Havana, Cuba has to be one of the most magical places I've ever been. I flew American Airlines (the ticket included health insurance but not a visa, I purchased it seperately) and we booked an Airbnb right in the middle of old Havana (a Cuban family hosted). We truly had a "person to person" experience like no other and I have to say I felt an amazing connection to the people and culture. We took toothbrushes, baseballs and toys for the children (don't go empty handed). Our trip happened to fall over the national mourning of Fidel which meant no shows, no music and no alcohol. But we listened to music in cabs or during our vintage car tour (a must). We road tripped to Vinales and road on horseback to a tobacco farm. We ate the most incredible food and drank the world famous coffee until our hearts desire. The most important tip is once you arrive there will be Cubans who want to act as your city guide/helpers (no internet or texting which means also no google maps) and I strongly suggest your find one and use them (pay in tips at the end of the day). We also stayed at a hotel our final night and hands down our Airbnb experience was the best. We loved our host and being in the middle of old Havana as opposed to being surrounded by other tourists at an overpriced hotel. Expect things to move slower in Cuba... especially at the airport. No credit cards can be used so take as much cash as you think you will need. It was an incredible experience I will forever cherish and I can't wait to go back someday.
Eat- La Guarida, Cafe Bohemia, any local restaurant and order the Ropa Vieja, Cafe Reilly for coffee. Rooftop of Hotel Ambos Mundos for lunch, La Floridita for drinks.
Do- Vintage car tour, Vinales Valley (horseback ride) , Varadero Beach (we didn't make it but everyone says its gorgeous), visit the 5 Plaza's in old Havana, Revolution Museum, Fabrica de Arte