence that only Habana Vieja can offer.

itinerary for cubaTake a break from the sun at La Bodeguita del Medio, the birthplace of the mojito & the late Earnest Hemingway’s favorite jaunt.

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Explore the Forts

itinerary for cubaBy the late 16th century, Havana had become the largest port in the region, so naturally the Spanish armada wanted to protect their gem of the New World. So what did they do? They didn’t just construct one fort, but four MASSIVE forts (and a few smaller ones) to defend the port from invasion. They are well-preserved and have fantastic museums inside.

Plaza de la Revolución

A tribute to Los Heroes de la Revolución (Heroes of the Revolution) like Che Guevara, Camilo Cienfuegos, & Jose Martí, this plaza was stage to some of Fidel Castro’s memorable speeches that galvanized the country against imperial powers.

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Everyone knows Cuban cigars are the best in the world. Viñales is where Cuba produces the finest of its cash crop. But it’s not just any old honey-pot, La Valle de Viñales (Viñales Valley) is surrounded by sugar-loaf shaped limestone mountains, forming a spectacular backdrop for any tour through the valley.

itinerary for cuba

Suggested time: 2 days

What to do:

Take a horse-back riding tour of the tobacco farms

itinerary for cubaTouring the tobacco farms that dot the valley floor can be done on foot as well, but I recommend the horse-back riding tours because the distance is substantial, it’s usually hot as hell, and you can’t beat the price ($4CUC/hour!). It’s very interesting hearing the farmers explain the entire harvesting & packing process, so if you don’t speak Spanish you may want to hire a bilingual guide.

Bay of Pigs (Bahía de Cochinos)

Widely considered as being the best scuba diving on mainland Cuba, taking a short detour to explore the underwater paradises of Playa Girón and Playa Larga is much easier & cheaper than chartering a flight or boat to Isla de Juventud or Jardines de la Reina. A few meters off shore, a coral wall plunges into an ominous, deep blue abyss – it was some of the best diving I’ve ever done! There are also various cenotes & caves to dive in the area.

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Suggested time: 1-2 days


The city of Cienfuegos is ok, it has some cool French architecture and serves as a good example of the real, working class Cuba. But it’s the sites around Cienfuegos that make it a nice stop on your Cuba itinerary.

itinerary for cuba

Suggested time: 2 days

What to do:

Go snorkeling at Rancho Luna

It’ll cost you $6 & 20 minutes from the city center to have the sand between your toes. The snorkeling & scuba diving is quality out here too.

itinerary for cuba

Cool off at El Nicho

itinerary for cubaIf you want some waterfall time during your trip to Cuba, El Nicho is the one. Crystal-clear blue swimming pools & multiple cascades wash the backpacker scent off in beautiful fashion. Taxis (about $40 roundtrip) can be procured from Cienfuegos, so find others to share the costs with!

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itinerary for cubaTrinidad is one of the most popular tourist destinations in Cuba, and for good reason. It’s colonial architecture, cobble-stone streets, colorful atmosphere, & close proximity to the beach are sure to keep the tourists coming for years to come.

itinerary for cuba

Suggested time: 3-5 days

What to do:

Bike Ride to Playa Ancón

itinerary for cubaAn idyllic beach, located about 12km away makes for a nice hour-long bicycle pedal, or $8 taxi ride.

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Sweat out those mojitos at Casa de la Música

My favorite Casa de la Música in Cuba (they’re in every city), Trinidad’s version has a big beautiful staircase out front with steps so wide they double as dance floors. You can boogie every night of the week if you want. Don’t like your dance partner? Hop down to the next step & find someone else!

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Cliff jump and swim through a cave at Javira waterfall

itinerary for cubaA unique, waterfall/cave combo with a refreshing green pool to take a dip in or cliff jump.

itinerary for cubaFor more in-depth information about Trinidad, see another article of mine about the 5 Best Things to Do in Trinidad, Cuba.

Santa Clara

For history buffs, & or those looking for a quick crash course in Cuban Revolution history, go to Santa Clara. This is the city that Che Guevara liberated, turning the tide in the Revolution & changing the fate of the nation.

Suggested time: 2 days

What to do:

Pay your respects at the Che mausoleum & memorials

itinerary for cubaThe remains of the world’s most famous guerrilla can be visited directly beneath his statue, and beside a very interesting & informative museum with exclusive photos. There are also other important, historical sites around town that those interested in better understanding the Cuban Revolution should visit.

itinerary for cuba

Get funky with the university scene nightlife

With a history so rich, and a thriving university nowadays, it’s no wonder that Santa Clara remains radically revolutionary. Political protests by day turn into funky fiestas at night, which begs the question – when do these kids sleep?


Located smack-dab in the middle of the island, Camagüey is a worthy stop to break up your cross-country haul. Nicknamed “La Ciudad Confusa,” Camagüey’s streets were purposely designed like a maze to confuse pirates and other potential invaders. Spend a day here meandering through the many parks and plazas, and taking in the interesting architecture before jumping back on the bus the next day.

Suggested time: 1 day

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Cuba has countless beautiful beaches, but many of the best ones are strictly regulated by the government, only accessible to people staying in expensive, beach resorts, & therefore lacking in true Cuban authenticity (I’m looking at you Varadero).

itinerary for cubaGuardalavaca is unique because despite being one of most beautiful beaches in all of Cuba, and despite having massive tourist resorts constructed on it, it remains open to the public. Cuban families & extranjeros (foreigners) are free to interact, adding a humble & authentic aire to the paradisiacal atmosphere. They are nearby casa particulares to stay at as well for the budget-minded.

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Suggested time: 3 days

What to do: Chilllllll

itinerary for cuba Santiago de Cuba

Santiago de Cuba is hot, loud, and assaults all of your senses simultaneously, but you’ll love it. The birthplace of the revolution, this city is surrounded by lush, green mountains, and filled with culture, music & street life.

itinerary for cuba

Suggested time: 4 days

What to do:

Wander through El Morro

itinerary for cubaCastillo de San Pedro de la Roca (as it’s officially known) is a UNESCO World Heritage site. This castle was constructed at the mouth of the Bay of Santiago de Cuba to defend the city from naval invasions. It gives you great perspective of the entire bay, and lots of interesting exhibits in the museum.

Cuartel Moncada

itinerary for cubaWhere it all started. The young Señor Fidel Castro & his motley crew assaulted these military barracks in 1956 in an attempt to overthrow the US-backed dictatorship. They failed, and Castro fled the country after being released from prison, only to return years later in spectacular fashion to spearhead La Revolución, take his country back, & change the world forever. Now the barracks are home to a grade school & one of the best museums in all the country.

Climb La Piedra Grande

itinerary for cubaTranslated literally as “The Big Rock,” it is…well, a pretty big-ass rock. This 70,000 ton boulder looks as if it was placed by the hand of God himself on top of a 4,000 foot mountain. Not only are the views of the city & ocean great, but the nearby Isabelica coffee farms are a UNESCO World Heritage site.

Dance, dance, dance

itinerary for cubaEverywhere you go in Cuba you’ll have opportunities to dance like you’ve never danced before, but Santiago takes it to another level. There’s no need to pay for salsa classes here, just take a stroll down Calle Heredia when the sun sets and you’ll find lines of Cubanos ready to take you for a twirl (disclaimer: don’t worry, they’ll be older than the group of folklore girl dancers above).


itinerary for cubaSecluded from the rest of Cuba in a hard-to-get-to corner. 29 rivers. Tropical, mysterious rainforest. Steamy, odd-shaped mountains. Hidden beaches. Local cacao & coconut-infused seafood cuisine. Welcome to Baracoa.

Suggested time: 4 days

What to do:

Climb El Yunque

itinerary for cubaIt’s only 575m (1886 ft) high, but climbing this table-shaped mountain was a right of passage for the indigenous Taino people, and should be for any tourist as well. Go early in the morning if you don’t want to sweat half of your body weight out.

Take a boat ride up Boca de Yumurí

itinerary for cubaThe Yumurí is a lazy, green river that winds through a deep canyon and flows out into the ocean. Locals wait at the mouth of the river to row you upstream. Get your camera ready, the towering canyon walls are home to many exotic birds.

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Cross Río Miel & explore the Fuentes farm caves

At the far end of the beach past the baseball stadium, you’ll find a bridge that crosses the river to a more primitive corner of Baracoa.

itinerary for cubaHere the Fuentes family runs tours on their farm in defiance of the government, and there is an extensive cave system to explore, including Cueva de las Aguas where you can take a fresh water dip in the pitch black dark.

itinerary for cubaAnd don’t forget the last part of your itinerary! An 18-hour Viazul bus alllll the way back to Havana.

Cuba is Not Just Another Country to Check off the Bucket List

I hope this itinerary has given you an idea of where to go & what to see during your time in Cuba, but the allure in this country doesn’t just lie in the beautiful beaches, cheap mojitos, awesome music, and time-machine appearance.

Traveling to Cuba has the ability to change how you think, put certain things back into perspective, and certainly shatter stereotypes. For me, it was refreshing to spend time in a society where technology & internet haven’t really penetrated yet, and it was a reminder of how rich real-life, human interaction can truly be. Furthermore, the resiliently optimistic attitudes of Cubans, in spite of having virtually no disposable income and limited human rights, is nothing short of inspiring.

I left Cuba with not just another country checked off the bucket list, but as a changed person with a greater appreciation for the simple things in life. I dare you to go spend a month in Cuba and tell me you don’t feel the same.

If you would like more detailed information for traveling to some of these destinations in Cuba, complete with contact information and insider tips, feel free to check out my 1-3 Week Backpacking in Cuba Itinerary & 4-6 Week Backpacking in Cuba Itinerary.

Who is the Gringo?


Ford Quarterman of Where’s the Gringo? is currently road tripping the Pan-American Highway from USA to Argentina over the next few years with a mission to learn Spanish fluently, shatter stereotypes & show that America is a continent and not a country. Follow his adventure at his blog or on his social media channels.

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