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A how-to guide to visiting Cuba that finally makes sense

Story highlights

  • The U.S. and Cuba have agreed to resume commercial air service between the two countries
  • 12 categories of traveler can self-authorize a trip
  • Tourist travel to Cuba is still illegal for U.S. citizens and residents

(CNN)Since President Obama restored diplomatic relations with Cuba, there have been endless headlines heralding the reduction of travel restrictions for U.S. citizens.

With a resumption of commercial flights coming soon and more loosening of restrictions in advance of Obama's upcoming visit to the island, excitement is growing faster than ever.
Unfortunately, the changes have been instituted by way of sometimes-contradictory bullet points outlining downright bewildering guidelines. With so much ambiguity, deciphering the new policies makes rocket science look rudimentary.
    Through a careful review of the reforms, we've managed to work through the confusion. Here's a dose of clarity for American travelers with Cuban travel aspirations.
    So ... American tourism is or isn't legal in Cuba?
    Though the U.S. and Cuba have re-established diplomatic relations, the two countries have far from worked everything out. General tourist travel to Cuba is still illegal under U.S. law.
    Until Congress decides otherwise, U.S. citizens and permanent residents are prohibited from traveling to Cuba for the sole purpose of basking on a beach and drinking daiquiris.
    If the U.S. Department of the Treasury were to discover that an American took part in such illicit activities, he or she could be subject to legal penalties.
    How rigorously illegal tourism will be monitored remains to be seen.
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    Why is everyone saying that more Americans can travel to Cuba?
    Before 2015, if an American wished to visit the island, e.g. a marine biologist studying Cuba's coral reefs (let's call her Jane Smith), she would have had to obtain a travel license from the U.S. Department of the Treasury via a lengthy application process.
    What has changed is that this lengthy licensing process has been retired for certain types of travelers, like Jane Smith, who is now free to book a flight to Cuba without acquiring explicit clearance by the U.S. government.
    As long as Jane Smith's schedule does not include activities inconsistent with a full-time research job, now all she has to do is obtain a tourist visa (different from a license) and -- if traveling directly from the U.S. -- sign an affidavit from her travel provider about the purpose of her trip (details below).
    She'll also need to keep records and receipts of her trip for at least five years, according to the Department of the Treasury.
    There are 12 broad categories of travel activities that have been granted permanent pre-approved status (PDF):
    • Visiting family
    • Humanitarian projects or to provide support to the Cuban people
    • Official business of the U.S. government, foreign governments and certain intergovernmental organizations
    • Journalistic activities
    • Professional research
    • Educational activities by persons at academic institutions
    • People-to-people travel
    • Religious activities
    • Public performance, clinics, workshops, athletic or other competitions and exhibitions
    • Authorization to provide travel services, carrier services and remittance forwarding services
    • Activities of private foundations, research or educational institutes
    • Exportation of certain Internet-based services
    On March 15, 2016, the U.S. government made another significant change to the rules around people-to-people educational travel. Before the change, Americans were required to be accompanied by a sponsoring organization subject to U.S. jurisdiction.
    Now, individuals can organize their own people-to-people trips as long as they have a full-time schedule of educational exchange activities.
    Traveling to Cuba is indeed easier for many than it's been in decades. It's just not the free-for-all it's been made out to be.
    Tourists take in the sights from a double-decker tour bus.
    What constitutes a valid reason for visiting Cuba?
    The stated purpose of your trip has to fit within the above 12 pre-approved categories.
    Fortunately, it seems that with the right spin, almost anything can.
    Some of the 12 categories are clear-cut, such as going to Cuba to "visit relatives" or "attend a professional conference."
    However, most are vaguely defined, such as "journalistic activities" or "providing support for the Cuban people." In the era of social media where everyone is a publisher, what qualifies as journalism? (PDF)
    On the one hand, such obscurity makes the criteria more inclusive, a seemingly welcome thing for prospective travelers.
    Yet, the ambiguity creates a murkiness that most would rather do without in a self-authorizing system that carries the possibility of penal consequences.
    Who decides whether I meet the criteria of these categories?
    You do. The traveler categories are self-authorizing.
    What was once a formal application system has essentially been converted into an honor system whereby you conclude whether you meet the categorical criteria.
    Though you don't need a license, you do need a visa to enter Cuba.
    Puerto Rican tourists visit Old Havana.
    Wait, a visa is different from a license?
    A visa is a completely different document from the retired travel license, and all U.S. visitors to Cuba are required to have one in hand before arriving.
    Getting a visa for travel to Cuba isn't as straightforward as faxing a form to the nearest embassy.
    By far the easiest way to obtain a visa is through a travel agent specializing in travel to Cuba, such as Cuba Travel Services or ABC Charters, which quickly process visa applications in-house.
    You can receive your visa in the mail (it takes up to four weeks), or you can arrange to pick it up at the U.S. airport from which you're departing.
    If you want to make all of your travel plans independent of a travel agent, you can book your flights on CheapAir.com, and the company will assist in obtaining a visa.
    U.S. visitors who travel to Cuba through a gateway country such as Canada, Mexico or the Bahamas do not need to organize a visa in advance, since they can be purchased at the gateway country's airport during the layover.
    Currently, visas cost about $25.
    Either way -- whether you're traveling through a gateway country or flying to Cuba directly from the U.S. -- if you're a U.S. citizen or permanent resident, you need to fit into the pre-authorized traveler categories to make your trip legal.
    Crowds of foreign tourists walk around on Old Havana.
    Can I fly to Cuba directly from the United States instead of going through a gateway country such as Canada or Mexico?
    The U.S. officially signed an agreement in February to re-establish scheduled air services between the U.S. and Cuba.
    In March, U.S. airlines submitted applications for specific routes. The Department of Transportation is expected to make a decision on the flights this summer.
    In the meantime, charter service will continue.
    Before 2015, there were only a handful of flights to Cuba from the U.S, all charters and strictly reserved for those granted travel licenses. In 2015, several direct daily charter flights from New York, Miami, Tampa, Los Angeles and Washington were added.
    Because the flights are technically outside the scope of the airlines' normal service, they can be booked only through the charter organizer or in some cases at CheapAir.com.
    All U.S. suppliers providing Cuba travel services, whether a travel agency or an online booking engine, currently require American travelers who fall within the 12 pre-authorized categories to sign an affidavit (a legally binding document) declaring the exact category with which they identify, e.g. visiting family.
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    The affidavit is normally collected by the supplier at the same time as the company is processing a traveler's flight reservation.
    Though the direct flight gets points for convenience, at this time it is still cheaper to opt for a two-leg journey: booking a round-trip flight from the U.S. to a gateway country such as Canada, Mexico or the Bahamas and then a separate round-trip flight between the gateway country and Cuba.
    Flying through the Bahamas is generally the cheapest option. To legally fly through a gateway, U.S. travelers must still fit within one of the authorized travel categories.
    Direct flights between the U.S. and Cuba are likely to become more affordable as scheduled commercial service resumes.
    Can I take a ferry to Cuba?
    Perhaps in the near future. Regular ferry service from southern Florida to Cuba is expected to commence in 2016.
    Inaugural voyages aboard small cruise ships are also slated for this year.
    Do I have to use a travel agent, or can I plan the trip myself?
    There a few ways to go about planning a trip to Cuba.
    You can certainly book your trip in a totally DIY fashion, arranging for flights and a visa online via CheapAir and accommodation through sites such as WowCuba, Cuba Particular and even Airbnb.
    With the growth of the sharing economy, more and more travelers are opting to stay in guest houses and vacation rentals, making the arrangements directly with independent Cuban property owners.
    Another option is to work with a travel agent only in the capacity of organizing flights and applying for a visa, in order to simplify the booking process, while autonomously planning all other activities.
    However, although you're not legally obligated to participate in an organized trip, to ensure full adherence to approved travel categories, this still might be the best bet for the time being.
    Many travelers suggest working with a full-service boutique tour operator, such as Havana VIP Tours.
    These organizations will not only handle flight and accommodation bookings, they design a fully compliant non-cookie-cutter itinerary that includes immersive activities like cooking classes, dance workshops, theater performances, architecture tours and volunteer work.
    Other important pointers:
    Cell phones: Cell phones with a SIM card from a U.S. provider will not work in Cuba, so don't expect to fire up your iPhone and roam like home upon arrival on the island.
    If your phone is unlocked, you can purchase a local SIM card that will allow you to call and text (no data).
    Internet access: Even with a Cuban SIM card, you won't have data on your cell phone, a stark change for ever-connected Americans. Internet access is limited across the island, available for purchase by the hour at certain locations.
    With the exception of a few wi-fi hot spots at higher end hotels, most connections are sluggish dial-up. As such, if you have any booking confirmations or other paperwork you need during your trip, you should print them out before departure.
    Cash: Some U.S.-issued cards now work in Cuba, but credit and debit cards linked to U.S. financial institutions are not working across the board.
    You should bring enough cash to cover all expenses and then some. Also, make sure to set aside cash for the exit tax that is charged when you leave the island.
    Money exchange: To get the best exchange rate, some travelers suggest converting U.S. funds into euros, British pounds or Canadian dollars before trading the cash for Cuban pesos.
    There is a 10% penalty tax on the exchange of U.S. dollars that isn't applied to other currencies.
    However, it's wise to crunch the numbers before taking this route to make sure that the gains from the first-step conversion don't outweigh circumvention of the 10% penalty tax.