Roberto and I definitely fall into the category of people who try to cram as much into a trip as possible. I know that there are travelers who might argue you could spend a week or two just in Havana and not scratch the surface, and I can totally appreciate that viewpoint. On the other hand, our vacation days are limited and our location bucket list is long. When we visit a country we do it knowing that we may never make it back. With that in mind, our goal is always to see as much of a country as possible. All this to say that this is a jam-packed itinerary, but we felt it allowed us to see various towns and topography in our limited time on the island. Once we had narrowed down where we wanted to go we had to figure out the order in which we’d do it and how we’d get from town to town. We used Furkot to map out our road trip around Ireland last spring, and I found it helpful in planning this itinerary as well since so much of our travel was done by car. Flying into and out of different airports saved us the unnecessary travel time of looping back to Havana. We arrived in Cuba on a Saturday and returned home the following Sunday, spending a total of 8 nights and 9 days (with two of those days being travel days) on the island. Here’s what we did:
Day 1 //After a short flight from Miami to Havana we found a cab driver to take us to our hotel in the Habana Vieja (Old Havana). Once we got checked in we were ready for lunch so we headed straight to La Bodeguita del Medio. After cooling off with our first mojito we set out to explore the rest of Old Havana on foot. We visited Plaza Vieja, Plaza de la Catedral, and Plaza de Armas. That night we enjoyed dinner at Esto no es cafe after freshening up (and a quick siesta). We had heard great things about Fabrica de Arte Cubano so we cabbed over after dinner, but were devastated to discover it was temporarily closed (and that we had spent our limited cash on a cab ride!).
Day 2 // Our second day in Havana was our only full day in the city so we were determined to squeeze in as much sightseeing as possible. After breakfast at our hotel, we decided to jump on the Hop On Hop Off bus tour thinking it would a be a good (cheap) way to see more of Havana. We got off at Parque Central where we (Roberto) were immediately sidetracked by a large group of men having a good natured argument about baseball (we were there during their World Series!). After checking out the Gran Teatro and Capital we popped into Hotel Saratoga to enjoy a Cubata in their gorgeous black and white bar. We spent the rest of the afternoon engrossed in the Museum of the Revolution. After dinner at Atelier, we headed to the home of the daiquiri, Floridita, to end the night.
Day 3 // Our day trip Vinales was one of the absolute highlights of the trip. It’s about a two-hour drive from Havana so we had an early start at 7 am so we could begin our horseback tour by 9 am. We spent the whole day with our guide visiting his family’s tobacco farm and touring the unimaginably gorgeous valley. We had reservations at 304 O’Reilly that night but lost our table after being late due to our little gas debacle (see TIC in my Cuba overview). Luckily we were able to get into their sister restaurant El Del Frente across the street which ended up being one of our best meals in Havana (remember what I said about it all working out?!).
Day 4 // On our last day in Havana we knew we had to take a ride in a classic car. We found a driver where lots of cabs hang out across from Castillo de la Real Fuerza and he took us over to El Morro and El Cristo Blanco. After our ride, it was time to say bye to Havana and make our way to Trinidad. The drive is about four hours so we had our driver stop in Cienfuegos so we could stretch our legs and have a look around. If we had more time I would have loved to have lunch or drink, but we were behind schedule so we continued on our way. In Trinidad, we checked in with Dr. Suarez and Senora Addys and felt immediately at ease after our many debacles early on (cash, blisters, gas, etc.). After getting settled we had dinner at Sol y Son and called it a night.
Day 5 // Senora Addys and her staff prepared us an amazing breakfast on the patio of fresh fruit and omelets before sending us on our way for a pedicab tour that she had arranged. Since we only had one full day in the UNESCO World Heritage Site designated town it was a great way to see a lot of the colonial city. We visited a cigar factory and this awesome pottery shop and even though there were tons of things we wanted to bring home we were afraid the items wouldn’t make it in one piece. We spent the rest of the afternoon strolling through the brightly colored streets. That evening we watched the sunset from the stairs off of Plaza Mayor with mojitos in hand from a little stall boldly advertising themselves as “The Best Mojito in the World”. Roberto and the bartender had a laugh about a money back guarantee, but guys… these really were the best mojitos in the world. After the sun went down we waited in line for a coveted spot at Restaurante San Jose where we devoured lobster, beans, and rice which were quickly becoming our Cuba staples. After dinner, we headed up to Casa de la Musica where we listened to live music and watched dancers (much more coordinated than myself) salsa the night away.
Day 6 // And just like that our time in Trinidad was already over and we had to hit the road for Cayo Santa Maria, an island off the island. Senora Addys had arranged a shared a ride for the three hour trip to the island chain and we arrived at the Royalton Cayo Santa Maria just in time for lunch. We spent the rest of the afternoon relaxing by the pool at the resort.
Day 7 // This day was a total veg day and it couldn’t have been more perfect. We walked along the beach, sunbathed by the crystal blue water, and took advantage of the free catamaran rides offered by the Royalton. After enjoying dinner at one of the resort’s restaurants we walked into the little island “town” for a couple rounds of bowling.
Day 8 – We spent the morning shopping for souvenirs in the resort “town” then soaked up the sun by the pool for the rest of the day. We stayed at the all-inclusive resort through dinner since the food was delicious (and we didn’t have money 😂). Afterward, we hopped in a cab for a two-hour ride to Santa Clara where we were flying out the next day. Once we had sorted out our little lodging debacle we took a quick stroll to Parque Leoncio Vidal to get a feel for the town before hitting the hay.
Day 9 – Our flight home was in the early afternoon so we set out to see as much of Santa Clara as possible that morning. We visited both the Mausoleo del Che Guevara and the Monumento a la Toma del Tren Blindado before stumbling on an awesome farmer’s market. After grabbing a bite it was time to say bye to Cuba and head home!
I’m planning to put together more details on each town but wanted to put our itinerary all in one place! Let me know if you’re planning on visiting Cuba and have any questions!