travelers exiting a taxi in Viñales Cuba

How to Plan A Trip to Cuba: A Guide For Americans

If you’re a U.S. citizen planning a trip to Cuba in 2024 and you don’t know where to start, you’ve come to the right place. This guide will walk you through the process of planning an unforgettable trip that directly supports Cubans, helps sustain Cuba’s growing private enterprises community, and complies with U.S. travel rules.

Our team has been living and traveling between the U.S. and Cuba for over 20 years. Sharing local tips and recommendations (and other really helpful travel tools) is our passion, as well as our job! Let’s get started—here’s our step by step guide to making your Cuba journey happen.

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Is Visiting Cuba Worth It?

Before we delve into the details, it’s worth mentioning that the extra effort involved in planning for a Cuba trip is, we assure you, completely warranted. Havana alone is a gem of a city—the history, architecture, and energy is all encompassing—and the island’s many regions offer infinite exploration of Cuba’s vibrant culture, stunning natural beauty and complicated national identity. (Think music, art, food, nature, history, architecture, politics, dance…you get the idea!)

All this to say, if you’re worried it is too much work, don’t be—it’s totally doable to plan a legal trip without a package tour, and it’s definitely worth it.

Confused about visas?

Our mission is to provide clear, accurate information on Cuba travel for Americans. Check out our article on visas or visit our site for more!

U.S. Travel Rules for Cuba

Travel to Cuba for U.S. citizens is restricted to certain types of activities, so if you want to see Cuba without having to apply to the U.S. government for permission, you have to follow the guidelines of one of the 12 legal categories of travel that are spelled out in what’s called the “general license.”

The categories lay out the rules for travel to Cuba to do things like journalism, business meetings, sporting events, family visits, and activities that directly support the Cuban people.

Purely touristic activities like spending the day at the beach are not permitted. But activities like guided tours, cooking classes, hiking, dance lessons, shopping at locally owned stores, meals at privately owned restaurants and attending cultural events like concerts, athletic events, and other performances are perfectly legal and easy to arrange. These types of cultural pursuits fit under the guidelines of the Support for the Cuban People category, so most U.S. citizens visiting Cuba choose to plan a trip in accordance with this category.

How to “Qualify” for Legal Cuba Travel

If your reason for travel aligns with any of the 12 categories, you don’t need to submit any paperwork or get prior approval from officials in the U.S. You don’t need to notify anyone or get any special documentation before you travel.

When you purchase flights and lodging, you’ll be required to make an official declaration that your travel activities will fall within the guidelines, and that’s it.

Since it’s then up to you to follow the rules, you will need to make sure you have a plan, and that your plan should show that your schedule of activities fits the guidelines for whichever category you’ve chosen. You’ll also want to save photos and receipts from your trip so you are able to demonstrate, in theory, that you followed the rules.

The “Support for the Cuban People” Category

Support for the Cuban People is the category used most frequently by American travelers. Why? Because it allows for the widest range of cultural pursuits—experiences that anyone might plan on an active vacation.

As long as each day you’re participating in a full schedule (breakfast to dinner) of activities that (a) result in meaningful interactions with Cubans and (b) directly support private businesses or other non-governmental groups, your trip will meet the requirements for legal travel to Cuba under Support for the Cuban People.

Here are some examples of qualifying activities under Support for the Cuban People:

In addition to these activities, which should form the bulk of your daily itinerary, you are also allowed to attend concerts, performances and sporting events. Only activities that are purely “touristic” in nature, like going to the beach all day, are not allowed.

The rules also prohibit U.S. travelers from staying in hotels that are owned and run by the Cuban government. Thankfully, they created a helpful list of all of the hotels and Cuban companies that are off limits, and the rules are very clear: if it’s not on the list, it’s fine to stay there.

Booking Lodging? Taxis? Activities? Restaurants?

We provide Americans with resources for independent Cuba travel. Our private business guide connects you directly to Cuban shops, restaurants, planning services, activities, and more!

Step One: Find Flights

The first planning step for a trip to Cuba is finding flights. As of right now, Delta, American, and Southwest are the only U.S. commercial airlines offering flights to Cuba. Most flight search engines like Kayak don’t show results for Cuba, so we recommend starting with Google flight search or going directly to airline websites to search and book.

Fortunately, the booking process is quite simple—it’s just like booking an international flight to anywhere, with one extra step in which you check a box stating that you plan to travel to Cuba legally under one of the 12 categories. (This is where you select “Support for the Cuban People.”)

Step Two: Get a Visa/Tourist Card

All travelers entering Cuba are required to have a Cuban tourist card, commonly referred to as a “visa.” This visa has nothing to do with the U.S. travel rules. There are two types of visas, one is pink and one is green, and the difference depends on where you’re flying from (not your citizenship).

When you book your flights, the airline will send visa information in their confirmation email. If your “gateway airport” (the last airport you go through before arriving in Cuba) is in the U.S., you’ll need the pink visa. If you are flying from an airport outside of the U.S., you’ll need a green visa.

Airlines typically provide travelers with an option to purchase the visa in the airport on the day of their flight, either at the check in counter or the departure gate. If you’d rather have it in hand ahead of time, the visa can be conveniently ordered online and shipped to you:

The visa is good for 30 days, and can be renewed once for another 30 days. We’ve written an in-depth guide on acquiring the Cuban visa if you’d like to learn more.

Step Three: Create an Itinerary

Your itinerary does not need to be fancy or official looking—a typed up Word doc, Google Doc, or spreadsheet will suffice. It simply has to demonstrate that you have planned out a schedule of qualifying activities for each day that you’re in Cuba. Typically, travelers aren’t even asked to show the itinerary to U.S. customs or immigration officials when traveling to or returning from Cuba. However, it’s good practice to have a digital or physical copy of it handy just in case.

Remember, your itinerary, along with receipts and photos from your trip, should be kept in your records after you return so you can demonstrate that your activities met the guidelines, should you ever be asked to show proof.

The best way to start putting together an itinerary is to go through the list (above) of activities that qualify for Support for the Cuban People, and search online for options that look interesting.

We provide a curated guide to Cuba’s private enterprises that allows you to directly contact and book restaurants, tours, and other activities to start filling in your itinerary. Airbnb Experiences is another great resource for this, and there is a Cuban company called AlaMesa where you can also find interesting options.

CAYOS: Cuba Travel for Americans

Our mission is to provide clear, accurate information on Cuba travel for Americans. Check out our articles or visit our site for maps, itineraries and more!

Book a Full Day Tour

You might also consider one or more full day tours. There are many Cuba tour companies that are based outside of Cuba—often owned by Cuban emigrants—that offer day tours and guide services. For example, Cuban Adventures is an Australian company that offers tours specifically for Americans traveling under Support for the Cuban People.

You can piece together your itinerary in this way to cater to your interests, whether it’s music, history, nature, art, dance, cigars…you get the idea. If you’re not sure or can’t decide, we humbly offer some recommendations:

Book a Tour of Old Havana

What to say about Old Havana—it’s a UNESCO World Heritage site, it’s a maze of human activity, a city within a city dense with history and change—it’s a must see, and the amount you get out of it with a guide versus without is immense. There is a free tour (tipping encouraged) and many different offerings on Airbnb Experiences and other tour companies. Find one that suits your fancy and add it to the itinerary!

Book a Classic Car Tour

If you’re from the U.S. and it’s your first time in Cuba, taking a spin in a refurbished American convertible from the 1950s will not disappoint. Even if the cars now have Chinese motors, even if the experience is a bit cliche…a jaunt around Havana in one of these cars about history, politics, and economics all at once.

And aside from that, as you enjoy the sun and breeze, your driver will take you to all of the major historical and tourist sites of the city. Plus, the tours are often operated by freelance drivers or local private companies, so booking a tour fulfills the Support for the Cuban People requirements.

You can find classic cars and their drivers waiting for clients parked in Parque Central, along the Malecón on the north side of Old Havana, or around most large hotels. A typical loop takes you past the Plaza de la Revolución, the John Lennon statue in Vedado, Bosque de la Habana, and Fusterlandia—all places that are worth seeing, and are on our touristy places map, but maybe not worth going out of your way to visit on their own.

Consider a Bike Tour

Havana is a visually stunning city, and taking it in on a bike is worth the experience. There are several private businesses that rent bikes and offer tours, which are particularly nice for travelers who don’t know the city well. Tours include helmets and guides and are a great way to see the city at a different pace and get some exercise. (And of course, they count toward Support for the Cuban People.)

Get a Tattoo

As anyone walking the streets of Havana will notice, tattoos are quite popular in Cuba—a recent phenomenon in the last two decades. There are several privately run tattoo parlors that have an online presence and are completely safe and sanitary, with unique artistic styles.

See If Your Airbnb Host Offers Activities

If you’ve booked an Airbnb, you can also check with the host to see if they offer any other services like guided tours and experiences, or know of any. Often they have connections within the local hosting community and can find options. Beware however, if you’re booking an experience through your Airbnb host it can be difficult to assess the quality or reliability of the what they are offering. Sticking to sites with reviews, upfront payment and clear cancelation policies make it easy to know what to expect.

Visit Museums

Once you have a some guided tours or experiences penciled in, check out museums and other cultural offerings. Havana has a renowned Cuban art museum, a museum of revolutionary history, and a museum dedicated to the history of the city that are all well worth a visit, with our without a guide.

Go Shopping at Privately Owned Stores

An afternoon of shopping at privately owned stores is another great activity to add to the itinerary, since it directly supports entrepreneurs on the island and a great way to find a memento to bring home from your trip. The CAYOS team has created a Google map of private businesses in Havana—part of our meticulously curated and constantly expanding collection of Google Map lists for Cuba travel.

Hire a Travel Planner

One way to make all of the planning easier and support the local economy at the same time is to hire a local Cuban travel planner (yes, they exist!). Working with a local (many who have worked for ViaHero or other travel planning sites) to plan your trip is a great way to have a point person who is familiar with Cuba and knows guides, taxi drivers and the general lay of the land. They can share opinions, help you find specific activities, arrange transfers, and generally be your sounding board for thoughts, questions and ideas.

If you work directly with a travel planner who is local to Cuba, you’ll need to sort out some of the logistics like payment and the final deliverable as far as what you’re getting, but it’s one of the best ways to both directly support the local economy and get valuable service that will make the planning process much easier and worry-free. Many planners charge a flat fee for each itinerary day that they include in the plan, making pricing easy and straightforward.

Step Four: Book Lodging

Once you have a basic plan ironed out, you can book lodging, which is a simple and straightforward process. Airbnb used to have a monopoly on the best lodging options, but these days you can find lots of great stays on Expedia and Hotels.com, from bed and breakfast style lodging in stately Cuban homes to full apartment rentals and boutique hotel accommodations. Bookings made on these sites directly support Cuban hosts and small private business owners, so they align with the rules for Support for the Cuban People.

The only thing to keep in mind when booking lodging is that you’ll need to avoid hotels that are designated as a “restricted entity” by the U.S (hotels that are owned by the Cuban government), but these options are not available on Expedia, Hotels.com, or Airbnb, so it’s not hard to avoid them.

Even if these hotels were available, there are several reasons why the smaller privately owned lodging options like boutique hotels and B&Bs are better than Cuba’s large hotels.

First, when you stay at a small privately owned hotel, your money goes directly to ordinary Cuban citizens, enhancing the benefits to the local community. Second, the smaller family-run hotels and B&Bs of Cuba are known for having terrific hospitality and relatively low prices.

For more details, our team put together a quick guide to booking hotels in Cuba, with links to our favorites.

If you’re booking lodging in Viñales, Trinidad, Cienfuegos or another smaller city, you’ll also find options on Expedia, Hotels.com and Airbnb. The range of choices is fewer and less fancy, but no less comfortable or hospitable. Of course, you’ll have to wait to book lodging until your daily itinerary is sketched out, but keep in mind that many of the best options get booked up weeks to months ahead of time, especially during tourism’s high season from late December to April.

Step Five: Explore Restaurant Options

There are lots of good private restaurants spread out across Havana, and most cities across the island have a small selection in and around the main plaza at the center of the city. In Havana, we recommend downloading our restaurants map to peruse the best options in different neighborhoods. Old Havana is walkable so you’ll run into many options if you are exploring on foot, but the neighborhoods of Centro, Vedado and Miramar also have a decent and random smattering of delicious options.

By restaurant we are of course referring to Cuban paladares—privately owned restaurants that U.S. travelers are allowed (and encouraged) to eat at under the Support for the Cuban People requirements. Paladares have been allowed to exist since the 1990s and are one of the ways that Cubans can benefit directly from your visit. In recent years, the quality of Cuban cuisine has improved markedly as paladares partner with local privately run farms and access to products from off the island become more accessible.

Still, running a restaurant in Cuba is extremely complicated, which limits the scope of what’s available. But there are still many great restaurants serving delicious traditional Cuban dishes and interesting takes on cuisines of other cultures—check out the guide we made with our list of favorites.

Whether you plan a trip to the more well known paladares like La Guarida or El Cocinero, or you choose to try a Cuban take on international food at Asian-inspired Jama or the Cuban-Iranian Topoly, we recommend contacting them in some form (email, WhatsApp, Facebook) to confirm hours. And for large groups, a reservation is a good idea.

Step Six: Arrange Transportation

Transportation is the trickiest part of planning—and potentially the most expensive. The price of gas has increased quite a bit in recent years, so the price of traveling between cities has also risen. Hiring a travel planner is one way to resolve the complexities of arranging transportation, but there are lots of options to consider.

Taxis

Within Havana and the other main cities on the island, taxis are relatively easy to find and flag down on main streets. In Old Havana, if you walk to the outer edges—along the Malecón on the bay side, or anywhere near Parque Central and the Capitolio—you’ll find lots of taxis. In Vedado, Avenida 23, Línea are the best places to find taxis.

Viazul Bus

Viazul operates clean, air conditioned buses for tourists that are moderately priced. You can book online on their website, and even though Viazul is a government run company, it’s not on the restricted list so it’s totally legal to book and pay online. The site is a bit glitchy, but it works. The downsides to traveling by bus are:

  • you’ll likely have to pay for taxis to get to and from the Viazul stations, which adds to the cost and subtracts from the convenience
  • you often only find one or at most two options per day, so your plan has to conform to the bus schedule
  • depending on the time of year, you may need to book far in advance
  • once you book all of your transfers, you can’t change plans on the fly during your trip
  • the Viazul website has periods in which it just doesn’t work for unknown reasons

Transportation Through Your Airbnb/Hotel

Often times your lodging contact (concierge or Airbnb host) will have contacts for transportation at a good price. Since hosts and concierges are aware that travelers will leave reviews, they are incentivized to give you sound advice, and will often be able to find and book transportation by taxi within Havana or between cities.

La Nave App

There is an app called La Nave that is basically the Cuban Uber—you enter where you are and where you’re going, and it shows you a price, and if you accept, a taxi comes to get you. The only difference is that you pay the driver in cash. Using La Nave is much more convenient compared to the uncertainty of hailing a taxi on the street, but before you get too excited, there are some complicating factors:

  • its only good for local trips, and only in Havana
  • you need a local phone number to use it, which means you need to get a Cuban sim card, which requires planning and may not be possible on newer phones

One convenient workaround is to ask your local host/concierge to use La Nave to book a ride for you. Since the rider pays in cash, many hosts will offer to do this for rides from the hotel/rental. Then you just have to hail a cab the traditional way coming back!

Online Taxi Services

It is possible to find taxi services for Cuba online, but it can be hard to verify their legitimacy and pay for bookings ahead of time. Oftentimes sites appear and disappear or are left outdated, and inquiries are sent but responses are never received. Due to these factors, we recommend choosing another option.

Local Taxi Drivers

Another good way to secure a reliable taxi during your trip is to start by hailing taxis and when you find a taxi driver you like, ask them if you can have their contact info. You can call them directly from your accommodations whenever you need a ride and typically they will be happy to come get you, as long as they have enough lead time. Or you can set a schedule and negotiate a price ahead of time for them to act as chauffeur for multiple days.

Step Seven: Post Trip Documentation

The travel rules specify that you should keep records from your trip for 5 years. In theory, officials could ask you to show proof that your trip fit within the guidelines of the travel category you traveled under (i.e. Support for the Cuban People). This means it’s important that you keep your itinerary, photos, receipts and any other documentation of your trip just in case you’re asked to show them.

In reality, the chance that this will happen is very close to zero, as the U.S. government’s policy is not to pursue individual travelers for violations. But storing your records somewhere safe will ensure that in the very unlikely that you are asked about your trip, you won’t have any issues.

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