Guest post by Cuba Travel Expert Tony Rubenstein

My buddies here at have asked me to share some of my expertise for new U.S. travelers to Cuba. I’ve been traveling to Cuba for more than 18 years, and have led many high-end and VIP tour groups in Havana and throughout Cuba.

Vintage Car, Havana Cuba

I am the executive director of ARTempoCuba, a collaborative effort between Cuban contemporary artists and curators and their U.S. counterparts to promote Cuban art worldwide. Part of that effort is our new guidebook “Cutting Edge Art in Havana” the definitive guide to Cuban contemporary art which profiles 100+ artists living and working in Havana today, complete with contact information, maps to their studios, and even suggested places to eat & drink recommended by our team of Cuban curators and artists. I also operate the website for Havana VIP Tours which provides trips, tours, and travel planning resources for English-speaking travelers to Cuba.

Although visiting Cuba may (for the time-being) seem novel and exotic to U.S. travelers, everyone else in the world has been traveling to Cuba for decades. Consequently, there is a well-worn Cuban trail of tourist traps and pitfalls, but these can easily be avoided with some advance preparation. With this in mind, here are my expert tips to Avoid Havana Bad Time:

1) Travel to Cuba with a purpose (its U.S. law!)
U.S. Government regulations as of January 15, 2015 require U.S. travelers to Cuba to have one of 12 specified reasons for authorized travel. You can check them out on the U.S. Treasury Department Cuba Sanctions webpage FAQ.

One of the best ways to travel to Cuba is to attend some kind of cultural seminar or special cultural event or happening. This will give a structure to your itinerary and put you into a network of “regular Cubans” as opposed to only interacting with Cuban Government tour guides, or worse, the Cuban tourist hustlers called Jineteros (pronounced hee-neh-tare-o).

For example, at ARTempoCuba we offer customized art tours to Cuba where our team of art historians and curators will teach you about Cuba’s great contemporary art and artists (a topic I’ll be covering in a follow-up blog post on this site.) We also offer week-long seminars in Havana to study printmaking and shortly we’ll be adding photography courses as well. You can also look around to find week-long courses for things like Spanish language, Salsa dance, conga playing, or music appreciation. Just be certain that you are honestly qualifying under the U.S. Treasury Department guidelines on the FAQ mentioned above.

One of the most important cultural events in Cuba is the Havana Biennial of Fine Arts. ARTempoCuba is offering an exclusive VIP trip to the Havana Biennial June 15 – 23, 2015 where our curators will show you all the best art and artists, along with the all the best historical and cultural attractions. We’ll be eating in the best Paladars, enjoying the hottest nightspots, and generally having a great, fun, interesting time. Space is limited to 20 people per group, and our first group has already sold-out, so sign-up now and join us in Havana!

2) Travel to Cuba as independently as you can while complying with U.S. laws. makes it easy to book your flights, and the information I provide here will get you pointed in the right direction to fill-in everything else you need.

Don’t be fooled by U.S. Cuba tour operators. Almost all packaged group “unique people-to-people” tours for Americans to visit Cuba, are exactly alike. And all will show you a Cuba that is laminated and vacuum-sealed. Though they’re called “people-to people” tours most of the only “people” you’re going to interact with are Government tour guides, drivers, screened guest lecturers, and carefully invited “guests”. I’ve seen it with my own eyes.

I won’t specifically trash my competitors by name, but I will say this: go with a smaller independent travel provider who specializes in your area of interest.

3) Plan to Allow Yourself Plenty of Time in Cuba.
We’ve seen many people who try to pack too much travel into too few days. As I’ll explain below, Cuba moves at it’s own inexorable pace. In Cuba, a travel day, where you travel between cities, for example, inevitably takes up the whole day.

My recommendation is plan for 5 nights in Havana and never less than 2 nights anywhere else. The colonial town of Trinidad, a UNESCO world heritage site on Cuba’s southern coast deserves 3 nights. Be sure to add full travel days between destinations farther apart than 100 miles.

4) Be prepared, have patience, and expect to un-plug from the grid.
Settle down Hot Rod. Life moves at a slower pace in Cuba. It’s partly do to societal limits and inefficiencies, partly do to cultural customs, and often due to the heat and humidity.

Expect that plans may go wrong: the rental car agency won’t have your reservation; the bus from Havana to Trinidad could be delayed; the line to change money could stretch a half-block long; and especially, you might not find anyone that speaks English. Any of these and more can happen. And all of it will work out fine. Be patient and flexible.

Welcome to what Cubans call La Lucha, the daily struggle against the inconveniences and annoyances of Cuban life. Even going through Customs and Immigration upon arrival at Havana’s José Martí International Airport can sometimes be a multi-hour experience. So just take a breath, and be patient. Bienvenidos a Cuba!

If you have any receipts, itineraries, or other paperwork that you might need for your trip, bring them with you – already printed-out. It is not a simple task to print something out in Cuba, especially if you need to connect to your Dropbox via your smartphone to do it.

Pack your bags to be as self-sufficient as possible. In Cuba there are no giant pharmacies, mega-camera stores, computer stores, much less any Apple Stores. Bring any medicines, hygiene products, camera and personal electronics equipment, and any supplies you might need for any seminars or events with you.

Instead of creating frustrations and hassles for yourself, expect to be disconnected from the web for your entire stay in Cuba, except for a few hours now and then when you might be able to connect via a slow and expensive hotel WiFi. Enjoy your forced digital detox. You’ll be OK. I promise.

Doorway, Old Havana Cuba

5) Avoid Staying in Hotels When Possible –Stay in a Casa Particular (a Cuban B & B).
Generally, the hotels in Cuba are over-priced for the quality of the accommodations, and seldom reach the standards to which U.S. travelers are accustomed. Instead, stay in a licensed Casa Particular which is a B & B privately owned and operated by Cubans. Think AirBnB a lo Cubano.

Comparing category-to-category and price-to-price, the conditions in a Casa are usually superior to those in a hotel. A 5-star Casa Particular will provide much better accommodations than a 5 star hotel for a better price.

All Casas offer home-cooked food service, and it’s often quite good. One meal you should definitely take every day at your place of lodging is breakfast. There just aren’t many breakfast places in Cuba, so eat it at your Casa.

Casa Particulars are also very safe. The licensing requirement that the Cuban Government places on owners of a Casa Particular, makes the Casa owner legally responsible for your physical safety and that of your belongings. And the penalties are severe. Many middle to high-end Casas have in-room mini-refrigerators, hotel-style digital strongboxes, and of-course en-suite private bathrooms. Even without the strongbox, you can safely leave your valuables and documents locked in your suitcase in your locked room in your licensed Casa Particular. If you’re still uncertain, you can always give them to the Casa Owner for safe keeping (get a receipt, even if hand written), and I promise you that she will defend your valuables with her life. To know whether a Casa Particular is licensed look for the symbol of the government issued seal which looks like this.

There are Casas Particulares for all tastes and budget levels from luxury penthouses with their own private swimming pools, to moderately priced private apartments, to economical private rooms in someone’s home. You can check out some examples of Casa Particulares on Havana VIP Tours site, and there are many online services for Casa bookings.

Tip: when booking through an online service avoid bait & switch scams by either demanding a satisfaction guarantee, or by pre-paying for only the first two nights of your intended stay so that you can find another place and move if you’re dissatisfied.

The best Casas enjoy high demand, so reserve well in advance for at least the first few nights of your arrival. If you’re going to travel from one city to another in Cuba and haven’t pre-reserved a Casa at your next destination, the Casa owner where you are initially staying always usually has a network of trustworthy Casas around Cuba, so ask his or her help.

6) Dine in Paladars (privately owned and operated restaurants).
With the exception of breakfasts (which you should eat in your Casa Particular) the food and service you’ll enjoy in a Paladar is much better than in Cuba’s government owned and operated restaurants. Do your research to find quality places. On you’ll find twenty of Havana’s Best Places to Eat and Drink selected by our team of Cuban curators and artists, complete with contact info and mapped locations. While there are many more Paladares to choose from, you cannot go wrong with our recommendations – they are where we eat ourselves.

7) Cash is King in Communist Cuba.
Bring Plenty of Cash, either U.S. Dollars or Euros. Travelers checks are not accepted anywhere, and while some U.S. based credit cards are now usable in Cuba, many places lack the infrastructure to be able to accept them. We’ve seen too many travelers not bring along enough cash thinking they could use credit cards or ATMs, only to end-up having to curtail their activities for lack of funds.

Tip: Set aside $25 CUC per person that will be required at the end of your trip for airport departure tax.

8) Only Change Money at a Hotel or Cadeca (Casa de Cambio).
Currency exchange scams are common. Confusingly, Cuba has two systems of currency, the Cuban Peso (CUP) referred to as Moneda Nacional, and the Convertible Peso (CUC). The CUC is roughly equal to the U.S. Dollar and is the currency foreigners use most. At current exchange rates, $1.00 USD equals $0.87 CUC. The CUP can be used by Foreigners and Cubans alike to purchase goods and services outside the tourism sector, and is valued at 24 CUP to 1 CUC.

Tip: The 3 CUP note and coin have a portrait of Ché Guevara on them and make for nifty souvenirs. They are often “sold” to tourists at inflated values as a scam. The value of 3 CUP in U.S. Dollars is 12.5 cents.

9) Average Taxi Fare in Havana is $6 CUC.
Negotiate cab fares up front and before you enter the car. A ride between La Habana Vieja and El Vedado should be about $5 CUC and a longer trip to Miramar around $7 CUC. No fare in greater Havana should be more than $10 CUC. The going rate to or from Havana’s José Martí International Airport is $25 CUC. When in doubt in Havana call a yellow government operated Cubataxi at 855-5555, and ask the driver turn on the meter.

10) Use Street Sense: Anyone who strikes up a conversation with “Hello My Friend, Where You From?” is not really your friend.
As a general rule anyone on the streets of Cuba who greets you using this phrase is a street hustler (JINETERO in Cuban slang). He hopes to somehow make money off of you, usually in the form of commissions paid by Casas Particulares and Paladares he’ll tout. If you adopt the right attitude, dealing and talking with Jineteros can be amusing. When the amusement wears-off, politely but firmly ask him to leave you be. If he doesn’t buzz-off, flag down the nearest police officer and “your friend” will disappear.

When it comes to protecting tourists and travelers on the street, Cuban Police are very effective and NOT corrupt (especially in comparison to other Latin American countries). In all other matters, however, like filing out paperwork for a lost passport, or a crashed rental car, put all your plans aside and expect mind-numbing hours of delay. Never try to bribe a Cuban cop. Period. ‘Nuf said.

Compared to all other destinations in Latin America, Cuba is very safe when it comes to violent street crime against tourists. Of course, there are always exceptions to the rule, so be cautious and use common sense.


Cuban Cigars, Havana

11) Assume That All Cigars Sold on the Street Are FAKES.
For travelers to successfully buy real brand name cigars on the Black Market is practically impossible. I repeat: All cigars you can buy off the street are F-A-K-E! And the cigars that your driver, tour guide, or new friend whom you met on the Malecón wants to sell you and swears are real, aren’t. Even if the box looks perfect and has the seals and everything. If you want real Cuban cigars, be prepared to pay handsomely for them, and only buy them from a Casa de Habanos, the official brand name of the Cuban Government cigar stores.

The most convenient place to buy cigars to take home to the U.S. is in the duty-free store in airport the departure lounge. They have all the popular brands and sizes, and you don’t have to lug them around your whole time in Cuba. U.S. travelers to Cuba may import to the U.S. up to 2 liters of Rum and up to 50 cigars for a combined total value of $100.00 USD.

All that being said, scoring cigars off the street can be a fun “clandestine” adventure. And they can often be good smokes. They’re still Cuban cigars, just not $400 Cohibas. If you decide to go for it, exercise common sense: be careful; bring a buddy; and assume what again?… that they’re not the real thing (no matter what the Jinetero selling them says). Spend only as much as you are comfortable LOSING. Around $25.00 per box is a good price.

12) Smile, Have Fun, and Dive-in deeply.
You’re visiting one of the liveliest, most fascinating places on the planet. Keep a positive adventurous outlook. If you want to dance in the streets with a group of Rumberos you stumble upon, then shake your booty – even if you don’t know the steps. If you want to discuss Proust over a game of chess with an old man in the park, have at it. And if you want to dive into the water off the Malecón seawall go for it (just be sure you jump where the Cubans kids do – where the water’s deep enough).

That’s all for now.

Feel free to contact Tony via ARTempoCuba or Havana VIP Tours with any questions you may have about travel to Cuba.


  1. Thanks for the info, it needs periodic updates, otherwise it could be very misleading, nevertheless, somehow, helpful!

  2. THANK U SO MUCH, Tony at Cheapair! This information is invaluable because its HONEST, whether the info u benefits Cheapair directly, or not! But, I guess, even indirectly benefits, too, bcuz I found this looking for Cuba travel info! But, now, cant wait to use Cheapair…so, new business! BIGHUG

  3. I am a solo traveler and want to travel to Cuba December or January or February, 2018. What if I book and then the current government tightens restrictions again? What would happen to monies spent? Do you have any single groups going to Cuba?

    • Hi Deena, That is an very interesting question. Should the U,S, government restrict travel to Cuba again, the airlines will certainly be obliged to return the monies to travelers. I would assume that this would come in the form of a refund or credit of some kind.

  4. Hi ,
    My husband and I are traveling to Cuba at the end of the month. We have dual citizenship, Brazilian and American. Which passport should we present at our arrival in Cuba?
    Thank you

    • Hi Silvana, It honestly doesn’t matter to the Cuban authorities. If you are returning to the U.S. on U.S. airlines, you should be prepared at Customs & Immigration to discuss your trip and let the authorities know which of the “12 reasons” your travel to Cuba was covered under. Many people are not questioned about their trip at all, but at the moment these relaxed rules do not allow for leisure travel and even travelers from other countries must be compliant to the restrictions when traveling on U.S. air carriers.

  5. Hi Cheapair, thanks for all your answers above, but I am too anxious. We are a Turkish family travelling to Cuba through the US independently. What exact documents are required at the airport in America? As we have special passports, we are exempt from visa to Cuba. I know a People to People travel affidavit is required. And a full time itinerary also?

    • Yes, it would be a good idea to keep a record of your visit as well as receipts from your activities. There is no “affidavit” required. These reasons for travel are all “licenses” on the honor system (so, in fact, you have no paperwork – you must self-identify).

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