Two weeks in Cuba is the perfect amount of time to get a diverse view of the country. Our two week travel itinerary for Cuba will bring you through cities and small towns and provide plenty of beach time. We recommend spending at least four days in Havana as there is so much to explore in Cuba’s largest city. This itinerary begins and ends in Havana and takes you on an overnight trip to Vinales, on to Veradero and then two days each in Trinidad and Cienfuegos.

Cuba’s surprisingly diverse terrain makes it a great compromising location if you are traveling with beach and mountain lovers. With our Cuba itinerary, you will get a good look at Cuban culture, enjoy some adventure and spend time relaxing without ever getting bored.

Keep an eye out for our latest posts on Cuba with all the information you need to plan your trip!

Day one: Havana

Days one through four: Most flights from the U.S. will land in Havana, so this is the easiest place to start (and end) your trip. If you want to exchange your money at the airport (you’ll at least need enough for a cab) you’ll need to wait in line at one of the exchange counters. If you prefer to wait and exchange most at a Cadeca (they may have slightly better rates), make sure you block off an hour to do this on day one or two.

Take your first day in Havana to get settled in your accommodation and walk around your neighborhood. If you get in in the morning, get right to exploring!

Day Two: Havana

Start at the Museo de la Revolucion (open 10 a.m. to 5 p.m.; 8CUC) and learn about Cuba’s revolution and the heroes of the movement. Allow about two hours to explore the museum, more if you’re very interested in the topic. Most labels are in Spanish, but there are plenty of photographs, maps and vehicles as well. Walk north to the Castillo de La Punta for a beautiful view of the ocean and the Castillo de los Tres Reyes del Morro across the bridge. From here, walk down the Malecon past several parks until you reach the Castillo de la Real Fuerza (6CUC). After your visit to the fort, walk through the used book market at Plaza de Armas across the street. End your evening with sunset mojitos at Hotel Ambos Mundos just two blocks down on Calle Obispo.

Day Three: Havana

Shop for souvenirs at Mercado Artesanal San Jose. There is also a Cadeca in this market where you can exchange for local currency (Cuban Pesos) if you wish. The market is full of handmade and traditional gifts, clothing and jewelry with eager salespeople. Be ready to say “No gracias” while you browse and haggle for the best deals. After your shopping spree, go next door to one of Cuba’s craft breweries, Antiguo Almacen de la Madera, for lunch (5-12CUC per person). If you’re lucky you’ll enjoy some live music with your coastal view.

Walk north to Plaza Vieja where you’ll be surrounded by lively restaurants and cafes (another option for lunch) and beautiful architecture. Keep walking to visit the Catedral de La Habana, which sits on a square surrounded by the historic homes of some of Cuba’s wealthiest families. Entry is free to step into the courtyards where a museum worker can tell you about the history of the home. As you look at the Cathedral, down the street to the left is a small bar called La Bodeguita del Medio where many famous patrons have signed the walls and the mojito may (or may not) have been invented.

If you’re ready for some nightlife, take a taxi to Bar Sarao for a club experience with Salsa and Reggaeton until 3 a.m. (10CUC cover charge).

Day Four: Havana

Visit the Che Guevara artwork near the Palace of the Revolution for a quintessential Havana photo op. Don’t forget to turn around to admire the towering Jose Martí monument. Venture over to Café Mamaine for lunch and enjoy this artsy eatery with a variety of refreshing coffee drinks. Next, spend some time strolling through the The University of Havana campus. The buildings are beautiful and you will have an incredible view of the city from the top of the stairs. Take the opportunity to chat with Cuban students eager to practice English and tell you their favorite places to visit in the city.

At night, visit the historic Hotel Nacional for drinks or head over to Fabrica del Arte Cubano (F.A.C.) for a trendy club experience inside an art gallery (10CUC, closed in January). Next door is El Cocinero, an upscale restaurant built inside a factory. If you don’t have reservations for dinner, you can still climb to the very top level to enjoy a drink inside the smoke stack, although, this may be best avoided if you have a fear of heights!

Days Five and Six: Viñales

Travel to Viñales and get settled in a Casa Particular. This town is small, so plan on spending your full day here taking an excursion such as a 6-hour horseback riding tour with stops at a tobacco farm, a cave and a cafe. You can also hire a driver for similar experiences or further excursions to beaches and larger caves. For meals, stroll along the main street to browse your options. We recommend El Olivo, which is well worth the wait, and Tres Jotas for tapas. If you have the option, take advantage of the breakfast offered by your Casa owner.

Days Seven through Nine: Veradero

Make your way to Veradero. Hire a private or shared taxi to take you to Veradero so you can make a couple stops along the way. The tiny town of Matanzas is home to Ediciones Vigia, a handmade bookshop where artists create collage covers for books and produce them in a limited quantity (closed Sundays). Between there and Veradero, you can stop at Cueva Saturno, a cenote filled with crystal clear water where you can stop for a swim (8 a.m. to 6 p.m.; 5CUC).

This famous beach town is home to several all-inclusive resorts, but there are also plenty of Casa particulares. If you are hoping for a few days of down time, you’ll have no trouble finding a spot on the beach. There is a great beach bar with music and chairs for 2CUC each at the end of Calle 29.

For a little more adventure, stop by the information stand across from The Beatles Bar to book snorkeling, SCUBA and more. For some history, take a taxi up to Mansion Xanadu (2CUC) where you can explore the 1930s vacation home of U.S. billionaire Irenee DuPont, now a clubhouse for the surrounding golf course. The bar that was once his entertainment room on the top floor is an idyllic setting for an afternoon coffee or cocktail. Later, take a stroll through Josone Park where you’ll find some quiet restaurants including an Italian one with friendly staff called Dante. Head back to The Beatles Bar at night for great live music and dancing with fellow tourists.

Days Ten and Eleven: Trinidad

Travel to Trinidad via bus will take about six hours, so be prepared for a long day. Trinidad is a beautiful town interwoven with cobblestone streets. An easy hike up a dirt road will give you a stunning view of the town and beyond to the ocean. You will pass the entrance to Disco Ayala where you can return after 10 p.m. to experience an underground club in an impressive cave. For another colorful view, climb to the top of the belltower at the Convento de San Fancisco (2CUC). To experience Trinidad’s traditional cocktail of rum, honey, lime and soda water, the Canchanchara, visit the bar of the same name on Real del Jigue. At night, visit the stairs at the center of the city and grab a cheap mojito or Piña Colada before heading into Casa de La Musica for live music and dancing shows.

Since you’re on the coast, take a taxi to the Marina and reserve a spot on a Catamaran tour that will leave at 9 a.m. and return at 4 p.m. Arrive about 45 minutes early to book. The tour includes a trip to Cayo Iguana, a small island covered in iguanas, snorkeling time nearby and a delicious seafood lunch.

Days Twelve and Thirteen: Cienfuegos

A bus ride or shared taxi from Trinidad to Cienfuegos will take just an hour and a half. Cienfuegos has beautiful architecture, so plan for lots of walking around here. Head down Calle 37 and stop in to admire Club Cienfuegos. You can relax in the restaurant and enjoy a drink or pay extra to sit by the pool. Turn down Avenida 10 or 12 across the street to see a hidden Lagoon filled with colorful fishing boats. Continuing down Calle 37, you’ll pass a sculpture park that is worth a photo op. If you’re in need of a beach break after your walk, there is a bar with a small beach at the end of Avenida 6.

Visit Parque Martí where you can see the Arco de Triunfo and people watch as locals gather to use wifi and enjoy the square. For a look into Cuban life away from the tourist centers, walk down to the Cementario de Renia, founded in 1837. A tour guide will take you into the walled cemetery for a fee.

Take a half day trip to El Nicho, the famous waterfall with several chilly swimming holes (10CUC park entrance). The falls are located along an easy path that takes you on a short walk through the woods. There is a restaurant near the entrance that is packed at lunch time as the park fills with tourists. The best swimming spot is across the street where the pools are warmed by the sun.

Day 14: Havana

Lastly, travel back to Havana for your flight home. Keep in mind you’ll need to arrive at the airport up to three hours early to get checked in, so plan your arrival in Havana accordingly. If you have time, pick up some last-minute souvenirs at the Romeo y Julieta cigar factory or grab one last mojito before you leave La Isla Grande!

Have you been to Cuba? What would you add to our itinerary?