10 Day Cuba Itinerary: The Best Of Cuba

Cuba is a destination that surprised me in more ways than one. I had heard such mixed reviews from people that I had started doubting whether this island I had always dreamed of visiting would not meet my expectations. But oh man, this was a case in point example of trusting your gut instincts and going somewhere anywhere. Cuba feels like entering another world, a world of vibrant colour, community, and enjoying the good things in life. I had always seen photos of Havana, with its pastel, faded buildings and candy-coloured vintage cars, but Cuba is far more than that. With turquoise Caribbean waters, bright Colonial towns, and landscapes full of green mountains and towering hillocks, the enormous variety will satisfy any traveller.



Although I wish I had spent far longer in Cuba, there was unfortunately only so long I could be on holidays for. Thinking that my ten days in Cuba would be more than enough to satisfy my curiosity, it has instead sparked an intense desire to spend longer here, so the plan somewhat failed (in the best possible way). The relaxed atmosphere is captivating and I am already planning a return to the country to explore it further, particularly to do some more hikes and see the Eastern half of the island. However, if you also only have limited time, then this is the ideal Cuba 10 Day Itinerary to hit the highlights of the West. It includes stunning cities, relaxed beach days, and is the best introduction to Cuba. This itinerary is possible to do independently but it is a common route followed by group tours like G Adventures and Intrepid, so if you are more comfortable to book with a group then you will still see all of this.


Arriving and settling into Havana takes a little bit of time. After clearing immigration and customs, head to the exchange desk or ATM to withdraw some local currency (you can’t get CUC/CUP outside of Cuba). Expect to wait some time to get this sorted out as the queues are long at the airport as almost everyone coming and going is exchanging!


The airport is only a half an hour taxi ride from the old town of Havana and, despite the drivers being a bit crazy, there is barely any traffic. This drive into the city is your first chance to see the vibrancy of the country you’re visiting. Marvel at the colours in the streets and the huge number of people socialising – no matter what time of day – in the cafés, on balconies, or over a spontaneous game of soccer.


Once you arrive at your casa, it will take a little while to check in, enjoy a welcome drink and get to know your hosts. If you have time in the afternoon, go for an orientation walk around the city to familiarise yourself with the layout.


If your flight was in the morning, you will probably have some left over time to head to some of Havana’s museums. These museums will give you insight into Cuba’s interesting and complex history. This knowledge will definitely come in handy during the rest of the trip where there aren’t always signs in English. Although a bit chaotic in its layout, the Museo de la Revolución is the most useful museum to visit and has a lot of information on the Cuban Revolution. Other great museums to check out include the Museo Nacional de Bellas Artes, Museo de Arte Colonial and the Museo de la Farmacia Taquechel. If you are feeling like learning more about Cuba’s national beverage of choice, you can also go to Havana’s Rum Museum.

If you are looking for a good first meal, friendly staff, and delicious cocktails to settle into Havana, look no further than El Dandy Café. Pull up a chair at one of the tables overlooking the square, order yourself one of Cuba’s famous mojitos, and enjoy some people watching in Cuba’s vibrant capital.

Side note on eateries in Havana

There are some seriously good eateries, bars and cafés in Havana if you know where to look. My favourite for breakfast was El Café. For tapas was Lamparillo 361. For lunch and dinner was El Dandy and Al Carbón. If you want to try a Cuban coffee with rum, then head to O'Reilly's.


Start your day off with a healthy and delicious breakfast at El Café and make sure you have a Cuban Cortado coffee. You will want all of your energy for exploring Havana today and keeping up with the colour and liveliness of the city.


The most common way to see the city’s highlights as a traveller is to hire an old-school Havana car and take a guided tour of the city’s hotspots. It might seem touristy, and even a bit cheesy, but it really is so much fun and you can get to places that would be hard to reach on foot or public transport. It costs around 35 CUC per hour and you can either pre-book one with your casa or head near the Capital Building and you’ll find plenty of drivers around.


Once your tour is finished, take to the city by foot and explore in closer detail. The newly renovated Capital Building is absolutely stunning and worth looking at from a few angles. After admiring the building’s facelift, head down Obispo Street which is a pedestrian only (mostly) shopping street with plenty of cool shops to explore. Eventually you will get close to Havana’s Old Town. After some serious restoration efforts, a lot of the colonial old town in Havana is in beautiful order and it’s easy to feel the history of the city. Highlights include the old city walls, Plaza de Arms, the Catedral de San Cristobal de la Habana and wandering around Cathedral Square.


Enjoy the sunset at the quintessentially Cuban Malecón, with colourful buildings looking straight out to the water and the fortress, and bright classic cars zooming past. It is a place where locals and travellers alike go to drink a beer and watch the sunset. Just make sure you don’t get hit by any of the waves going over the wall – or by cars when crossing the busy road.


Viñales is a rocking-chair-loving town nestled amongst towering hillocks of the fertile Viñales Valley. It only takes a couple of hours to reach the town from Havana and the road travels through stunning countryside. The luscious greenery is a welcome contrast to cityscapes and the phenomenal hillocks rival those of the Philippines and Thailand. The atmosphere in Viñales is relaxed than Havana, with the emphasis here on slowing down and enjoying the natural beauty that has blessed the region.


The drive here takes around 2 hours and you can stop in the colourful, Gaudi-inspired Fusterlandia. This is a home which is entirely decorated – by one man – in bright tiles and out-of-this-world statues, it’s really quite incredible. 

Once you’ve reached the town from Havana, you should have an afternoon free to get orientated to the city. There are some great bars and short walking trails which lead from Viñales where you can enjoy the spectacular sunset from a variety of different viewpoints. Because although Viñales is surrounded by breathtaking landscapes all the time, it is taken to another level at golden hour. 


After a meal in one of Viñales’ many delicious restaurants, you can head to the nightclub/salsa bar in town – you won’t miss it, it’s the only one – and dance off the morning’s drive. There is a singer and a group of very talented dancers to inspire you to hit the dance floor.


You can either enjoy another day in the mountain town itself or escape the heat and head out to the island of Cayo Levisa. This is usually a full-day exercise because the boat to the remote island only leaves three times a day and it’s just over an hour from town plus a forty minute boat ride. However, your efforts are well-rewarded. With only one lot of accommodation on the island, there aren’t too many people around, and with dazzlingly blue waters, white sands, and surprisingly cheap cocktails, it’s an easy place to spend the day. There are a variety of activities on offer on the island including snorkelling and kayaking, but if I’m honest, I just lay on the sand with a never-ending stream of mojitos delivered to my towel. No complaints.


Not only is the quaint township itself fun to explore, but there are a sprinkling of activities nearby which are quintessentially Cuban. Think horseback riding, the world’s best cigars, and even more dramatic natural beauty. The atmosphere in the Viñales Valley is unlike anywhere else and it is a great place to spend time and enjoy. It’s the kind of location where all the households leave their doors open, and everyone says a friendly hola as you pass. You won’t regret spending some time here to enjoy the town and its surrounds.


The land in Viñales is rich and fertile which means it’s perfect for growing Cuba’s famous tobacco. There are several tobacco farms surrounding the town and many of them are happy to show travellers around. You may have spotted some of the tobacco drying houses on your way to Viñales, these A-framed buildings made from dried palm leaves are abundant in this part of the world. The process for planting, harvesting, and drying the tobacco is complex and extremely time-consuming, it’s phenomenal to learn about. You can sample Cuban cigars dipped in honey and take some home for a bargain price.


Viñales’ hillocks are beautiful from the outside but also house dozens of underground worlds. There are many hillock caves in the area and even some with underground waterways. Only a short drive from the township, it’s easy to pick a cave from the bountiful selection and enjoy a different perspective of the landscape. Visiting the caves and taking a boat ride is usually around 3-5 CUC and is a cool activity to do.


Although I didn’t get the opportunity to try it in Viñales, there are several companies that offer horseback riding through the countryside. This is a typical activity to try in the region and a unique way to explore the mountains and agricultural areas of Viñales.


After a few days in cities and in the countryside, it’s time to head to some of the best water in Cuba. And Playa Larga does beauty in spades. The area is most well-known worldwide as being the site of the Cold War’s Bay of Pigs invasion in 1961. There are plenty of reminders of the deadly history here with memorials, gravesites and a museum dedicated to the invasion. It is a key place to learn more about Cuba’s Cold War history and the impact of this time period on the Cuban people.


Playa Larga itself is a small, sleepy seaside town with fewer than two thousand residents. The perfectly positioned beach is the pick of the region for both spectacular sunrises and sunsets. With crystal clear, warm Caribbean waters, it serves as a good base for those wanting to enjoy some snorkelling. Only a fifteen/twenty minute drive from the centre of Playa Larga, there is a spot called Cuevas de los Peces which is a fresh-water cenote swimming hole with a spectacular snorkelling spot only a few yards away. I have to say, drinking mojitos from a beach bar, watching a golden sunset, and doing a spot of night-time swimming, was up there as the highlight of the trip. 


En route from Playa Larga you should stop at Cienfuegos, a colourful colonial town with huge historic significance. Wander through the streets and down to the pier, admiring the beautiful buildings and the unique seaside city feel. It is a really nice way to break down the journey, grab some coffee, and re-energise.


The drive from here to Trinidad is relatively short and you’ll be there in no time. Trinidad is a touristic city in the middle of the island and a place where you feel the presence of other tourists far more than most places in Cuba. But, it draws crowds because it is phenomenally beautiful with brightly coloured houses, a thriving main square, and an abundance of nearby waterfalls.


The architecture in Trinidad is different to that of Havana, with the colonnades and faded paintwork replaced by clean lines, big windows and doors, and vibrant paintwork. Trinidad is known for having some great museums and views. Surrounded by mountains, the colourful streetscapes are the foreground to green mountain landscapes and it’s really quite beautiful. My favourite museum to grab great views – for only 1 CUC entry and you get to climb the tallest tower in Trinidad – is the Museo Nacional de Lucha contra Bandidos.


Grab dinner at Adita Café which has a great selection of food and drinks for a reasonable price.  At night, head to the main square to pay just 1 CUC to sit on the stairs and listen to amazing live Latin music. If you are good at salsa you can head in front of the stage and dance, although for uncoordinated people like me, it was just as enjoyable to watch. If you’re still feeling up to it, you can head to the nightclub in a cave. To be honest, it’s not the best nightclub experience you’ll ever have, but it’s a pretty unique thing to try.


You can either spend another day in town or explore some of Trinidad’s nearby offerings. Set beneath mountains and close to coastline, Trinidad has several day trips and half-day trips which are easy to get to. You can head to a nearby beach to escape Trindad’s infamous heat, go on a horseback ride through the mountains, or make your way to one of the waterfalls and swimming holes in the surrounding hills.



Personally, I was pretty tired by this point and enjoyed a day in the city sampling some of the best cafés and soaking up the street scenes. I actually really enjoyed staying back and having a more chilled out city day, but if I had another day in Trinidad, I would’ve opted to hike to one of the waterfalls.



Shortly outside of Trinidad is the Sugar Mill Valley which has a dark past as the site of large sugar cane plantations which were worked by slaves. It is a place steeped in history and a reminder of the colonial past of the island. I would recommend visiting to get a better understanding of this part of Cuba’s history. 


Getting back to Havana from Trinidad is a lengthy process and it pays to break the process up. Depending on which route you took to get to Trinidad, if you went to Cienfuegos on the way to Trinidad, you should stop off at Santa Clara en route back. Santa Clara is where the monument to Che is located, as well as his final resting place and memorial to the revolutionaries. Alongside the memorial is a museum which shines light on the history of the Revolution and is a really interesting place to visit.


Eventually after the long drive you will make it back to Cuba’s capital, Havana. It is a good opportunity to see whatever you didn’t have the opportunity to see in your first few days in the city. If you are happy with what you have seen already, just spend the afternoon wandering the bright streets, restaurant hopping, and people watching from hole-in-the-wall mojito vendors.


It is time to leave the beautiful island paradise of Cuba and back to reality. Enjoy a great breakfast at El Café (the best breakfast spot in Havana, for sure) and then jump in your classic airport taxi to the airport. You will no doubt be plotting your next return to the island!  



Cuba 10 Day Itinerary

Lucy Owens Travel Textbook


My name’s Lucy and I’m the junior doctor and travel writer behind the blog. If you’re a fan of scratching beneath the surface of travel, visiting interesting destinations, and exploring ethically, then you’re in the right place. Focusing on purposeful budget and solo travel, Travel Textbook hopes to inspire more young people to seek meaningful adventure.


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