Your Guide To A Long Weekend in Havana, Cuba

Cuba is one of the most magical places I’ve ever visited. It’s also one of the most colorful. I’ve always been fascinated by the pictures I’d seen of the mid-century cars in candy colors, and buildings painted in pastel hues. I just knew visiting would be a visual feast, and worth the complications of US-Cuba travel-restrictions. And it was! Note: Unfortunately since I last visited, these complications have become quite a bit more restrictive. It’s still do-able, and there are lots of blogs where you can find out just how to do this via gateway cities, so I won’t get into it here. I’ll just say that even with these new restrictions, I would still consider it worth the extra planning. 

I had read that in Havana, life is lived in the street. But I didn’t really understand that until I visited. The streets are vibrant and full of people- Habana Vieja is less a metropolis and more like a village. Residents greeting one another, fruit and garlic sellers pushing their carts, children playing. Surprisingly, a lot of Habana Vieja  reminded me of the beautiful buildings and boulevards in Paris, but in a state of beautiful ruin. Many deco architectural gems are crumbling from salt-water exposure along the Malecon. And others have just been neglected due to the financial state of the city. But it’s easy to imagine the Prado, the main boulevard, in it’s heyday. And that’s what’s magical about Havana- it is a place that captures your imagination- decaying doorways hide beautiful secret courtyards, musicians gather for spontaneous jam sessions on the corner, jewel colored vintage cars line up in the plazas like chrome rainbows. It’s a photographer’s dream city.

Cuba’s political history is fascinating and complex and has left an indelible mark on the country. There are still ration cards for staples like eggs, chicken, milk, etc. And there’s very little consumer choice, as you can see in one of the images below. There are also dual currencies circulating- one for tourists, the CUC, and one for locals, the Cuban peso. Because of the embargo and political situation, many consumer goods and services we take for granted are simply not available (ex: tampons). Bear in mind too that you may encounter infrastructure issues while you’re there. We had a blackout on the block where our Casa was located, which meant no lights or AC for the night. Also don’t count on your cell phone to work, except on wifi, but it’s actually a nice break from being plugged-in all the time. It may not be luxurious, but if you want a lively, colorful adventure- Havana is the place!

When we traveled, getting there was actually not too difficult.  First, we needed a good reason to go, and sitting on the beach did not count, unfortunately. Up until June 2017 there were 12 general ‘license’ categories you could align your travel with. We chose ‘professional research,’ as I wanted to research and photograph the colorful craft traditions in Cuba. Under the Obama administration, most people were using the “People to People” category, which was all about cultural interaction and learning. Unfortunately, as of June 2017, President Trump has taken that license category off the table now, so if your reason for travel doesn’t align with any of the remaining licenses, there is the old standby options of flying through Cancun, or another gateway city, if you’re concerned about the license issue. I worked with a travel agency to purchase tickets and secure my license- Cuba Travel Services– as you can’t buy them directly from the airlines via phone or internet. (MarAzul or Airline Brokers are also reputable agencies). The license takes a little bit of paperwork, but it’s quite simple. Next, you’ll need to plan your money. Honestly, I’d recommend taking all the cash you’ll need with you. It’s hit or miss whether your American credit cards will function. So better safe than sorry. I actually took down Euro, since Cuba actually puts a 10% tax on exchanging dollars, and it was cheaper to use Euro instead. You can exchange at the airport-  where you exit the baggage claim, there are cambio booths. If you do bring Euro, go upstairs to the booths there as the ground floor only exchanges US dollars.

Below, you’ll find my Havana quick-start guide…


  • Walk through as much of Havana Vieja as possible- it is an amazing section of the city. At least hit all the major plazas- Catedral, Central, Vieja, etc.but try to wander down some side streets too that have fewer tourist traffic. I felt very safe there, even off the tourist track.
  • Vintage Car Tour– we used Old Car Tours, since you can pick out your car:) We did a2 hours guided tour and it was one of the best things we did during out stay. It really helped us get to know the city very quickly.
  • Callejon de Hammel– It’s a street filled with vibrant art and installations. We visited here on our car tour, but we also went back on a Sunday. Sundays the’s a street festival, with music and singing and dancing- a celebration of the Yoruba religion. Some touts can be a bit persistent- they’ll try to bring you to their restaurant or bar, etc..Just be very firm with them. It’s very crowded, but it’s worthwhile just to hear the music and see the exuberant dancing.
  • Alamendares Forest– on the edge of the city is a beautiful forest area. Our car tour stopped there and we walked around a bit- it’s a nice change of pace from the city-quite beautiful. Accessible via taxi too.
  • Parque Central– the guys line up with their vintage car taxis here- go negotiate a ride! Or most are also just very nice and like to talk about their cars if you show interest and are happy to let you photograph the cars. it’s like a rainbow of vintage cars!
  • Walk The Prado all the way down to the Malecon (the sea wall). the Prado is a beautiful tree lined boulevard for walking only. It makes you think about how incredible Havana must have looked in it’s prime-  Parisian almost. If you have kids, it’s a great place to let them run and get some energy out since there’s no cars and sort of walls on the sides so they can’t run away.
  • Walk along the the Malecon before and during sunset. Everyone goes there and just hangs out- It’s like the living room couch of havana. You can buy little cups of weak rum (or BYO) and watch the sun go down. Buildings are amazing colors and textures along here too. Unfortunately,  the salt is just destroying them, but they’re beautiful and. amazing works of architecture nonetheless

To Eat/Drink:

  • La Guarida– It’s not really marked outside- the building looks crumbling and under construction, but once you head up the palatial staircase you’llget to the restaurant. Try to get a seat on the balcony out front to watch the street. There is a great roof terrace if you go outside and up a spiral iron staircase. 360 degree views of the city. great at sunset.
  • El Concinero– this restaurant is next to FAC, the arts warehouse and gallery. It’s delicious and the rooftop is a fun place to have dinner before heading over to FAC
  • Eat at a Paladar. Paladar’s are private restaurants, usually in someone’s home, sort of like the casas.  We didn’t make it to these two, but they both had good reviews: Versus 1900 & Atelier Paladar (make reservations). We also met a nice guy who had been down to Cuba a dozen or so times. His favorites were La Fontana and L’Esperanza, but we did not have time to check them out.

To Shop:

  • Plaza de Armas secondhand book market- books, small antiques, lots of screen-printed cuban movie posters for sale. I fell in love with these and bought several.
  • Clandestina design store- fun shop with modern cuban designed totes, clothing and jewelry. Very original design and presentation- not your average souvenir shop.

Que tengas buen viaje! (Have a great trip!)


Images copyright Dru Hilty and Ryder Carroll

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