For the average American, travel to Cuba is still restricted (as of Feb 2016). To my knowledge, the easiest and cheapest way (and the method adventerous Americans have been using for decades) is to enter Cuba from another country. Most Americans enter through Cancun. Simply purchase one regular ol' ticket to CUN, then a seperate ticket (most likely on a different carrier) from Cancun to Havana. We chose to fly through the Cayman Islands, as we wanted to stop over there for a few days. Really, any other country works. When you depart from your gateway country, you must purchase a $25 USD Cuban visa at the airport checkin counter. Once we landed in Cuba, I was a twinge nervous waiting to go through customs, but it was easy peasy. Breezed right in. I've heard you can request that your passport not be stamped (and Cuban border officials will oblige), but I didn't bother.
That being said, Americans can now enter "legally" (I use quotations only becaue the above method really isn't illegal, per se), by obtaining a visa for Americans prior to departure. I don't know a lot about this method, but legitimate reasons include journalism, tourism with an authorized agency, and a variety of others. We did meet one American couple who had obtained a proper visa simply by hiring a Cuban travel agent in the US and paying a $100 fee. This would make flight times shorter and easier (Havana is only a 45 plane ride from Miami- a flight that is generally reserved for Cuban citizens), but they paid upwards of $500 for just that leg of the flight, so it wasn't cheap.
All this being said, regulations are rapidly changing and it likely won't be long before Americans can easily enter Cuba. American airline carriers will follow suite by offering new flights and time will tell how these changes affect tourism (and life and culture) in Cuba.
Be prepared to step back in time- Cuba is a cash-only operation. If you’re American and/or have American-issued bank cards or credit cards, your cards will not work (as of Feb 2016). I tried. There are sporadic ATMs, but you will not be able to withdraw any type of currency with an American-issued card. For this reason, it’s important to calculate, create a budget, and bring the proper amount of cash with you. We brought Euros as we had read that we would be charged a surcharge to exchange U.S. dollars. (Interestingly, we met a Canadian couple who brought USD because they heard that was the best rate!) We paid a fee to exchange from USD to euros at home, then another fee to exchange from euros to Cuban convertible pesos (commonly referred to as CUCs) so I think it would’ve been about equal. Next time I’ll simply bring USD.
1 CUC is almost exactly equal to 1 USD. Our budget broke down as follows (per person):
• $100 5 nights lodging at casa particulares (we found these to be in the $30-40 range per room, which we were able to split between the two of us)
• $200 for 6 days of food, drinks, and bottled water
• $120 each for round trip private taxis from Havana to Trinidad
• $100 extra just to be safe
We thought $100 extra would be more than enough, given Cuba is inexpensive and we didn’t plan to do any excursions. However, we actually ended up being dangerously close to running out of money. Everything has a tourist price, and when factoring in unplanned activities and food that was more costly than planned, we were not able to maintain our budget. After a failed attempt to receive a Western Union wire transfer from my husband (Americans are not allowed to received wired money in Cuba, even though Western Union told us we could!), we eventually cracked the system by having my husband send the money to the Cuban family we were staying with.
Bottom line, in general, I would say $100 a day would be very comfortable and you could eat and drink at your leisure without worrying about budget too much. We started with $600, but by the time all of the exchanging was done, actually only ended up with about 530 CUC. You could definitely get by for much less if eating at food stands, avoiding alcoholic drinks (they really add up!), taking buses, or staying in one city. And better to bring extra cash, because if you have leftover CUCs at the end of your trip, you can easily change it back to dollars at the airport upon departure.
WHERE TO STAY
Casa particulares (which are rented rooms within peoples’ homes) are the way to go! Both for a more authentic experience, and to support the local economy (vs the government run hotels). However, a word of caution, the term “casa particular” seems to be a bit improperly used these days. Not all of the casas are actually in people’s home- some are run a bit more like small scale hotels. We booked our first casa in Trinidad, Casa de Elio Ramos, based off of recommendations on Trip Advisor. (We booked via Facebook messenger, and our host even arranged a private driver to pick us up at the Havana airport and drive us 4+ hours to his casa). While we enjoyed the casa in Trinidad, it was more like a small hotel vs a home. We were hoping for a more intimate experience. Nonetheless, the room was clean and beautiful, and had air conditioning and a private bathroom with hot water- things you want to be sure to ask for when looking for accomodations in Cuba. The location was great and we were easily able to walk all over the city center.
We only booked the first two nights as we weren’t sure how long we would want to stay in Trinidad. We debated stopping for a night in Cienfuegos or Santa Clara on the way back to Havana, but decided to skip those and head right back to maximize our time in the capital city. With only 6 days/5 nights we just couldn’t see it all.