In a nutshell, Cuba is magnificent. But planning a trip over to the jewel of the Caribbean from your sofa might be a little daunting, yet extremely fun. Therefore we put together this Cuba Itinerary to help you have the best of your visit.

While Cuba, unarguably, has one of the most gorgeous coastlines, stunning scenery, and rich heritage, in reality, it’s all about the people. We had a blast in every casa we stayed and found it to be the best option for us as a couple. Cubans are friendly and warm people and will make your stay at their home a truly unique experience. We do hope this will never change.

A Brief Overview of the 2 Week Cuba Itinerary

So you have 2 weeks in Cuba, we are very jealous! Let’s look at the Cuba itinerary overview and see how you can make the most of your stay on this timeless Caribbean island.

We suggest starting with magical Havana. The crumbling, yet incredibly charming city that lives and breathes culture has a lot on offer. But don’t just explore Habana Vieja, the newly restored old town, venture into the local, run-down streets. After all, this is where real life happens. Don’t worry, Havana is very safe. In fact, Cuba is one of the safest countries to visit.

To discover the real Cuba, make your way to Vinales. Explore the tobacco plantations, smoke fat Cohiba and sip rum all the while sitting on a porch of a Cuban casa. Pure bliss.

Trinidad, out of all the places should be included in your Cuban Itinerary. It’s literally an outdoor museum, filled with colour, music, and sunshine. A truly stunning place to visit. Imagine beautiful cobbled streets, salsa moves and balmy evenings. In our humble opinion, this city is built on romance!

A little away from Trinidad, you will find yourselves in classic Cienfuegos. This absolutely stunning French settlement will blow your mind. It is anything but typical Cuba and this is exactly why you should include it into your Cuba Itinerary. For the ultimate experience, stay in Punta Gorda, the upper-class neighbourhood.

Finally, your visit to Cuba will not be complete without visiting the coastline. Our poor experience of Varadero led us to exclude it from this Cuba Itinerary. In our opinion, Cayo Guillermo represents a much better value. If we had not made the effort to travel all the way to the Atlantic Ocean, we wouldn’t have known what a gem we nearly missed.

old town, havana, cuba

Discover Magical Havana

We promise to be understanding should you decide to completely ignore this Cuba Itinerary and spend your entire time in Havana. The city is picture-perfect, overflowing with music, rum, and beautiful people.

Architectural Heritage

Habana Vieja. Rehabilitated with some serious tourist money, the colourful old town is truly stunning and a massive contrast from the run-down streets in the rest of Havana.

As you enjoy the captivating Plaza San Francisco, take some time to admire the Baroque-style Havana Cathedral located in Plaza de la Catedral. The basilica is one of the eleven Roman Catholic cathedrals in Cuba.

Run-Down Havana. Whatever you do in Havana, make sure you spend some time walking along the crumbling streets of this incredible city. It’s the true face of Havana – crumbling away, yet absolutely stunning. Look around you and discover the day-to-day life of a Cuban.

If you see any shops while wandering around, don’t hesitate to buy something. See if you can find any pizzas or ice-cream sold right in someone’s home doorway. The tasty Guanabana (custard apple) ice cream cost us next to nothing! We can’t even work out how much exactly!

Hotel Inglaterra. Before you jump into one of the wonderful convertibles, pay attention to the grand and wonderful building right next to the Gran Teatro de La Habana. It’s the historic Hotel Inglaterra dating back to 1875. As a matter of fact, Winston Churchill stayed here as a military observer during the Spanish-Cuban war back in 1895.

The Cuban National Ballet School. To visit the biggest ballet school in the world wander off to the Paseo del Prado. The stunning 3-stories yellow building provides ballet lessons to approximately 3,000 students. Actually, Alicia Alonso, the first ever prima ballerina took classes in this very school.revolution museum havana cuba itinerary

Cultural Explorations

Castillo de la Real Fuerza. This massive star-shaped fort is considered to be the oldest stone fort in the Americas. The amazing UNESCO World Heritage Site was reopened as Cuba’s premier maritime museum back in 2010. It now houses an excellent exhibition of Cuba’s maritime past from pre-Columbian days. Additionally, it has fantastic panoramic views of Havana.

Museum of Revolution. Under no circumstances should you miss the incredible Museum of Revolution. It has a wealth of information and is one of the most bias museums we have ever visited. It’s brilliant!

Historical and Military Park. The park, built by the Spanish in the 16th Century, contains a selection of weapons and a massive catapult. Interestingly, soldiers dressed in 18th-century military uniforms fire a cannon across the bay every evening at 9 pm. Definitely, something interesting to include in your Cuba Itinerary. Here you will also find the house of Che Guevara himself. A selection of photographs and Che’s personal belongings are displayed in the house.

Also check out the 20-meter-high Cristo de la Habana statue by Cuban sculptor Jilma Madera, overlooking the bay in Havana. Ultimately, soak up the great panoramic views of the city from the park.

Glorious Revolution Square. Pay a visit to Cuba’s most noble heroes immortalised on the huge tower blocks in the square. See the Che Guevara and his counterpart’s Camilo Cienfuegos portraits steel wired on the building veneers. Also, wired on the facades are the famous quotations: “Hasta la Victoria Siempre” – Until the Everlasting Victory, Always and “Vas bien, Fidel” – You’re doing fine, Fidel.

Finally, try to take a good shot of the impressive 109-meter-tall José Martí Memorial that dominates the Plaza.

cuban cars, havana

Cuban Entertainment

Take a ride in a 1950’s convertible. This bit is as touristy as it gets, but sometimes it’s worth giving in. We look at it more as supporting the locals rather than a cheesy thing to do. Trust us, it will be great. The lovely Cubans will effortlessly whizz you through the streets of Havana and give you a great tour.

Join the Locals at the Malecon. Walk along the promenade Paseo del Prado which divides Old Havana and Centro Havana. This first-ever paved street in Havana will lead you down to the Malecon. You’ll see the Cubans fishing, smoking cigars or just unwinding after a long and sizzling-hot day in the city, join them. Sunsets here are a true sight to behold.

5th Avenue. If you want to see the upper-class neighbourhood in Havana, venture to the 5th Avenue. This Avenue of the Americas is considered to be the most beautiful area in Havana.

Parque Almendares. Havana might seem like a busy and dusty (yet breathtaking) city, but it, no doubt, has something for everyone. If you feel like chilling out in a green space, head to Parque Almendares also known as Havana’s Forest. The park is a recreational area complete with children’s playground, boating, and even mini golf.

Join the Rum Frenzy in Havana. One of the greatest entertainments in the capital city is, of course, indulging in some delicious Caribbean beverages at any time of day. While you are welcome to seat yourself in the more popular bars like La Bodequita (Empedrado Street) and El Floridita (Obispo Street), we would like to recommend Prado No 12.

It’s a tall, slim building on the corner of Prado and San Lazaro. Scan through their extended collection of wonderful rum and have it neat or order a Pina Colada. It’s simply fabulous!vinales, cuba

Chilled Vinales

It’s time to chill and nothing says “relax” better than Vinales. Surrounded by wonderful scenery and tobacco plantations, it is one of the most unique places in Cuba. Therefore, you can’t afford to miss it.

Here you will find interesting examples of colonial architecture, mostly wooden houses with porches. That’s what we call a true getaway.

Life in Vinales is a little different. The day-to-day life revolves around agriculture and, of course, production of the best tobacco not only in Cuba but in the world! For this reason, visiting the tobacco plantations is an amazing experience, let alone seeing the making of the famous Cuban cigars.

There are many other things you can do in this incredible place from horse riding through the hills to caving through some impressive grottos.

When exploring Vinales Valley, a UNESCO World Heritage Site, don’t miss out the incredible Mural de la Prehistoria, a mural painted over one of the valley’s limestone outcrop. However, a charge applies to see it up close.

If feeling adventurous, go on an all-day horse ride. Just check with your casa host for the best possible option.

Whether an avid climber, a beginner or just interested in climbing, you will love Vinales. It is a popular place for climbing due to the rich karst landscape. For an easier option, take a boat tour through the caves.

Check out the High Street music scene and listen to live tunes bursting on the street. You can never have enough rum and music in Cuba!

In reality, Vinales, just like the rest of Cuba is all about the people. Your most treasured memories about Vinales will be the warmth of Cuban hospitality found here.trinidad, cuba

Colourful Trinidad

Welcome to Trinidad, a one of a kind outdoor museum in Cuba. Declared a World Heritage Site by UNESCO in 1988, this cobbled-street, the picturesque place attracts masses of visitors every year.

Once upon a time, this Spanish colonial city was a prosperous centre of the island’s sugar and the slave trade. As a result, Trinidad is still home to many grand colonial mansions and churches of exceptional beauty built from local fortunes.

Architectural and Cultural Explorations

Plaza Mayor. This breathtaking terracotta tiled roof city is compact and the centre is pedestrianised, making it easy to explore on foot. Just take any of the picturesque streets and it will eventually take you to the Plaza Mayor. The neoclassical, pastel-yellow church, Iglesia Parroquial de la Santísima Trinidad, dominates the square.

Next to the church, you’ll see the Palacio Brunet overlooking the main square, built back in 1812. The mansion now houses the beautiful Museo Romantico which still displays the Brunet family’s belongings. For a few convertible pesos, you can get to the 2nd floor and enjoy the panoramic views stretching to the lush Escambray mountains.

The biggest house, Palacio Cantero, is now the Museo Historico Municipal. While exploring the museum, be sure to step out into the beautiful courtyard. Also, make sure you climb the dilapidated staircase for some fantastic views across Trinidad. Check the opening hours though, the tower closes pretty early.

Take a Private Tour. If you can spare a couple of hours and convertible pesos, you can take one of the guided tours which will take you around the main sites of Trinidad.

Take a Steam Train. For the ultimate experience in Trinidad, take the steam train to the Unesco-protected Valley of the Sugar Mills. You will get to explore the Hacienda Iznaga with gorgeous panoramic views from its tower. Additionally, you will have the chance to see the ruins of the saccharine empire.

cycling outside trinidad, cuba

Fun Things to Do in Trinidad

Chill at Casa de Musica. If you want to have a chilled evening, we suggest heading to the House of Music and join the crowds on the gargantuan staircase. As you start approaching the square, you will hear the wonderful Cuban rhythms from afar. Get your rum and chill. If you are brave enough, join the locals in the invigorating salsa dance. This was our absolute favourite spot in Trinidad.

Cycle to Ancon Beach. Spare a good chunk of your day for this cycling experience along the Caribbean Coast. You can either rent a gearless bike at Las Ruinas del Teatro Brunet or Hostal El Oasis. Alternatively, you can ask at your casa. Your host will most likely know someone who rents bikes in the area.

However, make sure you dress appropriately for this outdoor adventure. Apply plenty of sun cream if you burn easily, wear a hat. We highly recommend wearing a long sleeve shirt too.

The distance between Trinidad and Playa Ancon is around 12 km but there are many lovely beaches along the way. Bring along your swimwear! We stopped at every single beach and had a blast in the tea-warm waters of the Caribbean.

You will come across places to eat and drink, but we still recommend packing a few snacks. If you can, pack a picnic for your final destination at Ancon Beach.

To avoid the blistering midday sun, leave Trinidad early in the morning or later in the afternoon. We left the city just before midday. What fools!cienfuegos, cuba itinerary

Classic Cienfuegos

Situated on the Caribbean coast of southern-central Cuba, Cienfuegos, also known as Perl de la Sur is a fascinating place to visit.

The French Colonial Architecture of Cienfuegos. There’s nothing quite like it in the country as the urban historic centre of Cienfuegos. The splendid French colonial architecture surrounding the city centre is captivating. No wonder this exquisite part of the country became another Cuban UNESCO World Heritage Site in 2005.

Palacio Ferrer, cuba

The longest in the country, Cienfuegos Boulevard houses some of the most magnificent architectural compositions you will come across in Cuba. A few to check out are the Nuestra Señora de la Purísima Concepción Cathedral, the building dating back to 1869.

To the south of the park, stands the Nobel Palacio de Gobierno. It is, however, the Government Palace and there’s no admission for the general public.

Have a chilled stroll through Jose Marti Square and lose yourself in the sea of the refined historical masterpieces. On the western part of the Parque Marti, check out the elegant Arco de Los Trabajadores (Arch of Triumph) dedicated to Cuban independence.

Next to it, on the other side of the street check out the blue tiered mansion, a former Palacio Ferrer, designed by the local architect Donato Pablo Carbonell and completed in 1918.Teatro Tomas Terry, cienfuegos, cuba

Visit Teatro Tomas Terry. The Italian style theatre on the northern side of Parque Jose Marti is one of three vernacular theatres in Cuba. This national monument has won an Award of Conservation in 2008. Don’t hesitate to pop in. For just 2 CUC have a nose around the impressive 950-seat auditorium.

For a coffee break, make your way to the charming Teatro Cafe Terry wedged between Teatro Tomás Terry and Colegio San Lorenzo.Punta Gorda, Cienfuegos, Cuba

Explore Eclectic Punta Gorda

The Upper-Class Neighbourhood. Located around 3 km away from the centre, Punta Gorda is an incredibly stunning part of Cienfuegos. Follow the Malecon sea wall and you will reach it in no time, otherwise, hale the iconic Bici taxi (a bike taxi).

Situated at the edge of the Bay of Cienfuegos, Punta Gorda is a refreshing neighbourhood by the waterfront. If you can, rent a room at the end of the peninsula so you can enjoy the gorgeous scenery any time you feel like it.

Palacio de Valle, Cuba

This eclectic suburb houses some of the most wonderful and eye-catchy buildings like the sky-blue Palacio Azul, built in 1921 and the one thousand and one nights like Arabian Palacio de Valle. The latter, built in 1917, houses a luxury restaurant with a terrace bar.

Cienfuegos Club. Cienfuegos Club might come across as a sports-bar-like place for western travellers, but it offers fantastic views across the marina. At least check out the domed building painted in white & green, the colours of the Cienfuegos baseball team.

To get those old bones moving and experience the true Cuban spirit, come back here later in the day. Have a drink and dance your night away as the sun sets into the Bay of Cienfuegos.

marlin marina, cienfuegos, cuba

Marlin Marina. While wandering around Cienfuegos Club, pop into the marina for a refreshing sea breeze. The place is absolutely stunning. Book a boat tour around the bay or arrange a deep-sea fishing trip through Cubatur/Cubanacán. Alternatively, check out other operators in the nearby Jaguar Hotel.cayo guillermo, cuba

Stunning Cayo Guillermo

Cayo Guillermo will spoil you rotten with its coastline so much that you will not want to leave. This delightful stretch of sand is located on the northern coast between the Bay of Dogs and the Atlantic Ocean.

While visiting, be sure to check out the snorkelling and diving options in the magnificent Jardines del Rey archipelago just off the northern coast of Cuba. This spectacular 200-kilometre-long coral reef is well known amid water enthusiasts.

Things to Do in Cayo Guillermo

First things first, enjoy it! Chilling and beach lounging is compulsory. That’s why we included this place last in our Cuba Itinerary. After roaming the dusty, but gorgeous Cuban cities, you will thank us for leaving this paradise for last.

Visit Playa Pilar beach. This 500-meter-long finer-than-fine sand beach is an absolute star of the northern coast. I swear my jaw stayed lose throughout the day while we enjoyed the crystal-clear waters of this unbelievable shore. Spare at least a day to fully appreciate the beauty of this hidden gem.

Before you hit the beach, make sure you pack some snacks and water with you. Food-wise, there’s only one restaurant perched in the dunes. Next door you will find a bar-shack jammed with all sorts of lovely Caribbean rum.

There are 4 hop-on-hop-off buses per day, going between the resorts and stopping at Playa Pilar.cuban cigars on the beach

Enjoy Mojitos and Fat Cuban Cigars on the Beach. We couldn’t get enough of minty drinks at our resort. The bar staff were incredibly hard-working and entertaining, making the best Mojitos we’ve ever tasted!

We are not encouraging you to smoke, but you can’t leave Cuba without inhaling at least one puff of Cohiba. Good quality cigars will be available at your resort shop. We bought one for around $8 and shared it while enjoying the sound of waves of the Atlantic Ocean.

It was then that we realised we want more experiences like this so we made a plan. A plan to create our own travel lifestyle. Maybe a glass of rum and a cigar will inspire you too!jardines del rey, cuba

Sail the Jardines Del Rey. We really recommend a snorkelling trip around Jardines Del Rey archipelago. You will most likely see agents at the resort/hotel reception selling various sailing trips. For around $80, catamaran trips include pick up and drop off at your resort, snorkelling equipment, lunch, bottomless-rum bar (at least ours did) and a couple of swimming stops.

Otherwise, check the Marina at Cayo Guillermo directly for more options.

How to get to Cayo Guillermo Independently

Your best bet to get to this piece of paradise is to rent a car or hire a local taxi. If you are going to hire a taxi, we suggest asking for advice at your casa.

Cubans are extremely resourceful and will probably know someone local who can take you all the way to Cayo Guillermo for a negotiable price. It’s better this way because the pennies go to the locals’ pockets rather than the government.

Our journey from Trinidad took us around 3.5 hours at a hefty $120 USD. If you choose an official government taxi it will cost you much more. Of course, be cautious, if you don’t have a good feeling about the driver, don’t get into the car, but in general, Cubans are very trustworthy. To minimize the costs, if possible, share a cab.

You might also want to arrange a pickup from the resort with the same driver. We made arrangements with our driver to pick us up 3 days later and take us back to Havana. It took us around 7 hours at a cost of over $200 USD. Again, check at your resort if anyone else is going back to Havana on the same day. Try leaving a message at the reception asking for taxi buddies.

Alternatively, you can fly directly into the Jardines del Rey Airport located on Cayo Coco. Check with your resort if they can arrange a transfer which takes around 45 minutes depending on the stops.

Read more: Must-see places in Cubacuban casa particular

Where to Stay in Cuba

In our opinion, Cuba is best experienced when you stay in a casa particular. We’ve been lucky enough to stay in some incredible homestays and would highly recommend booking a casa for your trip.

Casa Rolando y Marisol (La Casa del Chef), Havana. This lovely casa is located in Habana Vieja, very close to the Malecon and the alluring Plaza de San Francisco. The best thing about this place was the welcoming atmosphere and the hosts. Both Rolando and Marisol were extremely friendly and accommodating.

Casa Ellios Ramos, Trinidad. Ellios casa is a beautiful colonial house complete with beautiful rooms and spotlessly clean bathrooms. After exploring the casa, we suggest booking a room on the second floor overlooking the street.

Casa Ariel y Maykelis, Vinales. For a complete experience in Vinales, stay in Casa Ariel y Maykelis. It has an amazing veranda with a beautiful view where you can enjoy a tasty breakfast and dinner or chill out on one of the rocking chairs after a day of explorations.

Villa Lagarto, Punta Gorda, Cienfuegos. It’s not a casa, but a fabulous place nonetheless to spend a couple of luxurious days while enjoying the offerings of Cienfuegos. The food, although not the cheapest is great and pina colada here is fabulous. Pair it with a rocking chair and stunning views over Cienfuegos Bay and you’ve made yourself some pretty unforgettable memories.

Iberostar Daiquiri, Cayo Guillermo. This all-inclusive resort is great for anyone, especially couples. At $100 per night per room, it was the perfect finale to our Cuban adventure. More so the food and drinks were excellent.cuba itinerary

Practical Things to Know When Travelling to Cuba

Visa and proof of departure flight are required by all nationals. If you are planning to travel to Cuba as a tourist, you will need to obtain a tourist card at your country’s Cuban Embassy. We had our 30-day tourist cards issued on the same at a cost of £20.

On arrival don’t forget to pick up a Customs Declaration Form as soon as you cross the border. We totally missed the desk with the cards and had to come back to fill it out.

There are 2 exchange bureaus as soon as you leave the airport. However, they can run out of cash and close the office right in front of you. It happened to us. To avoid the hassle, make your way to the second floor of the departures terminal where you will find an ATM.

Getting cash out of the ATM’s is not usually a problem anywhere in Cuba, however, sometimes they can be out of order. In this case, to withdraw money, go into the bank, but make sure you have your passport with you.

You are not required to pay the departure tax at the airport anymore. It’s now included in your airline fair, however, we still paid an extra 25 CUC at the check-in desk. You might want to have some spare cash just in case.

Booking a casa in Cuba can be pretty challenging, but don’t worry, we’ve put together a comprehensive guide to help you out. For more information, read Our Complete Guide to Booking a Casa Particular in Cuba.

If you really want to understand Cuba, you should read Cuba: A New History, the book by Richard Gott. It’s very factual but necessary to understand the historic events that happened in the country and why they happened. It goes a long way in explaining the current state of the country.havana-from-a-convertible-cuba

Getting In and Around Cuba

Buses. Viazul will be your main transport mode in Cuba. This national bus company is actually very efficient, reliable and comfortable. The prices are very reasonable too, but you will need to purchase your tickets at the bus station in advance.

We recommend buying tickets at least a day before your trip. But most importantly, don’t forget your passport, otherwise, you won’t be travelling anywhere.

An alternative option is to book transfer buses at a hotel, even if you are not staying in one. We booked a transfer bus from Havana to Varadero for around $25 each. We simply walked into a hotel and booked it at the reception. All we had to do the next day is to show on time.

Railway. Don’t even think of taking a train. Unless you enjoy rail journeys so much that you are prepared to spend over 10 hours on board from Havana to Cienfuegos. For up-to-date information check the excellent rail website.

Road. Road journeys can be extremely fun and time-saving if you know where you are going. However, bear in mind that the road signposting is not great. The road can also end suddenly, without any warning… as it happens in wonderful Cuba.

It’s easy to rent a 1950s convertible on the island. It will cost you over $100 per day but remember that they break easily too. On our way from Cayo Guillermo back to Havana our taxi lost the fourth gear… What we saw under the bonnet was incredible. We found the air filter tied up to the rest of the engine with a shoelace!

Eventually, we switched cars somewhere in the middle of nowhere. You’ve got to love Cuba!

Have you been to Cuba? What was your favourite thing about this island? Let us know in the comments below.

Cuba Itinerary - Our Epic Getaway to the Jewel of The Caribbean
2 Week Cuba Itinerary. Our Epic Getaway to the Jewel of The Caribbean