Travel Itinerary: The best of Cuba

So you want to go to Cuba and do it on your own? Well, I’m here to help make your Cuba dreams come true. This tried and tested (by me!) Cuba itinerary brings you the best sights and sounds that Cuba has to offer in 1 week. Have more time? Then custom tailor your trip with my extra day add on’s. Let’s Wander Cuba!

Day One:  Arrival

Today is your arrival day. Once you get past customs and immigration, head directly to the money exchanges located outside the arrivals and departures halls. Waits can be up to 1.5 hours to exchange money if multiple flights have landed at the same time. Pro tip: Arrange a transfer to your accommodation ahead of time and save time changing money at a bank or Casa de Cambio in town instead. Lines are usually shorter in town and the rates are the same. Settle into your Havana Vieja accommodation and get your bearings.

Stroll up Calle Obispo to enjoy the architecture and find a good place to eat dinner. Check out El Floridita and La Bodeguita del Medio two of Hemingways favorite watering holes. You can’t miss having a daiquiri or mojito in these lively bars. I recommend 304 O’Reilly for dinner and El Del Frente for drinks. The later has an amazing rooftop bar where you can sip the best piña coladas and mojitos in town.  Spend the night in a Casa Particular – a homestay run by a Cuban family. These offer the best rates and you get to immerse yourself in the Cuban culture by interacting with the friendly people who run these places. You can find tons of them on AirBnB. Get 40$ off your first stay by clicking HERE. I stayed exclusively in Casas for my entire trip to Cuba and it was the best experience ever.  

Day Two: Havana

Get up early and enjoy the day walking Old Havana. The best place to start any Havana experience is at Plaza de la Catedral. Stroll down Calle Mercaderes to Plaza Vieja and take in the view at the second floor cocktail lounge at Don Eduardo Alegre. You’ll be treated to 180 degree view of the entire plaza while you sip a mojito on the balcony. 

Get lost in the maze of the old town, it is one of the best preserved and was designated a World Heritage Site in 1982. The streets are lined with colonial architecture, 16th century fortresses and countless churches. Visit La Catedral San Cristobal de la Habana, the Palacio de los Marqueses de Aguas Claras and the Plaza de Armas. Also visit the Museo de la Revolucion, to learn about the history of the Cuban Revolution and see the infamous Hall of Cretins.

After lunch see the passion project of Jose Fuster, an artist who has turned an entire neighborhood into a lively and colorful series of mosaics. Known as ‘Fusterlandia‘, the inspiring and whimsical scenery is a perfect spot for pictures, and potentially have the chance to say ‘hola’ to the artist as he works!

Check out the Capitolio and Parque Central. These are the best places to see lots of classic cars and negotiate for a ride in one. Bargain hard! It’s usually 40-60 CUC for a ride down the Malecon and out to several of the main attractions in Havana. If you don’t have the money for a tour in one of the classic cars, you can get on the hop-on hop-off city site-seeing bus. These giant red double-decker buses depart from Parque Central and only cost 5 CUC. They go to all of the major sites in greater Havana including the Plaza de la RevoluciónHotel Presidente, el Cementerio de Cristóbal Colón and the University of Havana. After a long day seeing the sites I highly recommend eating dinner at Los Nardos. The food is cheap, tasty and the portions are huge, so don’t let them talk you into tons of appetizers!

Day Three: Havana – Viñales

Head out early to the Viñales Valley. It’s about a two hour drive to Viñales – situated in one of the most picturesque parts of Cuba, the Pinar del Rio province. The landscape here is dotted with limestone hills called mogotes. The town of Viñales is a small and culturally rich village, with friendly and welcoming residents. All of the houses in town are painted bright colors and it’s easy to navigate on foot. Once in town arrange your excursions for the following day.

The most popular way to see the valley is by horseback. Tours of the valley and the many tobacco farms can be arranged at the Finca Raul Reyes which is located down at the end of Calle Adela Azcuy Norte. You can also rent bikes or hike through the valley independently or with a guide. We rented mountain bikes and pedaled our way through the trails. 

After you have arranged your excursions, head up the hill out of town to grab lunch at the restaurant Mirador Balcón del Valle. The restaurant has 3 giant balconies overlooking the valley. A little further up the hill is the Hotel Los Jazmines. There are 360 degree views of the entire valley from the pool lounge or you can have a cocktail at the observation platform. It’s a great place for sunset. 

Day Four: Viñales

Head out on your excursion into the Viñales Valley. Spend the morning learning more about Cuban agriculture with a visit to a local tobacco farm on your ride through the valley. Learn about the tradition of Cuban cigars from a farmer and expert cigar maker. Get an insight as to how the communist system works, how much tobacco they keep, how much produce they give back to the government, and how they make ends meet.

Learn about the process of tobacco planting, cultivation and rolling the final cigar. Most horseback tours of the valley stop at a few plantations on the way. If you are exploring independently you can just pop into a farm and more than likely someone will be around to explain the process and show you the tobacco. For dinner I recommend eating at El Olivo. 

Optional Extra Day: Cayo  Jutías or Cayo Levisa

Have an extra day on your hands? Head out on a day trip to one of Northern Cubas two most beautiful beaches, Cayo Jutias and Cayo Levisa. Both are about 2 hours away by bus or car. There is an additional boat ride out to Cayo Levisa so it takes just a bit longer to get there than Cayo Jutias. Both offer up beautiful white sand and amazing crystal clear turquoise waters. Spend the day relaxing on the beach with a good book, or swimming in the turquoise water while you look for fish. Day-trips out to each of these locations can be arranged right in the town of Vinales at the Cubanacan tour agency. Other ways to get to the beach include taxi collectivos, rental car or scooters. 

Day Five: Viñales – Cienfuegos

Today head to Cienfuegos – the “Pearl of the South”, a city founded by the French, which lends it a distinctly European flavor, with wide Parisian-style boulevards and elegant colonnades. Like Havana, Cienfuegos has a beautiful Malecón, where anyone can pass a peaceful evening watching fisherman cast nets and locals socialize.

Check out the Parque Jose Marti, Museo Provincial, Teatro Tomas Terry and the Mercado Central in the old part of town and then walk down the Malecón to Punta Gorda to check out the Club Cienfuegos, Palacio Azul and the Palacio de Valle. Head up to the rooftop of the  for some great views and a cocktail! For dinner head to Casa Prado. They have a great rooftop terrace for dinner and an amazing paella! 

Day Six: Cienfuegos – Trinidad

Head to the beautiful colonial city of Trinidad. Trinidad is home to numerous churches and many beautiful colonial buildings. Located near the lovely Valle de los Ingenios (Valley of Sugar mills) and Playa Ancón.  The town of Trinidad is a UNESCO World Heritage site.

Head to the Plaza Mayor and walk along the cobblestone streets, visit the Museo Historico Municipal where you can head up the tallest tower in town to get a great view of the entire city, then take a walk in the Barrio Los Tres Cruces for some great people watching. Pro Tip: Trinidad is very compact so it’s main sights can get overrun with tourists quite quickly. To get great photos get up at sunrise and capture the first rays of sunshine on the architecture in town. 

At some point, learn about the cultural and social importance of the dance scene in Cuba. Check out the Casa de la Musica on the staircase next to the Iglesia Parroquial off of Plaza Mayor. There is a 10pm salsa show here. Nightlife in Trinidad is probably the most accessible and intense in all of Cuba, with numerous live music venues and many dance performances every day of the week, all amongst the enchanting setting of old colonial buildings and the cobblestone streets.

Day Seven: Trinidad

Take a second day in Trinidad to walk the beautiful streets and check out the neighborhoods outside of the old town area. Relax in a street side cafe and enjoy the music pouring onto the streets from every restaurant in town. Check out the Museo Romantico and the Galeria de Arte. If you have energy to burn head up to the Cerro de la Vigia. From Calle Simon Bolivar its about a 45 minute hike to the radio tower on Cerro de la Vigia and you will have views of Trinidad and the Valle del los Ingenios!

Optional Extra Day: Playa Ancón or  Topes de Collantes

Have an extra day to spare in Trinidad? Beach it or hike it by heading out to Playa Ancón or Topes de Collantes. Playa Ancón is only a short 15 minute taxi ride from Trinidad while Topes de Collantes 20km northwest of Trinidad, has some of Cuba’s best unguided hiking. The most popular hike is the 2.5km, 2½-hour round-trip trek to the Salto del Caburní, a 62m waterfall cascading into cool swimming holes.  Playa Ancón offers a long stretch of powder white sand with plenty of palapas for lounging the day away in the sun. 

Day Eight: Trinidad – Havana

Head back to Havana for your last day in the historic city. Wander the streets of Centro – Havanas most populated and lively neighborhood. The buildings may not be as restored as the ones in the old town, but the energy of this area is unbeatable. Head to the Real Fabrica de Tabacos Partagás. This is the official spot to buy cigars in Havana and the place to watch how the cigars are made by hand. Check out the Parque Historico Militar Morro- Cabana and stay for the shooting of the cannons in the evening. Stroll down the Paseo de Marti (Prado) from the Parque Central all the way to the Malecon. It’s a great place to people watch and check out the beautiful buildings lining the street. 


Day Nine: Depart Havana

Say good-bye to Cuba as you head back home.  Make sure to give yourself plenty of time to get to the airport and check in. Lines can be long and slow. 

Optional Extra Day: Havana

With so much to see and do, why not spend an extra day in Havana. Head out to the Vedado and have an ice cream at the famous Coppelia ice cream parlor. Wander around Barrio Chino (China Town) in Centro. Relax on the expansive outdoor patio at the Hotel NacionalDon’t miss the Tropicana Cabaret show, a Las-Vegas style open-air cabaret show with live music, beautiful costumes and lots of singing and dancing. 

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