Cuba, oh Cuba...what a place. The colors, the scents, the nature, the art, the people! But don't get me wrong, it takes a few minutes (or days) to get acclimated, though once you do—it will be the adventure of a lifetime. If in most places around the world light, pre-trip research would suffice. When it comes to Cuba I actually recommend a more in-depth preparation that includes saving info offline (your phones "notes" would work), and maybe taking some screen shots. While it is not as bad as some describe, Internet is still not easily available in Cuba and therefore having information about what areas of Cuba you want to explore, transportation options, money practices, Museum addresses and hours, restaurants, etc. will come extremely handy.

Traveling to Cuba with an American passport is a bit different. Let me start by saying that it is NOT AN ISSUE at all, super easy. However, it is very helpful to be prepared in advance. Here you will find all the information that you need to know—READ: information that is hard/impossible to find online or elsewhere. You're welcome.

IS IT LEGAL FOR AMERICANS TO TRAVEL TO CUBA?

Many Americans are still having a hard time figuring out whether they may or may not travel to Cuba, and you can't really blame anyone. The current regulations and process (as of December 2016) are vague, to say the least. Luckily for you, we (and many other American travelers) went through the experience first hand and are back to share it with you. So, is it legal to travel to Cuba? The answer is YES, but with a "catch". From the U.S. Embassy in Cuba website: "Travel to Cuba for tourist activities remains prohibited by statute". However, the Department of Treasury’s Office of Foreign Assets Control (OFAC) has issued general licenses for 12 categories of travel. Here is the LINK to the U.S. Embassy's site.

Now, it is very IMPORTANT to understand the following:

The 12 categories vary from journalistic activity (which we chose based on our travel site), to educational activity, religious activity, humanitarian activity, etc. As you can tell, those are very open to interpretation. Anyone can find a category that is relevant for them.
Note that the only time you will be asked for the category that you are traveling under is when you book your flight online. Other than that no one asks, no one cares, no one checks. Not when you leave the U.S. to fly to Cuba, not when you arrive in Cuba, and not when you fly back to the U.S.
I heard previous reports that Cuban immigration officers ask American passport holders if they would like to be stamped on the Visa card instead of the passport so they won't be asked any questions when getting back home. We weren't asked that, our passports were stamped, and we had ZERO problems.
We saw and met hundreds of American travelers in Cuba, even lots of families! So book your trip and have fun!

IS IT SAFE IN CUBA?

We never felt unsafe while traveling in Cuba. They also really love Americans and many times you will see American flags along side Cuban flags (like in most taxis for example). The only thing that is not safe in Cuba is drinking water. Always drink bottled water.

SHOULD I GO BEFORE TOURISM TAKES OVER?

Well, you should go soon, but not because of the tourism question. Cuba has been a hot traveling destination for years, so it's already quite "touristy". Tons of people from Europe, Asia, Latin America, and everywhere in between have been traveling to Cuba for a while. So, why should you go soon? Right now Cuba is still VERY much communist which makes for a lot of its magic. The life-style, the culture, the old cars, houses, stores, it will all change (not taking a side if for better or worse, it will just be different) in case politics will change. And to be honest, with Fidel Castro's recent death and his more "progressive" brother, Raul Castro in charge, plus the recent changes that the Obama Administration put in place, it smells like CHANGE is indeed in the air.

CAN I FLY DIRECTLY FROM THE U.S.?

Absolutely, yes! Unfortunately I think that 100% of the Americans we had the chance to talk to were too misinformed and booked flights to Mexico or elsewhere first and then from there to Cuba. Such a hassle (unless you spend a few days in Mexico for fun before flying to Cuba).

We flew direct from Miami to Havana with Frontier Airlines for around $100 each, and the flight duration was 45 minutes! No issues whatsoever. Many U.S. Airlines including JetBlue and American Airlines fly direct to Cuba.
It is important to note that as of December of 2016, the Visa cost is more expensive if you fly direct from the U.S. From Cancun, for example, it should cost you around $25 per person—while we paid a steep $100 each. It is worth mentioning that the cost may vary between airports and airlines, and to be honest, we got the sense that it's all quite new for the U.S. and that airlines are charging whatever they feel like at the moment. The best way to find out is to call and ask the airline before or after you book your flight.
PRO TIP: Most of the time you literally buy your visa at the check-in counter. This means that you will probably not be able to check-in online— even if you travel with only a carry-on, like ourselves. So what should you do? You should arrive at the airport early because the line is likely going to be longer than you are used to. Plus, make sure to ask an airline representative if you buy the visa to Cuba at their counter or elsewhere before you stand in line (or if you have a partner, one should secure your place in line and the other should ask). We flew Frontier and found out only at the counter (after 1.5 hours in line) that they want us to walk 10 minutes away to the American Airlines counters and buy our visas there.

The Cuban visa card you need to buy and fill out

IS THERE INTERNET SERVICE IN CUBA?

The answer is yes! But getting online isn't going to be as luxurious as you are probably used to. It also isn't free and will cost you about $4-$5 for one hour and twenty minutes. Here is everything you need to know:

Unless you are staying at a hotel, which you totally should not! (See the Accommodation section below), there is almost no chance that you will have Internet at "home".
Internet spots are usually at parks and hotels.
Hotels are usually pretty good with letting people hangout in their lobby for internet. Out of many times we hung-out in hotel lobbies, we were told only once that we had to be customers of the hotel or bar if we wanted to stay. So we bought a Mojito for $3, why not? ;)
It is ridiculously easy to spot a hot-spot based on the gathering of dozens and sometimes hundreds of people who are "glued" to their phones.
How to connect? First you will have to buy an Internet card that looks like this:

You can buy this card from an ETECSA center (their telecommunication company) or from any hotel's lobby desk. I recommend buying with the hotels, as those ETECSA centers always feature incredibly long lines of both locals and tourists and sometimes also run out of cards in the middle of the day, go figure... Note that the cost of a 1 hour card is about $2.5 at the ETECSA center and between $4-$6 at a hotel, depending on the hotel. But in my opinion it is worth not having to stand for an hour in line and risk the chance that they've run out.
The cards are advertised as "1 hour" but in reality give you 1h20m. I guess the extra 20 minutes helps to make up for the lost time when you try to logout and can't figure out how, or when the Internet service is spotty and your minutes are still counting down.
Interent service is not as smooth or as fast, but it works and you get used to it. Remember my recommendation of researching in advance and recording your findings offline? (Screen shots, notes, etc.)? Do it.
The card is pretty self-explanatory but here are some tips that will really help:

After you purchase a card, scratch of the designated area to expose your password and find a WiFi area (if you purchased at a hotel, the hotels lobby will have internet). PRO TIP: if anyone gets their hands (or eyes) on your username and password, they will be able to use your card—so be discreet.
The WiFi network that you are looking for is "ETECSA WIFI". If you can't find it, wait a few minutes and try again, or try moving around a bit.
Once you choose the network be PATIENT. A window with an ETECSA or NAUTA page will pop up and will ask you to enter your username and password. Sometimes you will have to enter it twice even if the first time was correct. Again, patience is a virtue in Cuba. But then, voila! You're logged in and the clock will start counting down from 1h20m. PRO TIP: To save time, prepare your Instagram photo and caption in advance, or anything else you plan to do online.
Troubleshooting: if you waited 20-30 seconds after choosing the WiFi network and the automatic window never popped up, try going to Safari or any internet browser you use and enter a random address like "www.apple.com". Hopefully the ETECSA page will appear in your browser. If that didn't work as well. Turn the WiFi off for a minute and then turn on and repeat the steps.
How to logout? This is much more cumbersome than it should be so again, patience. In some cases you won't be able to find the ETECSA page to do it. If you ARE able to find it, just hit the "Cerrar la sesión" ("Close session"). If not, turn your wifi off and on and check if you can still use the internet. If that doesn't work, turn your device off and then turn it back on. From there, check if you can still get online. Turning the device off and on should always work. I read in some places that entering the following web address (http://1.1.1.1) should take you to the ETECSA page where you can logout but it never worked for me.
NO. Two people can't login at the same time with the same card/user. You will have to buy two cards.

MONEY

What a topic! Cuba is probably the place where there is the most to discuss when it comes to MONEY! So, here it is:

There are two completely different currencies in Cuba. CUC (Convertible Cuban Peso) and CUP (Cuban Peso).
Both currencies are widely used, even by locals.
1 USD = 1 CUC. Easy, and don't worry, Cuba is still much cheaper than most western countries. A good accommodation will cost around $30 (30 CUC) or less, a mojito will cost 3 CUC, a good meal with drinks is under 10 CUC per person. You get the idea.
1 CUC = 24 CUP. Why not just use CUP? Isn't the CUC just "Tourist currency" and I won't I get screwed over? The answer is no. Not unless you plan on literally living like a local and buying only eggs and chicken from the markets without ever eating out. You will use CUC 99% of the time if not 100%. Even the locals use it. The restaurants, hotels, local accommodations, etc. everyone prices services in CUC, charges in CUC, and gives change in CUC.
IMPORTANT: American credit and debit cards will not work (as of December 2016) anywhere in Cuba. So be sure to take enough cash with you so you don't get stuck. Keep in mind that you don't have to exchange all of it. Just have it for an emergency.
Also nice to know: as of December 2016 (there are talks about it changing), exchanging USD in Cuba comes with an extra government enforced 10% fee. So if you have or can get foreign currency in advance it will save you some money. I believe the best currency to exchange there is in Euros, if you can get your hands on them in advance.
Exchanging at the airport when you land is easy. If you need to exchange again during your trip go to any bank but plan on spending an hour in line at least. Cuba has the local nickname, "THE COUNTRY OF LOST TIME"—as everything is very slow and laid back, and there is almost always a line.
IMPORTANT: If you do exchange money at a bank, make sure to bring your PASSPORT with you or else you won't be able to exchange.

MONEY SCAMS

Like anywhere around the world, you should get to know the currency and be aware of some common scams. With Cuba's dual-currency system however, things become a bit more tricky. A good way of telling the difference between the two currencies is to know and remember the following: CUC (higher value) = Monuments on the bill, CUP (lower value) = People on the bill.

Top: 10 CUC ($10), Bottom: 10 CUP (less than 50 cents).

So what should you be most careful of:

Paying in CUC and getting change in CUP (always check your change).
Paying in CUC and then being told that you paid in CUP (always make sure and be confident that you paid in CUC). Example: you will pay a taxi driver 12 CUC (10 bill and two single bills). He's sitting in the front of the car with his hands outside of your vision. He quickly switches your 10 CUC bill to a 10 CUP bill that he had ready in advance. He then turns around and claims that you accidentally gave him a 10 CUP bill. Unless you listened to my advice and were certain that you paid in CUC, it will be hard to argue. They will usually do it at night when it is more confusing and hard to see and most likely when several bills are involved in the transaction. You're welcome. :)

ACCOMADATION

The most popular accommodation option in Cuba, which I believe is also the best possible way to experience Cuba, are the CASAS PARTICULARES. What is a "Casa Particular"? It is basically a Cuban family's house that is licensed to rent rooms. It isn't fancy by any means but if "fancy" is what you seek, Cuba might not be the right choice in general. Here is why I believe a Casa Particular is the best option in Cuba, at least for now:

It is cheap ($20-$30 per night).
Most of the time you're allotted a private section in the house, with private bathroom and shower, towels, toiletries, and everything else you need for a simple, comfortable stay.
The hosts will make you breakfast and dinner upon request. It will be an extra cost (average of $5 per person for breakfast and $10 for dinner), but many times it is cheaper and even tastier than the restaurants.
You get to experience the life of a local first-hand AND practice your Spanish, which is worth money on its own!
The hosts will help you with everything you need, from recommendations of local restaurants and bars, to organizing transportation from/to the airport as well as other cities in Cuba, to setting you up with accommodations in the other cities, and sometimes even exchanging money for great rates! This is all priceless in Cuba where internet is scarce and you can rarely find or book anything online.
If there are multiple rooms in the house you get to meet other travelers and make awesome friends!
Hotels are usually really expansive (minimum of $200 per night) for lousy quality. The hotels are run by the government.
Is AIRBNB operating in Cuba? Actually it is. But the selection is currently limited and most of the time it's a little more expansive than a Casa Particular without all the perks of having a local host.
PRO TIP: Note that once you are in Cuba, you will not be able to book on Airbnb, some regulation prevents Airbnb from allowing you to book from within Cuba. You can still browse and then get in touch with friends or family in the U.S. or elsewhere to help you book if you have to.

How to find and book a Casa Particular?

We will share a few great options that we stayed at in Havana and Trinidad in this guide. You can also find a bunch of them on Trip Advisor and other websites and email the hosts (just google "casa particular Cuba"). Alternatively, if you are more adventurous, and travel light, it is not a problem to arrive in Cuba and find one instantly. Ask locals around and look for this sign:

TRANSPORTATION AND NAVIGATION

I believe there are two international airports in Cuba but you will most likely land in José Martí International Airport (HAV) in Havana. It is about 30 minutes from the center of Havana or Habana Vieja (old town). If you booked a place in advance, ask them to help you with transportation from the airport and provide them with your flight info. It might be a little more expensive ($30 vs. $20-$25 if you negotiate upon arrival), but it might be worth the "smooth landing" for the first time.
Remember to have the address of your accommodation handy offline, as you will not have internet.
SUPER PRO TIP: download offline maps of the areas you plan to travel in (Havana, Viñales, Trinidad, etc.) on the Google Maps App. Click HERE for instructions. If you can't find the download button, just tap the menu button on your Google maps app, choose the third option ("Offline Areas"), hit "Custom Area" and zoom out and scroll to the area in Cuba you would like to have available offline and hit Download. If you get a message that "the area isn't available offline", zoom out a bit. It should work. What does having an offline area mean? It means that you will be able to see where you are and navigate even without internet connection. Your GPS (that blue dot on the map) works even with Airplane mode turned on and cellular data turned off. Furthermore, you can find museums, restaurants, internet spots, bars, etc, in advance on Google maps and add flags known as "labels" (here is how) and that way you will be able to navigate to those places even without internet. Still have a question? Get in touch and I will help. :)
Generally however, I recommend having the exact addresses of the stores and restaurants you want to visit in Cuba handy. Online map locations aren't always accurate in Cuba.
For your flight back, get to the airport early. Locals recommend at least 3 hours in advance and I recommend even 3.5 hours to beat the rush of people coming 3 hours in advance, it will pay off. Remember reading that Cuba is the "Country of Lost Time"? Just trust me and get there early.
Taxis in Cuba can be a bit pricey in comparison to other things. They are around $10 to move around areas in Havana. SUPER PRO TIP: An awesome "secret" that not many know is the "Collectivo" Taxi service in Havana. If you can speak some Spanish and don't mind riding with locals, it is a great and extremely cheap option. What is this Taxi Collectivo? Taxis that drive back and forth along main streets and pick up and drop people off along the way upon request. The cost is set and it is 10 CUP per person, don't let anyone tell you otherwise. If you don't have CUP (local currency), it is 0.5 CUC per person (that's 50 cents!). So how to do it? Stand on the street and flag your hand for a taxi like you would in NYC. You can also see other locals flagging for taxis. Those "collectivo" taxis are usually the old classic cars you see in photos or the movies. When the driver stops for you, ask "collectivo?" and tell him where you want to be dropped off along the way, if it makes sense with his route he will tell you to get in. When he drops you off just hand the 10 CUP/0.5 CUC and leave. Do not ask how much! The price is set.

Transportation between cities in Cuba:

Best way in my opinion is again "Collectivo" taxi service. It is a bit different than the city ones I described above as this service will pick you up from your casa/hotel and drop you off at your casa/hotel in the next city. It is called collectivo because you share the ride with other travelers. This is an awesome way to meet new people! We made tons of friends.
Your host can help you booking this taxi service.
The cost from Havana to Trinidad, or the other way around (about a 4 hour ride) is around $30 per person. To put things in perspective, same car and same ride only without the other travelers (private) would cost you around $160.
The cost from Trinidad to Viñales, or the other way around (about a 6 hour ride!) is around $40 per person.
The cost from Havana to Viñales, or the other way around (about a 2 hour ride!) is around $15 per person.

LANGUAGE

To be honest, Spanish is really helpful in Cuba, as most people don't speak English and most restaurant menus are exclusively in Spanish. It doesn't have to be perfect Spanish though (ours isn't)! If you speak zero Spanish don't worry, many travelers don't and do just fine. Hopefully you are open to learn, laugh, and use some body language. :) Here are some tips that can help a lot:

Take a few Spanish classes in advance (nothing fancy), an app would do. I highly recommend Babbel. You can also download classes and continue learning offline in Cuba! With Babbel you do have to pay a little for a subscription but it is worth it. This app is really awesome and took my Spanish to the next level! If you are looking for a free option, Duolingo is also great.
Download the Google Translate App and then be sure to download the offline Spanish dictionary in advance. You will be able to translate even without internet! Here is how.
Be patient, positive and keep an open mind. Find the fun in miscommunication. It's bound to happen.

NETFLIX

As you may know, Netflix now has an option of downloading movies and series for offline watching. Best thing ever for flights and countries with no internet! :)

CIGARS

Many people will try to sell you cigars on the street. It is illegal and most of the time those are fake and are made with banana leaves or other ingredients that are not tobacco. Best way to buy cigars accompanied with an amazing experience? Visit Viñales where all the tobacco farms are at. You will get to meet the farmers and learn about the process first hand, and smoke hand rolled cigars (sometimes dipped in honey or whisky, which is an amazing tradition). They will also sell the real deal for about $3 a cigar (instead of much more elsewhere). Usually they will have a minimum purchase of about 20 cigars. They say it is legal to come back to the U.S. with up to $100 worth of cigars per person. You can learn more about Viñales below.

RUMORS

If you heard online or elsewhere about there being an "Exit Fee" or "Tax" at the airport when leaving Cuba, don't worry there isn't. There may have been in the past.
Another thing we heard is that Cuba requires proof of travel insurance prior to entering. While we do always recommend travel insurance (we use WorldNomads), no one asked us or anyone else for insurance at any point.

WHERE SHOULD YOU GO IN CUBA?

We spent 11 days in Cuba, starting in Havana for 3 nights, then Trinidad for 3 nights, from there to Viñales for 2 nights and then back to Havana for the last 2 nights. It worked pretty well. If you are into some Caribbean beach time then be sure to visit Varadero as well. We spent a full week at the beach in Turks & Caicos prior to arriving in Cuba so we skipped Varadero. Click on an area below to learn where to stay, what to do, where to eat, and more!

Havana

Trinidad

Viñales

Viñales, Cuba

Where to stay

Where to eat

What to do

How to Travel to Cuba: A Guide for Americans (and everyone else)