Thinking about a trip to Cuba and not sure where to start? We had a few moments of pure confusion getting there, from the visa paperwork to a long hold at Havana immigration, but careful planning is what turned it into one of our most memorable trips. These Cuba travel tips for Americans walk you through every step, from the legal category to pick, how we flew there cheap on points, the documents you need, where to stay in Old Havana, and the best Havana itinerary. We’ll show you exactly what we did, share the mistakes we made, and help you plan a smooth trip to Cuba.

Cuba Travel Itinerary Planning

Best flight deals	Price out whether it costs less to get to Florida first and then book a round trip to Havana. The difference can be significant.
Points options	Fort Lauderdale to Havana. We paid 5,000 Southwest points + $40 in taxes one-way, plus we had a SW Companion Pass.
Airport	Havana (HAV), via a Tampa, Fort Lauderdale, or Miami connection
Legal category	Support for the Cuban People
Where to stay	Privately owned casa particular in Old Havana (via Airbnb)
Best time to visit	Dry season, roughly November to April
Is it safe?	Yes for tourists, with normal big-city precautions. But resources can be scarce
Minimum time needed	24 to 48 hours for Old Havana
What to skip	Government-owned hotels and restricted-list businesses

Is It Legal for Americans to Travel to Cuba?

Yes, with a catch. Americans can’t travel to Cuba strictly for tourism, but you can go under one of 12 authorized travel categories, and one of them covers most independent trips. We traveled under the Support for the Cuban People category. You are not allowed to stay at government-owned hotels, rather you’ll need to arrange stays in a privately owned home or “casa particular” and also fill your days with activities that put money directly in local hands, truly in support of the Cuban people. The rules may shift with each administration, so check the current State Department guidance before you book.

Cuba Travel Pro Tip: You’ll be asked your reason for travel when you buy airfare and again when you book activities. The answer is the category name, support for the Cuban people. 

How to Fly to Cuba Cheaply From Florida

Flights to Havana look expensive, but you can break the trip into legs and even add a few nights in Florida. It’s just a 45-minute flight from Fort Lauderdale to Havana, and we found real savings booking segments instead of one round-trip fare. Outbound, we used 9,000 Southwest points plus $60 per person to fly Washington DCA to Havana with a layover in Tampa. Our Southwest Companion Pass covered the second traveler, so two of us flew out for 9,000 points and $120 in taxes total, which is amazing.

Coming home, we booked Havana to Fort Lauderdale and then Fort Lauderdale to DCA as separate fares because it was cheaper than booking all the way through. The Fort Lauderdale to Havana one-ways were 5,000 Southwest points each when we booked, with about $40 in taxes on the return. That low-fare option is common from Florida to Havana, so at a minimum, we suggest comparing the price on one itinerary to Havana vs. booking to Florida (Fort Lauderdale, Miami, or Tampa) and then roundtrip to Havana from there. You may find a huge fare difference.

But we have one caveat we’ll explain in more detail below: We had some trouble at immigration getting into Cuba, and we think it’s because we had two one-way tickets about 24-hours apart. It all worked out fine, even with a moment of stress. So if you do book in segments, maybe book a round-trip fare from Florida.

What Documents Do You Need to Travel to Cuba?

Beyond your passport, you’ll need two important documents, and Southwest laid both out clearly during booking, which took a lot of the guesswork out of it for us.

The first is Cuban travel medical insurance, which was bundled into our ticket price (in the taxes and fees we paid on the points fare). The second is the Cuban Tourist Card, which is sometimes called a visa. We bought ours in advance separately through Southwest’s instructions. You can buy the card at the airport before your Havana connection, but our Tampa layover was tight, so we ordered online in advance and had the documents mailed to us. We were really glad we did.

Cuba Travel Mistake to Avoid

A short layover will not give you enough time to sort out your Tourist Card at the airport. We had to show our documents to the gate agent in Tampa before we could even queue to board the plane, so if we’d waited to buy it there, we would have been scrambling. Sorting it in advance was a little more expensive, but it worked out much better. We had some gate confusion because we had to go to the airline agent first during our layover and get our boarding pass signed off after she checked our documents. But it all worked out and we boarded just fine. 

Now, about that immigration hold we mentioned earlier:

• When we arrived in Havana, they initially would not let us clear immigration.
• Everyone was friendly, but they did not give us an explanation. We tried twice.
• They took our passports into the back room. It was stressful in the moment but seems pretty reasonable when we look back on it.
• Our best guess is that we were flagged because of our points and miles savings strategy. We booked a 24-hour stay in Cuba on two separate one-way tickets. So, even though everything was done properly, this probably looked unusual to them.
• It all got sorted out, but it’s the reason we’d suggest a round-trip fare from Florida if you want to skip the stress and still save on the airfare.
• You should also have all your documentation printed and ready to show.   

Where to Stay in Havana: Casa Particular vs. Hotels

The support for the Cuban people category actually requires you to stay at a privately owned casa particular, which you can book through Airbnb. The point is spending your money with a local host instead of a state-run hotel. 

Our casa was a gorgeous loft in Old Havana, in walking distance to so many historical sites, with a few wonderful restaurants right downstairs. Waking up inside the old city instead of commuting into it made a real difference in how much we saw on foot, and we loved coming back to a home rather than a hotel.

Booking Tip: A well-reviewed casa particular in Old Havana usually costs less, satisfies the travel category, and puts you within walking distance of the sites you came to see. Read the reviews closely and message the host before you book, since they’ll become one of your best resources on the ground. They may have WIFI cards for you, help with transportation, and help you exchange cash if needed. 

Havana Itinerary: How to Spend 24 Hours in Old Havana

Traveling under this category means you need a documented schedule of at least six hours a day of activities that support the Cuban people directly. That might sound rigid, but we followed it precisely and it was wonderful. It can include cooking classes, historical walks, salsa lessons, eating at family-owned restaurants, riding in classic cars, going to art exhibits, and much more.

We booked everything through Airbnb Experiences, which kept the documentation simple and connected us with some amazing people. Print your itinerary, take it with you, follow it, and save it for five years. Here’s how we filled our day, and we highly recommend all of this:

Vintage Car Airport Pickup

Because, why not? Our driver picked us up right at the airport and took us to his restaurant, where we had a welcome drink and got local tips over lunch. We packed clothing and toiletries from home to donate in support of the Cuban people, and this is where we provided them. 

Cooking Class With a Local Host

Book a cooking class. Our cooking class with Raquel was the highlight of our trip, and it’s still one of our favorite things we’ve ever booked through Airbnb. Raquel is a delightful person and a seriously talented cook, and she even coordinated our taxi to and from her home in a local neighborhood. Her interpreter, Ivan, was a super cool guy who made the whole evening easy and fun. The house was beautiful and the food was delicious, but the reason we still talk about it is the people. We left feeling like we’d made real friends, rather than just booking an activity.

Walking Tour of Old Havana

On our last morning, before we checked out, we did a walking tour of the historical sites with a local guide who talked openly about daily life for Cubans. We saw the beauty and the hardship side by side, and it stayed with us. Our specific guide has since left Airbnb, but there are plenty of well-reviewed Old Havana walking tours in the Experiences listings, so you’ll find a great one there.

Best Time to Travel to Cuba

The dry season runs roughly from November through April, and that’s the easiest window for Havana, with warm days, lower humidity, and less chance of rain interrupting a walking tour. The wetter months from May through October bring heat, afternoon storms, and hurricane-season risks, particularly in September and October, so we’d steer you toward the dry season if your dates are flexible.

We went in April and it worked well. We hit storms coming back into Fort Lauderdale, but that’s a story for another post. Prices on flights and casas rise around the winter holidays and fall in the shoulder weeks of late spring and early fall, so if you watch the calendar, you may find some good deals at those times. 

Is Cuba Safe to Visit?

We felt safe in Havana. Violent crime against tourists is uncommon, and our recommendation is to follow the usual big-city safety precautions. We watched our belongings in crowds, booked transportation in advance or used registered taxis arranged through our host, and kept an eye out after dark like we would anywhere.

The bigger adjustment is scarcity, not safety. Shortages of food, fuel, and medicine are a reality in Cuba, and daily life for Cubans can be dramatically different than a tourist’s experiences. Bring what you need for your time in Cuba and be patient. Our Airbnb host and our driver were excellent resources.

Safety Note: Petty scams do happen, but it’s mostly friendly strangers steering you to a specific bar or cigar shop for a commission. A polite no usually works fine. But also, Havana was just not a place where we felt like negotiating for the best deal. Everything was reasonable and we were happy to support the Cuban people.

Cuba Travel Tips for First-Timers

Here are a few things we learned along the way:

• Bring cash for everything. Euros and USD both worked fine when we visited, and you can’t use US-based credit cards, so bring enough to cover your whole trip. We were told that Euros were better than USD but that seems to have changed. 
• Bring donations. We fit as much clothing and toiletries as we could into our backpacks and arranged the dropoff in advance. The support is genuinely needed and appreciated, so just ask your Airbnb host how to help before you go.
• Expect spotty Wi-Fi. We had Wi-Fi cards at the casa, but it came and went. Download offline maps and anything else you’ll need to navigate, just in case.
• Keep your records. Print your itinerary, follow it, and hold onto it for five years along with your receipts. The Support for the Cuban People category comes with recordkeeping requirements, and it also makes a nice shareable itinerary.
• Check the restricted list. The State Department publishes a list of businesses tied to the Cuban government that you’re not permitted to patronize. The general rule is to support family-owned businesses, and it’s worth a quick look at the current list before you go.
• Be patient. Supplies were hit or miss, and everyone is doing the best they can. One restaurant had an abundance of delicious Caribbean lobster but no water … so we just drank wine with dinner. You may feel a little overwhelmed at times by the realities of life in Cuba, and that’s part of the experience. The people we met were amazing, resilient, and friendly. It was emotional. 

Frequently Asked Questions About Cuba Travel

Can Americans legally travel to Cuba right now?

Yes, under one of 12 authorized categories rather than as tourists. Most independent travelers use support for the Cuban people, which requires a private stay and a full schedule of activities with locals. Check the State Department site for current rules before booking, since they may change with each administration.

What is the cheapest way to fly to Cuba from the US?

Booking separate tickets to get to Florida and then from there to Havana often beats a single round-trip fare from home. Price out your different options before booking a single itinerary. But we suggest doing a round-trip itinerary from Florida (Fort Lauderdale, Miami, or Tampa) that clearly shows your return flight to avoid confusion with two one-way tickets. 

Do you need a visa to travel to Cuba?

You need a Cuban Tourist Card, sometimes called a visa, plus Cuban travel medical insurance. The insurance was included in our airfare. You can buy the Tourist Card at the airport, but ordering it online in advance is smarter if you have a tight connection. Our airline provided all the details for us to handle smoothly. 

Is it better to stay in an Airbnb or a hotel in Havana?

For anyone traveling under the support for the Cuban people category, a privately owned casa particular is required, and it’s easily booked through Airbnb. It keeps money with a local host, costs less than state hotels, and an Old Havana location puts you within walking distance of the main sites.

How many days do you need in Havana?

You can see the core of Old Havana in 24 to 48 hours, which is why a weekend works well. You’ll need a full, documented itinerary of 6+ hours a day of activities supporting locals to satisfy the travel category. This includes cooking classes, historical walks, salsa lessons, eating at family-owned restaurants, riding in classic cars, going to art exhibits, and much more. Print your itinerary, take it with you, follow it, and save it for five years.

When is the best time to travel to Cuba?

November through April is the dry season and the most reliable window for Havana, with warm days and less rain. May through October is hotter and wetter, with hurricane risk peaking in September and October. Prices dip in the shoulder season.

Is Cuba safe for American tourists?

Yes. Violent crime against visitors is uncommon, and standard precautions are enough in Havana. The harder adjustment is scarcity, since shortages of food, fuel, and medicine are common. You may see some petty scams that are more about getting commissions, and who could blame them?

Should You Add a Havana Weekend to Your Florida Trip?

If you’re already heading to Florida, we really think you should add a night or two in Havana. Follow these steps:

• Read the most up to date requirements for the Support of the Cuban People travel category before you book, and make sure to follow the rules
• Book a casa particular in Old Havana through Airbnb
• Sort your Tourist Card and medical insurance before you fly
• Build a full daily itinerary of local experiences through Airbnb 

I first fell for Cuban culture back in law school in Miami, when I lived with a wonderful Cuban family. I’m so glad we had the amazing opportunity to finally travel to Cuba. We met so many beautiful and resilient people on our brief trip, and we left with full hearts.

Have you been to Havana? What was your experience? Let us know in the comments.

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