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As someone who lives part of the year in Cuba, a question I get asked all the time is whether spending two weeks in Cuba is too much. My invariable answer: no! Leaving aside the fact that I love the country, there are objectively many amazing things to see and do, so if anything a fortnight isn’t enough. But let’s assume 14 days is your time budget: what should you do and, most importantly, where should you go during your 2 weeks in Cuba?

Havana obviously, and then to the intriguingly called Oriente, which as the name suggests is the Eastern part of the island. Most independent tourists start off with the idea of visiting this region, then they take a look at the map, gasp at the distance, and quickly settle on the Havana-Varadero- Trinidad-Viñales circuit. These are all pretty places, but by virtue of being the default choice of the first timer they are also very crowded.

On the other hand, the opposite is true for the provinces of Granma, Santiago, Guantanamo, and Holguín, which brim with natural and cultural gems but are penalised by geography and an underdeveloped infrastructure. And yet, Oriente is perfectly explorable in two weeks and the following Cuba itinerary will show you how. Get ready to learn tons of Cuba Travel tips for your visit!

Best Cuba Itinerary - The Perfect 2 weeks in Cuba by a local

The perfect two weeks in Cuba itinerary

Oriente itinerary


Most flights from Europe and North America land in the evening, which means that Day 2 is when you can start exploring in earnest. I recommend that you lodge in a casa particular (small family run B&B) in Old Havana, or in one of the posh hotels around Prado and Parque Central. From here you will have easy access to the city’s rich colonial heritage and vibrant nightlife.

DAY 2: After exploring Habana Vieja’s restored plazas (Catedral, de Armas, Vieja, San Francisco), stop for a cheap and cheerful lunch at El Chanchullero in Plaza del Cristo, the only square in the Old Town still showing the ravages of decades of neglect. Note: There are plenty of ways to travel around Cuba on a budget.


Make sure you don’t overdo the daiquiris though, as the next stop in the itinerary is the Capitol building and if you are tipsy its opulent eclecticism will make your head spin.

This one-meter-longer-taller-wider take on Washington’s own interpretation of the Italian original was built in 1929 to house the government but has been barely used. Following a long self-imposed legislative exile by the revolutionary parliament, however, El Capitolio is now in the last stages of a thorough makeover and will be soon ready to reprise its role.

One hour should be enough for the visit, after which you can tranquilize your senses with a stroll along leafy Prado, hitting the malecón just in time to see the setting sun bath the city in a shimmery golden light.

For dinner head back to calle Habana, which is the street with the highest concetration of restaurats in the Old Town. Here you will find anything from pizza to lobster, even though my recommendation is for a comida criolla of fish or pork with sides of black beans and vianda, which is the umbrella word for starchy tubers like sweet potatoes (boniato) and cassava (yuca). Pro Tip: Check out my instructions for eating out in Havana

cuban food

DAY 3: Now that you have a good idea of the city center’s topography, you can delve deeper into its history by visitings landmarks such as the Morro-Cabaña fortification system (UNESCO World Heritage Site) and a couple of museums. I recommend the Museo de Arte Colonial for more insight into life in Spanish-ruled Cuba, and the Revolution Museum to gain a better understanding of the country’s recent history.

In terms of nightlife, lovers of the higher arts can enjoy a string concert by the all-female Camerata Romeu in the Basilica de San Francisco (10 CUC) or the ballet at the Gran Teatro de La Habana (30 CUC).

Those who aren’t satisfied by watching others perform and would rather do the dancing themselves can scope out the rooftop of the Hotel Inglaterra, the newly opened Salsa Habana in calle Muralla, the famous Club 1830 in Vedado, or the all-round satisfier Fábrica de Arte Cubano, also in Vedado, whose multi-genre musical offer is guaranteed to please everyone in your party.


DAY 4: If you believe that Havana’s only attraction is a rich colonial past, take a trip to its modern barrios and be ready to eat your words. You have two options here, depending on the depth of your pockets: the hop-on hop-off tourist bus (10 CUC) or the classic American convertible car (it seats 5 people at 40 CUC per hour.)

Either way, don your panama hat, whip out your camera, and snap away at the iconic engravings of Che Guevara and Camilo Cienfuegos in Plaza de la Revolución, the beautiful art deco mansions of Vedado and Miramar, the colourful Afro-Cuban murals of Callejón de Hamel, and the crumbling melancholy of the wave beaten malecón.



Bayamo is a befitting 666 km from Havana, by which I mean that given that the Carretera Central is not exactly a German autobahn, the devil’s number is an omen for things to come. Let me explain: although snail paced, the overnight Viazul bus that leaves from Avenida Boyeros at 10 pm is relatively pleasant, but if you choose to travel by camión you better get ready for a hellish journey.

This solution will save you 30 bucks, but it entails inching it to Oriente on a converted 1950s truck – charming for sure, but not something that I recommend to those without an iron back and a couple of spare travel pillows.

Coming from Queen of Chaos Havana, Bayamo will feel like Switzerland to you, with its pristinely conserved houses and spotless streets. Even if you are in desperate need of a nap, make sure that you don’t sleep away the whole afternoon since the city has plenty to offer.

For example, you could visit the Casa Natal de Carlos Manuel de Céspedes, one of the country’s most illustrious independence fighters and official Father of the Nation, before lightening the mood by checking out Cuba’s version of Madam Tusseaud’s. The museum is small, but the wax figures are well-executed and entertaining enough to keep you busy until dinner time.

And if Bayamo is not exactly a culinary destination, it is in this area around the colourful and mosaic-paved Paseo Bayamés – offically Calle General Garcia – that you will have the best shot at pacifying your stomach.

You might also like reading: Myths and Misconceptions about Cuba



DAY 6: Whatever your vehicle of choice (Viazul, camión, shared classic car) the trip from Bayamo to Santiago shouldn’t take more than a couple of hours, so setting off early in the morning means that you’ll have almost the whole day to gallivant in Cuba’s second largest city.

One thing I love doing as soon as I arrive in a new place is walking around to get a feel of my surroundings. This is a pleasure in Santiago, whose winding, steep streets are full of surprises behind every corner, from unexpected sea vistas and revolutionary slogans, to hummingbirds pecking the foxgloves and daylilies of a lush hanging garden.

If you take no joy in aimless wandering and are only at peace when walking with a purpose, march up to the Moncada barracks, whose attack by Fidel and his insurgent army sounded the beginning of the Cuban revolution.

From here you can then proceed to Santa Ifigenia, the resting place of mammoth historical figures such as Jose Martí and Fidel Castro as well as, much to the chagrin of the Bacardi family who fled the island in the early 1960s, the son of the distillery’s founder.

I suggest that you wrap up your instructive day by popping into the Cathedral, after which you can unwind with a mojito from the Hotel Casa Granda before sampling the local dance scene at nearby La Casa de La Trova.

DAY 7: Perhaps the region’s greatest cultural treat is the so called Morro (officially Castillo de San Pedro de la Roca), an early 17th century fortress erected at the mouth of the Bay of Santiago to prevent pirates from looting the city.


Given that the latter is 11 km inland the trip will take you the best part of the day, especially if you ditch the organized option in favour of DIYing it. In this case, you have two ways to reach El Morro: the comfy tourist boat (10 CUC, departures in the afternoon are not guaranteed) or the regular commuter lancha (1 CUP for Cubans, 1 CUC for you).

From the foot of the Cape you can then catch a camión or, if the sun is not in killing mode, leg the 1.5 km to the top. Here you will find one of the best preserved and complete examples of Spanish military architecture in the world, a distinction that in 1997 led to its inclusion in UNESCO’s World Heritage List.


DAY 8: Raise early on your last day in Santiago to visit the sanctuary of the Virgin de la Caridad del Cobre, Cuba’s patron saint and revered figure for both Catholics and Santeria practitioners alike. You can save yourself the 40+ bucks of a guided tour by catching a 1 CUP (5 cents) bus from the central station. After about 45 minutes you will reach El Cobre, a sleepy town whose life rotates around the large three-aisled basilica that dominates it from atop.

Pro Tip: I highly recommend a visit to this quiet and spiritual place, also because you won’t have to elbow your way into the church through throngs of tourists: for once, these are few and almost exclusively Cuban.


The central bus station is also home the camiónes that connect Santiago to Guantanamo, from where you can jump onto another truck or, if your backside has had enough, a more expensive but immensely more comfortable shared car (máquina). Don’t be fooled by the map though: it takes around five hours to reach Baracoa through the tortuous Viaducto de La Farola, so make sure you leave by 3 pm at the latest.

DAY 9: However picturesque Baracoa may be, there isn’t an overabundance of things to do in the town itself, which is most famous for the natural beauties that surround it. Those with a respectable level of fitness can tackle the ascent to El Yunque, a two and a half hour trek in the jungle through torrents, ravines, and scenic lookouts where a friendly guy will let you sample his selection of fruit for 1 CUC.

Or, if you are not that keen on physical exertion, you can skip the hike and splash around in the cool waters of Rio Duaba before heading to the nearby chocolate factory for a taste of Baracoa’s main export.

rio duaba baracoa

Speaking of eating, you will be pleasantly surprised by the range of sea produce in this region. Fishing is less restricted than on the coast near Havana, and this translates into menus replete with delicacies such as prawns, lobster, crab, cigal, octopus, scallops as well as tetí, a tiny, transparent fish believed to have aphrodisiac proprieties and unique to this corner of the world.

The best tetí I had was from the centrally located El Guajiro, but I also enjoyed a coconut flavoured crustacean dinner at El Buen Sabor, which had the added perk of a breezy terrace overlooking the town.

DAY 10 – 12 BEACH

After a coffee at the hotel El Castillo (for the view rather than the brew) head north for some well- deserved beach time. Your choice, in order of un-touristiness, is between wild Maguana, historic Gibara, and Varadero-like Guardalavaca.

Maguana is the closest to Baracoa and can be reached in less than one hour by máquina for 2 CUC or with a 6 CUC tourist bus. Amenities are basic here, so the location will suit people who are looking for quiet nigths, pristine beaches, freshly fished seafood, and friendly villagers. These will try to peddle meals and tours to you but the hassling, if it even classifies as such, is very well mannered.


Approximately two hundred km north-east of Maguana you’ll find Oriente’s answer to Varadero in Guardalavaca, a fully-equipped tourist area with both 5 star resorts and quaint casas. This is thus a great place for those who’ve had enough of adventuring and feel like going on autopilot for a couple of days.

Or, if Guardalavaca doesn’t sound authentic enough to you, drive around the bay that Columbus described as “the most beautiful land that human eyes saw” until you reach Gibara, which is pretty urban but a good base from where to visit the mostly foreigner-free Playa Concha and Playa Caletón.

DAY 13 / 14 – HOLGUÍN

The degree to which you’ll be able to explore Holguín depends on where you spent the previous night, since the journey takes just over one hour from Guaradalavaca and Gibara but six from Maguana – unless you rent a taxi in which case you’ll hit Holguín in three. Leaving for Havana the following morning will give you enough time to climb the 458 steps of La Loma de La Cruz for afull panoramic view of the city. On the other hand, if you’d rather spend an extra day by the sea and bus it back to the capital on the 21.15 Viazul, you may have just enough time to visit the Cathedral and then cool off with a Cristal in nearby Parque Calixto Garcia.



Most flights to Europe and North America depart in the evening, so provided that you are keen on getting up early (or, if travelling overnight, have enough leftover energy after dropping off your luggage at a hostel) you can checkout a few more attractions. Amongst the most worthwile are the national gallery (Bellas Artes), the natal house of Jose Martí, and Havana’s not very Chinese Chinatown (Barrio Chino). Or if you haven’t had enough of the island’s mesmerisingly clear waters, catch a 5 CUC tourist bus in Parque Central and say hasta pronto! to the tropics from the white sanded wonder that is East Havana’s Playa Santa Maria.

This is a guest post by: Barbara from the travel blog

AUTHOR’S BIO: Barbara went to university to study geography because she wanted to see the world. Twenty years and twenty times as many adventures later she is living her dream. When she isn’t evaluating development programs in exotic locations, she runs a travel blog and spends her time between Europe, South Africa, and Cuba.

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