My trip to Havana, Cuba was one of my all time favorite trips I've ever taken. I know a lot of people who have been to Havana and not enjoyed it as much, which I personally cannot fathom, so I want to share a handful of the things I did that I absolutely loved and would highly recommend.
Explore: Old Havana
I walked so much in Cuba, and spent a lot of time exploring Old Havana, where I stayed, by foot. Old Havana has the most incredible original architecture I've ever seen, and there is so much rich history on every block. This also allowed us to discover some of our favorite restaurants, bars, and shops that we never would have found otherwise.
Stay: Hostal Chez Nous
I stayed at Hostal Chez Nous which is a casa particular right in the middle of Old Havana. Our neighbor next door prepared a lovely and delicious 4 course breakfast for us every morning, which was only $5, and our room had a vintage balcony that looked out over Old Havana with a view of the capitol building. The room was nice, recently renovated, and super clean and to top it all off, there was a music school around the corner and they were constantly playing music at sunset while we got ready for dinner.
Play: The F.A.C. (Fabrica de Arte Cubano)
This is one of the coolest places I've ever been to in my entire life. It was a mix between an art museum, a nightclub, a live performance space, a bar, and multiple restaurants. It's really hard to explain it in words, but I will say that this is a place that you absolutely cannot miss- it is so unique and fun, and you won't find anything like it elsewhere.
Relax: Playa Santa Maria Del Mar
This place is such a hidden gem. I know a lot of people that have been told (incorrectly) that you have to go over an hour outside of Havana to get to a beach. This is not true. We took a luxury bus from Parque Central ($5 round trip) 15 minutes to this amazing beach and had table side resort style service with cocktails and food all day long. You have to bring your own towels, but other than that, there are beach chairs and table setups waiting for you. We had such a relaxing day laying out and swimming and eating and drinking at this beach.
Eat: Paladar Vistamar
We had the most amazing lobster and swordfish dinner as waves crashed over into the pool next to us. Everything was delicious and we had a really fantastic time sipping mojitos as the sun set. Definitely make a reservation for a nice/fancier night out (though it is still really inexpensive like most places on the island).
Drink: Hotel Nacional de Cuba
You have to check the Hotel Nacional off your Cuba list to say you did it. I've heard less than desirable things about staying there, and it's a car ride from Old Havana, which, in my opinion, is the best place to stay, but you should 100% stop by for a drink. We had rum cocktails and listened to a cuban jazz band while reveling in the history and nostalgia of visitors past.
Cuba was such a cool place to explore, so my best advice would be to take some tips from friends, but when you get there leave plenty of room for going off the itinerary. Bon Voyage!