Updated: May 11, 2018
Above all, I learned...
The whole country is bootstrapped, and the people really do rely on each other as a result. Internet is not widely available, so people talk to each other. New provisions are spread thinly, so no one has much to steal. The country has near-zero crime, so it's safer to socialize.
Cuba's iconic vintage cars are a perfect metaphor for the country at large. Though beautiful, most are literally held together with glue and paperclips. The American embargo and the retreat of the Soviet Union has left owners to make due with what they have and what their neighbors can lend them. As a foreigner, the Cuban people open up their lives to you like a neighbor. People gave us rides in their cars, let us stay in their homes, fed us at their dining room tables, and walked us from store to store in search of fried plantain chips. Did we almost get married off to a few daughters in the process? Maybe. The people really are generous.
Millennials are trying to improve the country. More Cuban homes are now listed on Airbnb. The Fabrica de Arte Cubano (FAC) is a thriving Millennial dance club, restaurant, and art gallery mixed-use building. The notoriously bad restaurant scene in Cuba is improving. And, we saw a boutique hotel under construction in Old Havana. I think the future is bright in Cuba. No need to worry about getting there "before America ruins it," IMHO.
Where to stay...
I fully recommend staying in a casa particular. Like Cuba, it's a little bootstrapped, but it's a very unique experience. You can't get any more "local" than this.
Our Airbnb in Havana. Stay in Old Havana, not here. The front porch was a nice place to relax, and Casa Madre was very nice (spoke zero English). The beds were not very comfortable, and we saw some ants in the breakfasts Casa Madre made for us. I will say, she made a great lobster dinner for us. I think you can find a better alternative. Though this neighborhood was quieter, it was annoying to hail a taxi every damn time we wanted to go somewhere.
Our Airbnb in Vinales. This house was not easy to find, but all the locals in town knew Yuneisis's name (the owner) and could direct us. We joked that she was the real mayor, because she's a real boss babe business woman. Loved her, she spoke very good English, and again, the porches and roof deck were clutch spaces to relax.
Where to eat in Havana...
El del Frente - Owned by the same people as O'Reilly 304 (across the street), but so much better. I was obsessed with the salsa they served with plantain chips as an appetizer that I asked if they would sell a jar to me. They did, and it was phenom.
At your casa particular! My lobster dinner was incredible and my friend drools over memories of the grilled chicken he had. Just let your Casa Madre know the day before so she can prepare it for you.
We ate at La Moneda Cubana (where Beyonce ate apparently), but I wasn't impressed.
On the ground, I heard that "Paladar Doña Eutimia," "Esto no es un café," and "La Guarida" were great restaurants, but I didn't have time to eat there. We had reservations at La Guarida, but they decided not to open the restaurant that day...hmph!
What to do in Havana (+ life tips)...
Fabrica de Arte Cubano (FAC) - I stood in a long line to get in, but it was worth it. This is a mixed-use space: part art gallery, part museum, part restaurant, part dance club, and part bar (with the largest mojitos in the country). Very Millennial, very sceney (for locals and travelers), very fun. Highlight of Havana for me.
Playas del Este - This is a 9km stretch of beaches east of Havana. Get there by bus from Parque Central, but plan on hailing a taxi on your way back; the buses get overbooked even if you have a "return" ticket. Pro tip: if you really want to ride the bus back, get off at the last stop (first stop for the return trip) at Hotel Atlantico and aim to catch the return bus 1 hour before the last bus. I walked the beach from Hotel Tropicoco to Mi Cayito (the gay beach), passing numerous beach bars selling coconuts and pineapples (that they'll fill with rum)...yums. Mi Cayito was a very shallow part of the beach; I preferred sections to the west. One even had a massage station.
Take a dance class at La Casa del Son - Get a drink beforehand and you'll be lubed up and ready to get down. I didn't get to do this, though many people recommended it. It's first on my list when I go back to Havana.
Drag Show at Cabaret Las Vegas - Saturday nights. Doors open at 11pm and the show starts at 1am. I was falling asleep in the booth by 12:30am, so I definitely recommend a pre-nap or a stiff dose of caffeine if you're a night owl like me ::sarcasm::. The crowd was definitely local and definitely gay male only.
Museo Hemingway Finca Vigia - This was Ernest Hemingway's home when he escaped to Cuba. It does a great job of transporting you to another time, just like everything in Cuba, TBH.
Havana Vieja - I mean, walk around Old Havana, but don't expect too much. The old colonial buildings are crumbling to the ground. I'm a history buff, and I thought I'd find something poetic and beautiful in the rubble. I didn't, but that's just me.
Change your money at the airport and at the bank - I read conflicting advice online about when and where to change money. I changed my money in the USA to Canadian dollars, changed them into Cuban convertible pesos (CUC - pronounced "kooks") at the airport, and then changed some of those into Cuban pesos (CUP - pronounced "coops") at a bank in Old Havana. There are two currencies in Cuba and it helps to have both on hand. If you can pay someone in CUPs, you tend to get a steep discount, because it is the local, non-tourist currency.
Where to eat in Viñales...
Finca Agroecologica El Paraiso - Seen in photo above, I could have eaten here every day for the rest of my life. I'd be 500 lbs and so happy. This is true farm-to-table realness; the food is so fresh. That pumpkin soup you see in the yellow bowl was my ulti-fave.
3J - This is a bar/restaurant on the main street through town. Everyone told me to try this place, and I'm so glad I did. I ordered the pork dinner, recommended by the waiter, and I housed it down.
What to do in Viñales...
Ride a horse - Am I a cowboy now?! This was the highlight of my trip, despite the extreme chaffing I got on my knees and inner thighs. Oof. We rode up hills, around tobacco fields, and through riverbeds.
Hike out to Cueva de la Vaca - this is rock-climbing spot is walkable from the center of town. I am not a rock climber, but the walk is scenic (you can stop in at Finca de Raúl Reyes for a beer on the way if you'd like). If you head there for sunset, you'll get an awesome view. Viñales is surrounded by "mogotes" which are giant, picture-perfect rock formations.
Bike out to Cueva del Indio - Viñales is surrounded by "mogotes" which are giant, picture-perfect rock formations. This bike ride will show you some of the most beautiful scenery in the country. At Cueva del Indio you can even take a small boat on a river into the cave.
Tour tobacco and coffee farms - Viñales is a UNESCO site, so everything is grown organically. The coffee is strong, and the tobacco is rich. You'll be able to try both for free with a paid tour. Our tour was part of our horseback ride. Finca de Raúl Reyes is another spot you can access via bike or on foot.
Extra Memories & Tips:
I brought $1000 (Canadian dollars) in cash. I spent about $500-600 of it buying dinners, drinks, transportation, and paid tours. I'm not a big souvenir shopper, and had paid for flights and Airbnb accommodations in advance.
Spanish is widely spoken; English is not. It is much easier to get around on your own if you understand basic Spanish. If not, be prepared to be patient, play charades, and smile, because submitting to frustration isn't very helpful.
When hailing a taxi, point at the ground, not in the air. If you want a bargain, ask for a taxi collectivo or "collectivo." "Collectivos" are basically ride-sharing services and a typical fare from Miramar to Old Havana is 5 CUPs (not CUCs!) per person. They will start the price negotiation at 10 or 20, but 5 is the fair price. You will likely pay more coming back from Old Havana, because they know tourists will pay more. I think we paid 7 or 8 CUPs a few times.
Do not roam the streets after 11:30pm on New Years Eve. This is the one night of the year where the locals decide it's ok to throw shit (literal poop, glass bottles, eggs, rocks, buckets of water, etc.) off their balconies at you and not get in trouble. There is no crime in Cuba 99.9% of the year; this is their purge.