Overview

With careful planning and strategic use of domestic transport, you can see the majority of Cuba in two weeks. Here are two options that cover all bases over 14 magnificent days. In the first itinerary, you’ll head east from Havana along the length of the island to the city of Baracoa, in Guantánamo Province. Laze on the sands of both Caribbean and Atlantic shores, roam atmospheric colonial cities, visit sites associated with key moments in history, and end with a cannon-firing at sunset in Santiago de Cuba.

Itinerary two is a “greatest hits” option that combines active adventures with history, culture, and cuisine. Explore the Sierra del Rosario and Sierra Escambray mountains, ride a horse and go caving in tobacco country, and snorkel or scuba dive Caribbean coral reefs. Plus, relax in colonial-era Trinidad, visit famous artists’ studios, explore key historic sites associated with Che Guevara and the 1961 Bay of Pigs invasion, and savor the finest of criolla (local) cuisine at the region’s best restaurants.

For these journeys, you’ll ideally have a rental car but you can stitch many of the destinations together using Víazul buses. For more on planning your Cuba trip, see this article.

#1 Havana to Baracoa

Day 1: Your adventure begins in Havana with a panoramic tour by classic convertible car or the HabanaBusTour; en-route, stop to photograph Plaza de la Revolución and Castillo Los Tres Reyes del Morro. Back at Parque Central, take a break for a light lunch at nearby Sia Kara, then explore the Capitolio, walk the Prado (main boulevard), and bone up on revolutionary history at the Museo de la Revolución. Treat yourself to a nouvelle Cuban dinner at La Guarida the most sensational restaurant in town.

Day 2: Start your day early to explore the main plazas of colonial Habana Vieja (Old Havana) on foot. Take a break to shop at Taller Experimental de la Gráfica, and for a refreshing beer brewed at Factória de Plaza Vieja. Now wander the off-the-beaten-track ecclesiastical district in southern Habana Vieja, which includes the beautiful Iglesia Nuestra Señora de la Merced. End your day with dinner at one of the new paladares (private restaurants) in the Cinco Esquinas area of Habana Vieja, followed by cigars and cocktails at the Hotel Nacional. For ideas about where to stay during your visit to Havana, check out this list of the city’s best boutique hotels.

Day 3: Reserve in advance for a 9 am tour of a tobacco factory (H. Uppman and Fabrica de Tobaco Corona are two of the best) before heading out of town to Museo Ernest Hemingway, the author’s former home. Continue three hours east via the Autopista for Playa Larga (Bay of Pigs), with a stop in adjacent Palpite for eye-to-eye encounters with bee hummingbirds at Casa de Zunzuncito—a “secret” gem! Playa Larga is a great place for lunch by the shore. Continue along the Caribbean shore 20 miles to Playa Girón—the main battle site during the April 1961 Bay of Pigs invasion of Cuba. Make the 90-mile journey to Cienfuegos with time to explore spacious Parque Martí before sundown.

Day 4: You don’t need to be botanically inclined to enjoy a guided tour of the Jardin Botánico—an arboretum outside Cienfuegos—before continuing along the coast road to Trinidad. After checking into your casa particular (private B&B) in Trinidad, your best lunch options are Vista Gourmet or Sol Ananda for good buffet and seafood, respectively. Now tread in the footsteps of conquistadores as you wander the cobbled streets of this UNESCO World Heritage Site. In the evening, check out the state-run live-music house Casa de la Trova (there’s one in every major city and town) and later, if you have the energy, head to Disco Ayala, a nightclub in a cavern!

Day 5: Rise early to experience Trinidad at its most enchanting before the tourist hordes hit the streets. Explore art galleries, such as Galería-Estudio Lázaro Niebla, and “secret” spots such as the Río Tayaba, where classic cars get washed in the river. In the afternoon, mount up for a horseback ride in the Valle de los Ingenios; or head to Playa Ancón to laze on the sand or snorkel.

Day 6: Head into the Sierra Escambray Mountains today, with time for an invigorating hike through the pine forests to waterfalls at Topes de Collantes. Continue on the winding road that leads via the town of Manicuragua to Santa Clara city. Visit the impressive monument, museum, and mausoleum of Che Guevara in Plaza de la Revolución, and in the early evening join the locals in Parque Vidal to soak in the relaxing ambiance of this edgy university city. The El Mejunje nightclub is renowned for drag shows.

Day 7: Continue through the tobacco country of Vuelta Arriba to the UNESCO World Heritage City of Remedios. Allow time to stroll the historic streets before visiting the nearby Museo de Agroindustria Azúcar (Museum of the Sugar Industry). From here an elevated causeway leads over coastal waters to the snow-white beaches and turquoise waters of Cayos de Villa Clara. You can drive the full distance between Santa Clara and Cayos de Villa Clara in 2.5 hours, so plan to arrive with plenty of time to enjoy the beach and bathtub-warm waters. For more beach ideas in Cuba, check out this article. 

Day 8: Journey along the Costera Norte (North Coast Highway) via the city of Morón, passing from sugarcane country into cattle country—gorgeously studded with Royal palms—as you head to Camagüey city. With its many cobbled colonial plazas and labyrinthine streets, its historic core is sure to fascinate. Don’t miss Plaza del Carmen, which features life-size representations of city residents, and Plaza Agramonte, with its 17th-century cathedral. Relax with a mojito or beer at one of the lively bars.

Day 9: Continue roaming Camagüey’s labyrinthine streets before setting out along the Carretera Central—Central Highway—via Las Tunas for Holguín, another provincial capital with intriguing colonial plazas and museums. The three-hour journey leaves plenty of time for exploring after enjoying a nice lunch. Holguín’s lively cultural scene centers on the Casa de la Trova. The Terraza Bucanero is for beer-lovers, and there are a number of discos for night-owls.

Day 10: This off-the-beaten-track route takes you through sugarcane country to Museo Conjunto Histórico Birán, the family estate where Fidel and Raúl Castro were born to a wealthy rural magnate and his housekeeper. Today it’s a fascinating museum—note Fidel’s desk, front row center in the little schoolhouse. It’s a full day’s journey from here along the deteriorated north coast road via Moa—a blighted mineral mining town—to Baracoa, founded in 1511 as Cuba’s first city.

Day 11: After exploring this charming time-warp town consider an excursion to a cacao plantation such as Finca Duaba for a demonstration on chocolate making. Or if you’re in search of adventure, sign up for a day-long guided hike to the top of table mountain El Yunque on the rainforests of Parque Nacional Alejandro de Humboldt. Baracoa boasts several excellent paladares—one of our favorites is El Poeta—and the Casa de la Trova is a great place to enjoy traditional music and dance with the locals.

Day 12: A newly built road from Baracoa has finally opened up access to Punta Maisí—Cuba’s easternmost point. After climbing the lighthouse here, follow the road through mountainous coffee country then descend a series of dramatic limestone coastal terraces to Cajobabo. A hike along the beach brings you to a rarely visited monument built into the cliffs at the spot where in 1895 José Martí landed to launch Cuba’s War of Independence. Lunch at hilltop Mirador La Gobernadora, which affords a view of the Guantánamo Naval Base, then marvel at the life-size stone carvings of animals at Zoológico Piedra before continuing via Guantánamo city to Santiago de Cuba.

Days 13 & 14: Steeped in Afro-Cuban influences, Cuba’s second largest city—and in a way its cultural capital—deserves two full days of your time. Explore the casco histórico (the historic core) plus hallowed sites such as Cuartel Moncada and Cementerio Santa Ifigenio, where Fidel is buried. Perhaps journey eight miles south to Parque Histórico El Morro, with a recommended side trip to Cayo Granma—a small island inhabited by a colorful fishing community. Plus, there are heaps to entertain you by night. Don’t miss the Casa de la Trova (yes, there’s one here too), and spend your final night enjoying a cabaret at the Tropicana. On your last day, transfer to the airport for your flight home.

To dig even deeper in Santiago de Cuba, see this article.

#2 Best of Western Cuba

Days 1 & 2: Follow Itinerary #1 above for your introduction to Havana, where the exciting and ever-evolving dining scene includes such stellar paladares as Doña Eutimia, in Habana Vieja; Casa Miglis, in Centro Habana; and, in Vedado, Café Laurent and El Cocinero. For more on hidden gems in Havana, see this article. 

Day 3: Head west from Havana on the Autopista Este-Oeste for Las Terrazas (90 minutes), a lovely mountain community. Here you can enjoy a specialty coffee at Café María before walking around town, allowing for breaks at the studio homes of artists Henry Aloma and Lester Campa. Following lunch at Fondita de Mercedes, spend the afternoon on a guided birding hike into the nearby coffee plantations and forest—you’re sure to see the tocororó, Cuba’s blue-red-and white national bird. Then cool off in the Baños del Río San Juan cataracts. Relax overnight at Hotel Moka or at a casa particular in nearby Soroa.

Day 4: Enjoy a short but steep hike to Soroa’s exquisite waterfall, then visit the orchid garden before continuing west for Cueva de los Portales, in Parque Nacional La Güira. Roam the picturesque cavern, with its lovely riverside setting, before continuing one hour to the famed tobacco-country town of Viñales. Enjoy a relaxed lunch here, then explore Viñales’ top sites by hiking, horseback riding, or even by ATV. 

Day 5: Viñales deserves a second day to fully experience its natural wonders. This morning head to Cueva de Santo Tomás to explore the stygian underground labyrinths on a guided excursion. Then add the thrill of a zip-line ride between mogotes (dramatic limestone formations). Since this is prime tobacco country, spend the afternoon learning ‘Tobacco 101’ at a local farm; a visit is easily arranged at local tour agencies. At night treat yourself to dinner and entertainment at 3J Tapas. For a more in-depth look at the Viñales Valley, see our Ultimate Guide to Tobacco Country.

Day 6: Beach time. Drive west to María La Gorda (two hours), at the tip of Cuba, to don mask and fins and snorkel or dive the coral reefs and—¡ojala! (if lucky!) as Cubans say, you’ll encounter some whales sharks. There’s time, too, to laze the midday hours away on the sands before a guided birding walk into Parque Nacional de Guanahacabibes. Overnight at the beach hotel.

Day 7: Rise early and get a head start on the six-hour journey east via Pinar del Río city to the Autopista Nacional and onward to Playa Larga, in the Bay of Pigs. Getting from one autopista to the other isn’t obvious so you’ll want to have a good map at hand. This nascent beach resort and fishing community lies at the gateway to Parque Nacional de Zapata, and there are plenty of quality beachfront casas particulares (room rentals) from which to choose.

Day 8: The Parque Nacional de Zapata is Cuba’s largest national park and heaven for nature lovers. In the morning take your pick of guided excursions—perhaps birding, hiking, or even kayaking. In the afternoon drive along the Caribbean shore, stopping at the museum (dedicated to the 1961 Bay of Pigs invasion) at Girón before arriving in Cienfuegos mid-afternoon with time to roam the charming Parque Martí. Admire its lovely French-inspired buildings; then walk the Malecón bayfront boulevard to Punta Gorda at sunset.

Day 9: Begin today with a visit to the Jardín Botánico, Cienfuegos’ arboretum with a vast collection of palms and other species; hire an English-speaking guide to get the most out of your visit.  Then cross the road to explore Pepito Tey, a former sugarcane processing community where visitors are virtually non-existent; be sure to peek inside the bodega (ration store) to view the incredible revolutionary murals. Now head to El Nicho at the base of the Sierra Escambray Mountains: after hiking to the waterfall, take an invigorating dip in the turquoise pool at its base. Continue via Manicagarua, and turn south to cross the mountain chain via Topes de Collantes, arriving in Trinidad in the late afternoon.

Day 10: Use itinerary #1 above to plan your time and gain the most of your full day and second evening in Trinidad. For more detailed information, see our Ultimate Guide to Trinidad.

Day 11: Continue east through the Valle de los Ingenios, stopping at Hacienda Manaca-Iznaga and Sitio Histórico Guaimiro—two distinct 18th-century haciendas recalling the colonial heyday of sugar. Taberna Yayabo, on the riverside in the city of Sancti Spíritus, is a great place to lunch on criolla fare. Nearby, the Casa de la Guayabera—one of the most intriguing places in the city’s historic core—celebrates the guayabera, Cuba’s classic pleated cotton shirt. Next, head north to Yaguajay to visit the museum honoring Camilo Cienfuegos, a comandante in the Rebel Army, then turn west to cross the pedraplén (causeway) to Cayos de Villa Clara.

Day 12: Beaches and ocean waters don’t come more beautiful than on Cayos de Villa Clara. Here you’ll be tempted to laze the day away or try your hand at fishing for tarpon or bonefish, or scuba diving on a pristine coral reef. Consider a dolphin show at the delfinarium and a guided excursion by scooter to Reserva Cayo Santa María, where you’ll see flocks of flamingos.

Day 13: Head back to Havana, but take time to visit the Museo de Agroindustria Azúcar, telling the story of sugar production, in a former sugar-processing mill outside Remedios. Then head to Santa Clara for lunch—we recommend the El Quijote paladar for its superb buffet. Also visit the aforementioned Plaza de la Revolución, with its massive monument to Che Guevara. A three-hour drive on the Autopista Nacional then returns you to Havana. Celebrate your journey with a final cigar, cocktail, and night on the town.

Day 14: Say farewell to Cuba as you transfer to the airport for your flight home.