The 10 Things You Must Know Before Traveling to Cuba (Part 2)

With the death of Fidel Castro in November 2016, President Obama’s recent groundbreaking trip to Cuba in March 2016, and the gradual relaxation of travel restrictions to the country, for the first time in over 60 years, Americans can realistically think about visiting Cuba for a number of reasons. But what are the important things to know and prepare for before visiting this gorgeous, historic, and Communist Caribbean island nation?

Street life in Havana, Cuba

A street vendor in Havana, Cuba

(Continued from The 10 Things You Must Know Before Traveling to Cuba)

6. Know what is a tourist scam and what isn’t a tourist scam in Cuba

Partagas Cigar Factory in Havana, Cuba

Buying Cuban cigars directly from the workers at a Havana, Cuba factory (like this one) is WAY more reliable than street-bought cigars!

Especially if this is your first time traveling to Cuba, or your Spanish skills are less than conversational, you’re likely to have a huge “sucker” tattoo written all over your American/tourist forehead. Sometimes it’s hard to figure out what is actually a scam in Cuba, and what’s actually legit.

An excellent deal on Cuban cigars sold by some local Cuban in the middle of a street or an alley? SCAM…Almost definitely they are fakes. Buying cigars from workers directly inside the factory, who are trying to make a few extra CUCs on the side? LEGIT…Each worker gets 5 cigars (a week I think) as compensation for their pretty horrible salary, and basically everybody sells them to make side money.

Getting brought to a must-see local bar or restaurant by a helpful local in the middle of Havana? SCAM…These touts are all over the streets of Havana, and get a cut/compensation for bringing in random parties, and this extra fee is often added to your bill as their commission. Plus the place will often have overpriced and lousy food and drinks. Making reservations days or weeks in advance on the phone in order to get to eat at that paladar you’ve heard so much about? LEGIT…(See Survival Tip #3 here). Also, make sure you check the bill when you get it at the end to make sure a lot of extras haven’t been added on, as sometimes happens in less reputable restaurants.

Flea market in Old Town Havana, Cuba

A lot of the cigars, art, and knick-knacks in the streets and markets of Havana, Cuba is vintage, but isn’t worth what you might pay…Do your research!

Finding a super friendly and romantically-inclined Cuban girl (especially in the bars/clubs/nightlife) or guy who wants you to get them into the club/restaurant, marry them, take them home to your country, etc.? Ummm…SCAM!!! #CaptainObvious. Most local Cubans can’t afford the entrance fee/cover for a lot of clubs or even the cost of drinks inside. There’s unfortunately a fair amount of Cubans who will basically offer a whirlwind Cuban romance and their body for the chance at a green card or a way out of the country. But a lot of them are essentially prostitutes/gigolos (or “jinteros” in Cuba).

Just keep your wits about you, be aware of anybody trying to offer something for way too cheap, and make sure you do whatever bargaining you can for souvenirs, art, etc….although in my experience, Cubans are not as likely to drop the price of something 40-50% with haggling, like their Moroccan or Asian counterparts. Most times they will only take one standard street price, except possibly for taxis where you can agree on a price. Cuba is in general a fairly safe country, except for minor petty crime, stealing, pickpocketing, because trust me, nobody…I mean, nobody…wants to end up in one of Castro’s prisons in Cuba!

7. Explore outside Havana if you have more than a few days in Cuba, but prep for transportation and lodging issues

La Melia Americas resort in Varadero, Cuba

The gorgeous entrance to the beach from the La Melia Americas resort in Varadero, Cuba

Havana steals all the history, praise, and beautiful pictures in Cuba, but it’s definitely worth getting out of Havana if you have the time. It’s a fairly large country, about the size of Virginia and with about 3 million people. In general, you can see a lot or most of Havana in 3 or maybe 4 nights max, so if you go for more than a week, you should take the chance to explore outside Havana somewhere.

A lot of tourists visiting Cuba end up trying to go to Varadero, which is a famous beach resort area just about 2 hours east of Havana. This is the beach playground of the rich and famous, sort of their version of Cancun. Although you can find casa particulares to stay at, most people stay at a variety of all-inclusive resorts, where for something like $150-$500 a night per person (depending on how nice a resort and suite you have), you have access to a huge beachside resort, with unlimited food and drinks. You get your choice of many different types of restaurants and buffets (TIP: Make reservations for these restaurants early to make sure you get the time/restaurant you would like). In general, stay away from ethnic foods like Japanese/Chinese/Asian; their Italian, American, western food is way better. We stayed at the Melia Las Americas for 2 nights, for about $150/pp a night (with 3 of us in a 3 person/3 twin bed suite for $450 a night), and it was a fairly decent experience, you can read my review here.

The beach at La Melia Americas resort in Varadero, Cuba

The best AirBnBs, resorts, and accommodations in Cuba will get booked very quickly…Plan and reserve in advance!

Even things such as beach chairs/umbrellas, kayaks, salsa and dance classes, and social activities (TIP #2: Reserve your all-inclusive Varadero resort early, they tend to sell out especially during peak months/weekends. Also, make sure to get down early in the morning to claim the best beach umbrella/chairs for you and your friends/family; people tend to come early and leave their towels there all day long, and at some point shortly after breakfast almost all of them tend to be taken. Remember to tip your servers for things like your unlimited drinks at the bar, it’s just common courtesy and means a lot to their salary…It’s got to be hard for your average Cuban worker to be surrounded by rich foreigners and sugar daddies with their 20 y.o. European girlfriends as they spend 15 – 50x your weekly salary in one night just to get a tan and get drunk. Just keep that in mind.

But if you talk to locals, most of them will tell you that they absolutely hate Varadero, because it’s just super overpriced and not authentic. Most of them will describe the coffee farms, gorgeous countryside, and stunning caves of Vinales as a must-see, and our two sets of friends who went the same time as us and visited there whole-heartedly agreed. . Other destinations, such as Cienfuego and Santiago de Cuba, are must sees if you want to see something else besides Havana and the beach resorts of Varadero. Just keep in mind that you’ll have to organize transportation through a private driver/cab or private transportation buses. A 2 hour taxi ride to Varadero costs about $90 CUC for the entire taxi, and it’s worth it if you have 3-4 people in your group. If you are traveling alone or with one other person, you can take Viazul buses between major towns, which are air-conditioned, comfortable, and slightly more cost-effective than a taxi. Car rentals are an option, but not that recommended, because again the car rental agency infrastructure in Cuba is just extremely poor, limited, and pretty pricey.

8. Make sure you have good offline Cuba guides, maps, advice, books

Old Town Havana Cuba Plaza

Having a good offline guide and map for Havana and Cuba will make all the difference for your trip!

The poor communication/internet infrastructure doesn’t help out with looking stuff up online in Cuba either. I highly suggest getting a well-written guide book for traveling to Cuba, because unlike other countries where you can look stuff up on TripAdvisor, Yelp, or just Google things, you’re going to realize that you may have no idea where you are, how to find something, and how stuff works in this country without a little offline help. And it’s really really difficult to get on the internet easily to just look things up.

The #1 thing I would do is get a well-written and reliable hard-copy of a guidebook. I highly recommend the Havana guide book by Moon, written by Christopher Baker. It’s supremely detailed, has a lot of insider info on how to survive in the country, restaurant/paladar recommendations, and tips on how to prepare during your trip to Cuba. While it doesn’t cover a lot of things outside Havana, it’s epic for surviving inside Havana on a short trip, like on a cruise stop-over or weekend vacation from Mexico or the U.S. I also got a chance to look at the Top 10 Havana guide book, in the DK series. Normally, I like this series of guidebooks for other cities and countries, but it’s pretty haphazardly written and not very helpful; Christopher Baker’s guide books are way way better and probably the best offline tour book about Cuba to get. Better than Lonely Planet or Top 10, in fact.

The #2 thing I would do is to download an offline copy of a guidebook as a backup, specifically TripAdvisor for Havana and/or Google Maps for Havana. Hell, do all of that, so you have multiple off-line maps and info as back-up! You’ll use TripAdvisor more for numbers and restaurants, and Google Maps more for directions/addresses and a searchable map as you walk around Havana. As in Morocco/Marrakesh, having an offline map, filled with restaurants/nightlife/sights you have bookmarked/saved, will make all the difference in not getting lost and finding your destination. You’ll have a wonderful, stress-free trip to Havana where you don’t get lost and you don’t waste time. Remember, you basically will never have internet your entire trip!

9. Find a local guide in Cuba instead of a normal group tour guide, especially if you need transportation

Fabrique de Arte Cubano in Havana, Cuba

Talking to the locals and cab drivers will help you find great local nightlife, like this underground art and live music venue (Fabrique de Arte Cubano)!

Especially if you are somebody that doesn’t speak a lot of Spanish, it’s way more worth it to try to find a private local tour guide who can also double as a cab driver around the city. Your typical tour set up through a hotel will cost about $20-$30 CUCS per person, and is usually a 3-4 hour affair that takes you on a drive of the Malecon and Miramar/Vedado, a stop at the awesome but fairly empty Plaza de Revolucion, a rum factory or outlet, and maybe a walking tour of old Havana. A lot of times the tour is bilingual, and they tend to speak way more Spanish than English, so you may leave the tour feeling kinda underwhelmed. They really don’t give you much more information than what is written in most tour books. But for the same price, if you have 3-4 people in your group, you could probably hire a local who can give you a much more personalized and one-on-one tour of Havana and drive you all around in a cab.

If I could do the touring of Havana and Cuba all over again, I would probably just have found and hired a private Cuban tour guide through TripAdvisor forums or word-of-mouth to take my group around. It would have been a way better use of time and money in Havana. I would say that if you had 3 or 4 days in Havana, you should consider hiring a local tour guide for at least one of those days in the beginning to get a more authentic experience. You can basically do this in each area or local city of Cuba you visit; again, the main challenge is finding someone who speaks enough English for you and who is reputable for the right cost.

In addition, if you are visiting another area of Cuba outside of Havana and decide to rent a cab, feel free to quiz the cab driver on all aspects of Havana, the other city you are visiting, the countryside you are going through, and life in Cuba. Some of the most interesting and educational stories I heard in Cuba came from these cab drivers. You already hired them for the ride, you might as well get some great insider local information from them!

10. Ensure a good back story for your 12 reasons to visit Cuba if you are American, in order not to have a problem with customs coming into Cuba or returning to the United States

Havana Cuba Airport Check-In Counter

Is it legal to travel to (and from) Cuba? Basically, Yes…And No! Read below!

Officially, tourism from America is still considered illegal and there are travel restrictions. But practically, nobody really cares, and there is probably a very minute chance you will get charged or fined for doing it. In a legal sense, you are legally allowed to travel to Cuba, but you’re not supposed to spend any money there. It’s kind of bizarre, antiquated, and with all the recent attention with American cruise ships coming, President Obama visiting recently in March 2016, it’s going to get a lot easier to travel to Cuba as an American citizen. Now, with President Obama’s blessing since the end of 2014:

– You don’t have to get pre-approved license to visit Cuba as long as you “fit” under one of their 12 general use license reasons
– You can now use U.S. credit cards and ATM cards (although I still think it’s way easier to bring in Euro in cash and exchange for CUCs for practical reasons, since most places in Cuba really run on cash)
– You can legally bring back up to $100 in Cuban rum and cigars and $400 in Cuban goods total

Although your trip still has to technically qualify under one of 12 general use license reasons, you no longer have to get pre-approved. And a bunch of the reasons are super vague and would work for almost every tourist, with a little bit of preparation. The official list of allowed reasons for travel are: (1) Official governmental travelers (2) Journalists (3) Full-time professionals who are doing non-commercial, academic research in their field or are attending conventions or programs in their field, and have a full schedule of non-tourist activities (4) Visiting Cuban relatives (5) Faculty, staff, and students of an accredited US undergraduate or graduate program traveling to Cuba for educational activities (6) Religious activities under a religious organization (7) Humanitarian projects that benefit the Cuban people (8) Activities that provide support for the Cuban people, as a part of recognized non-US government human rights and charitable organizations (9) Public performances, including concerts, clinics, workshops, athletic games, and exhibitions (10) Activities of private foundations or research or educational institutes (11) Export, import, or transmission of informational materials (12) Certain export transactions that are authorized under existing regulations and guidelines for visiting Cuba already.

Building ruins in Old Town Havana, Cuba

Going on an official tour to “study” Cuban architecture is a legitimate way to visit the country…But there are much easier ways!

So that all sounds pretty confusing, but here’s basically what you need to know: Anybody, and I mean literally anybody, can go to Cuba now…as long as you don’t do a few stupid things, which I’ll list later. Almost everybody qualifies for some reason to go to Cuba. For example, I went under a combination of reason (2) and (3), since I’m an official, published travel and food travel guide author and I laid out a full itinerary of restaurants, nightlife, and interviews I was going to as part of my “research” for an eBook I may or may not be writing eventually about the Cuban nightlife, food, and travel scene. Pretty convenient, right? 😛 Another girl I know, who just Instagrams travel pictures and has a big following went under the same reason with her mother, and they had no problems getting into or out of the country.

I had another friend, who was a doctor, who didn’t even go for medical professional reasons but just went in February 2016 when the Rolling Stones gave a free public performance and concert, which qualifies under reason (9). So basically if you find a good free public concert, art exhibition in a gallery or museum, dance performance, or heck, even a good baseball game or sporting event you want to attend, you legally qualify! That’s all it takes. Another old college buddy went more than 2 years ago in 2014, under reason (3) by just saying he was doing research into possible business investment, after hiring a local Cuban to guide him around Cuban cigar and rum factories. No problems getting into and out of customs also. In fact, out of everyone I’ve talked to who has visited Cuba as an American in the last 2 years, which is over 10-15 personal friends, nobody had any difficulty at all!

Getting into Cuba is simple. You’ll usually fly through Mexico City, Cancun, Panama City, or Montreal, or some city in another 3rd country, which is likely to happen for you until more direct flights are set up through U.S. airlines by the end of 2016. Search for flights on, because some websites like, won’t show results for flights to Cuba yet. Same thing with lodging, as websites like will show listings and lots of availability, but not places like or When you check into the first leg of your flight at whatever U.S. airport you take off from, you’ll have to sign the attestation form and pick one of the 12 reasons you are using to qualify.

Entry Visa for Cuba

The entry visa for Cuba costs only $20 and is bought at your departure (or layover) airport gate…You might not even get your passport stamped!

Then at your stopover, you need about $20 US to buy a entry/exit visa into Cuba at the check-in desk for your 2nd leg of your flight; I did it at Panama City airport, and it was no problem. Just fill it out before Cuba, and show it, along with your passport, to the customs officer at customs in Havana. If the Cuban customs guy is nice, he’ll ask if you want the passport stamp on your US passport or on the separate entry/exit visa paper. Some people don’t want it because they think it’ll help them avoid detection of going to Cuba, which is not true. I didn’t care since I had a legitimate reason to go to Cuba, and a stamp from Cuba on the passport is pretty bad-ass! 😛

You’ll need to show the exit visa on the way out of Havana, and then the bigger deal/more scrutiny will come when you are enter the US again back from Panama/Mexico/whatever third country you flew into. Even if you don’t have the passport stamp from Cuba in your passport, a good vigilant U.S. customs official will know you have been somewhere. This is because you will potentially have an entry and exit stamp from a country like Panama, Mexico in your passport from their customs and they will want to know where you have been to in the meantime.

Just don’t lose your cool during this process and you will be fine. The most important thing is that you don’t under any circumstances tell anybody in Cuba or while returning from the U.S. that you are coming just for tourism. Use one of the 12 reasons listed above, whichever one works best for you, and have a good story for it. That’s all it takes. The U.S. customs official didn’t blink an eye or even ask about Cuba on the way back for me.

I was, however, asked by a Cuban airport guard/customs person why I was there, and he asked “Are you here for tourism?” which of course I replied “No” to. I had a feeling that if I had said “Yes”, I would definitely have been questioned more or pulled aside. I had all my business paperwork, a pre-written out “Cuba eBook Travel Book Research” itinerary printed out with address, phone numbers, and schedule to show it wasn’t all tourism, etc., so I felt safe!

Also be careful about import/export rules to not get in trouble when you leave Cuba or enter the U.S. That includes how much cash and money you can take into and out of the country, as well as how much in cigars/rum or goods you can take into out of the country (e.g. $100 for cigars/rum in total, and $400 for all other goods; no valuable works of art, etc.)

Old Town Havana, Cuba

Gorgeous 1950’s automobiles…Slowly decaying buildings…Old Town Havana, Cuba is like something out of a time-warp. You have to visit!

In the end, I can’t tell you whether you individually can or cannot take the risk of going to Cuba. That is a both a moral, legal, and political decision you have to make for yourself. I’m just saying that the risk of being charged or caught for something as an American basically doesn’t exist anymore, if you plan it out carefully and have a legitimate excuse or reason. You don’t need to apply for a special license anymore, and you just need a good story, so it’s way easier.

Enjoy your trip and happy traveling…Que Bola!!!