As of June 17, 2017, there is a new policy for travel to Cuba. Click here for information about how the new regulations may impact your travel plans

U.S. citizens no longer need to be part of a group tour to visit Cuba. Sounds good, but what exactly does this mean for you? Well, it’s never been easier or more affordable for you to make the trip!

vintage car, Havana, cuba

You can book accommodations, flights (on CheapAir.com, of course, still the only online retailer selling airline tickets to Cuba for eligible travelers), and visit sites and enjoy the cuisine. 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, #5 “Educational Activities” in which you will have a full schedule of activities designed for people-to-people contact with Cuban citizens fits the bill.

Step 2
Book your flights on CheapAir. We have daily direct charter flights from Miami and a schedule of other direct flight options from Tampa, New York, and Los Angeles. Since many flights are sold out, you can also contact us for assistance. If you’re traveling from other cities, you’ll need to allow a bit more time for the flight connections. Commercial flights are also being ironed out as we speak (schedules should be out sometime this summer with flights beginning in the fall of 2016). You may also find it helpful to know you can book commercial flights connecting through Mexico City or the Cayman Islands using our site. Basically, our booking engine will serve up the best option based on your origin city. Easy peasy!

Doorway, Old Havana Cuba

Step 3
Arrange your accommodation. This is where it gets a little interesting! More and more Americans are making the trip to Cuba and the travel infrastructure is racing to keep up. There are a few high-end hotels in Havana, but they book out very early. If you’re looking for an alternative, you can stay 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.

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 sticker shock. The limited number of Cuban rental car companies are in high demand and command a high price. Be prepared to spend 2 to 3 times what you might spend in the United States for a week. The upside? You’ve got complete freedom to travel about the island’s uncongested roads, stopping wherever you like and exploring villages and cities on your own timetable. Having a car in Cuba is well worth the splurge if you want to get out of Havana and explore.

If you’re the thrifty sort or have a leisurely timeframe in mind, you can get around Cuba using buses like the locals, but it’ll be a less structured affair than you’re used to. In Cuba, local customers know where to catch the bus (sometimes unmarked highway underpasses for inter-city travel), and have a somewhat confusing (to foreigners) queuing system. Working knowledge of Spanish will help quite a bit, but even the most seasoned world travelers on our team have found getting around Cuba without a taxi driver or car, somewhat of a challenge. Cyclists have been doing it for years, and if you’ve got the legs for it, biking is another fantastic way to get around. Also, don’t underestimate local interest in you. Most of the time, the connections you make in Cuba can lead you to an unofficial “cousin” who drives his 1950’s era car around the island for travelers or a guy who knows a guy that can get you to Santiago on Sunday. The entrepreneurial spirit is alive and well in Cuba, despite what the government would have you believe. That leads us to the all-important consideration for Americans. Money.

Step 5
Plan to bring lots of cash. Lots of it. American banks are still not synced up to the Cuban banking system so this essentially means no ATM access for U.S. citizens (reports of Master-Card accepting ATMs in Havana are vastly overstated). Most businesses will not accept credit cards. Don’t let this point stress you. Just make a budget and plan to bring 30-40% more than you think you’ll need. Unplanned expenses always come up and you don’t want to be pinching pennies on your vacation. As a thank you for your visit, the Cuban government extracts a $25 fee from each visitor upon exit so don’t forget to set at least that much aside on the day you plan to leave Cuban soil (side note, on most charter flights this $25 is now collected upon departure from the U.S.).

Some people get caught up in what kind of money is best to bring. 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. Keep it official and you won’t get ripped off.

Trinidad, Cuba

Step 6
Research your trip thoroughly. Here’s where you put the trip planner – that persnickety person who likes to schedule things – to WORK. Cuban museums and cultural attractions are set-up as they are the world over, so you’ll want to have a plan of attack on how to organize your activities and keep a list of hours of operation and holidays that could affect those plans (you may not have an internet connection there to confirm the hours after you arrive). You should also keep a few activities as back up just in case Plan A gets derailed. 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. Though most of the time, no one will ask.

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 are two very straightforward documents that cause a lot of American confusion. First, the tourist card, which is what a lot of Americans call a visa. In some cases, when you buy a direct charter flight through CheapAir, our charter partners will help you procure the tourist card. If you buy a flight that routes you through another country (like Cayman Islands, Panama or Mexico), you’ll pay for the tourist card in the airport as part of the check-in process. If you aren’t sure which category your ticket falls into, never fear. Just give us a call and we can let you know if you’re going to need to get a card on your own.

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. Yep. If you have a tummy ache in Cuba, you’ll get to be up close and personal with socialized healthcare. But it’s a good thing. Cuban healthcare is respected around the world and their insurance is a pittance (under $10/day). 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.

Step 8
Enjoy your time in this amazing country! One last tip: for dining, experience paladar culture. Paladares are “unofficial” restaurants operated by citizens. They used to be quite secretive, and speak-easy style in people’s living rooms. But these days, there is more of a mutual understanding between the government and the restaurants. For a few of the best check out Artempo Cuba’s list of attractions. And while you’re at it, take a gander at the post 12 Helpful Tips for U.S. Travelers to Cuba. It was written by an expat American who works in collaboration with the Cuban people and should answer many of your questions about Cuban travel.

We hope we’ve been able to show you how simple it is to travel to Cuba on your own. CheapAir.com 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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178 Comments

  1. there is no doubt how you researched hard to get these points, really appreciate the efforts you have put in!

  2. I just returned from Cuba by the way it is great! The people are fantastic and will welcome you. What we found was there were no issues entering or leaving the country. Since the State department has not written its new guidelines, we can still travel under the “Obama rules”. So for the most part you can self qualify for the “license” you will use and should be able to go now. And please do go, people are not traveling and many of the small business owners are worried.

  3. Hello,

    I’m thinking of going to Cuba next month. How long will it take to get a travel card and are you positive that I can go there without tour group? I’m worried about getting in trouble.

  4. I’m somewhat confused and need help. I booked a flight to Cuba from the US. I chose People to People/ Education as my reason. However, I’m now learning I need a paid consultant or agent of the sponsoring organization to accompany me and wife. I’ve also learned that the paid consultant or agent need to travel with us from the US. Can some on please confirm? Any other recommendations would be great. I’ve already paid for my flight and I hate to lose money! Thx

    • Hi Naz, When was your flight purchased? If you bought before June 16th this year, you can still travel on your own without a group. Please carefully read this post that explains the new rules: https://www.cheapair.com/blog/destinations/travel-to-cuba-before-its-too-late/. The requirements for the various licenses are varied. Off the top of my head without hearing the kind of tip you’re planning, its difficult to peculate what sort of sponsor you might need.

    • This is totally in accurate. I just returned on Sunday the 29th of October and al was fine. My wife and I went by ourselves. If you desire book tours for when you land but don’t hire a tour company now. The airlines make most of it easy, the coordinate your insurance and exit visa. Go and have a great time.

  5. I’m trying to coordinate a student trip (college kids) on my own so I don’t have to pay inflated prices from a travel agency. Do you think it’s possible with the new regulations to make it happen? I’ve already been to Cuba and know exactly where I’d take the students –just need to secure some type of bus.
    If you have any suggestions please let me know! Thanks!

    • Hi Christina, It’s a little bit hard for me to say in your case. The new regulations, I believe, ONLY affect INDIVIDUAL people to people travel.If you’re putting together a university-sponsored group you should be fine.

  6. Thank you for all this info! Do you suggest any single day tour operators/locals that could involve educational snorkeling or any way to delve into that beautiful water? To be able to surf there would be even more amazing. My family will be there from 9am-7pm on June 19th, arriving by cruise. We will have grandparents and babies in the group. Grandpa will not be able to walk extensively and the kids (2, 6yo) will not be able to have attention span for 10 hours of museums. Appreciate any advice.

    • Hi JD, Not really off the top of our heads. Remember – leisure travel is still strictly forbidden. The only acceptable activities are those that facilitate person-to-person interactions; those interactions that promote cross cultural communication with the Cuban people. Now, once you get to Cuba it may be that you could participate in a conservation project working with Cuban scientists/ecologists, etc. but that may be difficult to coordinate in advance. Not impossible, but challenging. I would reach out to a Cuban cultural exchange agency (there are a few in Miami) and see what they suggest.

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