First things first, as American travelers coming to Cuba, we wish we would have been told...don't bring US Dollars, bring in Euros or any other currency. They take a 10% penalty fee for all US dollars (US dollars are the only currency that gets hit with an additional penalty fee) when exchanging to the CUC. So to avoid this, if you can, withdraw or exchange your money to a different currency. Also, no ATMs in Cuba.
Neighborhoods: Our favorite neighborhood to hang, eat, drink, and sleep was definitely Vedado. We felt that in this neighborhood you really get the feeling of REAL Cuba. It's only a few minutes in a cab to the beautiful, but touristy Habana Vieja, but far enough away for the prices to drop dramatically.
Lodging: The best places to stay in Cuba are the Casa Particulares. Many families rent rooms or even separate apartments in their home to travelers. We found ours through Airbnb twice and once just through people we met. Like every other Airbnb experience, we've always felt we see a better side of the city that we wouldn't have if we stayed in a hotel. Our rooms we rented were anywhere from $30-$45. Our lovely hosts are below.
-Hostal Aida y Monica http://www.casaparticular.com/casa/index/id/389/name/hostal-aida-y-monica
-Marcel and Veronica's (email email@example.com)
-La Paila: Our favorite restaurant in Cuba for authentic Cuban food, huge portions and stiff cocktails.Get the Ropa Vieja! (Drinks=$1.5-3, Meal=$4-6)
-El Chanchullero: A great hole in the wall spot for lunch and a mojito. Get the Fricase de Pollo! (Drinks=$1.5-3, Meal $5-6)
-La Catedral: One of the local restaurants we frequented for a good dinner with big portions, deep in a Cuban neighborhood (Drinks=$1.15-3, Meal=$4-6)
-Cafe Madrigal: Super cool bar above a house in Vedado with really cool atmosphere and a great Daquiri (Drinks=$3-5)
-Cafe Neruda: Nice place to stop for a drink while walking on the Malecon to soak up the sunset. The restaurant doesn't have a roof so make sure to go when the weather is good (Drinks=$3 and the food is supposed to be pretty good too, we just didn't try it)
-La Reliquia: A nice place to stop for a cold drink while walking through the touristy Habana Vieja, with random antique memorabilia throughout (Drinks=$2-3)
Transportation: You can definitely take cabs around the city but we found for shorter distance rides, that taking Collectivos (those old pretty rough looking 50s-60s cars filled with locals hoping in and out) were much cheaper. Just wait on the side of the curb for one to pull up, tell them where you want to go and they will add your drop off point to the list of where else they're dropping off. Should be 50 cents each, more for longer out of the way rides. ALWAYS negotiate first.
TIP! Internet is VERY rare in Cuba. WIFI just became a thing a few months ago, so you can only get it in a few hotels in the city and have to pay by the hour. We frequented Hotel Habana Libra and Hotel Capri for our internet needs.
EVEN BIGGER TIP! Hotels will sell you WIFI cards for $5-7/hour. You can buy these exact same cards for $2 at any ETECSA Phone/Internet provider, which is the country's national internet provider. Just look for the building with loads of local people outside on their cell phones or waiting in line. The smart thing to do is stock up with at least 5 that way you have them whenever you're in need of the internet throughout your trip and save yourself some dough!
Lodging: We rented a room at a lovely 3-story home, recommended by some local Cubanos we quickly became friends with, called Hostal Barbaro & Andrea. $25/night includes a clean bedroom with private bath and AC and is walking distance to everything. It's run by an adorable younger couple and their baby and spunky animals. Contact them at firstname.lastname@example.org or +53 4199 4330
-San Jose: This place is probably the most popular restaurant in the town. You'll probably have to wait 45min-an hour, but it's worth the wait at least once. The food is pretty good, big portions, and decent cocktails. (Drinks=$1.5-4, Meals $5-7)
Activities: We spent the majority of our Trinidad trip just strolling the rainbow streets, checking out the town squares, people watching, and popping in for beers and mojitos often to cool off. We were lucky enough to catch the town's 502nd Anniversary. There were obviously parties in the street, live music and dancing in the park, and vendors selling anything you can think of and even street gambling. Another fun thing to do is rent bikes and ride down to La Boca and Playa Ancon. Make sure to plan on being gone a whole day...it takes a while. Enjoy!