Women Who Travel Solo: Solo Travel in Cuba With Jessica Hill

women who travel solo Jessica Hill


With diplomatic relations between the United States and Cuba, American citizens will soon be able to legally visit Cuba for the first time in decades. Jessica Hill discusses her experiences with solo travel in Cuba on her recent visit in this week’s Women Who Travel Solo.

How did you get started traveling?

I always have a hard time with this question because I’m not sure if there was one thing that started my travel addiction. When I was 18, I moved from a tiny farm town of 700 people to Los Angeles, where I had an interesting introduction to culture shock. I guess that might have been the catalyst to my adventures because I fell in love with how in L.A. I could feel one vibe one minute, and the total opposite the next.

Solo travel in Cuba is safe and rewarding!

Why did you decide to travel to Cuba alone?

I enjoy traveling solo for several reasons, but one is because it allows me to completely soak in a destination. Alone, I’m more approachable and therefore I easily befriend locals, which allows me to fully immerse myself in the culture. I also love that traveling alone gives me the freedom to be in solitude when I want to be, and to meet other travelers easily when I’m in the mood for that.

Solo travel in Cuba is safe and rewarding!

Tell us about your experience with solo travel in Cuba.

Cuba was utterly fascinating, and utterly exhausting. I spent 18 months in Asia traveling solo, India included, and Cuba was nearly as exhausting with the constant want of the locals. There isn’t begging, per say, but everyone is trying to sell you something.

What recommendations do you have for solo travelers in Cuba?

Definitely go to Baracoa! It was by far my favorite destination because of it’s laid back charm and the variety of things to do. It’s right on the coast, with a gorgeous black beach, and it’s surrounded by mountains, national parks, hidden beaches and caves.

You’ll never have a difficult time finding a place to sleep, as almost every local rents out a room in their house. They’re called casa particulares, and they operate much like a bed and breakfast. They’re safe, convenient and provide a great glimpse into the local culture.

The food gets old, really quickly. It’s bland, since Cuba hasn’t been able to import spices or anything else for that matter. Note that fast food prices (like pizza and sandwiches) are almost always in local currency, not foreign currency (CUC), but nobody will tell you that. You just have to give them the local stuff.

Also know that in Cuba, if a local invites you to do anything (coffee, beer, dancing, etc.) you’ll be expected to pay for everyone involved.

Solo travel in Cuba is safe and rewarding!

What was the best part of your solo trip to Cuba?

I was in Cuba in June/July, when temperatures were 100 plus humidity, so much of my trip was spent chasing water. There were beautiful beaches all around, but those near Baracoa are memorable. There, I also swam in a natural cave pool (so refreshing!) and relaxed in a shallow (and gorgeous) river after an intense trek up Yunque mountain. All were spectacular!

What was the worst part of the trip?

Not only was I a solo female traveler, but I’m American. And I was in Cuba illegally, at the time. This meant that I couldn’t access my money from ATMs or banks on the island, and it’s still this way, as far as I know. So, I had to take enough to last me for what I hoped would be five weeks. But since traveling alone is much more expensive than traveling in a group, I ran out of money before I was ready and had to fly back early. I could have been a better planner, yes, but the constant stress of running out of money placed a whole new element of worry on me.

Solo travel in Cuba is safe and rewarding!

What are the safety concerns for women traveling alone to Cuba?

Cuba is a relatively safe destination. There is almost no theft and no crime. The only concern is that the men are very persistent and forward, so be prepared to handle that. They are mostly harmless, though.

 What advice do you have for female solo travelers?

Be smart, always pay attention to your surroundings, and listen to your intuition. Trusting your gut is the most valuable decision maker you have when you’re on the road alone alone.

Just go. Don’t let all the fears get to you. Conquering our fears is what makes us feel alive, and it is the most rewarding challenge in life.

Solo Travel in Cuba Malecon Watermark

About Jessica Hill

Jessica Hill

After teaching English and traveling around Asia for 18 months, Jessica started a TEFL agency, Teach English: ESL, where she recruits ESL teachers and sells TEFL certification courses in Thailand, Costa Rica, Nicaragua and the United States. The lifestyle allows her to continue her travel addiction while helping others begin theirs! Follow along on her adventures at Miss Adventure Travel.

Women Who Travel Solo

Women Who Travel Solo is a weekly column that shares the stories of women’s solo travel adventures in hopes of spreading the message that traveling alone is not only safe, but wildly rewarding. Inspire other women to travel solo by sharing your story with Something In Her Ramblings. Email Lauren at lsalisbury24@yahoo.com.

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This Post Has 15 Comments

  1. Jessica Hill

    Thanks so much for featuring me, Lauren! And for making me look like a badass. Ha. The interview looks great!

    1. Lauren

      Thanks so much for sharing your solo travel adventures in Cuba with us! You are very inspiring!

    1. Lauren

      Awesome! Cuba is a great place for solo travelers. I enjoyed my solo trip as well!

  2. Zoe Lucas

    Cuba is an amazing place to travel and explore. Being a solo traveler I myself had visited Cuba many times and in fact, by now I am almost a tour guide now. This article makes me remember those good old days! 🙂


    1. Lauren

      I agree! Cuba is an amazing destination for a solo traveler.

  3. Yajaira

    Thank you for sharing your experience. Would you go out at night? If so how was the night scene in Cuba?

    1. Lauren

      Yes you can definitely go out at night in Cuba. The night scene there is limited, however all of the major bars in Havana have bars and there’s a few watering holes in the old city as well. Definitely try Havana Club rum!

  4. Maureen Tucker

    Thanks for the info, l really fancy going to Cuba but being a solo female older traveller l needed some reassurance and you have helped me decide.

    1. Lauren

      That’s so great to hear. Cuba is a fabulous destination for female solo travelers.

    2. Kristina Smith

      Let me know if you’re looking for a travel partner Maureen! 🙂

  5. Ray

    You women have been an inspiration to me. I am gong to Cuba in one week. I feel more self assured, thank you. My male “ego” was wavering, I needed a boost as a solo traveler.

    1. Lauren

      I’m so glad to hear that, Ray! Have a great trip.

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