One Week Road Trip through Cuba

Cuban Building

Here’s a suggested itinerary for a one-week road trip through Cuba. Traveling through this beautiful and mysterious country can seem intimidating, but I promise, it is not as difficult as it seems. Cuba is a country of deep pride; pride in self, pride in music, pride in dancing, and pride in their overall way of life.  There are many things changing for this country, but ‘being Cubano’ is not one of them. We hope our suggested itinerary works for you!

Preparation for your trip through Cuba?

We Are Travel Girls has published two excellent guides to understanding visas, money, exchange rates, immigration, etc. Visit ‘13 Things to Know Before you Travel to Cuba‘ and ‘Tips for Traveling to Cuba as an American‘ to get an overview of what to expect.

In addition to the recommendations on the WATG blog, I would also suggest that you skip the checked bags as it can take up to 4 hours to get your luggage due to frequent brown-outs. Road trip through Cuba on your own, or go with a group – but packing light is always simpler.

The best part of Cuba, IMO

I think what was most striking on this road trip through Cuba was the warmth and sociability of the Cuban people. I guess this should not have surprised me all that much, as I have an old friend that is Cuban who took me in early on in my career and became my mentor, saving me from many newbie blunders. But I digress.

No matter what level of English Cuban folks knew, they wanted to strike up a conversation and would do so in creative ways, such as asking me the time, even though I clearly didn’t have a watch, or just coming up to me and asking where I’m from. The people expressed delight when I told them I’m from the United States. They would go on expressing their excitement and hope that both the US and Cuba could become friends.

If there is one thing that Cuba does well, it’s rice and beans; well, that and a stiff mojito. But, that suited me just fine since I’m a pretty picky eater and I don’t particularly like meat. And I really like a stiff drink.

The ‘Not so Easy’ Parts of Traveling through Cuba

A few things Cuba doesn’t do so well: roads, signs, maps, and directions, and GPS! Bear this in mind if you decide to rent a car as I did. In retrospect, maybe a hired driver for the road trip through Cuba would have been a better idea – but all’s well that ends well.

Thankfully, I had a stellar co-pilot to help navigate along the way. I spent time dodging people and horse carriages that were strewn across the road. Often, my rental car electricity died while in 2nd gear, effectively taking out the power steering and breaks.

There’s a phrase in Cuba that says everyone is ‘on Cubano time.’ So, as a person that’s career is literally all about making process and technology more efficient, I had to reset my expectations that any activity could take 10x the time or may not happen at all.

Also, you should have seen the faces of the locals as two women rolled into their town driving a stick shift…I’m pretty sure women do not drive regularly Cuba. There were offers of marriage, some falling to their knees and fake worshiping, and just a general jaw-dropping as we drove by.

Now onto what you should do should you find yourself wanting to explore more than just Havana…and I recommend that you do.

Getting Around on Your Trip through Cuba

As I mentioned, I rented a car to drive, but the flexibility comes at a price.  Rentals are quite pricey (ours was $400+ for a week), gas is expensive or relative to US prices, directions and street signs are scarce, roads can quickly become questionable, but you save on time.

A bus generally takes 2-3 more hours than a car but keep in mind that seats fill up fast and service can be variable. I talked to a few other travelers and they were able to hire a driver to get around Cuba. They said a trip from Havana to Trinidad was around $100. I think you could end up spending just as much as a rental but without the headache of driving yourself.

Road Trip through Cuba Itinerary


Once I landed in Havana, I picked up my rental car, which took about an hour, and drove to my Airbnb in Centro Havana. There isn’t reliable service, GPS, or roadsigns, so give yourself some time to read a map and get lost a bit. I was able to plug the destination into my downloaded map and follow the blue dot to arrive at the correct location (eventually).

Where to stay in Havana

I booked my first night at an Airbnb in a charming colonial house in Centro Havana. Later, I would find out that the house was chosen by ‘Vogue America’ among the 8 most ‘charming’ homes of Habana AND even Brian Chesky (founder of Airbnb) had visited. There were such beautiful touches around the entire place from beautiful fresh flowers in big vases, to the unique furnishings throughout. We ate fresh breakfast on the roof every morning and it was so delicious and a steal for the price. My favorite feature about this place was the rooftop tower that overlooked Habana and the Malecon.

My second night was spent at an Airbnb known as an artist and intellectual haven in Old Havana. The home is close to Plaza Veiju and all the great restaurants. The space is beautifully decorated with a number of birds (in cages) in the inner courtyard that makes the stay extremely charming.

Want $55 off your first Airbnb booking? Use this link to book to get your discount!

Green Vintage Car in Havana Cuba
Green Vintage Car in Havana Cuba

What to do in Havana

Day 1

I spent an entire day wandering the Malecon and getting lost in Centro Habana, and I have to say, it was my favorite day. Less touristy and a little gritty. There are plenty of little bars to hop in and out of, a lot of them without a proper name or on a map. I filled my day with tea, mojitos, and Hemingway’s “The Sun Also Rises.” The warm sea breeze and salty air were intoxicating. The day wouldn’t have been complete without ending it at El Floridita, Hemingway’s go-to place to quench his thirst. This is a must-visit destination for traveling through Cuba.

Day 2

On the second day of my Cuba trip, I ventured out to see more of Habana. Because Havana is quite spread out, I opted for the hop-on / hop-off Habana Bus Tour. Specifically, I wanted to see the Necrópolis Cristóbal Colón. This cemetery is hauntingly beautiful with Romanesque architecture. The bus also drops you at La Plaza de la Revolución where you can view the José Martí Memorial. You can’t possibly miss the two steel memorials of Che Guevara and Camilio Cienfuegos.

After being dropped off by the bus, the second half of my day was spent doing the normal touristy stuff in Old Habana. I wandered over to Hotel Inglaterra, sat down at the bar on the rooftop, and ordered (you guessed it) a mojito. After my refreshment, I spent some time at the Great Theater of Habana and the National Capitol Building. I then weaved my way through the old streets to land at Iglesia de Paula, a quaint and old Cathedral. The complexity between communism and religion is particularly interesting if you’re up for a history lesson. From there, I worked my way up to Plaza de Vieja, where you can see most of the old Habana buildings restored to their former glory. I ended my Habana history lesson at Castillo de la Real Fuerza, a harborside fort.

Havana Street
Havana Street
Day 3

On the third day, my friend joined me, and we went out of the city to Hemingway’s house. Truthfully, Hemingway’s work isn’t my favorite from the writers of that era. However, his estate is stunningly preserved and is known to be a haven for other artists.

Later that night, we went to the Tropicana Club. It’s quite expensive but the performance is iconic. You can save a few bucks by skipping the meal (it’s not worth it anyway). The show goes pretty late, so I recommend pairing it with a lighter day.

For some excellent Havana food recommendations, check out The Wayfaress’s suggestions.

Havana to Varadero

Day 4

Continuing our road trip through Cuba, on our way to Varadero, we stopped at Castillo San Severino Castle. This was quite atmospheric and made for some moody pictures while traveling through Cuba. The next pit stop was at Cuevas de Bellamar, an eerie (and extremely warm) cave with loads of stalactites and stalagmites and a swimming hole. FYI – both of these stops will charge you a small entry fee and camera fee.

Once you enter Varadero, sadly, you leave Cubano behind as the area is restricted to tourists, except for those who have special permission to work there. It’s pretty much a resort town. This is really unfortunate as there are excellent beaches there as well as Cueva de Ambrosio.

Varadero to Trinidad

Day 5

On our way down to Trinidad on the road trip, we stopped for lunch at Cienfuegos. Still, the real highlight of the trip was our arrival in Trinidad. I absolutely fell in love with this old colonial town.

Where to stay in Trinidad

We booked Casa Colonial Munoz through Airbnb.  Muñoz is a colonial house built in 1800 that has retained its original style and antique furniture. The Muñoz family also owns the restaurant Muñoz Tapas, located one block away. Guests can get a free welcome cocktail and a special discount on their meals. We opted for the homemade breakfast on the roof terrace with a magnificent view of Trinidad and surrounding mountains.

Horses in Trinidad
Horses in Trinidad

Julio, the homeowner, is a “horse whisperer”– sort of like Ceaser Milan but with horses. He offers horseback riding excursions to the mountain, valley, waterfalls, etc. Julio is also a professional documentary photographer and offers lectures and photography workshops. He’s basically an all-around Cuban renaissance man.

What to do in Trinidad

Day 6
Cuban Waterfall

Day 5 of the road trip we took an entire day to explore the Gran Parque Natural Topes de Collantes. Depending on where you enter the park, you find your way to two excellent waterfalls, El Cubano Natural Park or El Nicho, an excellent waterfall with chilling temperatures. The perfect dip after sweating through your hike.

Day 7
Cuban Beach
Cuban Beach

The next day, we relaxed at the beach as we were exhausted from all of the hiking the previous day. You will find that most of the beaches are empty but spectacular. All of the beaches are lovely but Playa Ancon is the fairest of them all.

Once we were back in the city, we pepped ourselves up with coffee at Cafe Don Pepe. That night, as we strolled the cobblestone streets as Cuban beats blasted from the bars. We had many offers from lively ladies to teach us how to dance Cubano style. Which, to me, this dancing was somehow an even sexier salsa. We got carried away and ended the night by dancing away at Casa de la Trova.

Day 8

On the last day of our Cuba road trip, we explored the city. Highlights to see are Convento de San Francisco de Asís, Museo Romántico, and Iglesia de la Santísima. Mid-afternoon we grabbed a delicious bite at La Botija. Then we hopped in our car to catch our flights to complete our travels through Cuba.

Restrictions on Cuba travel for US Citizens have been strengthened lately, and doing a road trip on your own now would be harder then it’s been in the past. However, another option for visiting Cuba – which includes not worrying about following all the rules while being there – is joining a group trip while there.

Jess Primavera

Jess Primavera

Jess is the CEO and Co-founder of Unbound. She is an entrepreneur, product builder, and world traveler.
You can follow along Jess' travels at @WanderlustPrima and her entrepreneurial journey @Jess.Primavera

There are group trips to Cuba available with Damesly, Legit Trips, and Heart of Travel on Unbound. Book your getaway today!
  1. Cuba With Damesly (women only) – Dec 2020
  2. Havana & Vinales with Legit Trips – Nov 2020
  3. Exploring the Past, Present, & Future with Heart of Travel – Nov 2020 & Dec 2020
Not sure if group travel is right for you, read our blogs
  1. Is Group Travel Right For You?
  2. What to Expect During Small Group Travel
And if you’re a host interested in joining Unbound, let us know here!


One Week Road Trip through Cuba

You'll also love...

Like this article? Share:

Share on facebook
on Facebook
Share on twitter
on Twitter
Share on linkedin
on Linkedin
Share on pinterest
on Pinterest

Leave a comment

Unbound App

Get Unbound Today!

  • Find the best hosted group trips 
  • Connect with experienced hosts
  • Book your dream adventure
  • All in one place!

Yes! I want to hear about Unbound.

We use cookies to improve your user experience. To find out more, read our privacy policy and our terms and conditions.