I’ve been in love with Cuban culture since my time in Miami when I lived with a wonderful Cuban family during my first year of law school. I had always wanted to visit the island country and was excited when travel got easier for Americans. Although the rules change periodically, and we were initially nervous about how to do it properly, we now know that travel to Cuba can be a legal, safe, and culturally rich experience if you follow a few important steps. And if you just want to check it out for a weekend, flying to Havana from Fort Lauderdale, Miami, or Tampa is inexpensive and easy to do. Here’s what you need to know to plan your weekend extension to Cuba.

In our “weekender” posts, we’ll tell you where we stayed and what we did on brief trips to interesting cities in the U.S. and around the world. We’re sharing these tips from our own personal experiences with the goal of making travel more accessible to a broader audience.

Plan Ahead

• While Americans can’t travel to Cuba strictly for tourism, you can travel in support of the Cuban people — which can include a wide range of enriching activities and has become even more critical after the pandemic left the island with fewer visitors and less resources.
• To plan your weekend in the vibrant capital of Havana, you’ll need to select one of 12 designated reasons for going to Cuba. We went in support of the Cuban people, which means the goal of our trip was to make meaningful connections with local people by staying in a privately owned home called a casa particulare (rather than a government-owned hotel) and having a full schedule of activities with locals.
• You can do some research about the specifics and should recognize that the requirements from the U.S. government change from time to time. We won’t include all that information here, but a Google search and a visit to state.gov are helpful to get the most up-to-date information. 

Researching Airfare 

• For our self-planned, independent trip, Southwest Airlines and Airbnb were our best friends, though you do have other options for booking.
• Flights to Cuba can be very expensive even though the flight time from Fort Lauderdale is only about 45 minutes. So, we did a little strategizing to make it affordable, and it was significantly cheaper to buy three separate legs. 
• We used Southwest points to book a one-way flight from Washington DCA to Havana with a layover in Tampa for only 9k points and $60 per person. (We also used our SWA companion pass, so the total was only 9k points and $120 in taxes for two.) 
• On the way home, it was cheaper to purchase a fare from Havana to Fort Lauderdale and then from there to DCA – so this is the key reason we recommend adding a weekender in Havana on your Florida vaycay. One-ways between Fort Lauderdale and Havana were just 5k points with Southwest when we booked (with an additional $40 in taxes on the way back)!

Preparing Your Documents 

Southwest did a great job of outlining everything we needed for our travels to Cuba. The two key things you must have in addition to your passport are:

• Cuban travel insurance, which was included in our ticket price.
• Cuban Tourist Card (also referred to as a visa), which we purchased separately through instructions provided by SWA. This was a little pricey. You can purchase this at the airport before your connection to Havana, but we had a very short layover in Tampa, so we bought ours online and the documents were mailed to us in advance. 

Remember that you will be asked your reason for traveling to Cuba as you purchase airfare and activities. The reason will be the designated category “in support of the Cuban people.” 

We had to go to the gate agent in Tampa to show our documents before we could queue up to board the flight. This was a little confusing, but we figured it out and were still able to snag the emergency exit row after boarding late.

We were held back for about 20 confusing minutes at immigration when entering Havana, but we think that’s either because our stay was for only 24 hours or because we bought separate one-way tickets. But after a little confusion, we were on our way to explore Havana!

Planning Your Itinerary 

Traveling in support of the Cuban people requires a full itinerary of activities connecting with locals. As mentioned above, this includes staying at casas particulares (local homes available through Airbnb), having dinner in someone’s home, taking a walking tour with a local, visiting art galleries, riding in a vintage car, taking salsa lessons, and participating in other activities focused on a true cultural experience.

Here are the highlights from our itinerary with links. All activities were booked easily through Airbnb experiences:

Airport Pickup in a Vintage Car

Because … why not?! Our driver promptly picked us up at the airport and took us to their restaurant where we had a welcome drink, got local tips and advice, and made clothing and toiletry donations in support of the Cuban people with items we brought from home. We highly recommend booking this service to start your weekend right.

Beautiful Loft in the Heart of Old Havana

Our casa particulare was absolutely gorgeous and in such a great location in the heart of Old Havana. We were in walking distance to so many historical sites and had a few wonderful restaurants right downstairs.

Cooking Class in a Local Home

This cooking class with Raquel was one of our most memorable experiences that we’ve ever booked through Airbnb. Raquel is a delightful person and amazing chef. She made everything easy and even coordinated our taxi ride to and from her home in a local neighborhood. She had an interpreter, Ivan, who was a super cool guy. The house was beautiful, the food was delicious, but more importantly, we felt like we made some wonderful friends.

Walking Tour of Historical Sites

In the morning before we checked out of our Airbnb, we did a fantastic walking tour to visit cultural and historical sites and to learn about the realities of everyday life for Cubans. With heavy hearts, we saw the beauty and the tragedy; the struggles and the resilience of the Cuban people. Our tour guide is no longer available on Airbnb, but this one looks very similar.

A Few Practical Tips

• Build an itinerary through Airbnb. You are required to have a full itinerary with a least 6-hours a day dedicated to supporting the Cuban people (once again, 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.
• Bring cash to cover all your on-the-ground expenses (Euros and USD were both fine at the time of our trip).
• Bring donations. We fit as much clothing and toiletries as we could into our backpacks and arranged in advance to deliver them. If you have questions, just ask the host of your Airbnb how you can best offer support.
• Be prepared for spotty Wi-Fi. We did have Wi-Fi at the Airbnb but it went in and out. So, make sure you download maps and have everything you need to navigate your experience – just in case.
• Don’t visit restricted businesses. Check with the U.S. State Department and do some research on this. The general rule is to support family-owned businesses.
• 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, for example. So, we just drank wine! But in all seriousness, you may feel a bit overwhelmed at times about the realities.
• Be ready to experience Cuban culture. We met so many beautiful and resilient people on our brief trip, and we left with full hearts.

Final Thoughts

We are so glad we took this short trip – which was truly in support of the Cuban people, and we learned so much from our new friends in Havana. We highly recommend adding a night or two to your next trip to Florida for an unforgettable experience.  

Have you been to Havana? Share your thoughts in the comments.