Here is the big question on every potential traveler to Cuba’s mind these days: “can I still go?” It’s easy to get confused. The rules are not terribly clear and the media has sent mixed messages. It’s true that effective November 9, 2017 individual travelers cannot no longer travel independently to Cuba under the educational, people-to-people license.

havana cuba

Those travelers must now visit the island as part of a group (the pre-Obama regulation). However, you can still travel to Cuba without a group if you choose the “Support for the Cuban People” license. Here’s all you need to know in order to do that legally (full disclosure: it’s totally doable). You can book private accommodations, flights (on, of course, still the only online retailer selling airline tickets to Cuba for eligible travelers), visit sites and enjoy the cuisine without running risk of running afoul of the law when you return. Here’s a simple step-by-step guide to a DIY solo tour of Cuba.

Step 1
Qualify yourself for travel. Review the 12 permitted reasons for travel to Cuba and determine which license allows your visit. For most people, #8 “Support for the Cuban People” in which you will have a full schedule of activities designed to strengthen civil society in Cuba will work. The official, 35-page Treasury Department FAQ states that under the amended license each traveler is required to “engage in a full-time schedule of activities that enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities, and that result in meaningful interactions with individuals in Cuba.”

Step 2
Book your flights on CheapAir. We have daily direct charter flights from Miami and a schedule of other flight options from gateways around the country. You may also find it helpful to know you can book commercial flights connecting through Mexico City or the Cayman Islands using our site. Our booking engine will serve up the best option for you based on your origin city. Simple!

Step 3
Arrange your accommodation. This is where it gets a little interesting! The new regulations restrict Americans from staying at the state-owned hotels in Cuba. Inexperienced travelers to Cuba might then infer that the trip is not possible. This could not be further from the truth. In fact, CheapAir and most Cuban tour operators have long steered travelers away from the bigger hotels that are simply not up to U.S. standards and are quite expensive besides! We always recommend staying at the Cuban version of the Bed & Breakfast – a Casa Particular. The Casas Particulares have been a cottage industry in Cuba for many years and are an amazing way to stay in a variety of Cuban homes and experience the real Cuba. It’s now very easy to book them, as Airbnb has scouted out the very best options for travelers. You book a Casa Particular exactly as you would any other Airbnb property. There is really no better way to “support the Cuban people” than to stay in a casa. It’s a very simple way to show you’re in compliance with the rules.

Step 4
Decide on an itinerary and determine your transportation needs. For some people, an introduction to Cuba might mean hanging out in Havana for a week. If you’re planning to just keep it local, you do not need a car. Taxis (both official and unofficial) are all you might require for getting around, and there’s a load to explore in Havana just within the historic center and along the Malecon. If you’re planning on going further afield, you might want to think ahead a bit more. You can actually book a rental car from the U.S. The only drawback to going this route is the cost. Cuban rental cars companies charge exorbitant rates. Be prepared to spend two to three times more than you would at home. If you’re the thrifty sort or have a leisurely timeframe in mind, you can get around Cuba using buses like the locals.

Step 5
Plan to bring lots of cash. American banks are still not synced up to the Cuban banking system, and with the new restrictions it doesn’t look like that’s going to change anytime soon. Keep things simple. Just bring U.S. dollars or Euros. There are plenty of money exchanges (Casas de Cambios) and hotels in Havana who will give you the best exchange rate at the time. Don’t ever exchange money on the street and you won’t get ripped off.

Step 6
Research your trip thoroughly and keep a full schedule of activities. This is where some of the confusion comes in and has people asking “what is considered a full schedule of activities under the ‘support for the Cuban people’ license, anyway?

The Treasury Department has described one such acceptable schedule as “a four-day trip that qualifies when an individual plans to travel to Cuba, stay in a room at a rented accommodation in a private Cuban residence (casa particular), eat at privately owned Cuban restaurants (paladares), and shop at privately-owned stores run by self-employed Cubans (cuentapropista).” In addition, the traveler “will complete his or her full-time schedule by supporting Cuban entrepreneurs launching their privately owned businesses.” Easy peasy!

CheapAir also has a great resource in Havana VIP Tours, where you can schedule inexpensive walking tours of Havana whether you’re interested in art, history or architecture. Keep your receipts for cultural activities to demonstrate your visit was filled with “authorized travel activities.” In layman’s speech, as long as you keep records of museums visited, local tours you took, cultural activities attended, etc. – you should be golden when you come back through customs.

Step 7
Take care of the red tape. If you’re going to Cuba you need two documents – the Cuban “tourist card” and proof of Cuban health insurance. These days, most airline tickets bundle these items in with the cost of your fare, but it’s a good idea to double check.

Cuban health insurance has nothing to do with any trip/travel insurance you buy here to protect yourself while on holiday. The Cuban government requires you to purchase Cuban health insurance so if you are on vacation and need to be seen by a Cuban M.D. you are covered for that visit. If you don’t have it before you land on Cuban ground, you’ll be required to buy it in the airport before being admitted to the country (it’s just a few dollars a day).

Step 8
Enjoy your trip! And for additional help with the new rules, you might want to read Changes to Cuba Travel for US Citizens. It was written by an expat American who works in collaboration with the Cuban people and answers a lot of popular questions we’re getting these days.

We hope we’ve been able to show you how simple it is to travel to Cuba on your own. has had a number of staff visit the country and their expertise has contributed to this post. We are proud to continue to be the only online travel agency selling charter flights to Cuba, and we aim to make your trip planning process as simple as possible.

That’s all for now. We’d love to hear from any other travelers to Cuba on your experiences and any updates to the information we’ve included in this post. Happy travels!

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  1. Being a traveling freak would like to say that this one found so much massive as mine one day trip from philadelphia. I am sure this will remain helpful for others as well.

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