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The Capitol in Havana, Cuba
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Ever since former President Obama eased sanctions against Cuba last fall, Americans have flocked to the island. U.S. visitors, however, must still meet the conditions of one of these 12 permitted reasons for travel. For most people, educational or “people-to-people” programs, in which you agree to have a full schedule of activities designed for interacting with Cuban citizens, is the most applicable. At this point, however, there isn’t much clarity around which specific activities constitute people-to-people contact, and it doesn’t seem like Cuba is closely keeping tabs on visitors’ individual itineraries.

One way you’re guaranteed to  meet the requirement: visit with a guided tour. You’ll find dozens of tour companies that will do this, but they can be expensive. Here are some tips for fulfilling the people-to-people requirement on your own, without spending a lot on a tour.

Create a comprehensive schedule.


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Start by setting aside time to see monuments, museums, and cultural attractions and any other pre-arranged tours or classes you might want to take (more on that later). But build in extra time for exploration, too. A little spontaneity often leads to connections you wouldn’t otherwise make — a friend who drives his 1955 Ford Thunderbird around the island for visitors, or someone who recommends the best place to go for live Jazz on Thursdays — which can lead to more opportunities to interact with locals. If you’re not sure what to book, we recommend looking at the schedules of tour groups as a model for activities, along with how much free time you can give yourself.

Stay in a family home rather than a hotel.


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At Casas Particulares (family-run bed and breakfasts), you’ll get an intimate look into Cuban life. The homes are more affordable than hotels and some include home-cooked meals (which will likely be the best food you get on your trip). This also allows for quality time with your hosts. You’ll need to book the most well-known casas early — sometimes up to six months in advance — but the introduction of Airbnb has made it easier than ever to arrange home stays. (Plus, you can pay by credit card).

If you are using Airbnb, message your host before you arrive and ask for recommendations for things to do in accordance with your cultural requirement. Also, ask to spend some time with them (some working knowledge of Spanish helps in this case). We found that our Cuban hosts were happy to share their perspectives on everything from relations with the U.S. to how to use the dual-currency system. By staying with local hosts, you’re also supporting Cuban individuals rather than the government — another goal of people-to-people interactions, as outlined by the U.S. Embassy.

Sign up for classes.

Whether it’s salsa dancing or printmaking, taking a class or two during your trip can give you a unique perspective on Cuban history and culture. For instance, while taking a two-hour class on Afro-Cuban drumming, we learned three basic rhythms in Cuban music, where they originated, which instruments were traditionally used to perform the songs, and how to play them on some of these instruments. Not only was it a lesson on the evolution of and influences on Cuban music, it was fun to put our learning into use when we went out to see live music later and could identify the rhythms of rhumba versus danzón.

Book a day tour.

While a week-long group tour might not be your speed, it is a good idea to book some guided tours during your stay. Havana is a surprisingly dense city, and there is a lot to take in. Pick a couple of elements of Cuban culture that really interest you — whether it’s the classic cars, political and war history, or contemporary art — and search for a tour that fits your preferred style of sightseeing. We opted for a tour with Sussette Martinez Montero (+53-7-267-7989), an art insider with connections to everyone in Cuba’s contemporary art scene. She offers half-day and full-day tours, during which you’ll ride around in a red 1954 Chevy and visit artists’ homes and private studios. On our tour, we spent nearly an hour with each artist, talking about their various mediums, the tools they use, and the inspiration behind their work. Many explore themes like emigration and the complicated relationship with the U.S., using symbolic and metaphoric images that allow them to express themselves freely in a country riddled with propaganda.

Keep a paper trail.

A few websites mention saving receipts as proof of your people-to-people activities. However, not many places (in particular local tour guides and business owners) give receipts, and all of your transactions upon arrival will be in cash. We recommend reaching out via email to book tours, classes, and other activities prior to your stay to maintain a paper trail. Keep contact information or business cards for hosts, guides, and anyone else you have meaningful work or interaction with who could be a reference for your stay.

Book your flights that include a tourist card and medical insurance.

Before you can enter Cuba, you’ll need two documents: the Cuban tourist card (which is sort of like a visa) and proof of Cuban health insurance. Arranging these separately is a hassle (we tried) and not worth it when airlines, such as JetBlue, include the cost and handling of both of these items in the price of airfare. This made the immigration process easy and seamless — and it actually ended up costing less than the prices offered by other Cuba travel services. Our flights with JetBlue also included the extra $25 needed to exit the country, which made pacing the money we spent toward the end of the trip easier.

Eat at paladares and shop at local markets.

Paladares are privately owned restaurants, usually run by a Cuban family informally out of their home. Like staying at Casas Particulares, dining at paladares directly benefits the Cuban people who own and run them. Plus, the food is often much better than what you’ll get at other (particularly touristy) restaurants, which serve mediocre food and have slow service.

We also recommend taking the time to go to local markets to buy produce, meat, and bread. It will spare you from having to take three lengthy meals per day, and shopping as the locals do is part of the learning experience — and the fun.

A couple more tips before you leave:

Write down addresses and basic directions to points of interest. It is very difficult to get working Internet in Cuba — you’ll likely have to plan your day around it — so it’s easier (and more refreshing) to go without it. To avoid any hiccups, print any addresses (and directions) before you leave, and make note of any public holidays that might affect hours of operation.

Convert your money in increments, and get rid of it before you come back to the States. The OFAC does not recognize Cuban pesos as legal currency in the United States. That means whatever you come back with, you’re stuck with. We opted to exchange currency in batches (make note of where your nearest bank is), to try to avoid changing over what we didn’t need. Pay a visit to the currency exchange at the airport to change back whatever is left over before you depart.

All in all, traveling in Cuba is an educational experience itself, but activities like these are enriching and help fulfill the necessary travel requirements for Americans traveling to Cuba. If you’re unsure whether one of your activities meets the legal requirements, you can always check with the OFAC directly.

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