Have you ever considered visiting Cuba? Oh man, you should absolutely go! I had such a great time in May of 2018. I landed on a Sunday afternoon and departed on a Wednesday morning and mostly stayed in Havana minus Tuesday when I bussed it to the beach.
AIRFARE
For airfare I turned to Google Flights and set a tracker for cheap flights. I found mine for $320 round trip, 4 weeks in advance.
When purchasing airfare you will be asked to pick 1 of 13 reasons for why you are traveling there. I chose "Support For the Cuban People" and was only asked about it once, at PDX.
TOURIST CARD
Along with a valid passport, I also paid $75 (cash/debit) for a "Tourist Card" at the United Airlines gate when I departed from Newark. It varies per airline.
ACCOMODATIONS
My Airbnb: https://www.airbnb.com/rooms/6358348?s=51
A 2-bedroom located in Old Havana with a wrap around porch and full kitchen. $41/night and the host family was so friendly and lived so close we would wave to one another from our balconies. There are tons of similiar rentals available in that area. As a first timer, I recommend sticking to Old Havana.
TU HABLES ESPAÑOL?
Do you speak Spanish? I spoke very little at the time but learned pretty quickly how to get around. I recommend downloading a translator app that works offline.
MONEY
For currency I read you should exchange US dollars to Euros before you leave the states, but I did not and it did not really make much of a difference (I spent roughly $300 while I was there). It says the exchange rate is 1: 1 but you pay a fee, I think it was about 13%, so for $100 US you get about 87 CUC (cukes) = Cuban convertible peso. This is tourist currency. The locals pay in CUPs, if you see an unusually high number it is CUP. Double check the change you receive. There is an exchange booth at the Havana airport, I took a photo of all of the currencies for reference. I did not use my debit card or any US currency there.
MAIL SERVICE
The post office (postcard stamps are .85 cents) and exchange office are located at the Plaza de San Francisco.
WIFI
There is limited WiFi in Cuba. You can purchase 1-hour cards for $1 /piece at the ETECSA Communications Store located in Old Havana. I believe it was on Obispo @ Habana. Get there early / be prepared to wait in line. To sign on, look for an "ETECSA" sign, usually at a public park, the few places people will be looking down at their phones.
PUBLIC TRANSIT
To get to the beach I caught a bus at Parque Central at 10 am (runs every hour) and paid $5 cash (CUC). I jumped off at the Mar Azul / Santa Maria del Mar stop, I believe it was the 3rd stop in. Get there early to snag an umbrella and devour some Cuban cheesy poofs!
CRUISIN'
I highly recommend taking a tour in one of the classic Chevys. I paid $40 for an hour and I learned a lot from my driver about Cuban history. He also showed me a handful of gems found off the beaten path, like Revolution Square and the John Lennon statue.
FOOD
As for food ... it wasn't that great! I say stick to the street food. You can find some cheap Cubanos. I ate at a place called El Chanchullero three times-- grilled swordfish with fresh salad and dinner rolls for six bucks, located near Teniente Rey @ Bernaza. There is a park that runs adjacent to it where you can find WiFi, too.
TRAVELER'S INSURANCE
Lastly, travelers insurance. I purchased mine through World Nomads for $20ish bucks and was never asked about it (they say you have to have it when you land in Cuba).
ETC.
Ummm ... also maybe download an offline map of Havana. I never did that and also didn't buy a map. I found it was more fun that way, but I also got lost one night in a "seedy" part of town and had to use sign language to find my way back.
SAFETY
On that note, I never once felt unsafe in any part of town. The locals are generally excited to see tourists, especially Americans, and want to help you as much as possible.
DO IT!