What is Waiting beyond Havana? The Ultimate Cuban Road Trip

Revolutionary propaganda murals remain un-scrubbed from crumbling colonial buildings. Vintage cars bellow as they make their way down dirty alleyways. Dive bars reek of rum and the sweat of salsa- dancing aficionados. The flare of Cuba will undeniably fill your senses, but a trip here can mean much, much more to those who look deeper.

Yes, Havana is a mid-century jewel beckoning to be explored, but the real flare of Cuba is beyond the time-warped colonial core of Habana Vieja, past the salty breeze of the Malecón, and further out than the golden sands of Canadian-filled Varadero. Cuba’s zest is dotted across the island – where verdant jungles meet limestone ‘mogotes’, before cascading into waterfalls; where tiny towns, with their own cultural flavors, are as varied as each of their winding, cobblestone streets; and where a new friend is waiting for you at each home-stay along your journey. The quintessential, yet unexpected Cuban experience is possible…on a road trip that spans the entire length of the country. Let’s take a look at the route that has something for all of your senses. And just like all good road trips, leaves room for spontaneity to turn down the road less-traveled where adventure may be hiding.

The Map:

To help you on your journey, there is a special Google map that accompanies this suggested 14-day route, with stops and driving directions included! It can be saved to Google My Maps for use on your trip.

The Accommodations:

The best way to immerse in the local culture is to stay in a “casa particular.” These are actually private homes offering guestrooms, where you can get friendly with their local owners. They are very likely to give you tips for your cross-country adventure! There are just two places on this route where I suggest staying in a resort or villa to truly experience the location the way it is meant to be enjoyed. The rest of the time, staying with locals will enrich your trip! It’s much more authentic and personable than staying in a touristy hotel.

The Journey:

Day 1 and 2

Arrive to Havana
This enchanting and compelling city is your home for the next two days. Its eclectic neighborhoods are a kaleidoscope of architecture and local flavor, with each district nodding to a different era of the city’s revolution. Most tourists are confined to the historic harbor side of Habana Vieja known as “Old Havana.” But, be sure to venture beyond this district as well. Gritty Centro Habana is home to the seaside Malecón. This oceanfront promenade leads to Vedado where there are an abundance of cabarets, cinemas and night clubs. It is also here where the dominating Plaza de la Revolución can be found. Lesser known Miramar mirrors 1950’s Miami with posh restaurants and music venues along lush, tree-lined avenues.

Suggested casa particular: Casa Ana y Surama
Located in Habana Vieja, this colonial gem was built in 1925. Its eclectic interior further adds to the charm of your stay in Havana.

Day 3 and 4

Drive to Valle de Viñales (distance: 2 to 3 hours)
In early afternoon, pick up your rental car in Havana to begin your cross-country road trip! Head southwest from the city toward Valle de Viñales – Cuba’s natural gem that was added to the UNESCO World Heritage List in 1999. Its jagged karst formations with steep edges slope down into the lush valleys below, where tobacco, taro and banana plantations lie. A fun activity for your first night in the small town of Viñales is to enjoy a local baseball game if the home team is in town.

The next morning, head out for a trek in the San Vincente area of the park.  Visit local tobacco farms and venture underground to Cueva del Indio, an underground river that can be navigated through by small dingy. Guides are suggested to make the best use of your time. You can easily arrange someone from your casa particular.

Suggested casa particular: Casa Ridel y Claribel
Hosts Ridel and Claribel have blown up trip advisor with great reviews because of their warm hospitality and great food! Stay with them to join their fan club!

Day 5

Drive to Matanzas (distance: 3 hours)
Bid farewell to your hosts in Viñales and journey on to Matanzas. Its hey-day may be over, but its former glory still shines through its colonial architecture. The Teatro Sauto, dating back to 1863, once hosted icons like the Russian dancer Anna Pavlova. Stroll to the 19th-century Museo Farmaceútico, still immaculately preserved with an eclectic mix of artifacts. Before you continue your drive, summit the hill in the center of town to Iglesia de Monserrate for dramatic views of the nearby valley.

Short detour to Cuevas de Bellemar (distance: 15 minutes)
Perhaps more stunning than its Viñales version, Cuevas de Bellemar offers hundreds of meters of awe-inspiring passageways below the earth. If you reach Cueva Saturno, you can swim or snorkel beside stalagmites and stalactites in turquoise waters.

Overnight near Varadero Beach Resort Area (distance: 30-45 minutes)
Now that you are soaked from your underground swimming session, make the short drive to the resort area of Varadero for a shower and some dinner.

Suggested casa particular: Surprise! Splurge for 2 nights and stay at a beach side resort
Only in Varadero would I recommend a resort hotel. When in Rome, right? It’s a nice way to spice up your trip and splurge on a hotel with pools and amenities right on the ocean. After all, you have a long journey ahead! I like cuba-junky.com for searching through options.

Day 6 and 7

Drive to San Miguel de los Banos (distance: 1 hour)
In the early 1900’s this town flourished as a luxurious spa town. Glamorous villas and hotels sprouted up including a replica of the Grand Casino in Monte Carlo! In the 1950’s, contamination from a nearby sugar mill brought this town to its demise. It now makes the perfect places to wander the ruined buildings through its Grand Hotel and Romanesque bath houses from its former life.

Continue to Cienfuegos (distance: 2 hours)
This waterfront community is known as the “Pearl of the South” and for good reason; it has a surprisingly elegant feeling with colorful architecture lining the sweeping bay. Stroll the Prado in the afternoon and don’t miss the Tomás Terry Theatre. Several good restaurants are available for a seafood lunch.

Continue to Trinidad (distance: 1.5 hours)
Trinidad is your final destination of the day – and as soon as you arrive, you will know why.  It’s a photographer’s dream! In fact, the entire next day is left free for you to enjoy this vivacious village. Visit the cobblestoned UNESCO city center, where music can be heard on every corner; hike in the Escambray Mountains, or take a dip in the blue sea off Playa Ancon. Once the sun sets, dance into the night at one of its several live music venues.

Suggested casa particular: Casa el Tulipan
Cuba-junky gives this home an “awesome sauce” certificate of excellence (whatever that means). I do have to say that their rooftop terrace is dreamy! It has loads of character and the hosts are there to cook scrumptious food and arrange fun activities for you, like salsa dancing lessons!

Day 8

Drive to Camagüey (distance: 3.5 to 4 hours)
Head out early this morning to make it to your next stop by lunch time. Coined “The City of Legends”, Camagüey for me is better known as the “Venice of Cuba” because of its winding streets. You are sure to get lost while trying to navigate its labyrinth of roads, but that’s part of the fun. Within the cobblestoned maze are handsome parks, crumbling churches and lively squares appearing with every unexpected turn. If you are traveling in June – Carnival here is a huge occasion not to be missed.

Suggested casa particular: Casa Caridad
The hosts of this casa are quite famous on trip advisor, making them the #1 guest house in the city.

Day 9

Drive to Pinares de Mayarí (distance: 4 hours)
Heading into the Northern Oriente, the earth rises up to form the emerald Sierra de Cristal mountains in Parque Nacional La Mensura. Very few tourists make it this far because of the condition of the roads, but the final destination at the isolated forests of Pinares de Mayarí is a fine prize for your efforts. Drive slow and carefully up the steep roads toward the little town of Mayarí, enjoying the crisp views of the bay and plentiful coffee plantations. Villa Pinares de Mayarí makes an excellent base from which to explore the forests, lake and pre-Columbian caves in the lush landscapes of this alpine region.

Suggested hotel: Villa Pinares de Mayarí
This hidden oasis is a locally-run property features 29 wooden cabins set on a small serene lake. The rustic, but well equipped rooms offer the perfect atmosphere for your mountain escape.

Day 10 and 11

Drive to Baracoa (distance: 2.5 hours)
Spend the morning enjoying La Mensura from the Villa. Then at your leisure, head a few hours east to the tip of Cuba’s coast.

Surrounded by an arc of mountains, Baracoa is the secret hiding place for many who say, “It’s the most beautiful place in Cuba.” Its seclusion has protected it from the negative effects of tourism, but its vibrant culture and gorgeous setting are sure to put it on the travelers’ circuit very soon. Spend today and the next, just wandering around the quaint streets. Everything is easily accessible from Parque Independencia. Watch locals gather around wooden tables playing pick-up games of dominoes, or head to the river to witness the women’s age-old laundry techniques.The countryside is a must here – explore its swimmable river systems studded with waterfalls, and visit Duaba Farm to see how chocolate is produced before a local lunch.

Suggested casa particular: Casa Colonial Gustavo Yalina
Centrally located, this casa has been in the family for generations, but has recently been renovated.  It’s a long time favorite for many travelers… who are raving online about the food long after they have returned from Cuba!

Day 12 and 13

 Drive to Santiago de Cuba (distance 3.5 hours)
Today marks the last leg of your cross-country road trip.  As you round the Oriente of Cuba you will have transversed over 960 miles of varied terrain and towns, but the people you have met along the way are surely the biggest highlight of your Cuban sojourn. Before you turn in your keys, celebrate your last few days in Santiago de Cuba – a fitting end to your journey. The town draws visitors from all over who come for its unique flavor. It is often noted as Cuba’s liveliest cultural city; so it’s no surprise that the city boasts the largest Afro-Cuban population and a prominent Afro-Caribbean vibe. Make sure to check out the music scene at Cabaret Tropicana Santiago or the Afro-cuban Ballet Folkorico Cutumba.

With two full days in the city, you might want to venture to the nearby Sierra Maestra Mountains to trek past the hidden bases of Revolutionary rebels that still remain. Other unique places are the fortress of San Pedro de la Roca del Morro and the ruins of French coffee plantations in the mountains east of the city.

Suggested casa particular: Hostal Raul y Cathy
Located in the heart of Santiago de Cuba, close to Plaza de Marte and Park Cespedes, this casa has cute wall art and a roof top terrace. Loads of character!

Day 14

Fly from Santiago or return to Havana for the trip home!


The Wheels:

Before embarking on your road trip you need to decide what your mode of transport will be. There are really 2 options for you: a rental car or using the government run Viazul bus (Cuba’s Greyhound). There are pros and cons to both. Of course a self-driven trip in a rental car will have more room for impromptu stops and a leisurely pace, but you will also need a confident driver to navigate the roadways. In general though, the island’s roads are not known to be too treacherous for travelers, just don’t drive at night.

Alternatively, a Viazul bus trip will be dependent on bus timetables and will leave less room for spontaneity. But, the local friends you could meet onboard will certainly add a layer to the adventure.

The main difference however is the price. Rental cars in Cuba are quite expensive at around $50 a day. There are several rental car agencies, which are in affect all government run. Some popular ones are Transtur/Cubacar, Via Rent a Car and Rex.

For this two week trip across the entire country, I suggest picking up your rental car at your starting point of Havana and dropping it off upon reaching your final destination, Santiago de Cuba. Depending on your flight schedule, you can either catch a 1.5-hour flight back to Havana or fly onward from there.



Feature Photo Credit: Thinkstock/istock/ Pedro Antonio Salaverría Calahorra


13 thoughts on “What is Waiting beyond Havana? The Ultimate Cuban Road Trip

  1. Hi Kari,

    Thinking of doing a small road trip through Cuba as well and have a trip booked for 2 weeks. Would you happen to know if there are scooter or motorbikes available for rentals in the country instead of doing a car road trip? Thank you!

    1. Hi Vivian,

      Congrats on your upcoming road trip! Please do check back in with our community once you return – we would love to hear how it went and hear your suggestions for the rest of us! I do not personally know of a specific scooter or motorbike rental place. But, once you arrive into the country you should be able to ask about this at the front desk of hotels in Havana. I always recommend reception desks and concierge desk for these types of questions. Don’t tell them you are not a hotel guest – just walk up and ask your question:)

      Enjoy your trip!

  2. Hi Kari,

    Is it safe to do the road trip alone? I mean I know Cuba is the safest. But would I be able to handel driving through thr country by myself? Thanks

    1. Hi Marina,

      Driving in Cuba is safe, but the roads are not the best of quality. I would suggest driving only in daylight and getting to your destination each night at a reasonable hour.

      Enjoy your trip!

  3. Awesome guide! I’m considering whether to rent a car in Havana, and instead of flying back to Havana from Santiago, drive to Santiago/Baracoa and then drive all the way back to Havana. Maybe focus on the southern coast on the way down, and the northern coast on the way back to Havana. What do you think? It would be a 14-15 day trip. Too much driving? I have a pretty high tolerance for drive time, but I don’t want to always be in the car.

    1. Hi Beau!

      congrats on your upcoming trip! I think your idea sounds great, especially if you have 15 days to do it. When do you leave? I would love to feature your adventure on the GC blog when you return. Email me at kari(at)globalcommute.com if you are interested!

  4. Hi Karie

    Thanks for the fabulous, informative guide!

    Do you know whether it is relatively easy to self drive in Cuba? Navigation, quality of the roads, etc. We are left side of the road drivers whereas Cuba is apparently right which obviously makes it a little tricky to begin with.

    Thanks so much!

    1. Hi Amy,

      Driving through Cuba is a fantastic way to see the country, but I wouldn’t categorize it as easy. The roads are not in good quality. If you decide to do a self-drive, I would be conservative with your itinerary – leaving time each day to “get lost” and to end the day before night fall. It’s definitely possible though if you are on the adventurous side. Otherwise, you could work with a company to design a program for you like http://locallysourcedcuba.com/

  5. Hi! thanks for the nice post! Do you know if cars are available with automatic transmission? Is it really 50 dollars per day because when I try to book one online it goes up to between 500 and 800 dollars for a week, which is ridiculous! Would it be better to book my car once I’m in Cuba? Which company?! I land in Holguin and leave from Varadero! Thanks!

    1. Hi Marie,

      Thanks for reaching out and congrats on your trip to Cuba! It all depends on when you are going and what the availability is. I would recommend booking in advance if you are going during high season, but of course when you wait until you arrive – the deals are better. It’s a gamble though right now because availability is low. This link will help you find a company for rentals at Holguin Airport: http://holguin.airportcuba.net/transportation.html. All the car rental companies you find there, will also be in Havana.

      Best of luck!

  6. Hey, Thanks for the really nice sum up and wonderful pictures. Me and my friends are curently also planning visit to Cuba and right now are looking for some tips for acoomodation in Havana. Your suggestion – Ana y Surama sounds great! Could you only let me know how much was it for a night? Thank you! Božena

    1. Hi Božena!

      I am so glad you found the guide helpful! I am sure you and your friends will have a great time in Cuba! Earlier this year, rates were around 35 CUC per night, but I would reach out to Ana and Surama directly to ask based on your dates. Good luck with your adventure! Where are you guys planning on going?

      Talk to you soon!


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