Cuba is a huge country and has a lot to offer for each type of visitor. I chose to backpack the island in two weeks. I soon realized that was not a lot of time but, thanks to recommendations of fellow travelers and locals I met along the way, I was able to capture the essence of this beautiful country in this short time period. Here you will find my cuba two week itinerary and short explanation per destination. You will also find links to stories of my experiences at each place and on the road. Enjoy and hopefully my experiences can help you plan your trip!

Day 1: Arrival in Havana

For my full Havana travel log check out Havana Nights, Cuban Days.

Most international flights will land you in Havana although if you booked with a tour agency some will land in Varadero (in which case you just shift the itinerary and start there). Find a place to stay somewhere in Havana vieja to experience the heart of the city. I stayed at Cuba 58 Hostel, which is as far as I know the only hostel type establishment in the city. Perfect for meeting other travelers and gathering tips and tricks for you trip. I arrived quite late but still went out to the wonderful Fábrica de Arte Cubano. Which made for a good introduction to the Havana nightlife.

Day 2: Habana Vieja

You need at least one full day to enjoy the essence of Habana Vieja. The hostel I stayed at is ideally located and you can easily walk the whole time, unless of course you really want a ride in one of those classic American Old Timers. There is so much history and culture packed together and the fun part is that a lot of it is not 100’s of years old. Colonial history and the modern stories about the revolution deliciously intertwine in these chaotic little streets. For more details on what to visit, check out my detailed reports on Havana.

Day 3: Modern Art and Revolution

Take one day to explore the more modern part of Havana. Leave the old town and venture into the many interesting corners of the capital. Explore the revolutionary history in the Museo de la Révolution. Have a whiff of the rich Cuban art scene in the Museo Nacional de Bellas Artes. Travel back in time with a visit to the Hotel Nacional and marvel at the community project in Callejon Hamel.

Day 4: Havana to Viñales

For my full Viñales travel log check out Venturing through the Valle de Viñales

This is a must-do in your Cuba Two Week Itinerary. Arrange a colectivo in your hostel or hotel or a private one if you’re feeling fancy. Most likely you will be cramped into an old Pontiac or a minivan held together with duct tape but eventually you will get there. Feast your eyes on the changing landscape when driving out of the city and into Viñales. 9 chances out of 10 they will make a stop in some tiny tobacco plantation as a pitstop. It is their version of a souvenir shop. Explore the tiny town after your arrival. Afterwards, hike up to El Balcón del Valle for an amazing sunset dinner view over the valley. If you don’t have a place arranged, your driver will definitely know someone to hook you up.

Day 5: The Green Valley of Viñales

Take a day to explore the many wonders of the Valle de Viñales. You can rent a mountain bike, do a guided tour on a horse, visit some caves and go swimming there. You can also simply just hike around in this wonderful landscape. I decided to go a bit less touristy but more about that in my detailed reports.

Day 6: To Playa Giron

Now here’s where i made the mistake of going to Cienfuegos first. So learn from my mistakes: it is wise to stick with the counterclockwise logic and do Playa Girón first. Although you have to note: this place is mainly popular for diving. There are some pretty beaches and entertainment but most tourist here are diving in the morning and drinking/relaxing in the afternoon and going to bed early. You will spend most of the day on the road, but if you still got some sunshine left, head over to Playa Coco to relax with a mojito.

Day 7: Diving in Girón

If you like diving, go to the Cubanacan and ask for the diving shop. Or make it even easier on yourself and stay at the Casa Particular run by Yvette and Ronel, the main diving instructor in town who runs the shop. They take a old yellow school bus every morning and offer 2 dives with several instructors depending on your level. In the afternoon you can head over to the Caleta Buena, where you pay about 10 bucks for a full afternoon of relaxing, drinks and lunch included.

Day 8: Cienfuegos

Take a colectivo or the bus two hours east towards this small city. It is worth spending one day there if only for the walk and sunset along the Malecon. Take a chill walk from the centre of town all the way down to Punta Gorda and enjoy the views over the Bahía. Make sure you’re around El Maleconcito at sunset and enjoy the views. Afterwards go for a Ropa Vieja in Las Mamparas just around the corner.

Day 9-12: Trinidad

By far my favorite place in Cuba, followed closely followed by Havana. This tiny city does not necessarily have enough to offer to need 4 days visiting it. But it is an essential part of the Cuba Two Week Itinerary. It is the perfect base for adventures around the region.

Plan a visit to the beautiful Playa Ancon (you can even bike there if you want). Go up into the Topes de Collantes to chase some waterfalls through the jungle. Take a steam train and visit a colonial sugar plantation. Take a catamaran ride and go snorkeling. There are numerous day trip possibilities around.

At night you start in one of the numerous sunset terrace restaurants in town. Walk to the lively Casa de Musica for some salsa and dance until the music there stops. If you still got some energy left (or the mojitos and canchancharans have not killed you yet), you can walk up to the Cueva, a genuine disco in a natural cave. Fun guaranteed.

Day 13: On the Road to Santiago

Now here I must note that Santiago is a huge detour from the rest of the Cuba Two Week Itinerary. I had my mind set on going and thought it was worth while. However you will lose about 24h sitting in a bus. So this day was spent entirely reading, listening to music and enjoying the varying landscapes along the way.

Day 14: M26-7 in Santiago de Cuba

Take a day to extract the essence of Cuban culture out of this remote city. This is where a lot of Cuban’s modern fame started and ended. The revolution took up arms here first and son and salsa have their roots here. It is also the final resting place of the nation’s greatest heroes: José Martí, Céspedes and Fidel himself. You can see the appeal of this city and why I had to go. However the city itself is less spectacular or pretty than Havana and Trinidad. A full day should be enough to enjoy the palpable history in this place.

Day 15: Varadero’s Infinite Beach

I took a night bus from Santiago to Varadero so I arrived kinda buzzed and tired. Now here you got 2 options: you either find a casa particular in town or you go more out onto the peninsula and book yourself a room in one of the all-in resorts that line the never ending white sand beach. Now I was traveling solo but there are plenty of lively bars and clubs to make friends in at night. However this place was a bit too crowded with package tourists for me. So I only spent one night here and headed back over to Havana to spend my last day with friends.

Day 16: Havana Bye-Bye

Spend your last day before your flight back where you started. Visit whatever you haven’t been able to do the first time around. If you are a beach person, stay a day extra in Varadero. Just make sure to take enough margin when you book a colectivo to the Havana Airport. You never know when that duct tape will fail. Go bar hopping for cheap mojitos in the cozy streets of Habana Vieja.

Full Itinerary Map

Below you will find a detailed Google Custom Map of my Cuba Two Week Itinerary. This not only marks the destinations I’ve visited but also all the places I’ve visited. I have marked down restaurants I liked, places I’ve stayed and route I took.