In three days, travelers can experience the highlights of Havana and take home an appreciation for the stunning architecture and rich cultural heritage of this ancient city. But a more relaxed pace awaits outside Havana, where mountain forests, beaches, lush tobacco country, sugarcane valleys, and colorful colonial cities await discovery.
A one week trip will enable you to explore the tobacco fields and stunning scenery of Viñales; go birding and hiking in Las Terrazas; visit the Bay of Pigs, Cienfuegos, and Trinidad; and/or head east to Matanzas and the beaches of Varadero. Two weeks will allow for a longer trip, perhaps taking in the central provinces, with a nature excursion and a visit to the Che Guevara Mausoleum in Santa Clara.
However, to experience Cuba at its fullest, plan on three or four weeks. This gives enough time to explore the entire island, including southeastern Santiago de Cuba, the easternmost city of Baracoa, and the Sierra Maestra mountains, including the trek up Pico Turquino—Cuba’s highest peak. Here are some itineraries, from three days to four weeks.
Cuba in 3 Days
Although Cuba has a dozen international airports, the vast majority of visitors who are not here exclusively for a beach vacation arrive at Havana. It’s best to stick to the capital city if you’re planning a short trip. Most of the city’s sights are fairly concentrated, and getting between them is easy. Habana Vieja's (Old Havana) colonial plazas, museums, and backstreets are teeming with architectural, historical, and cultural treasures. Spend the first day walking the four main plazas—Plaza de Armas, Plaza de la Catedral, Plaza Vieja and Plaza San Francisco—and the streets in-between.
On day two, focus your time around Parque Central and Paseo de Martí (Prado), including visits to the Capitolio (Capital Building), Museo de Bellas Artes (Fine Arts Museum), and Museo de la Revolución. For more off-the-beaten-path city destinations, check out Places Most People Miss in Havana.
Walk the Malecón seafront boulevard on day three, then explore the neighborhood of Vedado. Don’t miss the Universidad de la Habana, or historic hotels like the Habana Libre, the Nacional, and the Riviera. Be sure to stop in at Coppelia ice-cream park for a refresher from the tropical heat. In the afternoon, hire a convertible classic car and tour Plaza de la Revolución plus the Necropolis Cristóbal Colón, then head to the outskirts of town to visit Museo Ernest Hemingway, in the author’s former home, known also as Finca Vigía.
Cuba in 5-7 Days
With a week you have enough time to explore the highlights of the capital plus head west to Las Terrazas, in the Sierra del Rosario Mountains. Kick back in this peaceful rural community before enjoying some local activities. Perhaps whiz across the lake on a zip-line, or go birding and hiking with a local specialist guide. You’re virtually guaranteed to spot the tococororó, Cuba's national bird. You can overnight here at the lovely Moka eco-hotel overlooking the village, which has artists’ studios to visit.
Then continue west to the hamlet of Viñales via the provincial capital of Pinar del Río. Viñales is surrounded by sensational limestone formations enshrined within Parque Nacional de Viñales. There are three commercial hotels (two with stunning views), but we recommend staying in one of the many casas particulares (private B&Bs) in and around the village. Spend your time here hiking or enjoying a horseback ride in the country. You’ll also want to explore the underground labyrinth at Cavernas de Santa Tomás or Cueva del Indio. The Valle de Viñales is also the heart of tobacco country: several farms welcome visits, but our favorite is Finca Pinar San Luis, a private farm just a 20-minute drive west of Pinar del Río city.
With a week, there’s even time to head to the extreme western tip of Cuba, at Parque Nacional de Guanahacabibes. The dry forest here is ideal for eco-adventures, and the dive center at the modest beach resort of María La Gorda offers great scuba diving. Alternately, head to Cayo Levisa, a gorgeous cay off the north coast, with an excellent hotel and equally sensational diving.
Cuba in 10 Days
10 days lets you experience the week-long itinerary, plus it allows for heading southeast to the Bay of Pigs (a two-hour journey southeast of Havana) for a history lesson at the excellent Museo Girón, which recalls the CIA-sponsored invasion in April 1961. The area has several good beachfront restaurants and B&Bs.
Then continue to Cienfuegos, a tranquil and charming bayside city. The nearby botanical garden is a highlight, and this is a good place to take in a baseball game at the Estadio 5 de Septiembre. About 90 minutes’ drive to the east is Trinidad. You should dedicate two days to exploring this UNESCO World Heritage Site, considered the crown jewel of Cuba’s colonial cities. Spend the first day walking the cobbled streets, then head to nearby Playa Ancón for sunning and snorkeling; go horseback riding in the Valle de Los Ingenios; or take an excursion into the cool Sierra Escambray Mountains for birding and hiking.
Alternately you might prefer to combine Havana and the Viñales option with a visit to the Atlantic port city of Matanzas, about 90 minutes east of Havana. This culturally rich city is renowned for its Afro-Cuban rhythms and strong santería (Afro-Cuban religion) traditions. It’s best combined with a day or two at Varadero—Cuba’s premier beach resort, which stretches along eight miles of stunning beach. In September 2017, Hurricane Irma swept the region, causing extensive damage. But the recovery has been impressive and the resort is again resplendent. The offshore waters provide splendid opportunities for diving, and catamaran cruises are a popular option.
Cuba in 2 Weeks
With two weeks you can really gain a sense of Cuba’s diversity. After ticking off Havana, tobacco country, plus the highlights along either the Caribbean coast or Atlantic shoreline in the 10-day itinerary, you can then add a visit to Santa Clara. This peaceful city is intimately associated with Che Guevara, the guerrilla leader who captured the city in late December 1958, causing dictator-president Fulgencio Batista to flee.
If you love colonial history, the nearby colonial city of Remedios—another UNESCO World Heritage Site—will delight. If possible, time your visit for late December, when the town and neighboring villages explode in feverish fireworks celebrations called parrandas. The nearby offshore Cayos de Villa Clara will thrill anglers and scuba divers, and they boast more than a dozen upscale all-inclusive hotels.
For the most sensational beaches, you can continue east to Cayo Coco, now fully recovered following the devastation of Hurricane Irma. To the south is Camagüey, yet another historic city with cobbled colonial plazas and a rich cultural life. It’s a gateway to Playa Santa Lucia for scuba diving, and to excursions to the protected area of Sierra del Chorrillo for nature activities.
Cuba in 3 Weeks
Three weeks gives you time to explore part of the eastern provinces (Oriente), in addition to the above-mentioned itineraries. Follow the Carretera Central—the main highway—to reach Holguín, gateway to Oriente. It has plenty of historical sites, which can be seen in one day before heading north to relax in the weathered port town of Gibara, and on the white-sand beaches at the resort of Guardalavaca. The latter is a great place for scuba diving. A key draw is Finca Manacas, the Castro brothers’ birthplace at Birán. Here the former Castro family estate is today a fascinating museum. Combine it with a day or two in the pine-clad heights of Pinares de Mayarí—a cool alpine setting that appeals for eco-adventures.
If you want to explore somewhere more remote, you can head into the Sierra Maestra, Cuba's most rugged mountain chain, accessed via the well-preserved colonial-era city of Bayamo. These lushly forested mountains were Fidel Castro’s headquarters during the war to overthrow the brutal and corrupt Batista regime. You can base yourself at the eco-resort in the town of Santo Domingo. From here, it’s an exhilarating guided daylong-hike to Fidel’s former HQ at La Comandancia de la Plata; or, if you’re extremely fit, tackle the two-day round-trip hike to the summit of Pico Turquino, Cuba’s highest peak.
Cuba in 4 Weeks or More
Four weeks provides sufficient time to explore Cuba in its entirety and to immerse yourself in the fascinating eastern provinces. Base yourself in Santiago de Cuba, a hill city founded in 1515. Its architectural style is quite distinct from Havana, as is its culture, which is heavily influenced by Haitian and French immigrants. Take two or three days to fully explore the city’s sites, being sure to include the Moncada barracks, San Juan Hill, the Cementerio Santa Ifigenia, and El Morro castle. The city is a good base for half-day excursions to Basilica del Cobre, plus Parque Baconao and the Gran Piedra.
You’ll then want to head east via the city of Guantánamo, with a side trip to the Parque Zoológico de Piedra (Stone Zoo), where life-size animals are carved from limestone rock. The switchback road (called La Farola) over the Sierra Cristal offers fabulous vistas before you descend to Baracoa, Cuba’s easternmost and oldest city, founded in 1511. Surrounded by rainforest and soaring mountains, its bay setting is exquisite. Although it has several hotels, you may wish to base yourself at a local B&B. When you’re done soaking in the town’s aged ambiance, cap your visit with excursions to a cacao plantation, a boating trip on the Río Yumurí, and perhaps even a drive to Punta Maisí—Cuba’s easternmost point—where you can now overnight at a pleasant new motel.
Road travel in Cuba is easy, as the state-run car rental companies have outlets in every town and city. It’s expensive, but traffic is light and most Cubans are courteous and careful drivers. However, many roads are poorly maintained, and the many obstacles range from huge potholes to oxcarts and wayward bicyclists, especially beyond Havana.
Flying between cities is possible on two domestic airlines, Cubana and Aerogaviota, but reserve well in advance. Be aware that baggage allowance is limited on domestic flights. Note that Santiago de Cuba has an international airport, as does Holguín. So you may be able to fly out of either destination at the close of your trip.
A state-run bus company, Víazul, offers air-conditioned bus service between most cities and major tourist sites on a daily basis. Reservations are wise. If you’re adventurous and don’t mind the possibility of breaking down, you can even hire a private 1950s car with driver.