I traveled a lot this past year, but nothing has sparked more interest from people than my trip to Cuba. In this post I’m going to explain where we went, how we got around, and what all you should do to have the perfect Cuba itinerary!
For details on how you can independently travel to Cuba as a U.S. Citizen, check out my other post!
Here’s my detailed 10 Day Itinerary:
Day 1: Havana – Cuba’s capital city, Havana is the largest and most popular on the island. Founded by the Spaniards in the 1500’s, the city is divided into three main sections: Old Havana (“La Habana Vieja”), the area that you mostly see in photos with crumbling and colorful buildings; Vedado (a hip business district); and the wealthier areas of the city with neighborhoods like Miramar.
Arriving into the city, you’ll have to exchange cash into the local tourist currency (CUC). Then take a $25 taxi from the airport into town. If you’re from the US, to meet Visa requirements, you’ll have to stay at a Casa Particular. These are basically a home-stay with a local family, and yes AirBNB’s count!
Iconic Havana – The best place to get started is the area around Calle Obispo. These are the quintessential Havana streets with all the artfully crumbling buildings, old cars, and loads of charm. The nearby Plaza de Armas is another good stop, but just exploring on foot and wandering around is the best way to do it!
In the center, you’ll find the Capitol building across the street from Parque Central. There will be some inflated prices at restaurants around here, but it’s worth walking around and taking photos!
While in the area, stop for a daiquiri at El Floridita. This is the bar where famed author Ernest Hemingway spent his days, and supposedly where the daiquiri was first invented!
Make your way next to the Plaza de la Catedral. While touristy, it’s still beautiful. The church,live music, and ubiquitous fruit carts you pass along the way make it worth it!
For dinner, check out Van Van – a pricier retro place right downtown. If you don’t mind a line or bigger crowds, next check out Bodeguita del Medio – a bar made famous by its well-known patrons in days past.
Lodging: Casa Particular Colonial with Pablo
Day 2: Havana – We started our day out at the Fábrica de Tabaco Partagás, where my husband got his fill of Cuban cigars. It’s a cool old building- worth a stop! In Habana Vieja, we decided to do the Hop-On, Hop-Off red bus tour. I’d heard from other bloggers it was worthwhile, but in my opinion it was an unnecessarily long ride that took us too many places. For just a bit more money you can rent a private old car- I recommend doing that instead!
On the tour, we passed the El Morro Fortress (built in 1589), Plaza de la Revolución, the abandoned US Embassy, several old Soviet buildings, The Colón cemetery, and wealthier homes in Vedado.
We grabbed street food for lunch, then started the Lonely Planet guidebook’s walking tour. This took us to the scenic Plaza San Francisco, Plaza de Armas, La Fuerza Fort, and Havana Club Rum Museum.
The Cuban heat will get to you, so we cooled off with some daiquiris at Bar Bigote Gato. Next was an early dinner at a small, family owned paladar, with a very friendly staff, called Dos Pelotas (lol). Paladares are the non-government run restaurants in Cuba, and typically have more authentic food. Support these if you can, it isn’t easy to run your own business in Cuba and these families are some hard workers! Especially if you’re from the US, it’s important to support these places- in fact, it’s most likely part of your Visa requirement!
Around sunset, stroll Havana’s social waterfront walkway, El Malecón. There we bought some flan (sold by a lady out of her living room window!), watched some teens reeling in fish, and got a great taste of the vibe of local life.
Lodging: Casa Particular Colonial with Pablo
Day 3: Havana → Trinidad- No trip to Cuba is complete without riding in a colectivo (a share taxi), and since it’s one of the only ways to get from one city to another without navigating their complex public bus system, you’ll likely get plenty of experience with these! We rode in a private colectivo from Havana to Trinidad. It was an old car with no AC or seat-belts. This is common. We paid $50 each for the 4 hour drive. Our driver tried to “price scam” us by stopping at two terrible and overpriced restaurants, but the joke was on him because we packed our lunch! If you can, ask your driver to stop for lunch in the town of Cienfuegos. Ours wouldn’t take us, and we really regret not getting to see this town!
TRINIDAD: Trinidad is a colorful, beautiful town with a slow-paced way of life. It has that classic Caribbean vibe, and its 500 year old cobbled streets constantly remind you of its past. In fact, the whole town is a UNESCO World Heritage site. With horse carts, pastel-colored buildings and elegant plazas, Trinidad is a truly memorable place.
In Trinidad, we started out at our home-stay: Hostel Azalea y Alfredo. These two are a married couple who rent out their home, and I have nothing but amazing things to say about them! They were SO friendly and welcoming, and I had so many great chances to converse with them in Spanish and get all their insights and opinions on a variety of topics.
The city is very pedestrian friendly, so get out and explore! Stroll its hot and vibrant cobblestone streets. Drink one-dollar piña coladas sold by a guy on the front steps of his house- Why not? Lonely Planet has a residential walking tour map for views of the streets, and it was definitely worth it! It takes you from the crumbling buildings to the updated, and from the local to the touristy. This was one of my favorite things we did in the city.
Get the Views– We visited an 1820’s era mansion, El Museo de Historia Municipal, then climbed the steps of the house for an epic city view. After sunset, we had dinner at Ochun Yemaya. There, we ordered the local drink called a chinchirrada (rum with honey in it) .
At night, relax and get some WiFi on the square by the Casa de la Música, along with live music and people watching. There’s plenty of rooftop bars too, so find a nice view and take it easy!
Day 4: Trinidad – Playa Alcón We tried to take the local bus to Playa Alcón in the morning, but we couldn’t find it. Naturally, we gave up. Then, I ended up talking with a local guy loitering by the church, and he took us for $8 in his old 1955 car. When in Cuba!
Playa Alcón is about 15 minutes away from the city. It has beautiful sand and water, but limited facilities. There are no restrooms, no places to change, no faucets to rinse off sand, and no food options around (except pizza which is rumored to make you sick!), so come prepared. We used a random hotel’s beach chairs for 2 CUC and napped, read, and swam in the surprisingly cold water. We ended up leaving the beach early because we were hungry, so the moral is: pack a lunch!
Back in town, we did more aimless strolling (the best part about Trinidad!), and found a fabulous ice cream parlor (Heladería La Dueña- go and give them some business!!). We also visited the Santeria Museum Yamalla. It was a little creepy with the dolls everywhere, but it was still neat to learn about the local voodoo religion and understand why you see so many women wearing all white!
We had dinner at the popular La Botija, which I loved. It’s a good idea to get there early though- it has long lines thanks to its great ambiance, service, and food choices. The slave shackles on the wall were a bit strange, but pay homage to the city’s often violent history.
After dinner we hung out in the square, and found some local guys promoting “1 drink for 1 CUC”. We ended up chatting with these guys, shared said drinks, and eventually helped them advertise and draw in some fellow tourists! 🙂
Day 5: Trinidad- Topes de Collantes- Early that morning, we took the taxi we arranged in the square the night before with “Leo”, and headed towards Topes de Collantes National Park. We paid $30/person round-trip (our driver waited on us at the park and drove us back). It was a scary, twisty, uphill drive in a car from 1970, but the fast changing scenery was great!
We spent the afternoon hiking an easy trail that culminated in a 500 meter steep downhill hike to the Vegas Grande waterfall. There were not many signs, but it was easy to follow. Along the way we passed several oxen and also went inside a cave.
We were the first people to arrive, so had the falls to ourselves for a bit. By noon though, thirty people had made the 1.5 hour trek there too. My husband swam under the waterfall, but it was too cold for me! The hike back was straight uphill (rough!), but we had sandwiches our house-mom had made for us to boost our morale! On the drive back to town we stopped at a Mirador for a panoramic city view, and saw a wild tarantula! I also saw a super tiny “bee hummingbird”, which our driver said was called a “tsum tsum”.
Back in the city, we had a home-cooked meal by our casa owners, Azalea and Alfredo. We tried to use the Internet at a public park, but again it wasn’t working. Defeated, we headed back “home”. On the balcony, I talked to Azalea for hours about religion, marriage, death, her job and retirement, life under Fidel, American politics, the “”mierda” economy of Cuba, its good schools and health care, her thoughts on Raúl Castro, her fears for the ever changing “juventud”, and her liking US tourists over Europeans! It was honestly so fascinating to hear her insights, and I was so excited that I could talk that long in Spanish!
Trinidad → Viñales-Today is colectivo taxi time yet again! This time, we were super cramped because it was oversold (make sure to check on passenger numbers when you book a colectivo!). There was still no AC, and at $40/person for a 4 hour ride in a car from the 1950’s, it was a long drive! We stopped in Havana and our driver slowly switched passengers. Then we drove for another 3 hot, sticky, miserable hours towards Viñales. Once there, we checked in with our casa particular host named Sady.
VIÑALES– This town will give you insight into life in the Cuban countryside. It’s the “real Cuba”- the one that shows you what the majority of the island’s population lives like outside its big cities. It’s a tourist town, no doubt about it- but it still has a natural, unspoiled vibe. Located in the Pinar del Río region, Viñales is the best place to go if you want natural beauty and a slow paced rural lifestyle.
We booked activities for the next day through Sady (even though it was WAY pricier to go with her inflated rates!!). In hindsight, don’t book with your homestay, find vendors in town! The “town” of Vinales is essentially one main street, but is filled with shops and restaurants. We had a great Italian dinner at El Olivo, then found cheap drink specials after!
Lodging: Casa Estrella y Celestino
Viñales Valley– The main draw of coming to Viñales is seeing its valley, and the easiest way to do that is with a horseback ride. We likely overpaid, but at 30$/person our 3 hour tour still felt fair.
After a super brief “training”, we rode the horses in the morning heat out to a tobacco plantation with free rum samples. The surrounding hills and natural beauty there were fantastic! We then trotted our way to a “cigar making” workshop and a demonstration by a local family. The whole day was full of beautiful views. Overall we spent about 2 hours on horseback with our guide, admiring all the mogotes (rounded, tower-like hills) and peaceful countryside.
Views & Caves: Back in town, and off our horses, we had lunch at Paladar La Cuenca. Next it was time for our tour with an overpriced private driver (30$). Our first stop was the famed Hotel Los Jazmines. This is THE place to come for stunning sunset viewpoints of the valley. We contemplated swimming in the hotel pool with its great view, but it didn’t look the cleanest so we skipped. From there, we went to Cueva del Indio. For $9 you can go inside the cave, and take a short boat tour around its cavernous interior.
We finished up at the Instagram hot-spot “Muralla de la Prehistoria”. This is basically a massive mural painted on the side of a cliff. It took 18 people 4 years to complete, and some of these painters actually trained under the famed Diego Rivera! While it might be a bit odd and quirky, I still though it was a fun and worthwhile visit. Plus, no joke, the BEST piña colada (not just in Cuba) of my LIFE was found at a stall at the base of the hillside! Highly recommend!
Lodging: Casa Estrella y Celestino
Viñales → Havana : We said goodbye to slow-paced Viñales and started our 3 hour colectivo drive back to lively Havana. This time, we were in a comfortable and private share taxi that we had arranged with Sady. For $20/person, this was my favorite colectivo of the trip.
In Havana, we had lunch at the trendy El Chanchullero. There was a long wait, but it was worth it! We then roamed the busy streets, found some artsy shopping areas, and of course colorful rows with incredibly photogenic old buildings.
Propaganda: We decided to explore some areas we hadn’t seen yet, so went towards the water and the Plaza de San Francisco. We made another visit to the Malecón too. Since our curiosity was piqued, we decided to check out the Museo de la Revolución ($8). This proved to be extremely interesting. As US citizens, seeing this alternate take on communism was easily one of the most educational parts of the trip. I strongly recommend a visit here, but be sure to read the signs!
Lodging: Casa Particular Colonial with Pablo
Havana- Since it was our last day, we decided to splurge! We went for one of the heavily advertised vintage car hire driving tours (you can pick one up right by La Floridita). For $45 total for an hour in a 1954 pink convertible, we felt it was worth it. It was far better than the tourist bus, and we had some great chats with our guide who rode along with us! We made another stop at Plaza de la Revolución and got photos with the giant memorials to Ché Guevara, Fidel Castro, and José Martí as well.
For dinner, my husband suggested a place he found on TripAdvisor. It was in an old house with no signs, so I was hesitant at first. We figured out it was a paladar though, and once inside I immediately relaxed. Called “Somos Cuba”, this was the most authentically Cuban place we dined during the whole trip. The owner tells you what he has, cooks it up in front of you, and joins the crowd of 10-15 guests while you eat! Definitely memorable!
For the finishing touch, we went to the rooftop of Hotel Saratoga to watch the sunset at Bar Piscina Mirador. Beyoncé stayed here while she was in Cuba, so we knew it would be nice. It had a great view of the capitol building, and some tasty drinks too!
Adios a La Habana: After a lively Easter morning in Havana, we took a $25 taxi to the airport and said farewell! That’s a wrap for my ideal Cuba itinerary!
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As always, all reviews and opinions are my own. However, this post may contain affiliate links. This means I may receive a small commission should you choose to book any of the lodging listed above.