I recently had the opportunity to go to Cuba on a group travel trip. This was my first group trip ever, and I was pleasantly surprised that I genuinely enjoyed myself! I was able to experience things I normally wouldn’t on my own, as well as learn from so many different people. Continue reading for the itinerary of the trip, a pros/cons list, and my overall impressions.
BOOKING THE TRIP

How did I find out about this trip you may ask? I follow Dr. Kiona on Instagram [handle @hownottotravellikeabasicbitch]. She posts educational posts, raising awareness on topics deemed generally ‘uncomfortable’ by society. When she posted she was hosting her first group travel trip in Cuba, I knew I had to go. When news hits that Americans were now allowed to visit Cuba, I was interested in going and learning about the country, so when this opportunity came, I knew I had to take it.
The trip wasn’t promoted as visiting the most popular attractions and finding the most ideal locations for picture-taking, which I’m definitely not against by the way. Instead, the trip focused on supporting the Cuban people by connecting with them and learning from them. That, is what drew me into the booking the trip.
Originally, there were only two dates available and they sold out before a blink of an eye. Dr. Kiona decided to add more travel dates, and that is how I was able to go on trip. There are more dates being added for 2020, although you may want to check it out soon as they do go fast!
ITINERARY
This trip consisted of a 6 day / 5 night journey. Of course, you had the option to fly in a few days before, or stay a few days after. Several people in our group opted for one or the other, but also people, myself included, came in the day the group trip started, and flew out the day it ended. I’ll give a day-by-day breakdown of what we did. Every day was jam-packed with so much information and activity, and honestly I wouldn’t want it any other way while trying to maximize my time in Cuba.

Day 1: Arrive in Havana, Cuba
The day we arrived, we headed straight to lunch to meet up with two Cuban journalists, Ernesto and Daario. They discussed the history of uba, what it’s like to live there today, and more! We definitely gained a different perspective from listening to them speak about their country.
Afterwards, we had time to relax before heading to Proyecto Cultural Muraleando. Pictured above, the building used to be an old water tank that the community started using as a trash pile when it no longer served as a water tank. Now it stands, full of pride and joy, as the art-focused community center. Various art pieces line the streets as well as the inside and outside of the building. SOme of those pieces incorporate old typewriters and chairs found during the massive cleanup of transitioning to what it is today! How cool is that?!
We ended the evening at a club, where a famous band was scheduled to play. Before they came on, dancers filled the stage and amazed us with their flawless moves. Unfortunately, I was tired and headed home before the band came on, but I heard they were fabulous!

Day 2: Casa de Africa + Dancing
Our day started off with visiting Casa de Africa. From a university professor, we learned about the slave trade, the sugar industry, the revolution, and the influences brought from Africa to Cuba – which are still present today. We learned how primary schools are being incorporated into museums, and there was a class taking place during our visit. The students were so interested in what they were learning, they barely gave us a glance. At the end of our visit, we witnessed several different African-inspired dances which represented the various important gods in their culture.
Afterwards, we headed over to the Carlos Acosta Dance Company to watch the ballerinas practice It was amazing to see the dedication and passion for dance. Carlos Acosta himself, the founder of the company and the Royal Ballet’s first black principal dancer, was on the dance floor as well. Before we left, they rehearsed a piece so powerful, it brought tears to my eyes. The whole experience was beautiful!
Then we had dance lessons for ourselves! We met up with Tropicana dancers who broke down the dance steps for us. I’m actually really bad at dancing, and I was genuinely dreading this part of the day, so I was surprised to find how much fun it was! The dancers were so patient and supportive while teaching us the various steps.
We ended the night by eating delicious food at a neat restaurant called Michifu. After dinner, some of us headed to a house party, which was being put on as a fundraiser to support artists. Honestly, how much cooler can Cuba get?! There was a good number of people there, a DJ + a dance floor of course, and drinks being sold!

Day 3: New Cuban Art Scene Tour + Beach + Dinner + Concert
Started the day with a walking art tour led by a local artist who specializes in photography. We focused on contemporary artists, visiting galleries exhibiting pieces of artists alive today. In some cases, we even had the chance to speak with the artists directly! Many people in our group ended up purchasing pieces throughout the tour – and that was cool!
We just happened to be at the right place, at the right time because we had the privilege of experiencing the grand opening of an Afro-Cuban shop, Beyond the Roots. It was packed! There was barely enough room for people to walk, so it was great to see so much support for this new store!
Afterwards, we headed to the beach. We splashed around in the water, enjoyed a delicious lunch which included lobster, and relaxed on the sand. It was a great time for a break, rehydrate, and connect more with the people in our group!
We headed back to the hotel after a few hours to get ready for dinner. We met up with a doctor and a medical student, who took time to discuss the Cuban healthcare system with us. It was interesting to learn how involved the doctors are in their patients’ lives, how the system is focused more on prevention, and their thoughts on various health aspects. And of course, the food was delicious!
We ended the night by heading to the Malecon, where a huge outdoor concert was being hosted. There were people everywhere – talking, laughing, dancing!

Day 4: Head to Viñales + Horseback Riding Tour
Our first day in Viñales, we met our hosts who put together a delicious lunch for us. While eating lunch, we received a lesson about how the food on the table made it there. We learned about the farming process, the availability of lobsters on the island, and more! It definitely gave us a deeper appreciation for the food we were consuming.
Following lunch, we headed to our horseback riding tour. I’m not going to lie – I was a little nervous to go horseback riding, as I hadn’t done it since I was young. But Pancho [my horse] and I ended up having a blast!
During the tour, there were multiple stops for us to learn more about the Cuban culture. Our first stop was a tobacco farm where we learned how Cuban cigars are made, then we watched one being made! We had the opportunity to try one ourselves and to purchase for family/friends back home.
Our second stop took place overlooking the three valleys in the Viñales Valley National Park. We learned about the different valleys – The Republic of Chile, Silent Valley, & The Valley of the Palms – while enjoying the magnificent views and delicious drinks the spot had to offer.
During our third stop, we learned about coffee, honey, and rum-making processes. We had the opportunity to sample each and purchase for family/friends back home.
Tip: If you plan on buying honey and/or rum, make sure you have enough Cuban pesos to check your bag when you are heading home.
Our fourth and final stop of the night was for dinner. The original plan was to arrive for sunset to take in the view and see the garden from where the restaurant sources their ingredients. Unfortunately, we didn’t get to see that as it was dark by the time we arrived, but the food was phenomenal!

Day 5: Sunrise Hike + Rock Climbing + Block Party
Our day started super early with a morning hike up Los Acuaticos in the dark. Using our phone flashlights to guide us up the mountain, we made it to the top. While we waited for the sun to make its appearance, we enjoyed some coffee and mango juice. Then we saw the most spectacular sunrise through the clouds over the mountains and across the valleys. So worth the early wake up call!
After our hike, we had breakfast and our group split up to do various activities. Some people went horseback riding again, some went cave exploring, and some went rock climbing.
Although I’m scared of heights, I opted for the rock climbing. To me, it seemed like an amazing opportunity to try something new. We met up with our local guide who supplied us with the necessary equipment. We went on a mini hike [jumping over fences, crawling under low trees] to reach the side of the mountain we were scaling. Our guide was hilarious and very patient, answering “UP” every time we asked where to go. I didn’t make it all the way up to the top, but I’m surprised at how far I did make it! I’m really proud of the group of us who went!
After relaxing for some time after the various activities, our hosts threw us a block party – scrumptious food, delicious mojitos, Cuban dominos, and just a lot of fun! We ended the night by visiting several bars and dancing the night away. It was the perfect way to conclude our trip!
Day 6: Leaving Viñales + Heading to Airport
Our last day in Cuba, we woke up, ate breakfast, and piled into the van to head straight to the airport. It was bittersweet saying bye to everyone – it was so great to meet everyone and get to know them, but it was sad to know how trip had come to an end.
PROS
- The entire trip is geared toward supporting the Cuban people, hence the activities involved support the Cuban people. You will be able to see where your dollars are going, and who it is helping.
- You gain a different perspective of Cuba from the people who live there. Sure, you may have learned about Cuba’s history and current state in your own country, but aren’t there always two sides to every story? You may be surprised to learn you don’t know the whole story.
- You get to meet people, not only from Cuba, but from potentially around the world. The group will be diverse, and that provides an opportunity to learn from so many different people.
- There is rest time scheduled into the itinerary. I am an introvert, so I definitely need me time to recharge and keep going. I was thankful that was thought of while creating the itinerary. You can also opt out anytime you want to/need to.
CONS
Honestly, in my experience there weren’t any cons that were a direct result of the group travel. Everything I would deem as a ‘con’, could not be controlled by anyone. But I will go ahead and discuss them here:
- Bad rooming situation. Obviously with a group trip, this could become an issue. Thankfully, we did not have that problem with our group, and I personally loved my roommate! [I guess technically this one can be controlled if brought to the attention of the trip organizers, but you get what I’m saying here].
- Hot weather. It is hottttt in Cuba. Like sweat through your shirt on the daily, hot. You’ll grow used to the fact that you’re sweating so much because you’ll realize so is everyone else. Make sure to bring a bottle of water with you and stay hydrated throughout the day.
IN CONCLUSION

How Not to Travel Like a Basic Bitch and Like a Cuban curated an amazing group trip experience! I would definitely go back again and again. Although they have a tentative itinerary, each trip is different for several reasons:
- Your Group – The individual members of the group contribute to the group vibe. Thankfully, we had an amazing group who brought experiences from all over, had open minds, and wanted to dive in head first in this experience!
- Time of Year – Depending on the time of year, certain attractions may be open or close; special events may be taking place; people may be hosting concerts/parties. What is happening at the time, reflects what the overall itinerary looks like.
- Pop Up Events – One of the coolest things in my opinion, was that Rita would hear about something happening that night, and we would shift our plans to attend. Whether it was a house party to support an art fundraiser or an outdoor concert that filled the streets,
All in all, I would recommend travelling to Cuba on this group trip. I met some of the most incredible people on this trip; I had the opportunity to see Cuba from the perspective of people who were born and raised there; and I learned so much! Are you interested in going to Cuba? Does this trip sound like something you would enjoy? Let me know in the comments! I’d love to hear from you!
Hi! I just signed up for this tour for Memorial Day weekend and I’m so excited but also a bit nervous! Did you have any issues with visas? How involved/helpful were the guides? Seems like I’ll get there a couple days before the actual tour starts and I’m a bit nervous about being there solo, but SO excited for the trip
Hi Nausheen! I am so excited for you – you’re going to have a blast! If you’re flying from the United States, the visa is included in the flight ticket. I flew JetBlue and just had to go to their main desk inside the gate area and get it there. Super easy. The guides on the trip were super helpful and involved. They answered any and all questions and were happy to explain anything in detail. We learned so much! I personally flew in the day of the tour, so I can’t speak to being there before, but there was a girl on my trip that did the same and she had a blast! Maybe reach out to Rita and see if she has any recommendations for things to do while you’re there. The communication line is super open and everyone is really nice!