Traveling to Cuba has changed on paper – but not so much in reality.
Are you looking to travel to Cuba but don’t know how? Here is everything you need to know.
Like many things on this sleepy island nation, change is slow to come. Though President Obama has normalized relations and you can now “self certify” for a travel visa, in real life, traveling to Cuba is exactly the same as it has been for the last several years.
HOWEVER, if you follow my advice, you can see Cuba just like any other tourist, no need to go on a people to people trip where you are ferried from one government approved activity to another. I have been to Cuba twice in the last year. The first time as a guest of cazenove+loyd on one of their small Inspired Journey trips, the second trip was a gift to my husband for our anniversary. We booked through cazenove+loyd and paid for the trip and experienced it just like any other client.
What you need to know to travel to Cuba as an American
Getting a license: You still need to get an OFAC license from a people to people organization to book a charter flight from the US. How do you get a license? Work with a great tour operator like cazenove+loyd and they will expedite the process. We applied for, and received, our license in just over a week. It cost $250 per person as a donation to the organization. Though we traveled under their permit, we were not required to travel with them or be on a pre-planned itinerary. The law is very gray here, if you are a small group of Americans (say under 4) the governments is far less interested in your travel plans and a good travel planner can organize a trip for you that allows you to stay where you want and do what you want. The new regulations allow travelers to “self certify” in 12 categories which means you don’t technically need a people to people license. But here’s the catch: charter flight operators don’t accept self certification yet.
Currency and credit cards: Though the regulations have changed, there are still no American credit cards accepted anywhere in Cuba, it will take time for infrastructure to catch up. You can pay for hotels and most activities through your travel planner, but you will still be paying cash for food, drink and local expenses. There is a 10% fee to exchange American dollars for Cuban currency. Savvy travelers bring Euros or Canadian dollars (the exchange cost is only 1%). Also, tourist tips are what most Cubans depend on for survival, they also have to pay an exchange rate for US Dollars, tip in the local currency.
Where to stay: Accommodations are very basic, even the five star hotel patronized by Jay Z and Beyonce is a bit rough by American standards. On our recent trip we stayed at the Hotel Saratoga made famous by the hip hop moguls. The rooms are comfortable, the rooftop pool swank. and the pool bartender a dream. The hotel offers surprisingly good wi-fi and American TV. Last spring our group stayed at the Hotel Santa Isabel right in the center of town. The rooms were a little more rustic than the Saratoga but the views of the Plaza de Armes from our balcony and the al fresco breakfasts made it my favorite hotel. If you have the time I recommend a trip to Trinidad, the most quintessentially charming Cuban town. It’s about a six hour drive, you can stop at Che Guevara’s mausoleum on the way. The best place to stay is the Finca Kenia, a ranch/bed and breakfast with beautifully renovated rooms, an outdoor pool and a stable of working horses.
Where to eat: New paladars (private restaurants) open daily. The food is good in Cuba, but many tourists still get sick. Though La Guarida is the most famous of the Havana restaurants having been the set of Fresa y Chocolat and the top every restaurant list on the web, I found the food average and my husband ended up on the floor of our hotel with terrible food poisoning after eating there. In my opinion, the best restaurant in Havana is the brand new Cafe la Flauta Mágica, it occupies a 10th-floor penthouse-with-pool turned jazz bar. From the terrace you have a view of the US Interests Section (in lieu of an embassy) on the Malecon. It also serves food from the former chef of one of Havana’s best paladares. A few other don’t miss restaurants are Ivan Justo and Rio Mar. Make reservations and be sure to have cash on hand, meals are not cheap, most entrees were around $ 20 US. This is the pool and owner of the fabulous Flauta Magica, far and away the swankiest restaurant in Havana. The last photo is our small group having lunch at Ivan Justo, it’s small and difficult to find, the only indicator is a small sign over the door in the alley.
Staying healthy and what to do if you get sick: It’s best to drink bottled water and make careful food choices. Though I’ve never been sick in Cuba, my husband has and I’ve heard many anecdotal stories from other travelers. There is a health center for tourists only and the Hotel Nacional has a doctor on staff should you need medical care. The night Jeff was sick the staff at our hotel called the doctor at the Hotel Nacional, she came over and cared for him in our room. At no cost.
How to get around: Taxis are plentiful and easy to find, if not always in great condition. It’s a myth that all of Havana is rolling with perfectly preserved mid-century American cars. Given that many of these cars are now at least 60 years old and the embargo has included car parts, only the most clever of mechanics have kept their cars in mint condition. There are many cars and drivers that you can hire on an hourly or daily basis. We paid to have an Audi and driver at our disposal during the entire trip. I think the cost was few hundred dollars a day and more than worth it. We never had to wait for a cab and hope it had air conditioning (most don’t) and our driver served as a personal tour guide taking us to his favorite places and making sure we made it everywhere we needed to be on time. 
What you can bring home: You can now spend unlimited amounts of money on the island, but outside of food, drink and hotel, there is very little to buy. Art has never been a part of the blockade and many Americans have been collecting Cuban art for years. You are now allowed to bring $400 in in merchandise back to the US. No more than $100 of the merchandise can be tobacco or alcohol. In fact, no one checked our luggage, but we still stuck to the rules. There is not much in the way of souvenir goods to buy, you’ll find mostly antique books and posters. I did find Havana Club glasses at the airport on my first trip, but none on my second trip.
How to buy art: Buying art is easy if you have the right guide. Through cazenove+loyd we hired curator Susette Martinez. She has great relationships with some of the most famous artists in Cuba as well as connections to emerging artists. Roberto Diago is one of the more well known artists and was interviewed in the New York Times about the future of Cuban art should travel restrictions truly change. I am saving up for an original Diago and have filled my home with pieces by my favorite artist, Douglas Perez Castro. Seriously, art is more than a paragraph. Contact me if you want more information. A photo of me with Diago, and the piece I dream of owning. A shot of Douglas with the piece that Jeff fell in love with, a very cheeky interpretation of the Disney machine. And a few of the art in my home. I love, love, love Douglas’s work.
The total cost of our recent trip, which included hotels, car, driver, art curator, and salsa lessons was roughly $ 8,000 for two people for four days. Our flights to Miami were relatively cheap, the charters were $800 round trip each and we paid for all meals out of pocket. Please comment with questions and I’m happy to help you plan your dream trip to Cuba.