Next Stop, Cuba!

Filed Under: Travel

Over the past few months the major U.S. airlines have begun flying to Cuba. We’re going from one extreme to the other, as we’re going from an embargo for Americans to travel to Cuba, to suddenly having thousands and thousands of airline seats a day between the two countries. Given the limited hotel capacity, this is causing the prices of everything to skyrocket.

Why I haven’t been in a rush to travel to Cuba

I know a lot of people were excited about being among the first Americans to visit Cuba, though I’m not sure I have the same urgency. I actually sort of have the opposite approach, and my initial impression is that waiting a bit longer might make sense:

  • A ton of Americans are suddenly traveling to Cuba out of interest, though I suspect demand will be lower a year from now rather than higher; those who really wanted to go are doing so ASAP and paying the exorbitant prices
  • After the initial interest of visiting Cuba wears off, I think it’ll be at least a decade before we see a bunch of new mega-resorts opening up or see things changing in a substantial way

From friends who have visited Cuba so far, the general consensus seems to be that it’s interesting to see, though it’s far from a seamless experience; you’ll wait for a long time at immigration, won’t have cell phone reception, can’t use credit cards, and almost everyone in Havana is trying to rip you off and charge crazy prices, because they know they can.

So on one hand I don’t feel like there’s a huge rush to travel to Cuba since I don’t see much changing over the coming years, though at the same time with tickets costing ~$100 roundtrip between South Florida and Cuba, I figure I might as well check it out, as I explained in a post a couple of months ago.

Well, now it’s finally happening, as I just booked my ticket yesterday.

I’m headed to Cuba!

I’m headed to Cuba in a couple of days, which I’m excited about. I only have a limited window where I can visit due to other commitments, so I’m just flying from Fort Lauderdale to Havana for a couple of days.

I’m intentionally going into this trip mostly “blind.” Of course my goal is to see Havana, but beyond that my goal is to document what the actual process of traveling there is like as an American — what’s checking in for a flight to Cuba like, do you get questions from immigration officers in Cuba or the U.S., how expensive is stuff, what’s the food like, is Havana actually a city worth seeing or just interesting to see because it was forbidden for so long, etc.

I’ll be going in a couple of days, so if anyone has any tips (whether it’s great restaurants, sites, negotiation tips, or just general warnings), I’d love to hear them!

Like I said, there’s a lot of misinformation out there about Cuba, especially since right now American can only visit on a “wink wink nudge nudge basis,” as you have to travel to Cuba for one of 12 approved reasons (the most common of which is “support for the Cuban people”).

I’m really excited about this adventure!

  1. I visited Havana at the beginning of the month. My trip happened to fall during the mourning period of Fidel Castro’s death, so things were somewhat low key in public.

    Don’t expect to get as much blogging done as usual while you’re there as internet access is restricted to specific hotspots, which you need to buy internet cards for at large hotels, post offices, or mobile phone service kiosks.

    Interestingly, internet censorship exists but for sites you wouldn’t expect. Ebay is blocked and so are Google business accounts (Google prevents access, not necessarily Cuba itself). And my internet actually kept timing out when I tried accessing an article on OMAAT about AA reducing flights to Cuba. A VPN should get you around that, but it really is a hassle.

    If you have sensitive lungs, be careful. The old cars are good, but that means the air is subsequently dirty. I was there for only two days and actually coughed up blood in my phlegm.

    I was never asked for traveler’s insurance, although it appears to be a rule for American tourists. (Maybe use your German passport instead if you’re worried).

    If you happen to have a non-USD currency like Euros, Pounds, Canadian or even some Yen, bring them as they don’t suffer a 10% penalty like the USD does when converting to Cuban Converitble Pesos.

  2. As a canadian, we have had the privilege of visiting Cuba any time. Havana is a magical city. Find a walking tour (private). What you can learn by those living there is amazing! In Havana check out Hotel Nacional de Cuba Habana! The back veranda is awesome and it feels like time stopped since 1961!! Lots of AMAMZING restaurants!! If you stay in a resort town, the locals will invite you to a meal in their home for a small fee. If this happens to you, GO!!!


  3. I went about three years ago via Mexico and just got back from an trip last week.

    It’s a beautiful country with great people. Of friends I’ve talked to that have gone, the only ones who were disappointing were the ones who had completely unrealistic and mis-aligned expectations.

    Immigration, like in most international hubs, depends on how many planes land when yours does. Travel insurance is required but only spot checked. I did not purchase it but was asked about it and made to purchase it upon arrival. I believe it was roughly ~$5/day. On the upside the kiosk from which I purchased it let me exchange money there. To that end, if you have Euros, bring them. If you don’t though I don’t think it’s worth it to exchange USD for them. The USD receives a 10% penalty when exchanging it. Bring a lot of cash, your credit and debit cards will not work.

    I’d emphatically recommend staying in a casa particular, though there are many boutique, if not overpriced, hotels around.

    I’d also recommend getting out of Habana Vieja for a good spell. It is gorgeous there, but hyper-touristy and not really representative of the country.

    In terms of restaurants, by far the best meal I had was a paladar called San Cristobal in Centro. Not far from there is a coffee shop that I also enjoyed called Cafe Arcangel. I enjoyed walking through Centro to these establishments and then returning via the Malecon.

    Also, I highly recommend Fabrica de Arte Cubano in Vedado. It’s a huge converted warehouse with multiple bars, art exhibits, terraces, and is overall super interesting. Go not long after they open (8pm I believe) to avoid lines.

    I flew SW home with some hiccups. Their route was only a few days old so their systems were not “connected” yet and were relying upon wifi to get folks checked in. It looked like United and JB had their stuff together a bit more.

    You can exchange money after security as well, fyi.

    I’m not sure this would be an issue for you, but to anyone what reads this, you cannot bring bottles of rum (or any duty free liquid) through security Stateside. Southwest said multiple times that this was permissible. Basically not having to stuff the duty free booze into your suitcase after clearing customs at home and rechecking. Apparently this is a great deal of misunderstanding about this. Many folks have had no issues but I was turned around because, as explained to me by the least friendly TSA agent imaginable, the bottles have to be in the sealed bag (check), with a receipt (check), that is date-stamped (fail). The duty free from which I had purchased my rum from in the airport did not have a date on the receipt so they promptly.

    Anyhow, just a few thoughts from a recent trip.


  4. My advice to you: pack enough tissues and maybe some hand sanitizer. Don’t give out handouts (shampoo, pens or such), make sure that you get back the currency you can actually use (CUC, not CUP), make sure when asking your hotel to call you a cab, to specify which one. The oldtimer cabs are much more expensive.
    One thing you will definitely need: Patience.
    Auf meinem Blog gibt’s auch einen Post für “Kuba – Warum wollen da jetzt eigentlich alle hin? Reisetipps & ein offenes Wort. “, der könnte vielleicht hilfreich sein 😉

  5. Was in havana couple of years ago on holidays. From Australia. Safe place with plenty of cops on the street, people generally don’t try and take advantage of you if you keep a low non touristy profile. Tip: hire a driver to drive you around havanas touristic sites (fortification, forest thing I don’t remeber) in one of the classic old American cars. Took an awesome pink chevy for 2 hours, driver was a great guy who knew so much and he showed us local sights for just $50 USD. Food is a bit tricky as due to rationing and restrictions – choose restaurants before, and have snacks on you. Also try churros on the street – 2 dollars for a life times supply, best thing I’ve ever had. Enjoy Cuba before it changes! Looking forward to reports.

  6. Working with a non-profit, I’ve been to Cuba about 25 times since 2006. There is lots of misinformation out there, like the stuff that your friends have told you.

    Long immigration lines? Compared to where? Lines in Cuba are as good or better than most Latin American countries. No cell phone? That’s changed a lot in the last year or so; most companies now offer you roaming in Cuba. Or bring an unlocked phone and pop in a Cuban SIM card. (Internet coverage has improved dramatically, but it still lags far behind most countries)

    The part about credit cards is true. Will people try and rip you off? Some. But if you’re friendly to the people around you, they’ll see that you’re not taken advantage of. And you don’t have to worry about muggings or violent crime like you do in most of Latin America.

    Shun the hotels; use Airbnb or something similar to stay in private homes. A hotel won’t show you Cuba and won’t measure up to standards in other countries. The private homes I’ve stayed at will do almost anything to insure that you have the best stay possible.

    If you’re looking for luxury, Cuba isn’t the place. If you’re looking to go to a place with fascinating history, beautiful scenery, and locals who are truly glad that you’ve come, you’ll love Cuba.

  7. Immigration lines are fine, checking in is easy just fill out a simple visa for $50. Stay in Airbnb’s not hotels. Try to get the local currency from the banks as it will be a lot cheaper this way ( there are two currencies there the tourist and local) if you use the tourist Cuban peso you will be ripped of a lot. The pollution from the old cars is really bad. Very safe though with little crime.

  8. ONLY way to do this is with a local guide. Otherwise you will miss all that is good about Cuba (people, music and culture). All the best stuff is things/places you will never find if just there for a short time. Also having a guide lets you really get to see how locals live and visit them in their day-to-day lives. All the normal stuff (hotels/transport/food) that you normally cover in your reviews is no good in Cuba. a few years back we had an ex-Olympian bring us around the country for a week and not alone had he great stories about competing in the Games, but brought us to all sorts of great places (even brought us into his parents apartment to meet his family). Not to mention hitting the town with his buddies one Saturday night, and some fantastic private home/restaurants.

    If you do this like you normally visit places, it will be a disappointment.

  9. I disagree, sort of, in the sense that having “a guide” for your whole trip will be suffocating. If you travel as I suggested, saying in casas particulares throughout the country, you will get a decidedly local experience everywhere you go, eating local food and sleeping/showering/waking as the locals do. Additionally, the owner of each casa will organize your activities for you, which will go through local guides and companies by default. You’ll get shots of local experience when you need them, but overall have a free and elastic trip.

  10. Hi – went to Cuba on a journalist visa a few months ago to cover a fishing tournament. If you are writing do you plan to get a visa?

    Folks who want to go before it is too late are too late. Havana is filled with folks who are targeting naive Americans. Get out of Havana. It is a different country when you get away from the hustlers who are everywhere. And they are all over you, mad if you don’t cough up money. Even had a guy who was a ringer for Pres Obama in a coat and tie approached us in a nice restaurant for cash. We thought he was the manager, but he just calmly walked out the door with the money.

    Agree with all that hotels are the worst, casas particular much better bet. Book through AirBNB. Hotels are staffed with folks making less then $20 monthly and problem solving is not their thing – important when the electric/internet go down. We stayed at one of the top 3 business hotels because I was on deadline. No wifi for 3 days. Really spotty AC. No water pressure. That’s an issue when it is 90 degrees+ and humid around the clock. The casas particular are owned by the folks who run them, many of them have been doing it for years, and they want you to enjoy and respect their country and hospitality.

    Was really surprised to see folks throw bottles, chips wrappers and more in the street and on the beach, and see trash floating in the water.

    We heard that Starwood was taking over the management contracts in August for 2 of the top hotels. Would be really interesting to know if the hotels have changed, and what they see now given the election.

    Good luck, enjoy.

  11. I just got back from Cuba having spent 12 days there.

    Since I was allowed to take two large suitcases in addition to a carry on, I decided to fill my suitcases up with baseballs and gloves I bought through Amazon. Baseball is the #1 sport in Cuba. The kids basically have nothing. One of the best experiences I had was giving away the periodic baseball/glove to incredibly grateful kids. I hear dolls are valued by girls as apparently they are also hard to come by.

    #1 WARNING: Havana Airport. We waited FOUR hours to finally get our bags and make it through security. No officials there seem to care. I almost got myself arrested as my 73 year old dad had to go through security again. Then on the way out, my AeroMex flight watched as ONE guy for two hours, offloaded and onloaded the luggage. The flight captain over the loud speaker announced “Havana Airport is a disaster!”.

    #2 Exchange your money at a CADECO which is the state run offices. Some hotels will rip you off on the exchange rate.

    #3 Good luck with the WIFI! The Cuba gov still blacks out websites too.

    #4 Make sure to tour the waterfront. HavanaJourney’s is pretty worth it for a day tour in a 57 Chevy.

    Keep an open mind. Have fun!

  12. oh, and we tried to do the official thing “people to people cultural exchange.” Usually that means if the US gov asks, you should be able to give them something to prove you in fact did that instead of laying on the beach. We did a tour where the tour provider gave us an itinerary in case we were asked. US Customs asked why I was in Cuba and told them I wanted to see it before Trump laid an egg on it. Never asked anything more than that.

    Most Americans I met there, requested at the Cuban Customs “Please don’t stamp my passport” and Cuba will do you the courtesy of stamping a separate piece of paper. That way, Americans don’t have to pay 600% more by taking a tour. This only works if you go through another country like I did stopping in Mex City. Then evidently you just say you were only in Mex and there is no documentation to say otherwise.

  13. Many of these comments are correct but some are very subjective. I work for a company that specializes in travel to Cuba and here are some thoughts:

    HOTELS. Yes, avoid the hotels if you can as they are extremely expensive at this time, especially for what you get. AirBnB lists all of the casas particulares and are hit or miss – some will run out of water, many do not have A/C, and almost all do not have wifi. Most are run by families who will provide you a great authentic experience, and some have become boutique hotels with a full staff. Email me if you want specific casas to book that are amazing.

    FOOD. There has been a food revolution, and the top restaurants are excellent. There are about 15-20 very good ones, but you must book early as they are supposed to only have 50 seats by government regulations, so you can imagine how packed they are during the current peak season. Those who go to Cuba and eat randomly off the street or walk into any “official” (state-owned and state-run) restaurants will encounter horrible but cheap food.

    REGULATIONS. I would recommend NOT to go for “Support for the Cuban people”. Many people have not read the fine print, and you will see this category is for travelers who go to specifically work with NGOs that benefit the Cuban people – this is not simply going and saying by spending there, you’re helping society. Also, for any category, you must have enough activities to meet a “full time schedule,” which the US government has implied is 6-8 hours/day. The category that most travelers go on is Category 5b, People-to-People Educational Exchange. That is the safest category to go on.

    INTERNET. You simply buy wifi cards for 1.50 CUC each for an hour, and use those to log in to wifi hotspots around town. One poster said that eBay is blocked but that is because they block themselves as does Google paid services and pretty much any transactional and banking website due to the embargo – they are NOT blocked by the Cuban government. Remember the US embargo is still in place with harsh penalties and sanctions for any entity and country that transacts with Cuba. Get any online banking done before you enter the island. Also, the AppleStore and AndroidStore self-block as well, too, so get any iOS/OS/app updates before you visit.

    IMMIGRATION. You must tell the US government you’re going on 1 of the 12 categories. You must tell the Cuban government you’re going as a tourist (which is illegal under US law), and hence the Tourist Card you will buy as your visa.

    VISA. One poster said the visa can be bought for $50. That is partially correct. You can buy it for $50 from Delta and JetBlue. United is $75. American, Southwest, Spirit, and Frontier are all $100. This can change at any time, though.

    ENJOYMENT. I completely agree with the last poster, if you don’t have a great time, it won’t be Cuba’s fault. It is still a fascinating place and a local guide is key to learn about the craziness there. Since your trip is short, I strongly advise getting a guide for a few days if not the whole time.

    SHOPPING. Contrary to what happens in most countries, grey market cigars are legit – a local can tell you why. Also, for Cuban rum, you must try Santiago de Cuba 11 year – that’s the best in the country even though it’s not the most expensive (only 40CUC per bottle) – tastes more like a cognac than a rum and is delicious.

    NIGHTLIFE Lucky, I’ve followed your blog for some time and think there might be some places you’d be interested in hitting. Email me for details.

  14. I’ve never been to Cuba, but almost everyone I know has gone. Most of them many times. Cuba is THE favourite winter destination for Eastern Canadians — westerners go to Vegas. My understanding is that there are a ton of very good resorts, and everyone I hear from loves the trip (except the sardine class flight on Sunwing).

  15. I was just in Cuba over the weekend for 3 hours as part of a Delta mileage run. No questions from Cuban immigration coming/going, and using global entry back in JFK allowed me to bypass talking to an US immigration officer. Brought back $80 in cigars, which was my only purchase.

  16. We spent 7 days in Cuba this March We stayed at a casa and they were so nice. We took guided tours and learned from our guides what reasonable taxi rides around Havana are (5 CUC from Old Havana to Centro) and from Centro to Vedado and the Tropicana ran around 10. Haggling isn’t tough, basically we said take us to XXX for 5? OK. Done!
    The best Restaurants do tend to book up. We had someone book the whole trip for us but we thought dinner at Ivan Chef Gusto was the best meal we had, was amazing. We ate on my wife’s birthday and she got a whole lobster for around 25 CUC. The place is more Spanish seafood based and also makes a mean G&T.

  17. I cant wait to hear your trip report. Please write about everything this time! Cuba is on my list to visit for years but I am waiting for the hype to die down a bit.

  18. Was just there two weeks ago. Everyone is NOT trying to rip you off. I had one guy “accidentally” give me the wrong change. No problems with anyone else.

    My American cellphone worked for most of the time in Havana.

    WIFI is available in public parks, but you may or may not be able to connect. It’s very frustrating. The lobby of the Iberostar hotel at Parque Central had the best connection.

    HAV airport is the worst airport I’ve experienced int he 50+ countries I’ve been to. Immigration on arrival was fine, but then they make you go through security on arrival, for god knows what reason, with metal detectors, x-rar machines and hand held metal directors. Returning home, there is no online or kiosk checkin, so there was a 45 wait to checkin, followed by a 45 minute wait at immigration and then another wait for security. People were repeatedly cutting the lines, pushing, yelling, etc…. After security, the bathrooms had no toilet seats, no TP and no soap. Everyone was exhausted by the time they boarded.

    I hope you have nice weather, but if you happen to be there on a stormy day, watching the waves crashing on the malecon is awesome. Also, check out Plaza Vieja in the old city. It’s sunny and pretty in the day and then there’s great live music in the restaurants at night.

  19. I visited Havana, Camagüey, Santa Lucia and a couple of other places in Cuba several years ago. I agree that patience is essential, especially if you’re going for some of the more authentic experiences and not just the pre-packaged tourist stuff. While Havana is nice for day trip, I didn’t find it particularly charming beyond the few touristy renovated streets. Most of the city is borderline derelict, air pollution is really bad and there’s a general tendency to rip off everyone who looks just a little foreign. In contrast, I found the less visited parts of Cuba to be much more hospitable and way less pushy.
    Many western visitors do the mistake of intentionally leaving stuff behind as a sort of misguided charity. This only works to promote the black market and sets wrong expectations among the locals. On the other hand, don’t be afraid to negotiate vigorously, especially with taxi drivers, who will constantly try to overcharge. If you’re not getting a reasonable deal, just walk away.

  20. As a European I’ve always been able to visit Cuba either using direct flights from Europe (e.g. IB, AF, or one of the many leisure airlines such as DE, WK) or via Canada (on AC) or via Central America (e.g. CM via PTY).

    Now, in theory, it should also be possible to travel via the US. But there is a rumour that non-US citizens are not allowed to travel from the US to Cuba (vv). Indeed, DL refused to sell a ticket to a (remote) friend of mine on the basis he’s not a US citizen. Obviously, he has ESTA, so he’s allowed to travel to the US.

    Lucky, can you confirm (or otherwise) that US citizenship is required to travel from the US to Cuba (vv)?

  21. @Andy: The US carriers now sell flights to Cuba to anyone. In the past when the only direct way was through charter companies, there was a rule that tickets could only be sold to US citizens, but no longer. So many commercial scheduled flights have launched that there is a fare war between the airlines, and AA has already announced they are reducing future inventory with smaller planes and reduced number of flights. It’s a good time to buy air to Cuba, but hotels and the best casas are very difficult to book due to high demand and hence high prices.

  22. @Anthony You’re wrong. As a Non-US citizen you are not allowed to buy a ticket from the US to Cuba, because there isn’t supposed to be any “touristic” travel.

    @Andy. That’s correct. Had that confirmed to me by UA just last week.

  23. @Marina The commercial airlines sell tickets to Non-US citizens EVERYDAY. Feel free to call UA/AA/DL/WN/B6/NK and ask them. Non-US citizens can declare on the Cuba travel affidavit they are still going under 1 of the 12 approved categories, and the airline could care less whether their purpose is real or not. With the low loads on flights to Cuba still, filling seats is the priority at all of the airlines.

  24. @Anthony Did you read my comment? As I mentioned, I did just that. I work as a travel agent in Germany. My info from UA (from last week) was that they are not allowed to sell tix to non US-citizens. Some US Airlines even sent newsletters informing travel agencies of that fact, as the demand for a USA/Cuba combination is pretty high.
    I even know of another travel agent who did issue a ticket from the US to Cuba for a German citizen, but had to cancel it at her own cost, because of said issue.

  25. @Marina I did read your comments and you never mentioned you called the airlines. Perhaps the local offices in Germany of the US airlines are telling agencies in Germany something different but my agency here in California and all of my peer agencies sell air tickets on the US carriers to non-US citizens everyday for the USA-Cuba flights. We send groups every week without problems (besides frequent delays). We have clients that have flown these routes with various passports: México, China, Taiwan, Canada, Hong Kong, Australia and New Zealand to name a few. OFAC clarified this is allowed in one of their updates earlier this year. AA is selling the most since they have the most routes – you should be able to sell them without problems for your German clients. Danke.

  26. @Anthony I see no point in repeating myself. Just because it has been done by ppl w/o consequence, doesn’t mean that it’s “allowed”, so I will not take that chance. Since I have the info directly from the airlines, I trust them to know best about their own policies.

  27. @Anthony Just received a consolidator newsletter, I’d share it with you (specifically). Feel free to put it in google translator and read for yourself

    “Inzwischen haben mehrere US-amerikanische Airlines regelmäßige kommerzielle Flüge nach Cuba aufgenommen. Entgegen der missverständlichen Darstellung in manchen Medien wurden die bisherigen Beschränkungen allerdings keineswegs vollkommen aufgehoben, sondern bis dato nur gelockert. Das bedeutet, dass vorläufig bestimmte konkrete Gründe angegeben werden müssen, die die Ausstellung eines Tickets erlauben.
    Dabei ist es für den praktischen Ablauf erforderlich, dass diese Gründe bei Buchung als SSR-Element in die Reservierung eingetragen werden.
    Anderenfalls ist die Airline gehalten oder sogar gezwungen, die Buchung zu stornieren.´”

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