Start Planning Your Trip to Cuba Now

December 23, 2015

First, answers to the big questions: Yes, you should go now
. No, we didn't have friends there, nor were we part of an organized trip. Yes, it would have been difficult if we didn’t have some Spanish skills
. And no, we encountered zero U.S. or Cuban governmental complications

Sunrise in Old Havana.

Cuba: The TL;DR Version

For me, there is always a vacation conundrum. Find a grand adventure with my sons to keep us all on our toes or find a beach and a napping station. This year in particular, there was a real need for some decompression. When the recent news broke of a renewed relationship between U.S. and Cuba, I knew we had to go—and that felt a bit adventurous. But with all my might, I also needed to plan some serious down time. Success! Here's how it all went down.

Planning: So how can you go to Cuba? It's now legal to go to Cuba provided your trip falls under one of these twelve reasons: family visits, official business of the U.S. government, foreign governments, and certain intergovernmental organizations, journalistic activity, professional research and professional meetings, educational activities, religious activities, public performances, clinics, workshops, athletic and other competitions, exhibitions, support for the Cuban people, humanitarian projects, activities of private foundations or research for educational institutes, exportation, importation, or transmission of information or information materials, or certain authorized export transactions. Obviously, I was going for journalism purposes. But here’s the thing: No one asked me or anyone else to explain or prove. And there are a lot of nebulous definitions in the above list. And that is all I am going to say about that.

Shop the Story

How to get there: We simply bought plane tickets online. We then received an email from Cuba Travel Services informing us of the process to receive a visa. They sent over documents which we completed, along with paying additional processing fee, and that’s all it took. We arrived in Miami, stood in a gigantic line, and lo and behold, our visa and tickets awaited.

Melvis House, Havana

Lodging: All internet research pointed to avoiding hotels. There are many “casa particular” which allow you to stay in neighborhoods, eat better food, meet families, and try to understand a little more of real Cuba. Don’t get me wrong; I love a good fancy hotel stay. But the hotels reviewed online all seemed over-priced and under-serviced. Recently, Airbnb started listing apartments and we used this for Havana. Here's where we stayed:

Join The Conversation

Top Comment:
“Even though there are few Americans in Cuba, the Canadians and Europeans have been going there and have invested in many hotels and businesses. So, they usually assume that you are Canadian if you speak English. I would love to return someday soon!”
— dymnyno

Melvis House in Old Havana for 2 nights; simple and lovely with incredibly nice hosts.

Casa Isorazul in Varadero beach for 3 nights. Great location, fun and helpful hosts, great breakfasts.

Maison Cuba in Old Havana for 3 nights. Absolutely incredible. Prices already going up.

Casa Isorazul
Maison Cuba
More Maison Cuba

Money: U.S. debit cards and credit cards don’t work. Because that’s not complicated enough, there are two currencies in Cuba, one for tourists and one for locals. (“CUCs” pronounced “kooks” and “pesos cubano” in the vernacular). It worked out fine, but it did require more planning and a little additional stress while we were there. More on that below.

Language: I downloaded Duolingo approximately 14 seconds after I bought the tickets because I was silly and romantic in my youth and studied French exclusively. Did it help? Absolutely. I had a vague sense of what was happening around me and could understand menus (VERY IMPORTANT), signs, and some basic conversations—but if I didn’t have my high school son, who is competent and conversational, it would have been very hard. Many people did speak a little English, of course. But because culturally there were so many confusing signals, and formal information was not often correct, we were constantly asking questions and running into roadblocks.

Packing: It never serves you well to dress like a tourist, but really try to keep it low key here. Also: The roads are bad and wet and dusty and broken and you’ll be walking a lot. (I broke two pairs of sandals and almost devolved into wearing sneakers with my sundress but in the end, couldn’t pull the trigger. Judge away.) It is very difficult to find supplies, extras, and clothing, so careful packing is important.

Information and Communication: There is very limited internet. Like really: none of any use. And U.S. cell phones don’t work. For someone like me—no Google maps, no search, no online dictionaries, NO TWITTER—this was daunting. So I did what normal humans do (okay, not really) and I printed long, incredibly detailed excel documents with information on addresses, directions, phone numbers, hours of service, and tips. I bought 2 different print maps for no particular reason—one detailed of Havana and a general Cuba map; I downloaded a dictionary app that you could use offline. I loaded up my iPad mini with dozens of New Yorkers, books, podcasts. I was in full media and information panic. It turned out much of the travel information I compiled was outdated or just plain incorrect. Travel planning for Cuba is hard. But it's worth it. Below are some of the highlights from our trip.

Havana Highlights

Museum of the Revolution: In Batista’s former presidential palace, this museum had stunning architecture and great views, even without the exhibits. Inside, it was chock full of history, propaganda, and full-on America vitriol. You could see the staircase where Batista made his escape from the revolutionaries. We loved it all.

National Museum of Fine Arts: There are two locations—one with an international focus and one with a Cuban focus. We went to the latter. It was utterly amazing and I was ashamed I knew few none of the artists. We particularly fell for Tomas Sanchez.

Old Cars: Duh, right? No, you don’t understand. It’s not like there are dozens, or hundreds. There are thousands and thousands of old American cars everywhere in every color, model and condition. A favorite memory is our very discounted taxi which required our driver to hotwire the car at every stop.

Electric railroad from Havana to Matanzas: It’s ancient, hot, crowded, uncomfortable, and slow. The train broke down dozens of times. You must do this. 

Malecon: One night, the boys and I walked for miles from a restaurant to our rental along this stretch of sea wall and it was such a fun, lively scene. Picture thousands of Cubanos simultaneously making out...with food vendors, and booze, and lots of selfies. 

Just walk in Havana. Walk and walk and observe life. 



As mentioned above, we took the old Hershey railroad from Havana to Matanzas. A 80-mile trip featuring multiple breakdowns, a random film crew, shared snacks with our neighbors, and a few rocky times we were sure we were going to derail. 4 hours later we arrived in Matanzas, found a taxi to Varadero, and arrived at one of the most beautiful beaches I have ever seen. All the mega-resorts are also on Varadero at the end of the strip, but we never got close. We stayed downtown and everything was walkable and wonderful. It was low-key, not crowded, shaded by palm trees, and had warm calm waters.

Where and How to Eat in Cuba

Generally you get the sense that Cuba is cut off from food culture and that it is very difficult to get supplies, even for the rich tourists. Varadero had better food than Havana (that we were able to find); my host in Varadero recommended some really good small restaurants. As she seemed to live a fairly middle class life, I asked her which ones she liked the best and she laughed. “Cubans do not go out to eat. We are too poor.” So the restaurants, even the paladars, which are private, family-run (not state run), were really solely there for us. And you felt that.

There were many secret windows and small storefronts selling very cheap food to locals. I wish I could say we found some interesting things, but really it was a tough go with no variety: meat is in short supply, vegetables are not great. There were a lot of cheese and meat-like sandwiches. The Cubans depend on home cooking. Most of it is tasty and simple: beans, rice, fish and pork with cilantro, garlic, limes, etc. One of our best bites was a sandwich from our host in Varadero, after she let me pop into her kitchen and see what was brewing on her stove. Moments later we had pork in green sauce on soft buns.

Every place we stayed made breakfast for us and it was great. Eggs, tons of fruit, some sweet bread and coffee coffee coffee. I’m not proud to tell you my teen is now a coffee drinker. “I learned it from watching you, mom!” Fruit was abundant, varied, delicious and people made wonderful use of it all, and I did find some local markets. And in general drinks were pretty damn good—we drank piña coladas, mojitos, and daiquiris of all stripes.

Restaurants we’d visit again:

  • Salsa y Suarez: (Varadero) I’d say our best meal in Cuba.
  • La Vaca Rosado (Varadero): Fun vibe on a roof.
  • Cafe de los Artistas (Havana): Lovely service, excellent drinks, nice menu.
  • Otra Manera (Havana): The fanciest place we went. El Bulli pedigree, international wine list, and a great story that this is the owner’s mother’s paladar that she is reviving. It was good, but the food did feel a little dated in a European way. It was also our last night and I think we ordered poorly. Plus, we were severely under-dressed and my son Oscar was really sick of translating. I'd try this one again.
  • Paladars: We had many simple, inexpensive meals of fish, meat, rice, and beans at various paladars. Perfectly lovely.
  • El Floradita: Hemingway’s haunt. Yes, touristy, but pretty cool nonetheless. Daiquiris were good, if lacking in any discernible alcohol. Just drink there...and gawk.

Other random interesting things, observations, and tips about Cuba.

  • Water, in general, was an issue. We knew it was not potable and that didn’t bother us. In all of our rentals, water for general use was also an issue: It was barely a trickle in the showers. (Note that we were in the old part of town. Possibly other neighborhoods or hotels would have a different situation.) Also, it isn’t super easy to find large bottles of water. You can go up to private places that sell food and water, but they don’t always like to take the tourist pesos.

  • Conservation and resourcefulness: Even in 95+ temperatures, locals drank small amounts of water, slowly. Waiters didn't come back to try to sell you more drinks or offer dessert. Portions were small. Everything was being fixed. Everything was being resold. People were beyond resourceful. Almost every taxi we took had a mechanical issue. Once we blew out a tire on the road, and the driver had it fixed perfectly, I swear, in 6 minutes. Our hosts were on the roof repairing a water tank one day.

  • Music: Part of the essential DNA of Cuba, it's constantly streaming out of homes, apartments, shops, taxis, churches. I felt like our vacation had a soundtrack. One of our hosts attributed this to the high level of music education in the country. It was varied and wonderful. If you heard anything from Buena Vista Social Club, you knew you had entered a tourist vortex and ran for the hills. One evening on our terrace, we blasted Miles Davis' Ascenseur pour l'Echafaud into the night to add to the cacophony, and when it stopped, different people all over were calling out for more. I will always remember that.

  • Money: Carrying all the money you need for 8 days in cash, including for expensive things like lodging, is stressful. Figuring out when to exchange money and how much was also constantly on my mind. There are lines, and significant fees, and you forget when you have no debit card to fall back how much cash is flowing out of your pocket. Amazingly, I budgeted pretty much exactly how much we needed.
 But being a tourist in Cuba is not cheap: Because the local economy is complicated, we never really figured out how to buy things like a local. I wanted to unravel the mystery but needed more time, more Cuban friends, and better language skills.

  • Safety. You’ll notice I offered no warnings because I never felt any threat. Some people would try a small hustle, but they are quite obvious. The guy selling you bread in the morning is trying to hustle you in the afternoon. The nice guy who helps clean the pharmacy across the street is the next day trying to get you give him money for a private tour of something. Generally by day three, everyone left us alone because we didn’t look so ridiculously helpless. People in Cuba are poor and they are trying to catch a break. That is all it really seemed.

  • Bring gifts for your hosts. The boys thought it was weird, but we were staying at family homes so I brought them and was glad I did. Because our hosts really acted like hosts, I wanted some way to show them we were grateful beyond the tip transaction. We also brought some frisbees to leave behind with kids.

Cuba is a puzzle. I won't pretend to have deep insights after eight days, but I will say that it taught us lessons. I did not expect to feel so emotionally attached; it was both inspiring and heart-breaking to be there. The sense of community and generosity and civility is hard to describe. One of my coworkers sent me this upon my return, and it accurately describes the vibe there better than I ever could. Viva Cuba.

Cruising Cuba-style #latergram

A video posted by @bridgetwi on

See what other Food52 readers are saying.

  • roryrabbitfield
  • dymnyno
  • FJT
  • Jeremy Beker
    Jeremy Beker
  • Carmen Ladipo
    Carmen Ladipo

Written by: BrooklynBridget

Flawless mother, sublime cook, zippy biker, COO at Food52


roryrabbitfield May 18, 2016
Is it possible to buy a ticket from an American city directly to Havana? I can't find a way to do this online.
BrooklynBridget August 22, 2016
3 months later, just seeing this! Yes we did. We booked through Cheapair and I hear Jetblue is now flying directly.
dymnyno December 24, 2015
We went to Cuba in 2007 through the "back door". We loved it! We did stay at a very nice hotel (The Saratoga) which was located directly across the street from the old Capitolia. We hired a car and a guide. The black market system is alive and thriving which is what Cubans need to survive on the meager pay and food allotments that they receive each month. It is at every level of Cuban life, from guides with cellphones to fresh vegetables which are smuggled into Havana, to hawkers selling cigars. Walking through old Havana is an amazing tour. They are slowly restoring the old city, but have a long way to go. Havana was incredibly opulent in its day. It looks like Palm Beach with 60 years of deferred maintenance! Hitchhiking is a way of life and there are long queues everywhere and they take names and people wait their turn. Few people can actually afford cars so when you fly into the airport, you will look down on empty highways. Even though there are few Americans in Cuba, the Canadians and Europeans have been going there and have invested in many hotels and businesses. So, they usually assume that you are Canadian if you speak English. I would love to return someday soon!
FJT December 23, 2015
I've been to Cuba and I agree that it's definitely worth a visit. We went in 2010 - we wanted to go before there was a Starbucks or Big Mac on every corner. Beautiful, interesting place.
Jeremy B. December 23, 2015
I've been looking forward to this article since you got back. Exciting!
Carmen L. December 23, 2015
Allison December 23, 2015
This was a wonderful article! My husband is Cuban and we so want to go. I'm emailing it to him right now so we can start planning!