Every superlative you’ve heard about the storied destination of Cuba is true. From its evocative colonial cities, revolutionary sites, stunning beaches, and sprawling mountain ranges, it has an earned reputation as a travel hot spot. Plus, the nation's cultural scene is staggering. Where else can you enjoy a diversity of music and dance styles—everything from ballet and jazz to salsa and the vibrant percussion at the heart of santería religious rituals? Then there’s the time-warp ambiance, including all those 1950s American cars.
Havana offers a bit of everything, but a week-long itinerary lets you combine the capital with other nearby destinations. This provides a full breadth of quintessential Cuban experiences. Below are three itinerary options that will get you pretty far and guarantee an unforgettable seven days. If you've yet to embark on your Cuban adventure, be sure to check out this article on planning your trip.
#1 Havana, Las Terrazas, Viñales
This classic itinerary focuses on Havana and the easily accessible tobacco country west of the capital. This gives you a taste of almost everything Cuba has to offer. Start your adventure by exploring Havana, making sure to enjoy the rapidly evolving culinary and cultural scene. Start with the HabanaBusTour open-top double-decker sightseeing bus, which explores all the main sights. You can hop off and on at any of 41 stops along the route. Two can't-miss sights are the Plaza de la Revolución and Necropolis Cristóbal Colón. Then explore Habana Vieja (Old Havana) neighborhood on foot, taking in the main squares like sprawling Plaza Vieja. Important buildings include the newly renovated Capitolio, plus museums like the Museo de Bellas Artes (Fine Arts Museum) and Museo de la Revolución.
During the day snap some pictures as you ride along the Malecón, Havana's iconic waterfront thoroughfare, in a classic convertible car. By night take in the cañonazo (cannon-firing ceremony) in Fortaleza de San Carlos de la Cabaña—a must-see when combined with a visit to the castle of El Morro. The Vedado neighborhood is full of hip new private restaurants (paladares) and nightclubs, plus it's home to the Coppelia ice-cream parlor (a truly Cuban experience). If you can, catch the ballet or a classical music performance at the stunning Baroque Gran Teatro, learn to salsa at Casa de Música or splurge on a traditional Cuban cabaret like the Tropicana. (For more things to see and do, check out this article on sights and activities in Havana.)
Then you're off to tobacco country. It's a three-hour journey west of Havana and can be done in three ways. Either drive yourself, take the Víazul tourist bus or hire a car-and-driver through a state tour agency. In any case, we recommend allotting at least two nights for your stay. On the way, make a stop at Las Terrazas, an ecologically-minded mountain community great for birding and hiking. It’s a great place to have lunch or even overnight at a hotel with views of the lake.
Continue on to the provincial capital of Pinar del Río, with a diversion west to Finca Pinar San Luis, the most famous tobacco farm in Cuba (arrange in advance for a guided tour). Then continue north into the Sierra de los Órganos Mountains and the Valle de Viñales, in the very heart of Cuba’s premier tobacco growing region. The town of Viñales squats in the valley, framed by spectacular limestone formations called mogotes. It’s evolved as a popular activity center: hiking, horseback riding, and even ATVs are options for exploring the tobacco-growing region. Plus, you’ll want to explore the Cueva del Indio, a cave located in a subterranean river, by boat. There's also the nearby Cuevas de Santo Tomás, best explored on foot with a guide.
For lodging, you might choose one of two state-run hotels with sensational views over the valley, but you can also stay with families in the village and enjoy that fussed-over-by-mom feel. From Viñales it’s a short drive to the north coast, where you can catch a twice-a-day ferry to Cayo Levisa to round your week with a day or two relaxing, snorkeling or scuba diving at this lovely beach-lined cay. Havana is a two-hour drive east once you return to the mainland.
#2 Havana, Bay of Pigs, Cienfuegos, Trinidad, Santa Clara
Start this adventure by exploring Havana based on the itinerary above, allowing two or three days for the capital before heading southeast to the Bay of Pigs (known in Cuba as Girón, for the site of the main battles during the CIA-sponsored invasion of April 1961). As you head out of town on the Autopista Nacional (freeway), stop in at Museo Ernest Hemingway, where the author’s home, formerly known as Finca Vigía, is kept as if he still lived there.
After a couple hours of driving, you'll arrive at Playa Larga at the head of the Bahía de Cochinos (Bay of Pigs). This former fishing village is now a popular stop-over resort with a lovely beach at the gateway to Parque Nacional de Zapata—a paradise for birders, nature lovers, and anglers. You’re now on the Caribbean Sea, with coral reefs just offshore, tempting you to stop and snorkel or scuba dive at one of the several roadside facilities renting flippers and other gear. For more of Cuba's most stunning beaches, check out this article.
A 75-minute drive east through farmland brings you to Cienfuegos. It’s worth overnighting here. You'll have time to view the main plaza and the Palacio del Valle (a Mughal-style former mansion that’s now a restaurant). Also, ask locals if there’s a baseball game scheduled. If so, it’s worth going to the 5 de Septiembre stadium to enjoy this quintessential Cuban experience.
Continue east to the colonial city of Trinidad. It can get crowded with tourists in the winter months, but this UNESCO World Heritage Site’s popularity is justified. It boasts stunning 18th-century architecture (the historic center is entirely preserved), an enduring cowboy culture, a lively cultural scene, plus tremendous paladares (private restaurants) and hundreds of casas particulares (B&Bs). Spend another day here for excursions into the nearby Sierra Escambray Mountains, scuba diving off Playa Ancón, or exploring the remains of ancient sugar estates in the Valle de los Ingenios.
All these regions are easily accessible by road. When returning to Havana, add a stop in the city of Santa Clara (choose a route either via the Sierra Escambray or the Valle de los Ingenios). The Revolution, in all its manifestations—social, political, etc.—is a huge part of Cuba’s appeal, and especially so here. It was in Santa Clara that Che Guevara’s Rebel Army came out of the mountains to capture the city, causing dictator-president Fulgencio Batista to flee. The de rigueur visit is to Che’s tomb, beneath a massive monument of the revolutionary hero in the Plaza de la Revolución.
#3 Santiago de Cuba, Guantánamo, Baracoa
Some 500 miles east of Havana, at the eastern end of the island, is Santiago de Cuba—Cuba’s second largest city and its first capital (founded in 1514, it pre-dates Havana). The region is dominated by rugged mountains (the Sierra Maestra and Sierra Cristal) but also includes semi-arid, desert-like zones. Santiago de Cuba is known for its predominantly Afro-Cuban based culture. Plus it was here that the Cuban Revolution was spawned. It's off the tourist trail yet is served by an international airport, with direct flights from the USA and Europe. Domestic air service, plus the Víazul bus system, also link Santiago de Cuba to Havana.
Plan on three days for the main sites in and around Santiago de Cuba, which has several hotels plus a good choice of casas particulares. The dining scene may not be as exciting as in Havana, but culture vultures will be in their element. Key sites include the Moncada barracks (site of the attack in July 1953 by Castro's revolutionaries that launched the Revolution), San Juan Hill (of Spanish-American War fame), Cementerio Santa Ifigenia, El Morro Castle, and Parque Céspedes (the main square).
Know that Santiago is a hill city—although the historic core can easily be walked, many of these sites are spread far apart, so you may wish to rent a car or use taxis. As for culture, Son (Cuba’s traditional music form, made famous by the film Buena Vista Social Club) was birthed here at the Casa de la Trova, where musicians still perform. Try to catch a performance of the Tumba Francesa or one of the other Haitian heritage cultural groups. There’s even a Tropicana nightclub, as in Havana, offering sensual Vegas-style cabaret.
For excursions outside the city, head 40-minutes northwest to the Basilica del Cobre. This cathedral is Cuba’s main religious site and is rich with the folklore of the "Black Virgin," or Virgin of Charity. Then head east and stop in the city of Guantánamo. The British West Indies and Haitian heritage are strong here, as cultural centers keep the spirit alive. Then it’s up and over the Sierra Cristal via a switchback highway—La Farola—that literally clings to the mountain (use caution if driving).
Baracoa awaits on the Atlantic shore. Founded in 1511, it's Cuba’s oldest city, surrounded on three sides by rainforest-clad mountains, including flat-topped El Yunque. Hiking to its summit can be arranged. Other adventures include boating on the Yumurí River, birding in Parque Nacional Alejandro de Humboldt, and horseback riding. This region also has distinct cuisine—a legacy of the Taíno indigenous culture, who made good use of tiny fish called teti. It's also rich with coconut milk and cacao, grown locally—hence the local chocolate industry. Reason enough to visit!