Here's some starter reading: http://kottke.org/16/04/a-brief-history-of-america-and-cuba
If you ask the Internet, every forum and travel advice article will tell you you could never do Havana justice in 3 days. There's just too much throw-back splendor to take in to step outside downtown.
I call B.S. No, a day and a half is not enough time to go to every museum, club, and cigar shop in the city but it's plenty to get the vibe of the city and even fully take on a few top attractions. And that leaves a day and a half to experience one of the country towns (of which there are many, Cuba is way bigger than I ever realized. The biggest island in the Caribbean,believe it or not.)
Here's what Maria and I did:
- Fly from Cancun to Havana, get settled, walk. We stayed in El Centro (the area just outside the touristy downtown) since Old Havana was booked up. This area lacks the Unesco World Heritage funds and tourist attention of Old Havana so I like to think it's more real. As in lots of scrappy dogs, 5 cent pizza vendors and seriously dilapidated buildings. As with many hot countries, there's a bazillion people in the streets (doing what I'll never know. Squatting, hurrying, whatever) but I was surprised at how few shops and restaurants were open air. There must be some law about it?
- Head east to the beaches. At the edge of Old Havana is a cheap bus to the beaches, which were, honestly, not that different than any other beach I've ever been to: beautiful white sand, warm ocean, chairs and drinks for sale for a couple bucks each. A great place to forget that you woke up at 3 am again. On the bus to Playas del Este we met a solo traveler, Alfred, who is Egyptian American living in Columbia who was fun and interesting and happened to know Maria's boyfriend. I also had mediocre lobster and a fantastic nap.
- Have dinner and enjoy nightlife. One of the things I'd read about Havana is that there is music on every corner. It's true! Old classical Cuban groups straight out of Buena Vista Social Club were mostly in restaurants (in Old Havana, and down Obispo street which we walked end to end, restaurants were much more open air and shop doors wide open). Everyone is smartly dressed and charmingly flirty, as only sharp-dressed old Cubans singing along with a stand up bass and trumpet can be. We ate at a restaurant with a classy band and salsa dancers and then had dessert a few blocks down where a man and woman were serenading. It was very romantic flan.
- There's a ton of clubs to go to if you don't follow old lady hours like maria and I do. I don't do late nights well so I missed out on Havana's infamous dance scene #sorrynotsorry #sleepwins
- *Newbie tip: exchange all your money at the airport. The exchange rate in town isn't much different and the money change lines are long.
- *Cuban food isn't great. Low expectations made meals much more enjoyable
- Old Havana shopping, sites, and wandering. There are about a hundred museums to choose from. We chose the Museum of the Revolution (mostly because I realized once I got there that I actually had no idea about Cuban history, Fidel, Che, or really anything about the country besides samba and Cuban sandwiches (which are apparently Barely a thing outside the US) and El Morro, the fort across the bay, which we ended up seeing with the help of a Cuban guy who I'm sure was trying to seduce us for a night on the town until he realized he picked two old ladies who don't drink or party and are pretty cheap, but are really nice anyway. Jose got us onto the apparently Cubans only allowed public buses and filled in a bunch of blanks for me about Cuban history, culture, and how excited everyone is Obama came ("progress finally!")
- Salsa lessons from Omar Chocolate. Yes, that's his name, and for 10 bucks a piece
- Walk the Malecon and nightlife. There's nothing particularly interesting going on except fresh air and half of the city wandering the 3 mile long promenade. Besides an uncomfortable number of beggars (which I feel totally complicated about, especially in a communist country) and would-be Romeos (seriously, we're babes, I get it, but never have there been so many romancers anywhere else I've been (our casa owner had warned us emphatically about hangers on and apparently he wasn't exaggerating)). Lesson for the night: I just love maria. She's so fun, smart, thoughtful and amazing and I'm lucky to have traveled with her and to have her as a friend.
- optional: more nightlife. Guess what we did?
- *newbie tip: the antique market in the park has the only non-trinkety things to buy, but it's not cheap! Since there are no atms and us credit cards don't currently work, we counted and recounted the cash we brought multiple times a day. If I'd brought more cash I would have bought a could pocket watch or something.
- Head to the country. We chose Vinales because the pictures looked amazing and it is close enough for a day trip. Ultimately we decided to stay overnight due to some mix-up with our reservation and I'm so glad we did.
- Nicolas, our casa owner from Havana, set us up with his friend who arranged another casa for us and a horseback riding tour through tobacco country, including a cigar rolling demonstration, swim, and cave visit. Even for a non smoker who hates the smell of cigar smoke, the cigar farm was the coolest. Riding the horse itself was pretty great too, even if the last hour was excruciating on my tailbone, knees and hips and I walked funny for a couple days after (oddly like postpartum pain...). Pancho, our guide was rugged and charming and also amazed at my dedication to fidelity (Cuban men, who knew!)
Day four:Head to the airport and home