Everything you need/want to know to visit Cuba, 2019/2020, we just returned for a 13 day trip from NJ.
Yes! USA citizens can still legally visit Cuba for the reason of "support for the Cuban people". Visa, you get it at the airport before checking in. $75 for United at Newark($25 fee and the $50 visa card). Your health insurance in Cuba is covered by a mandatary surcharge in the airfare. We had a fantastic time during the Christmas and new year time on the cheap. Averaging more than 20k steps a day, and more than 3 cocktails a day. Had more straight rum than I could have ever imagined. Cuba is extremely safe and it's public health is better than most counties in the Americas.
A: US credit and cash cards do not work in Cuba. CUC (peso convertible) is pegged 1:1 to USD, but 10% surcharge for exchange USD to CUCs in the airport or other official places. UA uses T2, which is the old terminal. There is an ATM outside, if you have non-US ATM cards, you can get CUCs, 3% commission (I got 400 CUCs, receipt says 412 USD, CMB). there is no line for ATM, so I did not change my euro (as insurance to have enough money, more later) to CUCs. It is said there are always long lines at the money exchange at the airport.
Many restaurants and taxi drivers (but not all!) prefer to get USD (1for1). You will need some CUCs leaving the airport for taxi, but USD should be good as well,flat rate 25 CUCs to town. you can easily get 1:1 conversations with private exchange near city centers or in some restaurants (we changed a few hundreds). We ran out of USD, and got another 400 CUCs from ATM on the tenth day (again, it's 412USD, BOC). Like all trips, you will always spend more money than you think. This is a cheap vacation, we had a great time. It costed ~$150/day/2p (400+400+$800 for 13 days, spent all of the cash, so easy to calculate, Airbnb prepaid $250, visa $150) not including airfare, but bought some liquor and cigars. Please have more means for money or bring more cash than you think you will need and put in different places, otherwise, you will get stuck!!!!! Western Union is extremely costly to get money. We lent 100 CUCs to someone (we did not know) from Miami on blind Faith as he lost his wallet. He paid back through Venmo upon returning.
B: Transportation: we tried everything, bus most comfortable and slowest (station to station, >20% more time), private taxi fastest and most expensive, shared taxi is the best compromise (point to point, and slightly more than bus). Do not rent a car. It's cheaper to get taxi than renting a car. Viazul bus tickets can be booked on the net many weeks before using US credit card (use IE, chrome doesn't work).
C: Stays, use Airbnb to book casa particulars (Cuba does not have the hotel infrastructure to accommodate the tourists, so they let private home owners to rent out their rooms, there are more casas than tourists, so never worry you will arrive without a place to stay. I normally use booking.com, but it doesn't have reviews for Cuba hotels/casas. My 3 criteria for stay: close to town center (all about location!), With private bathroom; and good ratings with good rate. I paid $10-40 a night for a room. Booked five places, all good. I did not see any difference between the $10 or the $40 casas.
D. Internet (wifi) cards, officially $1/h, but if you don't want to be in lines, just pay $5 for 3, or $2 for one from the scalpers, hotels charge $4/ card. Do not buy multiple hour card, as if you forget to log off, you may run out the entire card. Use settings, wifi, forget network to log off. 10-15 minutes is all you need per day for uploads and downloads. You have to have everything written up before. The price is not the worst part, you have to find the wifi spots (maps.me has the info), and you may not be able to log on, even the signal is strong. Even if you get everything right, it may not let you log in, and you will have to find another place(we thought the cards were bad, bought two additional ones at two eqch before realizing the issue). It can be very slow if many people are using the same spot. Do it early in the morning, it is really fast. Somehow we had best luck at the La Bodeguita del Medio in Havana (the Hemingway Mojitos bar), and went there many times for the internet and Mojitos ($5 a piece, Hemingway is right). It's a good place to treat internet or WeChat addiction.
E. Download maps.me and offline Cuba map before you leave. It is a life saver, good for offline use, has ratings on most restaurants and attractions. Contribute by write reviews!! Google maps is not good in Cuba. Make sure everything works in airplane mode before leaving the US.
F. Food, surprisingly good if you do it right, otherwise awful. Some are US prices, you have to do your homework to get good food, and may have to wait in line even in mid afternoon. Drinks: Mojitos is the national drink and it's good. They put in twice as much rum as in the US. I had more cocktails in the trip than I had many years combined. 3 in an average day! They serve rum in the morning! We did one meal a day (I have been doing intermittent fasting for a year, lost 30 pounds), and sometimes go to the next restaurant to eat if first one has small portions (restaurant hoping). We ate well, paid $10-45 for meals for two. More expensive does not mean better. Los Nardos in Havana is the best. Lots of food and 10 CUCs a person with cocktails.
G. Cubans are very nice and helpful! However, there are small time swindlers that try to bring you to really expensive places to earn money. We fell to one, and had mojitos that are 6x more expensive than the cheapest we had. I knew it half way, but went along with it as I was having a great time seeing him acting. So it is worth the time and small amount of money ($15 over spent, but that's big money for Cubans, half a month's salary).
H. Leaving Cuba. Taxi to the airport is 25 CUCs. You can buy some food before entering security, better yet, eat before going to the airport. Make sure to change all your CUCs to dollars! once past security, CUCs cannot be used. Price of liquor at the duty free shop is similar to outside stores, and are marked in dollars, but if you pay with USD adds10% extra. Better to use euro or Canadian. The duty free shop has the name brand cigars, similar price to the city, apparently USD can be used without surcharge, they want to poison the Americans. Off brands are a lot cheaper. We don't smoke, but bought some for friends.
I. Cuban rums are much better than those we get in the US. I tried Bacardi on my flight back for comparison. So buy the most rum in Cuba as the US customs allow (which is a lot!).
J. If you have an over the ear noise cancling headphone, bring it. Will be useful for the noisy taxi rides.