The Havana Half-Marathon: Adventures on a Small Island


Last weekend, I finally made it to Cuba!

It was a significant trip for me, since Cuba was my final country in all of the Americas. I now have only 19 total countries remaining, and this was an especially fun one.

During my time on the island, I ran a half-marathon with a friend, spent another couple days walking around Havana, and made sure to sample mojitos from as many restaurants as possible.

Keep reading for the full report, or click any image for a larger version…

How to Visit Cuba as an American

When I came back and mentioned I was in Cuba, lots of messages popped up for me on Twitter and Google+ asking the same question: “How did you do that? I thought Americans can’t visit Cuba?”

Ah yes, here’s the thing. Americans aren’t “supposed” to visit Cuba without a license, which is kind of like a visa. But it’s weird, because the visa isn’t issued by Cuba—on their side, Cuba is happy to welcome Americans with no hassle and very little paperwork. Immigration officials will even go out of their way to avoid stamping your passport to ensure there is no evidence of your visit. Instead, it’s the U.S. government that doesn’t want its citizens visiting the small island 90 miles south of Florida.

When I first began my travel quest five years ago, I always assumed I would wait until I could get a license to visit Cuba. After hearing reports from many other travelers, however, I finally decided to just go for it. Almost every report said the same thing: the travel restriction is no big deal, no one has ever been prosecuted for visiting Cuba, and besides—it’s an amazing place. Don’t wait!

With that advice in mind, I reconciled myself to visiting Havana without the license, and I almost made it there earlier this year during the Axis of Evil trip when I visited Libya, Afghanistan, and Iran. On the way home from Kabul, I stopped off in Chicago and flew down to Cancun for the connection. Alas, my AA flight was two hours late due to a maintenance issue. While we were taxiing in on the tarmac, I saw the Cubana jet take off for Havana. Foiled!

I had been traveling for two weeks by then and had already made it to several police states, so instead of waiting a few more days for the next available flight, I spent the night in Cancun and returned home to the U.S. the next morning.

Visit with Wandering Zito

It was probably for the better that I didn’t visit earlier this year, because when I started planning the return attempt, my longtime friend Stephanie Zito decided to come along. Stephanie has been to more than 100 countries of her own, and was one of my original inspirations when deciding to visit every country in the world.

Traveling with Stephanie is fun because we are each experienced travelers in our own way, but we both tend to forget things. For example, even though we had planned to run the half-marathon, neither of us had done anything about registering for it before we got there. No problem, right? We had cash with us and figured that they wouldn’t turn away two healthy runners who showed up at the runners’ area the night before.

Unfortunately, the first guy we talked with didn’t seem especially eager to help. Our cumulative Spanish was fairly limited to phrases like “Dos más mojitos,” which didn’t help us with this guy who ignored our entreaties and kept motioning us to leave.

Steph and I looked at each other and silently decided on a common travel strategy: when things aren’t going your way, wait it out and see what happens. Just keep standing around looking friendly, and more often than not, all will be well.

The strategy worked. The marathon organizer, who also didn’t speak much English, came out to see us and kept repeating “Welcome to Cuba!” over and over.

“Dos más mojitos!” I replied.

We were now on friendly terms, but still had no way to register for the race. Eventually a third person was fetched, who grew up in Miami and was happy to help us sort out our registration. Success! We were officially ready to go.

The Half-Marathon: Tour De Havana

The next morning we woke up early and headed for the race entrance. At least two thousand runners were there, mostly from Cuba and other Latin American countries. A troupe of dancers was positioned on the steps of the capitol building, and everyone was full of energy.

We set off at 7am, and the crowd thinned out after the first kilometer or two. After the first 5k or so, I was slightly worried as the temperature rose. I usually run at least 10 miles every Sunday, so a half-marathon (13.1 miles) shouldn’t be a huge challenge, but running in the rainy Pacific Northwest is a lot different than running on an island in the sun. Fortunately, all was well—after warming up around 7:30, it was still hot for the rest of the morning, but never become unmanageable.

We ran past the seafront, into New Havana, and through a bunch of different neighborhoods. We had heard that the water stations were sparse and poorly run, but this wasn’t the case at all: Almost every kilometer or two, eager volunteers were handing out small bags of water that you open with your teeth and then drink.

We ran a slow pace, which was a good decision since neither of us felt super exhausted toward the end. In fact, we rounded the corner to the finish sooner than we were expecting. All of a sudden, it was over. A volunteer marked our number as completed, and another volunteer gave us a medal. Victory!

At the end of the race, several runners approached us and asked for our shoes. We had read online that this request was common, and when we saw the shoes that most Cuban runners wore for their races, it wasn’t a hard choice. We picked out two guys based on the poor quality of their shoes, made sure ours were a good fit for them, then handed them over.

Havana Photo Walk

After the marathon, I felt slightly dehydrated and took a short nap after drinking lots of water. Stephanie has endless energy, so she left to explore the city and take photos. After a while she came back to fetch me and I joined her for the second half of the excursion.

My grandpa was in Cuba in 1941 right before Pearl Harbor. The funny thing is, I’m not sure how much has changed. Due to the U.S. embargo, almost every car in Cuba dates back to the 1950s or even before. Walking around Havana is like visiting a car show, although some cars need a little work.

Random Facts

  • The Cancun airport has no transit section, despite seeing a lot of travelers transit through to third countries, usually Cuba. Ironically, the Havana airport does have a transit section… for everyone traveling on to Russia or China, I guess.
  • There are essentially two economies in Cuba. Our trip wasn’t super-cheap because we paid tourist prices: taxis are mostly fixed-price, and restaurants are clearly divided into tourist spots and non-tourist spots.
  • With employment opportunities being fairly limited, almost every restaurant in Cuba has a band. There is no Burger King in Havana, but if there were, I’m sure it would have a full salsa band at the entrance as customers ordered their Whoppers.
  • The unofficial “mojito index” ranged in price from $2 to $6, depending on how far one walks from the main tourist areas. Perfectly reasonable.
  • If you’re an American hoping to visit Cuba, check out Cuba Travel Network. They arranged my flights and hotel, and ensured that my credit card was charged in a country other than Cuba. (This wasn’t a sponsored trip of any kind, and I paid full price.)


The only problem with our trip came when we almost missed our flight back to Cancun and on to Dallas. Yikes! It was totally my fault, as it almost always is. For some reason I thought we were leaving at 3:15pm, but our flight (the only one to Cancun) actually left at 1:15. Oops.

Thankfully, after a mad dash to the airport, a successful attempt at jumping the queue at the Cubana Airlines check-in counter while avoiding eye contact with fellow passengers, and impatiently waiting through a long immigration process, we made it to the gate just in time. In fact, we even had a moment while boarding to exchange our final ten Cuban dollars for Mexican pesos, which could be put to good use with another friend of mine in Cancun.

If you’re looking for a place where time stopped in 1941 and hasn’t looked back, check out Cuba. As many independent travelers said to me, don’t wait.

Oh, and … only 19 countries to go! Wow.

Question: where are you going on your next trip?


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  • Stephanie says:

    Exciting, Chris! I’ve always wanted to go to Cuba and now I have no excuse, even as an American 🙂

    I’m off to Vietnam and Singapore the second half of December. I’d love to meet up with others if they’re in the area!

  • calceola says:

    Nice Article, and it is funny to hear from you, still running. Your long run to all countries still came to an end, you may see the finish line. But you are well trained by the last years, so the best is yet to come. Wish you all the best.

  • John Sherry says:

    Cuba sounds great simply because it’s had less influence from modern life and has that original latin flavour and taste of a more laid back era flowing through the streets. You can almost hear and feel it in your post Chris. My next trip for winter and New Year – Holland! Even colder than here in the UK but the people are as warm as they come and that’s the difference isn’t it. The people in the places.

  • Sarah Russell says:

    Fascinating!!! I guess I was one of those people who thought that you couldn’t visit Cuba, but your beautiful pictures make that something I’ll definitely reconsider 🙂

    As for my next trip, it looks like it’s going to be a road trip around Lake Michigan (hitting Chicago, Ann Arbor, the Upper Peninsula of MI and Northern WI) to see family over the holidays. In the middle of December… In a Jetta… (Don’t blame the insanity on me – this one’s totally my husband’s idea!)

  • Lisa Newton says:

    What a great way to finish out the Americas. Having just moved to Florida, I’m looking forward to experiencing “Cuba” via Miami, soon.

    As to my next trip, I’m just getting settled into Florida after living for several years in LA. Two different worlds in the same country, but different coasts.

    I’m excited to read more about your adventures!!

  • Artur Ciesielski says:

    Question: where are you going on your next trip?

    Mountain biking in Peru followed by mountain biking in Croatia and I can’t wait to be worn out from riding.

  • Monique says:

    Since I am on a quest to “run the world”, I must add Cuba to my list of must-do races.

  • Glenyse says:

    Chris, you have given me even more gumption to skip over to Cuba the next time I am in Jamaica. I’ve always been chicken because of the license issue. (I just couldn’t see myself paying the $10,000 fine if I got caught coming back into the country). But Cuba has always been on my bucket list, and I can’t wait to see it.

  • Chris says:

    I must say Cuba is somewhere I would love to visit! Wow that sounds like such an amazing trip to make overall. The pictures as well make it come to life!

    My next big trip will hopefully be to Patagonia. We will see how that works out though, 4 kids is a lot of people to drag down to the edge if the earth!

  • Annah says:

    I really want to get into the exclusion zone at Chernobyl for the abandoned town photo opportunities. And well, probably also for the adventure and shock value. Everyone thinks I’m crazy but I’ve done the research and you can get an organised tour and the radiation is lower than flying longhaul (if you stay in the right places). Has anyone been?

  • Chris says:


    I haven’t been, but I know some people who have been. It looks very easy and safe, once you get to Minsk or wherever your starting point is. Google it to find the main tour operator.

  • Shefgab says:

    My next trip (on Sunday!) is to Moldova. I’ve been waiting years for a cheap flight, and finally found one (£106 from London). Off to Burundi and Rwanda in January. I spent 3 weeks in Cuba last summer – nice place, although the way the Cubans are treated as second class citizens in their own country is saddening.

  • Kate Rodde says:

    Well done for just going for it – sometimes it’s the only thing to do….and the most rewarding!
    Which of your 19 left is going to be the hardest by the way?

    Fingers crossed my next trip is actually a country move to Singapore next year – We are just gonna make it happen… again a long held dream and somewhere from which it is so easy to travel to so many more places, cant wait!

  • alua says:

    From what I have heard from American friends who have done degrees in law, the US wouldn’t want to prosecute any American travelling to Cuba – it wouldn’t be a case they could argue and win apparently (I can’t remember why though).

    I’m impressed you’ve only got 19 countries to go. Wow!

    My own next trip: well, Austria during the winter holidays, then Hungary and Romania, the latter of which will be a new country for me. (I’m woefully ‘undertravelled’ for Eastern Europe, so I’m excited.) More travel plans for 2012 – determined to make it to Spain & Portugal (never been), plus Tunisia (never been). And hopefully Asia again. We’ll see. Money & time are always an issue!

  • alua says:

    *impressed (sorry, not a fan of typos)

  • 50+ and on the Run says:

    I’m so glad you got a chance to get to Cuba–and doing the half is a bonus!

    My next trip is through Buenos Aires to Ushuaia and Antarctica–can’t wait.

  • Willow says:

    Wow, what a trip! “What did you do this week?” Well, I went to Cuba, ran a marathon, then hitched a plane back to Cancun.

    Another inspiring post, as always, and beautiful photos, too! Thanks for sharing.

  • Tracey says:

    Havana looks AWESOME!! I have a rough plan to do a several month trip to vietnam, indonesia, phillipines. This is a very rough plan, but the idea of it keeps me sane in Toronto. Stephanie, please let me know how you like Vietnam, I have heard only positive!

  • Saad Bhamla says:

    Awesome. Good job on the half. Wonder what your time was?

  • Chris says:

    It was a leisurely 2:08. We’ll aim for the world record next year. 🙂

  • Sam says:

    I love that you combine two of your passions, running and travel, seemingly everywhere you go. As a woman, not always safe to do, but I try! My next planned trip is skiing at Jay Peak, Vermont in January. April will bring either the Amalfi Coast, Costa Rica, Belize or Jordan. I know, I know, what a mishmash of choices. Half the fun is doing the research then deciding!

  • Tom Pinit says:

    Leisurely 2:08, that’s fantastic in the heat and humidity! I’m usually struggling to break two hours here in the Northwest 🙂 Phenomenal photos, thanks again for the trip report Chris.

  • Alex Berger says:

    Absolutely fantastic shots of the old cars. One of the things I really want to see before everything gets opened up completely and they vanish into history.

  • Sophia says:

    wow .. only 19 countries to got. And, I am adding Cuba to the life list right now. Our next trip is in the spring to Spain. Very excited. Still figuring out how we can get some tickets to see Barcelnoa or Real Madrid play …

  • Lauren says:

    Seems like a wonderful trip! I’m off to India on my next trip!

  • Joe Lalonde says:

    Sounds like an awesome time in Cuba. You have almost made me want to visit Cuba.

  • Catherine says:

    Reading that has just absolutely made my morning! I’ve always wanted to go to Cuba, but given that I’d have to get home through the USA, I was too scared to try and go on my last trip!

    Might just have to pop on over and try again!

  • Steven says:

    So…the photos are awesome. Not sure why this isn’t something you’ve done all along. 🙂

  • Chris says:

    Ah, it’s because:

    1. I finally have an iPhone (never traveled with a camera before)

    2. Stephanie is an actual photographer

  • Heidi says:

    What perfect timing! I’m spending the winter in the FLA Keys and have been hoping to make it to Cuba. My dream (well, one of many) has been to spend my January birthday in Havana. This was a sign to make it happen! Thanks Chris

  • Darlene says:

    @Annah – Trey Ratcliff has! Email him or follow him on Google+ and ask him. He’s really good about answering questions.

    @Joe – almost? Why wouldn’t you wanna go?

    It’s funny this post comes now. I’m actually trying to plan a trip, photo tour, for a group of people right now. See us Canadians can just hop on a plane any time we want and head to Cuba! 🙂 There are some benefits of living north of the border, LOL.

    @Chris are they your photos or Stephanie’s? Great shots, love the people. So where was THE best mojito in Havana so I can try for myself?

    My next trip: wherever I can get a cheap package to in the next 8 days. Just gonna get away for a few days – sand, sun, myself only! Might be Puerto Vallarta or Laguna Beach. Maybe Cuba if I can get a smokin’ deal!

  • Darlene says:

    @Catherine, where do you live that you have to return through the US?

  • Roy Marvelous says:

    Thanks fantastic Chris. I’ve missed these travel reports of yours! I was just telling a friend today about your mission to visit every country in the world and how your almost there 🙂

    As for me, my cruise ship has just started it’s a trans-Atlantic journey from the Med to Florida. And I hear another one of your readers is onboard!

  • Joe Lalonde says:

    @Darlene – Yeah, almost. I’m unsure if I would be able to talk my wife into going. She’s a rule follower, I’m a rule breaker.

    So trying to talk her into going without the “correct” paperwork would be difficult and I’m not sure if it would be worth it.

  • iktomi says:

    Wonderful for you to share your trip. Best wishes as you continue your quest for visiting 19 more countries. It is a an admirable desire. I would be happy to make it to the Oregon Coast next spring/summer…time has given me few options and they continue to get fewer!! Enjoy every moment of your adventures.

  • Andrew Seher says:

    The photos are wonderful. Like the thought of a salsa band at the local Jack-in-the-Box.

  • Stephen Johnson says:

    Hey Chris – I totally loved reading this! Sounds like Cuba was an awesome experience. The 1940’s time warp you describe has totally inspired me to make a trip there (not to mention el cheapo mojitos 😉

  • Stephenie Zamora says:

    I’m hoping to come to Portland for the World Domination Summit on my next trip! 🙂 Thank you for continuing to share your travels, you are such an inspiration. xo

  • Stephanie says:

    This is my first time visiting. So glad I did! I’ve been putting off the trip to Cuba. Just confirms that I’m headed to Havana…NEXT!

  • Ame' says:

    I’m currently working in China, but as soon as my contract is up in July I’m headed to Hong Kong, the Phillipeans, and Thailand. It’ll be my first true backpacking trip. My parents are terrified, and I love it! 😉

  • Janna says:

    Sounds like so much fun! Reminds me of my experience running two half-marathons in Spain – there’s no better way to run a half-marathon than in a foreign country. Though at least I speak Spanish and could explain to the officials the fact that my friend mysteriously lost his runner’s chip, and translate their anger back to him.

    I’m hoping to visit Nicaragua next, because I have a friend there. But you make me tempted to find a way to get to Cuba. As a salsa dancer here in California, I kind of want to visit if nothing else but to see the salsa bands in every restaurant 🙂

  • Erin says:

    Ooh! Cuba looks stunning! I’ve always wanted to visit, and the extra information from you is encouraging!

    As far as what’s next? Diving in Roatan, Honduras and then two weeks outside of Cape Town, South Africa! Both are new countries for me!

  • Marie-France Roy says:

    Congratulations Chris! I visited Cuba in 2008 (as an independent traveller) and liked it a lot. It sure is different. But I was under the impression that it got frozen in time in 1959 (when Castro took over), not 1941…

    My next trip: Hong Kong, Malaysia, Cambodia, Laos, Thailand, Philippines (66 days, leaving Dec 25). That will be my first time in both Cambodia and the Philippines. 🙂

  • Victoria says:

    What a great story! And it was such fun to read it this morning over my coffee. Made my day.

  • Chris says:

    Awesome dude! Congrats on the progress. Planning my RTW for departure in mid-January!

  • Kerry Murray says:

    Felicidades, Chris! For your trip to Cuba, your half marathon, and heading in to the homestretch for those last 19 countries. Rock on!

    The photos are fantastic. So appreciate your iphone and Stephanie’s skills.

    For my next trip, I just got invited to Kruger National Park (South Africa) as my aunt and uncle are coming to visit. Not a big jaunt as we do live in Cape Town, but we haven’t been beyond the Eastern Cape yet, so looking forward to it.

    Then a meeting in Nice, France (that will require a week’s stay 🙂 and is expenses paid) a conference in Amsterdam (also paid!) and then off to Portland for WDS II. Planning on some adventure and will be in Ethiopia or Namibia by the end of 2012.

    All with a 6 year old in tow who just lost one of his front teeth and is wowing the crowd with his grin 🙂 (People, don’t let the children keep you home, they are awesome ambassadors!)

    All the best to you as the world tour continues!

  • Cynthia Morris says:

    Great article! I love that you participated in a half marathon. What a great way to be part of something and to run through the city like that…very cool.

    I love the photos of the buildings. They’re gorgeous. For some reason I love images of cracked-out buildings. It reminds me of Lisbon.

    Thanks for this report from Cuba!

    My next trip is back to Denver in two weeks where I shall settle in with little travel plans other than to publish my novel.

  • moom says:

    New Zealand. I’ve never been, despite living in Australia for 10 years. Going in March for a meeting and will try to do at least a little sight-seeing. Unless something else comes up in the meantime… This year was a big year for me travelwise with Austria, Korea (first time), India (first time), and the USA.

  • Tim says:

    Italy! Going in the Coast to Coast marathon from Sorrento down the Amalfi coast to Maiori. Then kick back, explore, eat seafood and drink limoncello with my family before returning to Dubai for a food-coma Christmas with friends.

  • Emily in Chile says:

    Sounds like a great trip! I really want to get to Cuba before it opens up much more, and I’m planning to go before we leave Chile. The flight from all the way down here is longer but direct on LAN, which sounds nicer than flying to Mexico from the US and trying to coordinate with Cubana.

  • Patricia Giacona-Wilson says:

    Congratulations on completing the half marathon! It’s so exciting and unbelievable that you only have 19 more countries to go.

    What stuck out to me in your post was: “When things aren’t going your way, wait it out and see what happens.” That’s a small nugget of travel wisdom I’m going to keep in mind.

  • Bill McArthur says:

    Nice article. I was there in a group of 21 Americans with Insight Cuba.

  • Judi Vreeland says:

    Chris-Thanks for sharing this trip. I have wanted to go to Cuba for such a long time. I don’t remember how many times I have been on a cruise ship rounding the tip of Cuba wishing we could sail into port. Once the ship captain was very daring. He took us inside 5 miles. There were so many passengers out on deck it’s a wonder the ship didn’t roll…….

    Keep on enjoying your journey and sharing.

  • Susan says:

    Hmmm… I’m surprised you didn’t mention while you can’t be ‘prosecuted’ you can be fined for going to Cuba. I know someone who got fined 10k by the IRS for visiting and spending over the alloted amount Americans are ‘allowed’ to spend while visiting. Again, a US rule and not Cuba. He managed to reduce it quite a bit with the help of a lawyer.

    Either way, I think it’s great you went for it and enjoyed it. And I didn’t state the above to indicate other people shouldn’t go, but you should research everything and also know you can easily go through volunteer efforts via humanitarian projects, as a journalist, or to visit close family.

  • Nicolaï says:

    Congrats on your milestone, Chris. 🙂

    You make me want to visit Cuba. As for me the next trip is to Taiwan, although I’ve been there already. Next unvisited country: maybe Vietnam.

  • Matt says:

    I could totally see you saying “Dos más mojitos!” in response to “Welcome to Cuba!” Haha. Made me laugh.

    Haven’t done much thought on international travel yet, but Thailand is near the top of my list.

  • Leen Celis says:

    I love to read your traveljournal, tips and trics…
    I’m longing for Cuba now! 🙂

  • Joe says:

    Thanks for the recap Chris! Sounds like an absolutely amazing holiday. I especially enjoyed the pics and hope that you will do some more in the future…

    As for next travel plans? Sadly, I have no scheduled travel plans right now, which is scary! The passport is getting dusty! My wife and I always try to get away in Jan/Feb, as the New Jersey winters can be harsh. Thinking Central or South America.

    Thanks again for an awesome post and the travel inspiration!

  • Scott says:

    Cuba is great. Just like going back to early 1950. I first went there in 1997. Another way for Americans to go is by way of Canada. Just remember when you go thru customs—no stampe no stampe.

  • Tyronebcookin says:

    There’s yet another EASIER way to do it: back when traveling to Dominican Republic there are “cruises” that last on average 3 days that go from DR (in this case it was Puerto Plato) to Jamiaca, and Cuba, and back to DR. THE ship holds the passport (or a copy of it and u hold the real one) they do not have it stamped while the cruise ship is in port in Cuba. — Chris, if u remember me, you know how I know this…and I know there were several other people on one of those cruises that you probably know.

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