International travel always requires preparation, but if you are going to Cuba, there's a little more to consider.
before you go
Check visa requirements based on your country
Get cash - Cuba primarily does business in cash only
Download maps.me and country map, save destinations beforehand
Download a full spanish english dictionary on your phone. If you don't speak spanish it's essential to have a full dictionary available offline. I speak Spanish, but in a pinch I use Word Magic ($4.99 in the App store).
Pack sunscreen, bug repellent, toiletries, and hand sanitizer. These things can be hard to find and are overpriced.
So you're a US citizen?
As of November 9, 2017, Trump's new restrictions on travel to Cuba take effect. What this means for you is that you probably cannot travel individually to Cuba and must go through and officially licensed tour group. Additionally, there is a list of hotels, restaurants, and stores Americans are banned from attending. Proof of all transactions is required.... but business in Cuba is largely done in cash and American bank/credit cards will not work there....so good luck with that.
IF YOU BOOKED PRIOR TO NOVEMBER 9, 2017: (accommodation or airfare) these rules will not affect those reservations and you can continue to Cuba by your damn self. This is due to the previous policy under the Obama administration, when restrictions were lessened for US citizens traveling to Cuba. You were permitted travel under one of 12 general licenses that did not need preapproval. Under the 12 approved reasons established during Obama's campaign, anyone could travel under Education - People to people exchanges or Support for the Cuban people. Trump has removed these 2 allowances, however the other 10 still exist.
10 of the 12 allowances for traveling to Cuba still stand, meaning if you have family there, or are going for research for example, you do not need an officially licensed tour operator. (Lucky!)
Visa - Easiest way to get this is at the airport during check in. With JetBlue it cost $50.
Health Insurance - Mandatory, but usually included in flight cost. Your boarding pass typically serves as proof of insurance.
Your credit and debit cards will not work. Do not try to use them. Do not notify your bank of your trip or they may lock your account. Withdraw enough euros in the US to sustain your entire time in Cuba. Why Euros? Read on.
If you're American, the most important thing to know before going to Cuba is that your credit and debit cards WILL NOT work. You will need to withdraw enough cash to sustain your entire trip. If you exchange American dollars, you're losing an additional 10%. If you exchange at a hotel they will add more fees on top of this (typically 3%). I went to my bank a few days before and withdrew euros, then upon arrival in cuba converted the euros to Cuban Convertible Pesos (CUC) at the airport. In the Havana airport there are multiple places to change money. When I was there, the 2 exchange counters upstairs, inside the airport would exchange money from the cuban local currency to foreign, and the 2 outside, downstairs (exit the main doors and there is one to the left and right) changed foreign currency to cuban currency. I'm sure this fluctuates as some of the counters are closed at times. If you have trouble finding one, just ask for Cambio de moneda.
Book your accommodations online and pay with credit card if possible to decrease the amount of cash needed while traveling. We budgeted about $50.00/person/day in cash, however if you are interested in doing any pricier excursions, research the price beforehand and add that in additionally. There are 2 currencies accepted in Cuba, the Cuban Convertible Peso (CUC) and the Cuban Peso (CUP). You will primarily use CUC, but CUP is also accepted and its helpful to understand the conversion rate.
1 USD = 1 CUC = 25 CUP
Tourists typically use the CUC. If a price is listed in CUP you can still pay in CUC, but just be aware for the conversion when paying and receiving change. We ate at a few places who used CUP and I typically didn't see other tourists there and the food was cheaper (and better).
What if I run out of money?
If you are from the US and you run out of cash, it is possible to have someone you know in the US send money via Western Union, but only to a Cuban national. If you are staying in a casa particular, you could ask the host if they would be willing to receive and pick up funds for you. There is also an agency called Asistur that aids travelers with this for a fee.
Crime rates are low and Cuba is a generally safe country, however it's important to realize the average monthly salary is 20 CUC. Just like anywhere else, don't leave your belongings unattended in public and lock your valuables in the room in a safe or your luggage. I have heard of a common scam where someone befriends you in the street and suggests you get drinks together, which you will inevitably pay for, and for which they will receive a commission. This was not my experience - I only encountered the expected tourist price hikes. The best way to avoid price gouging is to research expected prices before you go or to ask a local what the service should cost. Additionally, always agree to a price before taking a good or service. Often a local would tell me a taxi ride would cost 1 CUC and someone would try to charge us 5 CUC. You should expect to pay a little more than the locals, but if you are over quoted it is perfectly acceptable to haggle. If they won't negotiate, let them move on- they'll likely turn back around for you or someone else will come along who will agree to a fair price.
A taxi from the airport to the city center costs about 20-25 CUC. If you plan on venturing out of Havana (I highly recommend it), there are 3 main ways to do this. Always add a few hours to every road trip and be sure to plan to arrive in your departure city the day before departure, because you'll probably break down at some point. Don't get irritated, just expect this is an expected part of the journey through Cuba (the one downside to so many badass classic cars).
The viazul bus line is used by both tourists and Cubans (more tourists in my experience), and is typically the cheapest option. If you don't speak any spanish this is a good option as the itineraries and prices are listed and you don't have to worry about haggling for a fair price or explain where to take you. Its easy to look up the location of the bus stations on maps.me to find where it is in relation to your casa or hotel. If possible, buy your tickets a few days in advance, they tend to sell out in high season.
Typically will cost a little more than a bus ticket, but always faster (unless you break down) AND they will take you right to your destination (remember to save it on maps.me!). The easiest way to find a colectivo is to ask the host of your casa particular and they will always know someone providing this service who can pick you up from the house.
A private taxi will cost the most but will be the fastest and most comfortable. Taxis typically charge per person and never use meters. As a tourist you will likely be over quoted on price and it is common to haggle. If you know what it should cost, then just offer up front the amount you have and see if they will agree. ALWAYS agree on price beforehand, and clarify whether the price is for the entire car or per person.
Where to stay
During your stay in Cuba, your options for accommodation include hotels, resorts, and casas particulares. Resorts are only options in certain areas and will be your most expensive. Hotels are also expensive in Cuba and generally overpriced for the amount of luxury provided (remember most of the infrastructure is antiquated). I recommend staying in a casa particular. Some are available on AirBnb, with the added benefit of paying ahead. Be aware that usually the people you correspond with on AirBnb are rental agents and do not actually live in the house, they just handle bookings for the hosts the house. There are also some listings for the entire home, without hosts in house.
Didn't book in advance? It is not hard to find people on the streets or outside bus stations, advertising their homes for arriving travelers. You can also just go door to door of those advertising rooms for rent. Every host we had was friendly, trustworthy, and very helpful. Whether we wanted to go horseback riding or find a colectivo for the next day, our hosts always hooked us up. They also cooked some of the best meals of our time in Cuba, prices ranging from free - 10 CUC.
Spanish is pretty much necessary. You will find more english speakers in havana but it's still essential to know a few phrases to get around.
If you're female, the Cuban men WILL holler at you. Unless you are in the company of another male, expect to get many compliments and kisses blown your way.
Traveler SIM cards are available to rent in cuba, but they are expensive and don't offer data. its best to put your phone in airplane mode and purchase wifi cards to use at public internet sites (typically public parks or hotels). The cards can be purchased at Etecsa centers and passport is required. You can purchase one hour for 2 CUC or 5 hours for 10 CUC. I've heard there is a limit to the number of cards you can purchase and lines are often long, so its best to buy the 5 hour card. Scratch off to find the username and password that you will enter into the screen that pops up once you connect to the etecsa network (it may take a while).
If you're going in high season (December to April) - I recommend booking accommodations in advance and expect to pay a little more during this time.
Dry season is November - April, hurricane season is June - November.
Always have a stash of TP on you while traveling in Cuba. Toilet paper is not available everywhere. if you forget there may be a bathroom attendant you can tip for some.
You cannot drink the tap water in Cuba. Remember to include this in your budget - 1.5L bottle typically cost 1.50-3 CUC.
It is standard to tip 10% with meals unless a service fee is included.
The best way to plan excursions is to ask your host. There are also agencies, such as Cubatur, that can arrange these as well.