Our hosts explicitly said, "Do NOT drink the water, or you will get sick." So, what did I do? I brushed my teeth with bottled water.
What did the boys say? "You can brush your teeth with the water. You spit it out. It's fine." Guess who wasn't fine at the end of the trip? All three of us.
Word of advice: avoid Cuban tap water like the plague.
Jokes aside, I mean, we felt horribly at the end, but everything we experienced up until that point was amazing. The Cuban people are so friendly, and walking the colorful streets of Old Havana is something I will never forget. If "People to People" visas are ever available again to visit Cuba, I really hope you are able to go. It's a cultural experience like no other.
Pre-trip Notes
The first step was to acquire a visa. In 2017, Americans could still purchase individual People to People visas for $85 USD via Cuba Travel Services. Now, it appears that you can only purchase such a visa if traveling with an organized group.
Once we had the visas, we booked our flights and Airbnb. When booking these as an American, you must provide which type of visa with which you will be traveling. Remember, you'll want to have this visa on you at all times while traveling . . . just in case.
Our flight routed through Miami, and you must get your boarding pass stamped. During this time, it was still technically legal for Americans to visit Cuba, so our passports were stamped. We had no issue getting back to the States and were only asked if we had anything to declare upon return. Aside from the obvious and more outrageous items, TSA mostly wants to know that you aren't bringing back more than $800 USD in souvenirs and/or cigars.
Cash: As an American, your credit and debit cards don't work in Cuba. So, this means you have to take a bunch of cash with you. We witnessed an American at the Havana airport try to get money from the ATM. I'm assuming he had a nice stay at the airport.
CUP: The Cuban Peso Nacional is the local currency. There is a much better exchange rate with the CUP vs. the CUC, but the CUP is really not meant to be utilized by foreigners.
CUC: The Cuban Convertible Peso is used in the tourism industry, so this is predominantly what we used.
We were able to exchange our US dollars at one of the Havana airport's currency desks (CUCs).
Several articles we read prior to our trip suggested bringing a list of cultural activities you may attend or visit, as well as some back-up material explaining our right to be there under the People to People visa. We were never asked for such information, but I felt better having it just in case.
Phone apps:
Map of Cuba Offline (or, something similar. I had a Google phone at the time) is absolutely necessary while visiting Cuba (unless you have a paper map, of course). We weren't confident that our cellphone service would work when we got there, so we played it safely by downloading the app to avoid getting lost. Really important: American phone service doesn't work in Cuba, but the government sells Internet access cards. With these, we were able to use Wi-Fi while in the Airbnb or at local hotspots.
Google Translate was better to have than not, even though Cuban Spanish is quite different from the Spanish you might know.
What We Did
Havana Vieja (Old Havana)
Stroll Havana Vieja: I don't recall everything we did in Havana, but most of our trip consisted of simply walking and taking in the city. Havana has some of the most interesting graffiti art I've ever seen. We'd stop to eat and have a drink in whatever square we could find and enjoyed the weather and people-watching. Make sure to get a few Cuba Libres! The city is incredibly run-down, but it's taken care of since the Cubans have made-do with what they have. It really shows in their personalities and gives you some perspective on your own life.
El Capitolio and the Gran Teatro de La Habana: We only walked by the Havana capital building and the grand theater. Hopefully I can return someday to see a Cuban ballet, but at the very least, experiencing the buildings' architecture was worth a visit.
Castillo de San Salvador de la Punta: One of multiple castles/fortresses that has great views of the city and the ocean.
Finca Vigía: Hemingway's home in a suburb of Havana. Such a beautiful and informative place to visit.
Street art: I'm a sucker for street art. However, I bought a couple pieces only to find out at the airport that there is a fee for exporting such goods out of the country. I think it was $20 USD total that I had to pay after going through security. It seemed sketchy at the time. But after paying, the man stamped the back of each piece, and I was on my merry way.
Beaches: We went to a beach just northeast of Havana for only an hour, since the purpose of our trip was cultural connections rather than relaxing oceanside. It has incredibly beautiful white sand, and it's clean. It was really nice to rest our feet and take in the view for a short while. We never went to Varadero, which is where cruise ships and all non-Americans typically vacation in Cuba. But if the beach we visited was any indication, I'm sure they're incredible.
Valle de Viñales
Classic cars: Our Airbnb hosts have a friend who drives a "classic car" and was willing to drive us anywhere we needed to go. Aside from our cab from the airport to our apartment, which was very easy to hail without worry of getting ripped off, we had this guy drive us around the entire trip. He didn't know any English, but with my broken understanding of Spanish and the boys' hand gestures, we made-do. Also, he was very enthusiastic to at least try conversing via Google Translate!
As for the classic cars, they aren't very fast, fuel-efficient, or safe (no seatbelts). But they are pretty cool to experience, so don't hesitate to take a tour around the area in one.
On our way to Valle de Viñales, our driver stopped a couple of times for us to get drinks, shop, and buy some cigars from a tobacco farm. While at the tobacco farm, we briefly toured the drying house and watched how the cigars are rolled.
Rock Mural: A colorful representation of evolution in Cuba, envisioned by an artist and made a reality by several individuals.
Indian Cave: A fun walk and boat ride through a cave that has a few sculptures and a quick musical show at the end. On the way to the cave, a comedic actor insisted he place a bird of prey on Nick's head.
Playa Larga
We wanted to go to the Bay of Pigs Museum, but another cab driver warned our guy that the roads near the museum were covered in crab skeletons that could pop vehicle tires. So, our cabbie improvised and took us a few different places nearby.
Criadero de Cocodrilos: Crocodile breeding program/farm created after they nearly went extinct.
Taíno: A recreated native village that offers some history and beautiful views.
Playa Larga: Once we reached the Bay of Pigs, we had a couple of drinks while enjoying this gorgeous beach and ice blue water.
Food
Havana Vieja (Old Havana)
BelleVue Deauville Hotel (breakfast each morning): The food wasn't anything to get excited about, but it was a cheap and healthy 5-CUP buffet meal to start our day.
Floridita: Said to have been frequented by Ernest Hemingway, this is a popular tourist spot for a refreshing Cuba Libre, mojito, or daiquiri.
La Bodeguita del Medio: The place that lays claim to the origin of the mojito, so it's usually very crowded.
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