Cuba Great Itineraries

Highlights of Cuba in 8 Days

Cuba is not only the largest island in the Caribbean, but it may also have the most sights and attractions scattered across its diverse landscape. It could easily take more than two weeks to see the natural wonders of its mountains and forests and experience the culture and history of its towns and cities. The following itinerary takes in many of the island's best attractions across several regions, with recommended lodgings in each, offering the first-time visitor an exciting introduction to the country.

Days 1 and 2: Havana

Cuba’s amazing capital is the first port of entry for most visitors, and it could keep you occupied for days. Spend your first day strolling the famous seaside walk El Malécon. A good starting point is Antonio Maceo Park, just east of Hotel Nacional. Continue east about 2 miles (3 km) until you reach the beautiful Baroque Catedral de la Habana. The next day you can take in a trio of terrific museums —the rum-themed Museo del Ron Havana Club, the fine arts Museo Nacional de Bellas Artes, and the Museo de la Revolución.

On either day, be sure to save some energy for the night. Visit the famous El Floridita (aka the cradle of the daiquiri) bar. Although touristy, it provides a classic Cuban night, with hot live music and cool daiquiris and mojitos. Or head to Casa de la Música, one of Havana's most popular night clubs, featuring many of Cuba's biggest modern acts.

When you're finally ready for sleep, you could stay at the historic Hotel Nacional, where pre-revolution anybody who was anybody stayed. For a contemporary feel, try the Hotel Meliá Cohiba with its modern amenities or the intimate Hotel Raquel.

Days 3 and 4: Trinidad

The colonial town of Trinidad dates from 1514 and remains Cuba’s best-preserved colonial architectural gem. Its streets, with their pastel-colored houses, are an attraction on their own. The Museo de la Lucha contra Bandidos houses a Revolution-themed museum in a former monastery, the Convento de San Francisco. Like all things Trinitario, religion rubs shoulders with Revolution here. The Iberostar Grand Hotel Trinidad is your best lodging choice in the city.

Days 5 and 6: Camagüey

Camagüey’s labyrinth of streets reputedly confused invading pirates, and they continue to do so with visitors. Keep asking for directions; you’ll get where you need to go. A pair of 18th-century churches, the Iglesia de Nuestra Señora de la Merced and the Iglesia de Nuestra Señora de la Soledad have both gone through numerous renovations and restorations through the centuries but have remained pretty faithful to their original constructions. The Hotel Colón evokes its 1920s heyday and is one of Cuba’s snazziest city hotels.

Days 7 and 8: Santiago de Cuba

Like Havana, Santiago could keep you occupied for days. The beehive of life that is Parque Céspedes is best observed from the venerable Hotel Casa Granda, the best people-watching post in the city; it and the modern Meliá Santiago de Cuba are two great, affordable, places to stay. Three terrific museums sit in the center of the city: the Museo Provincial Bacardí Moreau documents Santiago’s history; the rum-themed Museo del Ron acquaints you with the life and times of Cuba’s best-known beverage; and the Museo del Carnaval portrays artifacts from Santiago’s Carnival celebration. (Try to time that last one for late afternoon when the museum stages a mini-carnival performance.) Don’t forget Santiago’s environs either. Cuba’s Revolution began at the Antiguo Cuartel Moncada, military barracks outside the city. Pay your respects to revered Cuban poet José Martí at the Cementerio Santa Ifigenia where he is buried. Cuba’s patron saint, Our Lady of Charity, is revered at the Basílica del Cobre. The imposing Castillo del Morro fortress sits out on the coast and protected Santiago from pirate invasions during colonial times. Any of the regional sites warrant a half day and can be reached by taxi. Back in the city, an evening of drink and music at the Casa de la Trova or drink only at the Hotel Casa Granda are relaxing ways to cap off a day, even if you don’t stay at the latter.

Vintage Cuba in 5 Days

Americans are often enamored with Cuba's antiquated appearance, the sense that little has changed since the early 1960s when a series of trade sanctions effectively froze the island in time. Follow this itinerary for a glance at old Cuba, beginning in Habana Vieja and ending in Remedios .

Days 1 and 2: Havana

Spend your day in Cuba’s cobbled Habana Vieja. The El Morro-La Cabaña Historical Military Park stands guard over the old city on the north side of Havana Harbor, just as it has since its construction in the 16th century. Wander the ramparts of the star-shaped fortress that once kept foreign ships out of the harbor by way of a chain stretched across to the other side of the harbor. You can climb to the top of El Morro Lighthouse for a stunning view of all of Havana and the Straits of Florida, 90 miles of water that separates Cuba from Key West, Florida. Back in Old Havana, you’ll want to pop into the Cathedral of the Virgin of the Immaculate Conception. The cathedral’s Baroque exterior dates from its construction in 1748; a renovation in the early 19th century gave the interior a Classical look. Have lunch at one of Hemingway’s favorite haunts, La Bodeguita del Medio. Quench your thirst with a mojito, just as Papa did, have a sandwich and bask in the memories of the famous people who preceded you, depicted in wall posters: Hemingway, Carmen Miranda, and Errol Flynn. Museum hop in the afternoon—vintage favorites include the Rum Museum, the National Fine Arts Museum and the Museum of the Revolution—and then take a taxi along The Malecón, the 5-mile (8-km) seawall, to your recommended accommodations, the landmark Hotel Nacional. The pink, twin-towered hotel was built in 1930 and has long connections to Batista, the mob’s Lucky Luciano, Winston Churchill, and Marlon Brando.

On Day 2, venture out of Havana to Cojímar. The seaside village east of town is home to the Fuerte de Cojímar, a tiny fort, alongside of which is a bust of Ernest Hemingway. Here it was that Papa docked his boat, Pilar, chatted with fishermen, and got the inspiration for his classic The Old Man and the Sea. Fill up on a seafood lunch at La Terraza, Hemingway’s favorite when he was in town, before taking off for Finca Vigía, Hemingway’s home and office. Bull-fighting posters, the heads of game animals, and Pilar remain at the estate, all of it original to the time that the author lived here. Back in Havana, take a spin in a classic car, a 1956 Chevrolet Bel Air or a 1957 Ford Fairlane, en route to an evening of dinner and jazz at Café Oriente. Cap off your evening with one last toast to Hemingway: a daiquiri at La Floridita, the author’s favorite watering hole.

Day 3: Santa Clara

A three-hour drive from Havana, east on Autopista Nacional, takes you to the village of Santa Clara where the pivotal battle to topple the Batista regime occurred, and it's here that you'll find the Monumento Ernesto Che Guevara. It’s impossible to miss the larger-than-life bronze statue of Che beneath which are the words, “Hasta la victoria siempre,” “Onward to victory, always!” attributed to the beloved Cuban revolutionary. Interred beneath the memorial are the remains of Che and a small museum dedicated to Guevara and the revolutionaries who fought alongside him. Spend time exploring Santa Clara's Parque Vidal, where most of the town's museums and monuments are located. The main plaza and surrounding streets are closed to traffic, and in the evenings you can experience local entertainment, watching concerts that take place in the plaza's main kiosk or on the street in front of the Casa de la Cultura. For a bargain lodging option right on Parque Vidal, you can stay overnight at the Santa Clara Libre hotel. On your way out of town, pass by the Tren Blindado, a memorial park commemorating a Batista troop train that was blown up by Che and his gang.

Day 4: Remedios

From Santa Clara continue east on Carretera a Camajuaní for about 45 minutes to Remedios, one of Cuba's oldest towns, founded in 1515. Small, but culturally rich and remarkably well preserved, Remedios is widely known for its las Parrandas festival in December, an all night celebration with homemade lanterns, fireworks, brass bands. The town’s chief attraction is its Parroquia de San Juan Batista, a 17th-century Baroque church. Inside is a carved cedar altar with gold leaf and two rare statues of the Virgin Mary, one heavily pregnant and the other depicted as a mulatto. The exquisite ceiling is of hand-carved mahogany built to resemble the hull of a ship. The late-19th century inn Hotel Mascotte is the only hotel option, but there are several casas particulares, most of which are west of Plaza Martí.

Day 5: Caibarién to Havana

About 15 minutes east of Remedios on Circuito Nte./José Martí is Caibarién, where ox-drawn plows and horse-drawn carts are commonplace in the sugarcane fields near the town. Spanish colonial-era buildings surround the town square called the Parque de la Libertad, where you can dine on cucina criollo, authentic Cuban cooking, at a family-owned paladare. Listen to the local orchestra perform in the town’s plaza (they play each weekend), then visit the Reforma, a historic sugar mill that has since been converted into a museum. Sample a cup of guarapo (sugarcane juice), with or without a shot of rum, then head out back to see a dozen late 19th- and early 20th-century steam locomotives, reminders of a day when trains rumbled through here regularly to load up on sugarcane, refined sugar, and rum.

If you choose to rent a car for this itinerary, the return trip from Caibaríen to Havana via the Autopista Nacional without stops should take about 4 hours.

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