Couples Vacation Kisses

While visiting family in Miami, Scott’s Cheap Flights showed a flight deal with a direct flight to Havana, Cuba! After a quick search to confirm that US citizens could travel to Cuba, we were ready to plan our Cuba itinerary.

Check out my “How To Catch A Flight Deal” post for the strategy I used to catch this flight deal.

✔️ Click here to sign up for Scott’s Cheap Flights and get flight deals delivered to your inbox daily, from your selected airport(s) ✔️

To our surprise, our Cuba itinerary quickly filled up with things to do in Havana and the surrounding areas. Thus, with our 4-Day Cuba Itinerary, we chose to maximize our time there by focusing on things to do in close proximity to Havana.

Traveling to Cuba from the US

Traveling to Cuba from the US is legal; however, not for strictly tourist activities.

This means that you are required to purchase a tourist visa and declare one of the 12 categories of authorized travel to Cuba:

  1. Family Visits
  2. Support for the Cuban people
  3. Official government business (and certain intergovernmental organizations)
  4. Journalistic activity
  5. Professional research and professional meetings
  6. Educational activities
  7. Religious activities
  8. Public performances, clinics, workshops, athletic and other competitions
  9. Humanitarian projects
  10. Activities of private foundations, research, or educational institutes
  11. exportation, importation, or transmission of information
  12. Certain authorized export transactions

We chose “support for the Cuban people” which is pretty easy to do by staying at locally owned lodging, supporting local restaurants, volunteering, etc.

You can get these visas directly from the airline, either online or directly at the gate. The cost of a visa starts at $50 and can increase depending on the airline and if you buy it in person.

We purchased ours directly at the Delta gate in Miami airport for $50. There was no pushback or questions when filling out the travel visa form.

Additional Requirements for Traveling to Cuba from the US

In addition to the travel visa and declaring one of the 12 categories, you must have travel insurance, customs, and health declaration, and fulfill any travel restrictions required by the pandemic.

Visit for more detailed information.

Cuba Itinerary 2024 Overview

Day 1
Early morning direct flight from MIA to HAV, 90 minutes
Toured Museo de la Revolucion
African Cuban Culture Tasting
Fabrica de Arte
Day 2
Vinales Tour
Stroll El Malecon
Dinner at La Guarida- a nice upscale restaurant
Day 3
Explore Plazas in Old Havana
Plaza de la Revolucion
Photoshoot and Tour
Day 4
Beach Day- Playas de Este

Day 1: Things to do in Havana

Museo de la Revolucion

If you want to learn about the Cuba/US relationship from the Cuban government’s perspective, a visit to Museo de la Revolucion is a nice addition to your Cuba itinerary. It gives a very clear perspective of how the Cuba government feels about the United States.

There were a few galleries that explored Cuban history- key players, influencers, etc.- but the majority of the galleries (at least it felt that way) detailed how the US attempted to sabotage their country. The remaining exhibits reinforced how much the Cuban government helps and supports its people.

Please note that most of the Cubans I’ve encountered do not agree with the sentiments of the museum. In fact, some discourage visiting the museum due to how the government treats their citizens, causing many to be in poverty with a lack of basic necessities.

Personally, I wanted to get an understanding of the Cuban government’s perspective as I’m always leery of the US narrative about other countries. In my attempt to get a full perspective, our next adventure of the day was an Afro-Cuban Culture Tasting. It was the opportunity to get the actual local Cuban people’s reality.

Afro-Cuban Culture Tasting

There is no better way to learn about a culture than to go to their home, cook, and eat with them. This is exactly why the experience with Beyond Roots, which you can find here, should be on your Cuba itinerary.

We had first-hand exposure to the Afro-Cuban religions, learning the various customs, and foods they offer to the gods. I must admit, I was a bit nervous as we entered the house. I mean, we were at a stranger’s home, in a foreign country.

To make the experience even more “interesting,” they instructed us to wash our hands at the outdoor sink. We were greeted by live chickens. Being city people, it took us by a bit of a surprise.

I’d recommend this experience to anyone, hands down! Beyond the religious enlightenment and delicious food, our hosts, two local women and a few others that would stop in occasionally were so open. We honestly could ask them anything. This gave us a great perspective on how the Cuban people live.

Having a true, local, Cuban experience was a key goal of our trip. This experience gave us just that.

Fabrica de Arte

Fabrica de Arte is such an interesting place- an art museum meets a performing arts center, meets a concert hall, a restaurant, and a bar. Literally, every form of art is represented.

We went a bit early, around 9 PM, right after our Afro-Cuban experience. There was artwork, structures, live music, a DJ dance hall, and even a live play- and of course bars and a couple of restaurants. In all my travel, I haven’t been to one location that had such a variety of artistic entertainment.

Day 2: Things to do in Vinales, Cuba

Vinales Day Tour

Cuban Vacation: Tiffany
Hey Tiffany, our 1954 Classic Car for the day

Pinar del Rio is located in the Westernmost part of Cuba, the beautiful countryside known for the country’s tobacco production. It’s about a two-hour drive from Havana.

We took a private tour with VC Tours, which you can find here. Our tour guide picked us up from our Airbnb in Tiffany, a beautiful 1954 Tiffany Blue Chevy. This car was pretty dope- until after the first hour on the interstate and my mid-30s body started to feel every bump we drove over.

But honestly, it was “vale la pena”- worth the pain.

Cuban Mogotes: Limestone Formations

Cuban Vacation: Mogotes

After a short break at Las Barrigonas Travel Plaza with a fresh pina colada, we arrived at the beautiful limestone formation, Mogotes. Man, what a beautiful view!

We spent a few minutes taking in its beauty before we headed to the main event, the tobacco farm.

Cuban Tobacco Farm

Cuban Vacation: That Smoke

As we neared the tobacco farm, we saw huts without any windows which are used to dry the tobacco leaves. 90% of the farmer’s tobacco leaves go to the Cuban government. The remaining 10% is used by the local farmers to make their own cigars, which are actually organic and 90% of the nicotine is removed.

Did you even go to Cuba if a Cuban tobacco farm isn’t on your itinerary?

Upon arriving at the tobacco farm, we took a quick tour of the facility to learn more about the process. Soon after, it was our turn to roll cigars and smoke them!

I WAS SO NERVOUS as I had never smoked anything- not a cigar, cigarette, or anything similar. My mind kept telling me that I was going to choke and make a fool of myself.

So I dipped my cigar in the honey (a Cuban method that helps filter the remaining nicotine). Then I slowly put the cigar to my lips, and to my surprise, I was fairly good at smoking a cigar (once I realized you blow with the exhale…don’t judge me!)

Cuban Indian Cave and Prehistoric Mural

Couples Vacation: Indian Cave

After the tobacco farm and lunch, we explored the Indian Cave and Prehistoric Mural. The Indian Cave was a pretty amazing short boat ride experience; I recommend that you add it to your Cuba itinerary.

On the contrary, the Prehistoric Mural, which is basically roped off to the public, only allows you to see the mural from afar, on a funky side angle. This makes the experience pretty mediocre. Skip it if possible.

Stroll El Malecon

El Malecon is a 4-mile esplanade that transverses through multiple Havana neighborhoods with the communities on one side and the shore on the other. This promenade embodies the culture of Havana with locals gathering to listen to music, dance, and enjoy one another’s company. You’ll also run into some trying their hand at fishing as well.

This path through the city isn’t shaded and becomes very hot during the day. Therefore, it’s recommended to come around sunset so you can see the sun setting over the water while the heat of the day slowly starts to dissipate. If you can’t make it around sunset, you can come in the early morning, before the day’s heat arrives.

Day 3: Experience Havana’s Plazas

Old Havana Plazas

Old Havana, La Habana Vieja, includes 4 main plazas that embody the history and culture of Havana. Each plaza has its own vibe and offers different elements of Cuba. You can visit the plazas via a tour if you’d like to understand the history from a local’s perspective or take your time and walk through each on your own terms.

We did the latter.

Plaza de Catedral– One of the busiest places in Old Havana. Plaza de Catedral is home to the Havana Catedral which is open to the public. If you’re a lover of architecture this is the perfect square to visit to take in the restored, historical buildings.

Additionally, you can find local Cuban Cigar Ladies dressed in their traditional garments. If you would like, you can take a picture with them, for a fee.

Plaza de San Francisco de Asis– Located across the street from the cruise terminal, Plaza de San Francisco de Asis embodies a lot of Cuban history as the Spanish would stop here on their journey from the Indies to Spain. Here you can find Fuente de Los Leones (Lion Fountain), statues, a cathedral, cafes, galleries, restaurants, and more

Plaza de Armas– The “birthplace of Havana” as it encompasses the legendary location that Havana was founded in 1519. Similarly, it’s home to Carlos Manuel de Cespedes, the “Father of the Nation” who was the initiator of Cuba’s independence in 1860.

Additionally, it’s home to the oldest castle of Havana, Royal Force Castle, and Parque Cespedes, a beautiful green park with plenty of seating and shade to people-watch or enjoy a snack from the various street vendors.

Plaza Vieja– if you’re looking for a lively plaza filled with music, dancing, performers, and more, Plaza Vieja is the one for you. In addition, you can grab a cold beer and a bite to eat at one of the numerous restaurants.

Plus the architecture is filled with so much color and vibrance, similar to the plaza’s ambiance.

La Plaza de la Revolucion

La Plaza de la Revolucion is not located in Old Havana and is not within walking distance to the above-listed plazas. In fact, it’s about a 10-15 min ride from Parque Central (right outside Havana Vieja.)

It’s basically the location where Castro and other political figures addressed Cubans (by the way, we learned that Castro gave a 7-hour speech from here!!) The key attractions are the steel memorials of Che Guevara and Camilo Cienfuegos.

It’s also the location where most of the classic cars line up for tourists to take pictures.

Couples Vacation Photoshoot

The Ancient Fortress of San Carlos de Cabana

We had to document this experience, our first couples vacation since our twin boys! And oh man, our Airbnb Experience Photoshoot with Manuel at Cuban Soul Pictures, which you can find here, was A-MAZ-ING! Not only was it a photo shoot where he took BEAUTIFUL pictures of us (like magazine worthy) but the tour by itself was worth the money.

We toured Havana Vieja, actually very close to our Airbnb. The real experience for us was two things: 1) the convertible car ride to The Ancient Fortress of San Carlos de Cabana and 2) Chatting with Manuel to learn Cuban history and experience from a young local that has lived in Europe and visited the US frequently.

The Ancient Fortress of San Carlos de Cabana

The Ancient Fortress of San Carlos de Cabana is an 18th-century fortress complex, located on the elevated seaside of Havana.

The history. The beauty.

Man, it’s a must-add to your Cuba itinerary. Here, you will witness groups of locals hanging out and enjoying the scenery and their families and friends. As a matter of fact, I didn’t see a lot of tourists.

If you want a calm, relaxing, and historical place to relax in Havana, THIS IS IT!

Day 4: Beaches Near Havana- Playas de Este

Playas de Este

The water at Santa Clara Beach is beautiful!

The beach is a must-add to your Cuba itinerary, especially on a couple’s vacation. Unfortunately, with our limited time in Cuba, we didn’t have time to take a day trip to Varadero Beach (about a 2-hour drive from Havana- and detailed below in the day trip section).

We were happy to find out there is a bus (T3) that leaves from Parque Central in Havana to a cluster of beaches about 30 minutes or so away from the city. The best part is the bus is only 5 CUC (about $5)  for a round trip! It’s recommended to get off at Santa Clara Beach or Santa Maria del Mar.

We got off at Santa Clara Beach which was a nice beach with beautiful water. If you’re looking for resort treatment with beautiful cabanas and whatnot, this is not the beach. It’s not touristy at all.

You can get beach chairs and an umbrella for only $6. The same guys who sell the chairs will grab food for you, for a fee of course. We realized they were going around the corner to the restaurant, a 3 min walk, where the food and drinks were 25% cheaper.

At this point of the trip, we were super broke (see the below section about currency to understand why). So every dollar made a difference.

Day Trips from Havana Cuba


Varadero is known as the best beach destination in Cuba as it’s filled with white sand beaches and resorts. If your goal is relaxation and drinking Cuban rum, you’ll be in the right place.

There are several buses from Havana to Varadero which take about 3 hours. If you hire a personal driver or go via a tour company, the ride will be about 2 hours.

✔️ Want to learn about the hidden beaches in Varadero, click here ✔️

Playas de Este

If going to a Cuban beach is a must-do on your Cuban itinerary, but you don’t have time to go to Varadero, then take the Hop-On-Hop-Off bus, a 30-minute ride to Playas de Este. I mentioned some of the details above in the Day 4 Cuba itinerary.


I mentioned Vinales above during our private day trip to the Cuban tobacco farms in the Day 2 Cuba itinerary. If time permits, you should also do a horseback riding tour through the hills. So beautiful!


Want to experience the authentic spirit of Cuba? Then Trinidad is a must-add to your Cuba itinerary.

The history of the enslaved Africans who once occupied this now Declared World by UNESCO, is still alive today. If you want to learn more about the enslaved experience, book a Sugar Tour. Similarly, the beauty of the architecture’s vibrant colors and 50 mansions are worth the day trip itself.

If nature is more of your vibe, check out Parque Natural de Topes de Collantes’s beautiful waterfalls, Sendero Vegas Gardens, and the beautiful city of Cienfuegos.

The trip to Trinidad is a bit long with a 4-hour drive each way. Most likely you’d like to make this an overnight trip.

How Many Days Should you Spend in Cuba?

The number of days you should include in your Cuba itinerary varies depending on which things to do in Cuba best align with your interest. If it’s your first time in Cuba and you’re on a limited timeframe, then 3 or 4 days should suffice. This will give you the opportunity to have Havana as your base with 1-2 days exploring Havana, which is a must-visit in Cuba, and 1 or 2 day trips from Havana.

We chose to do 2 days in Havana and 2 day trips- 1 to Vinales and 1 to Playa de Este.

If you’d like to include more day trips or stay overnight in Vinales, Varadero, or Trinidad, then you’d want to add at least 2 or 3 more days to your Cuba itinerary, making it closer to a 7 or 10-day trip.

Best Time to Visit Cuba

The best months to visit Cuba is October to May as there is minimum rain and the weather is warm. June begins the start of hurricane season in the Atlantic and lasts until November. If you want to avoid hurricane season altogether, visit Cuba from December to May.

Things to Know About Visting Cuba

Currency Exchange

When we travel, especially on our first couples trip since becoming parents, we want to live- eat, drink, do activities, and buy stuff freely. Well, we did just that the first day until we realized that if we kept spending at that rate, we would run out of money.

US citizens have to bring all the cash that they think they will need while in Cuba. Unfortunately, no US credit cards, debit cards, or access to US banks is available from Cuba. To make matters even more stressful, most activities must be paid in cash, excluding those booked via Airbnb.

Therefore, between the 12% currency conversion rate, giving tips, and buying souvenirs to support the locals, we were spending more money than we expected. The day before we were supposed to return to the US, we were literally counting our pennies.

PRO TIP: Do not convert all of your money. Before paying for something in CUC, ask if they accept USD (or Euros) and at what exchange rate. If they do accept your currency, it’s most likely at a 1:1 rate- saving you the astronomical fee.

Spotty Wi-Fi

The other challenge is the Wi-Fi. It is not readily available.

First, you have to find a place with Wi-Fi. Secondly, you have to purchase a WIFI card to actually access the internet. It costs about $5 for one hour.

Perhaps, it doesn’t sound ridiculous, but as a mom of then one-year-old twins back in the US, I needed to see them. Unfortunately, the connection is pretty slow, so FaceTime cut in and out. Honestly, I think if I didn’t have the boys and I was on a couples trip, I wouldn’t have minded the limited and slow internet.

Leave as much as You Take

It’s undeniable that many Cuban citizens are suffering from poverty and a lack of resources. Therefore, when visiting be sure to leave as much as you take from the country. That can look like a variety of actions:

  • Stay at a vacation rental owned by a local
  • Bring personal items, food, and supplies for locals
  • Support local, privately owned businesses, i.e. tour companies (we found ours through Airbnb experiences)
  • Eat at local restaurants (i.e. not in a global chain hotel)

Where to Stay in Havana

Did you even visit Cuba if you didn’t go to Havana?

Where you choose to stay in Havana really depends on what vibe you’re looking for. There are 3 main Havana neighborhoods: Old Havana (Habana Vieja), Central Havana (Centro Habana), and Vedado.

Old Havana is home to many tourist attractions like plazas and museums. If you’re looking to stay in an area full of Havana’s culture and within walking distance of many of the attractions, Old Havana is the neighborhood for you.

Central Havana gives local vibes. Here is where you’d find the average Cuban living life. You’d be able to truly experience what it feels like to be Cuban- eating at local restaurants and walking to local attractions. Central Havana is home to the capital and sits between Old Havana and Vedado.

El Vedado is the central business district and the most modern and upscale area of Havana. The Malecon is on the northern edge of the neighborhood.

Please note that US Citizens can’t stay in Cuban government-owned hotels. Therefore, if you prefer hotels, you need to find one that’s not owned by the government or stay in a vacation rental- which is also support for the Cuban People.

✔️ Click here to research hotel options in Havana, Cuba ✔️

Best Airbnb in Havana- Apartment Chacón 201

Cuba Itinerary_Balcony view in Old Havana

Sit on the balcony of Apartment Chacón 201 and take in all the vibes of Old Havana. This beautiful Airbnb is centrally located to walk to all attractions including the plazas, Malecon, Museo de Revolucion, and more.

Best Luxury Hotel in Havana – Iberostar Parque Central

Best Luxury Hotel in Havana_Iberostar Parque Central is a must-add to your Cuba itinerary/

Iberostar Parque Central is smack dab in the midst of the Havana action, located in Central Havana, a few blocks away from Old Havana. Not only does the architecture and decor exude luxury but the service and views do as well. If you don’t stay here during your Cuban vacation, you have to at least stop at the rooftop bar which offers amazing cocktail options and views of the capital, city, and more.

Best Budget-Friendly Hotel in Havana- Casa Colonial Yadilis y Yoel

Taking a picture in front of the Cuban flag is a must-do!

Clean, safe, and friendly accommodation located in the center of Old Havana. The staff is extremely friendly and helpful, it’s like having a friend in Havana. Plus, enjoy a delicious breakfast on the rooftop terrace and take in the views of Old Havana.

✔️ Click here to learn more about Casa Colonial Yadilis y Yoel as they are rated 5-Stars with over 1000 reviews on Tripadvisor ✔️

Is It Okay To Travel To Cuba with Toddlers?

Honestly, I would travel with my boys to dang near anywhere that’s safe, of course. Cuba is very safe. It may look a bit shady, but that’s because some of the buildings are worn down & some streets aren’t necessarily the cleanest.

With that said, I would bring the boys to Cuba. However, our Cuba itinerary would have been different.

We probably would’ve exchanged the Vinales/Tobacco Tour for a day trip to Trinidad or Varadero Beach- because toddlers at a tobacco farm just don’t seem right. The museum, the walk to the plazas, and the majority of the other things on our Cuba itinerary would’ve worked with the boys.

Yes, the streets aren’t the smoothest. Therefore, using a stroller may have been a challenge; however, that’s not a big deal to me. I live in New Orleans and our streets aren’t smooth here either but that doesn’t stop us from going out.

Conclusion: Cuba Itinerary 2024

There are so many unique and fun things to do in Cuba. Literally, there is something for everyone- history, nature, culture, rum, cigars, and so much more.

If you consider yourself an open-minded traveler that enjoys destinations that may do things differently than what you’re accustomed to, then Cuba is a must-visit. The people are friendly and welcoming, and the vibe is so warm and vibrant.

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