How to Backpack Cuba in 16 Days

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Ahhhh Cuba… sweet rum, delicious cigars, and too many pearly white beaches to count! There are so many reasons to backpack Cuba.

Aside from the obvious appeal of paradise, Cuba is an incredibly interesting travel destination. You can feel the 1940’s in the air and the spirit of the people bring to life a vibrant culture that’s intoxicating.

Alizé was one of the many friendly, and fun Cubans we met along the way. He showed us his favourite jazz bar, and a great local restaurant served out of the owners home!

…or maybe that’s just more of the cigar smoke!

Well lucky for you wandering soul because this island is easily visited in two weeks! In April of 2016, Jordan and I backpacked the country head to toe for around 16 days and had the time of our lives!

There are tons of buses and collective taxis available that will take you all over the island and makes travel really easy. The route we took helped us to see the true colours of Cuba, and experience everything the beautiful country has to offer. So if you are looking for an interesting getaway and can spare a couple of weeks in your calendar, this Cuba travel itinerary is exactly what you are looking for!


Let’s talk numbers for a second. First off, Cuba is an incredibly affordable destination and you can get by comfortably on $60CAD a day (the Cuban Peso for foreigners, CUC, is the same value as the USD). Our whole trip cost us about $1600CAD, which was a little bit more than we planned but that was thanks to some expensive excursions (catamarans and private islands? why not spoil yourself atleast once!).

Fun tip! If you are able to get your hands on some of the local Cuban pesos, the CUP, you can pay for goods such as market groceries, food items from stalls, and other small goodies for LITERALLY pennies! Try not to get confused between the two currencies.

Remember that sharing is caring! The most inexpensive way to travel Cuba, or even tour around nearby sites, is to hire a shared taxi with some friends. Negotiate a fair price that makes everyone happy and enjoy the hassle-free adventure.

Day 1: Varadero

Varadero is mainly a beach resort destination, and is great if you are looking for an all-inclusive resort, but to be honest, we only flew into Varadero because of the large number of resort-goers and vacation deals help to lower the price of our flights!

We didn’t stay too long in Varadero because we were anxious to get exploring Havana, the country’s capital city! The best way to get there is to track down a bus at the exit of the airport and grab a ticket for around $15.

ALTERNATIVE: Jordan and I decided to take the scenic route to Havana by stopping through the the nearby town of Mantanzas! All you have to do is wave down a taxi and you’re on your way! From there you can take the Hersey Train to Havana, an old sugar line that transported workers along northern Cuba. For roughly $2 you get an incredibly scenic ride! It takes a bit of luck though because the trains times are infrequent and unpredictable. We suggest you try!!

Days 2-4: Havana

Wander the streets of Havana

We could wander the colourful streets of Havana all day long.

Take your time and soak it all in. Havana offers an energy like no other, and it really hits you when you see your first antique American car. Wandering the streets of Centro Habana, Habana Vieja (Old Town), and the Vedado neighbourhoods could keep you occupied alone. We spent most of our time in the crumbling central district, and I say that is the best way to do it. This unique neighbourhood captures the bustling energy of Havana. Heck, we even caught a local bus to the beach one morning (and you will soon learn that wherever you go in Cuba you can find a beach to lounge on.)

NOTE: Be sure to stay in a local Casa Particular to get an authentic feel for the life of Habaneros and the best insider tips for fun and food throughout the city. Click Here to read about our incredible experience staying with local families

You could easily spend more than 3 days exploring the various museums (especially the revolutionary and Havana Club Rum museums), and hopping from restaurants to bars to dance clubs. Just ask any of the friendly locals or your homestay host and they will be able to point you the right way! By doing this we ended up in a hole-in-the-wall jazz club filled with locals dancing the night away.

Day 5: Viñales

A great escape from the excitement of the city is only two hours away. Viñales is a picturesque region decorated with fields of coffee plants lying the in the shadows of grand limestone scale cliffs. It is truly a sight to see!

Horseback riding through Vinales

A ride out into the valley is a must-do! Visit coffee fincas, tobacco farmers, and take some time to explore limestone caves in the hills!

Some of the best activities you can do here include horseback riding into the Viñales Valley national park. One trip will cover a whole afternoon as you visit local coffee and cigar fincas, as well as go spelunking through one of the many cave systems that run through the hillside. One moment we were tasting hand-rolled cigars, and the next we were chasing down runaway horses who had just broken out of their pen. And don’t forget to look around at the stunning scenery!

I cannot emphasize enough that this is a must-have experience in Cuba! There are some nearby tourist attractions that were lots of fun like the Cuevo de Los Indios if you have the time, but the peaceful town is a pleasant stroll in itself.

The main attractions of Viñales were easily covered in two days/one night. You could easily spend more time relaxing in the valley, but other adventures await.

Day 6-7: Santiago

This leg of the journey is where things got interesting. Santiago de Cuba is on the very southern tip of the island, and you need to cover some distance to get there. The best way to do this is to return to Havana and take an overnight bus.

The travel time is more than worth it. Santiago offers a totally new afro-Caribbean vibe you will not find anywhere else in the country. We wish we could have been here in July for the crazy Carnival festivities!

A walk down to the water will give you a good sense of the laid-back lifestyle of the city. But like I mentioned, the city lights up at night! Tons of Salsa and Bachata dancing is to be found, especially at Casa de la Trova.

We took some time to explore the historic fortress outside of town called El Morro to learn about the history of the port and pirates. We took a cab for the day, and asked our driver nicely to bring us to a secluded beach nearby for some sunbathing.

Catching some sun on a secluded beach. A quick drive out of town towards the El Morro castle, and relax with some cigars.

If you can, it is worthwhile to spend more time in Santiago! Enjoy the easy way of life, and hang around the many bars for as long as possible.

ALTERNATIVETrek through the Sierra Maestra National Park and follow in the footsteps of revolutionary leader Fidel Castro. From the town of Bayamo, northwest of Santiago, you can catch a taxi or tour into the park and make your way to the hideout of the rebellion that started it all.

Day 8-11: Baracoa

If you are looking for adventure, this is the real reason to travel the to south of Cuba! Chalk full of rushing rivers, waterfalls, and untamed jungle to be explored, Baracoa will keep you around much longer than expected. Even the crazy bus ride through the Oriente mountain range to get here is exhilarating.

Baracoa: Cuba's Jungle Paradise

The beautiful bay of Baracoa seen from the lookout at the anthropology museum.

The sleepy town of Baracoa is mostly cut off from the rest of the country, and is set in a gorgeous bay. There is no better place to feel like you are in the middle of nowhere. Or maybe the middle of paradise!

One of the most exciting excursions we did was the trek up to El Yunque, a tabletop mountain that overlooks the bay with an amazing panoramic view of the city. We also did a DIY adventure with some friends we met to the Rio Yumuri which was interesting to say the least. Sadly there is not much of a river in the dry season!


Baracoa is best described as the hidden gem of Cuba. It takes a lot of commitment to get here, but if you backpack Cuba it should not be missed!

Day 12: Holguin

Holguin was more of an unexpected stopover on our journey. The surprises it had in store made the trip even better!

After an off-roading taxi ride North from Baracoa to Moa then to Holguin, we made it to this pleasant city for a quick break. You can find Guardalavaca nearby if you are looking to spend the day on a beach resort like we were.

After getting a nice sunburn head back to town and catch the sunset on top of the Loma de la Cruz lookout situated over the city.

Day 13-15: Trinidad

We spent the final stretch of our trip in the beautiful colonial town of Trinidad. Cobblestone streets and pastel buildings are everywhere you go. All around the main square there are open-air bars where you can sip your favourite Cuban special be it the Cuba Libre or the world’s best mojitos.

Nearby is the fantastic Topes De Collantes National Park that is definitely worth a hike! We also stepped on the extravagant side and took a catamaran trip to a small island for a little tropical getaway and some snorkeling. We thought why not treat ourselves before the end of our trip?

Topes de Collantes National Park is BREATHTAKING

The BEAUTIFUL Topes De Collantes National Park is full of tropical wildlife, and pristine waterfalls that make for the best spots to cool off.

We danced our last night away in the one-of-a-kind cave nightclub called Disco Ayala. Who knew Cubans were such huge fans of Justin Bieber? Anyways, the good times went all night in this amazing bar literally built inside a cave!

Day 16: Varadero

We caught a collective taxi to Varadero in the morning of our final day in Cuba. The driver kindly dropped us off at the nearest public beach, and we spent our final hours relaxing by the ocean. A perfect way to finish our whirlwind trip through what is easily my favourite country I have visited; Cuba.

I have so many great memories of Cuba and the amazing people we met along the way. By the time I left the country, I realized that if we all adopted even just a fraction of the happy go-lucky vibes of the Cuban locals, it would make our world a little bit brighter!

Have any questions about my two week Cuba trip? How about any suggestions? Feel free to leave a message in the comments below!

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