ViaHero Cuba: My real experience and review

ViaHero planned a 10-day Cuban vacation for my new fiance and I in November 2018.

Special concerns as a US citizen

As a travel blogger, I have always organized my adventures on my own. But, because I’m a US citizen, I was nervous. The more I researched, the more I worried about the technicalities—especially the many different visa types and their various requirements. After all, the “Cuban travel ban” only recently ended during the Obama era and the rules have changed a couple of times since then. The Secretary of State’s site listed Cuba as travel advisory Level 2: Exercise Increased Caution.

Discovering ViaHero

I stumbled across ViaHero’s website again and again as I looked for answers to my questions about traveling to Cuba from the USA. Finally, I got curious enough to click on the rates for having a Cuban local plan the whole thing for me.

For only $25 per day, ViaHero would provide me a custom itinerary that would both suit our interests. Plus it would be guaranteed to meet the American “Support for the Cuban People” visa type.

Ethan and I purchased planning services for our full one-and-a-half-week journey. After paying, we received an extensive survey to fill out with all kinds of questions about our travel styles and interests. 

First to final draft of ViaHero itinerary

We received several draft versions of our itinerary in the month before our vacation. Our “hero” (guide) made a rough outline and we were allowed to make suggestions from there. Honestly, she did a good job of understanding our tastes based on our survey input. We hardly had any changes, other than less eating out and more meals with our three amazing Airbnb hosts

We were the most impressed with our final itinerary. It was more detailed and helpful than we could have expected.

Legal guidelines

After the itinerary pages, there was even more helpful information. It included safety tips and info on common scams. Our hero also let us know how much rum and how many cigars (the answer is lots) we could bring back to the United States with us. Because of all the superstition and rumor surrounding Cuba, we had no idea we could bring those items back. We were glad for ViaHero’s guaranteed advice that we knew would follow legal guidelines.

Even though we had offline access through ViaHero’s app, we printed everything out in case we were ever asked to show it to Cuban or American authorities. Interestingly, no one asked once during our entire vacation, even upon entering or exiting Cuba or the United States.

Booking accommodations through Airbnb

The biggest and probably only real mishap was in booking our accommodations. Our guide suggested Airbnb stays for each leg of our journey. They were all perfect for us. Unfortunately, though, our hero had selected the wrong month and they were actually completely booked for our dates. We sifted through the listings ourselves and ended up with some great choices. Maybe they were even better for us than the ones she selected—who knows? The moral of the story, though, is that it all worked out in the end.

View the itinerary

Using our Hero’s itinerary

Nevertheless, traveling with a set itinerary was really useful. Cuba’s very limited internet access made this especially true. It was so helpful to have all the addresses and suggested modes of transportation written down. Better yet, we had both Spanish and English descriptions available to us in the itinerary. That way, we could show them to our drivers and hosts when we did not know enough Spanish to communicate. 

To be honest, I wasn’t really into the idea of having someone else plan my itinerary. For me, planning is part of the joy of traveling. But it was also amazing to have a taxi driver pick us up at the airport with a sign with my name on it (a first for me). 

Our hero truly gave us a well-rounded look at Cuban culture through her plans.Trips were well organized, especially since she arranged the transportation, and our days flowed nicely from one activity to the next. For example, she had us visit an artist collective’s shop, Clandestina, specializing in screenprinting. Then, later that night, she had us visit the Cuban Art Factory where their work was currently on display.

My ViaHero review: Criticisms

Because I promised an honest review in the title, I want to share a few negatives we experienced having our trip planned by ViaHero.

My biggest issue was the number of very touristy activities the ViaHero planner put on our itinerary. We ended up at multiple restaurants and tourist attractions that were clearly completely inauthentic. That was not what I indicated I wanted in my survey. At the same time, I understand that actual Cuban locals cannot afford to go out to eat very often and therefore there aren’t a lot of actual authentic restaurants. Looking back, I would choose home-cooked meals from the host every single day.

To ViaHero’s credit, you can always skip what’s on their itinerary and do what you like instead.

But I also want to note that these were small issues. And I am only speaking from my own experience. I truly believe that, if I were to book another trip with ViaHero, it would be completely different and maybe even better as they are a growing company. 

My ViaHero review: Positives

My partner and I only know a little Spanish, so I can say, with confidence, that having ViaHero build our itinerary saved us a lot of time and headache. Maybe we could have arranged the taxis and tours on our own, but I’m sure we would have had many more misunderstandings and probably would have gotten lost a lot more often.

Also important to note: Cuba has very limited internet access and therefore many places do not have websites. This was not the kind of vacation we could have planned in advance back home. 

Overall, my vacation would not have been a true vacation without ViaHero. It would have involved a whole lot of work. I’m glad that I decided to have a local plan our first trip to Cuba and I would definitely consider it if I were planning a visit to one of their other countries. 

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2 thoughts on “ViaHero Cuba: My real experience and review

  1. I’ve never used a blog before but want to use all your knowledge on my trip to Cuba july5 to July13-already booked. Whats the easiest way to get my tourist card?
    I’m a clinical therapist for older adults and want to research Cuban programs for seniors (I’m 72), son music, cigars and be near a beach for some soaking. snorkeling would be a plus. do you have a hero to recommend?
    Excited, Fred Fischer comò Federico Pescador

  2. My Hero was named Lisbet, but I’m sure they’re all good. What country are you coming from? America? If so, I would recommend ViaHero’s resources. Their business relies on knowing the travel rules, so their site is a great source of readable info: It sounds like only cruises have been affected. They can build you an itinerary around pretty much anything else you want to do.

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