Traveling to Cuba Alone: Travel Bloggers Experiences

  >  Cities   >  Traveling to Cuba Alone: Travel Bloggers Experiences
Since Cuba is becoming a popular destination, we asked different travel bloggers about their experience in the island.

If there’s a place that is getting the curiosity of almost every traveler around the world is definitely Cuba. Being from Puerto Rico, and out of my curiosity (and since I am totally dying to go soon!) I decided to ask some fellow travel bloggers about their experiences visiting the island and this is what they had to say. This is a summary of their experiences and why you should consider traveling to Cuba alone.

Since Cuba is becoming a popular destination, we asked different travel bloggers about their experience in the island.

Traveling to Cuba alone: Janine – Fill My Passport

Cuba - + Fill My Passport

Vintage Cars in Cuba

When many think of a vacation in Cuba, automatically vintage cars, aged rum, and cigars come to mind. I knew the first time I traveled here that I would get my fill of the notorious rum drinks, eat delicious Cuban cuisine, and grab selfie upon selfie beside 50’s vintage Pontiacs. A novel destination with unique qualities and untold stories…I asked myself the second time around – “would this be an ideal honeymoon destination? I have already drunk the rum, explored Havana, and paid tribute to Desi Arnaz. And also traveling to Cuba alone would be a great option. Then, I discovered landmarks and brought home the souvenir magnet. I thought I had experienced everything Cuba was known for and had to offer.  But Cayo Santa Maria was different.

Traveling to Cuba alone: Cayo Santa María – Cuba’s luxury side!

An island accessible only by one road across the sea, this beautiful region of the country brings travelers the taste of sea salt as they bask in the sun, sipping Pina Coladas, and eat delicious local cuisines till their hearts’ (or stomachs’) content.

Cayo santa maria beach - Cuba - + Fill My Passport

Cayo Santa Maria Beach

This secluded area of Cuba is strictly for travelers and tourists. Locals are restricted at the entry gate unless they can prove employment at one of the luxury resorts on the island. The area screams luxury for couples and families wishing for a trip of sheer relaxation and romance, unplugged from technology and stress. Also, consider it if you are traveling to Cuba alone.

Cayo santa maria beach - Cuba - + Fill My Passport

One of the resorts I highly recommend is the Royalton– a couples-only five-star resort with all the amenities and perks you could want.  Enjoy a private beach, nightly entertainment, three restaurants, and swim-up bars with unlimited cocktails and wine. This paradise is perfect for the tired traveler traveling to Cuba alone, the newlywed couple, or that golden anniversary’s highly deserved celebration. Interested in seeing the traditional Cuban highlights too? No problem! The resort offers guided excursions via bus and plane to Havana and also to explore Trinidad.

Traveling to Cuba alone: Daniela – The Lost Romanian


Havana, Cuba - + The Lost Romanian

I went to Cuba last year, for one week. It seems like a short time, but it didn’t feel like it. I went for a few days to Havana. It looks lovely, with colorful cars and buildings and cheerful locals. There is a nice promenade and live music in Old Havana. I stayed at a casa particular (local host). It was very interesting to get to know the local lady and learn more about what locals think and do.

Speaking at least a bit of Spanish can make things easier. I would say the downside is the catcalling. It’s quite annoying for a solo female traveler traveling to Cuba alone. And the internet has very limited coverage, it’s expensive and extremely slow.


Viñales - Cuban lady rolling tobacco - + The Lost Romanian

Viñales – Cuban lady rolling tobacco

Then I went to Viñales, about 2-3h from Havana. It’s a small village, but quite touristy. I joined walking trips in the area, so I went to a tobacco farm, a cave, and a viewpoint, and ate mangos on the way. On one of the nights, there was a blackout. This allowed a stunning starred sky to shine, one of the best I’ve seen while traveling to Cuba alone.

Traveling to Cuba alone: Varadero

Varadero, Cuba - + The Lost Romanian


The last stop was Varadero, for (almost) two days. It was just for relaxing and tanning. The beach is great, but the area is quite boring in my view. For transportation, I took taxis colectivos (shared taxis) between cities. They take you from any point A and leave you to any point B, at any time. They are super flexible and easily make arrangements, just ask your host. Cuban people pride themselves on how welcoming and safe their country is, which is both true. And they are very reliable and pleasant. Traveling to Cuba alone is great, for the history, for the places, for the people and … for the rum! 🙂

Traveling to Cuba alone: Linda – Indie Travel Podcast

Cuba - + Indie Travel Podcast

Hola? – I shouted into the phone. It was a terrible connection.
Si? – came the reply.

With a bit of repetition, I managed to communicate that I was coming to Cuba in three weeks, that I’d been given this number by someone, and that I wanted to book rooms for five people.

Si, está bien.

I repeated the dates, asked the price and address, was assured that it was all successfully booked, and hung up the phone. After years of booking all my accommodation online, it felt strange to do it by phone, like I was missing a step.

My worries were unfounded. We arrived in Havana traveling to Cuba alone, caught a taxi to the address I’d carefully written down, and were welcomed into the house by Arsenio and his adult son — who just happened to be a Cuban pop star. (True story.)

Traveling to Cuba alone: The Casa Particular experience

It was our first experience of a casa particular, but by no means the last. In fact, we stayed at casas particulares every night of our stay in Cuba, and in my opinion it’s the only accommodation option that makes sense. 

Throughout the country, local people can make money by renting out rooms in their houses. They almost always have a double bed and a single, so are great for couples or two or three friends traveling together — especially because the price is per room, not per person. When we were there, we paid around $25 per night per room; up to $35 seemed to be an acceptable price. 

There are hotels in Cuba, but those that can be booked online are ridiculously overpriced. Much better to get into the casa particular system and let it look after you.  And it really does look after you: when we told Arsenio our next destination, he called acquaintances there to secure rooms for us. They in turn found us a place to stay in the next city, and so on. Back in Havana for our last night, we were once again in Arsenio’s house — a full circle. 

Each house is a private home, so facilities vary. Most offer breakfast for an extra charge; some also provide dinner or lunch. It’s worth taking advantage of the dinner option at least a couple of times during your stay, to try real local food; plus it may create an opportunity to spend time with your hosts and get to know them a little. 

If you don’t get given a phone number for a casa particular by a random acquaintance, head to to find your first place to stay and start traveling alone in Cuba. Then, let the network look after you! 

Traveling to Cuba alone: Joanna – The World In My Pocket

Cuba - +

Cuba left a very big print on my soul and once again, I left a little bit of me there. I didn’t know what to expect traveling to Cuba alone before I landed on the small island bordering the Caribbean Sea. After a 48-hour commute, from Europe, changing 4 planes, being denied boarding because of overbooking, and with my luggage lost, I remember stepping out of Havana airport at midnight, in chaos. The arrival hall was full of taxi drivers and it was so difficult to spot my transfer (who had my name spelled wrong on his paper). It was too hot and humid and I was wearing my winter clothes, the only ones I had left.

Traveling to Cuba alone: The Real Cuba

But then, the next day, something incredible happened. I got to experience Cuban hospitality and get invited to a local’s home for coffee. He wouldn’t speak a word of English, I would speak in Italian and we still got along. We met randomly, at the shop, when he advised me to buy water from a cheaper place. And then, in the evening, I met him again in another part of the city, waiting for his bus home. He took it as faith and invited me for coffee. And for the next couple of days he showed me his real Havana, invited me to his sister’s house, and took me to the local neighborhoods of the city.

I spent two weeks in Cuba, traveling to different cities but also visiting touristy Varadero and I loved every bit of it. Everywhere I met great people and got the unique chance to experience the real Cuba, through the locals. It’s astonishing how big the gap between our and their way of life is. Cuba has however its charm and I know that it will lose it soon, with the afflux of tourists it is experiencing at the moment. For me, traveling to Cuba alone was a small paradise.

Traveling to Cuba alone: Wendy – World Wide Wendy

Plaza de la Revolución - + World Wide Wendy

Plaza de la Revolución

It is a beautiful city with majestic buildings, large squares, cozy narrow streets, and lots of pastel-colored houses, that’s Havana. Unfortunately, large parts are in terrible condition. People die regularly from collapsing houses. If you try to imagine what it looks like when everything is restored, you know that Havana can compete with cities such as Paris, London, or Rome. The city breathes history. The state for now owns almost everything. Things will change now since they lifted the embargo. Hopefully (foreign) investors will see the potential of this fantastic city and restore it in all its glory. If they still can keep its authenticity, that would be totally awesome.

Traveling to Cuba alone: Explore Old Havana

Habana Vieja or Old Havana is the most interesting part of the city. The historic city center is UNESCO world heritage since 1982. The city was neglected (not taken care of) for centuries, but the restoration works are ongoing.

Some highlights:

Plaza de la Catedral: one of the main attractions of Cuba. The highlight is the Catedral de San Cristobal, according to many the most beautiful cathedral in Latin America.  The plaza is surrounded by palaces from the 18th century. Look for the video that I made on the spot and it looks like you’re standing on the square with me.

La Bodeguita del Medio - + World Wide Wendy

La Bodeguita del Medio

Bodeguita del Medio:  one of the side streets of the Plaza de la Catedral (Calle Empedrado) leads you to Bodeguita del Medio. Halfway (del medio) this street a grocery store opened its doors in 1942. Later, the store expanded with a bar where the local politicians, intellectuals and artists came to drink their rum or cocktail. Obviously, Hemingway was a regular customer here.

Convento de Santa Clara:  Founded in 1664, this gigantic monastery accommodated the city’s poor girls. The austere exterior would stand in contrast to the beautiful inside. Again, however, we faced a closed door because of restorations.

Convento de Belen: restoration works are ongoing. The workmen allowed us to take a peak? and it already looks beautiful. According to their information works should have been finished (April 2017) . If you’re in Havana, please take a look and let me know if a Cuban month lasts as long as ours.

Calle Obispo: This is one of the most lively and characteristic streets of Havana, between the Plaza de Armas and Avenida de Belgica. They restored most buildings in this street. Especially the old pharmacy is worth visiting.

Plaza de Armas: here you find yourself several centuries back in time. On the square, you can find many artists selling their paintings and books about Havana.  The wonderful Palacio de los Capitanes Generales was built at the end of the 18th century for the Governor. It served as a chapter house and later as a prison. Today it is a museum.

Need more Havana tips? Check this guide!

To explore the old town you can rent a riskja. A bit sorry for those poor cyclists? Take a coco taxi. These funny yellow scooters are everywhere in the city.

It took us one day to visit Old Havana.

– Check Wendy’s articles on Havana, Viñales and Trinidad

Need more tips to plan your trip to Cuba? Check Rebecca’s tips!

Liked this post? Don’t forget to Pin it!

Since Cuba is becoming a popular destination, we asked different travel bloggers about their experience in the island and why you should consider traveling to Cuba alone.

Brenda: + 34 years old + Puerto Rican + Viajera Boricua + Master in Cultural Tourism + Foreign Language Major + Hispanic Studies Minor + Portuguese + Italian + Russian + Literature Freak + ♥’s Indie Music + Volleyball Enthusiast + Tricolor do Morumbi(SPFC) + San Antonio Spurs +


  • July 29, 2017

    Great post! I’ve always wanted to visit Cuba, but I’m not sure that I’ll ever get there.

  • October 10, 2019

    I would love to visit Cuba! Looks like an amazing country!

  • Cornell

    March 28, 2020

    I know this site presents quality based articles and additional information, is there any other
    web site which provides these kinds of information in quality?


post a comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Que Ver en Belgrado, Serbia Mejores Hoteles en Punta Cana Festivales de Verano en Cataluña Películas para viajar por Puerto Rico