- Cruise around Havana in a classic car and tour a cigar factory
- Ride a horse through the tobacco farms of Viñales, then go caving
- Hike to coffee farms and waterfalls in the Sierra Escambray
- Soak in the vibrant Afro-Cuban culture of Santiago de Cuba
Founded in 1519 on the west side of a sweeping bay, Havana is one of the great historical cities of the New World. Each district has a flavor all its own, with buildings in an astounding array of architectural styles - from classical colonial mansions to stunning Art Nouveau and Modernist structures. Plan on at least three days in Havana (even a week isn't too much, as there's so much to see and do). There are three main districts you won't want to miss: Habana Vieja, Centro Habana, and Vedado.
The logical place to begin is Habana Vieja (Old Havana), with its beautifully restored cobblestone plazas, centuries-old castles and palaces, and dozens of other intriguing sites. On Habana Vieja's western fringe, explore around Parque Central and the Prado, a sweeping tree-shaded boulevard flowing down to the Atlantic shoreline. Sites not to miss here include the Capitolio and the exquisite baroque-style Gran Teatro. Nearby, you'll find Museo de la Revolución - housed in former dictator Fulgencio Batista's presidential palace - and the adjoining Museo de Bellas Artes, displaying beyond-impressive artwork up to the present day.
Havana's gritty street life doesn't get any grittier than in densely populated Centro Habana, just west of Habana Vieja. Formal tourist sites here are few - but it's the setting for some of Havana's top paladares, or private restaurants. And no visit to Havana is complete without strolling and hanging with Cubans along the superbly scenic (and always thronged) Malecón seafront boulevard. On weekends, you can dance to Afro-Cuban rhythms at Callejón de Hamel, also known as "Salvador's Alley."
Further west you'll find Vedado, a sprawling and airy district laid out in the early 20th century with tree-shaded boulevards and grandiose mansions. Many of the best nightclubs are here, along with mobster-era hotels still worth a visit: the Hotel Nacional, Modernist Hotel Habana Libre, and Hotel Riviera. Roam the Universidad de la Habana and the astonishing Cementerio Colón necropolis. And, of course, savor ice cream with locals at Coppelia Park.
Other activities are countless: visit a cigar factory, splurge for a night at the Tropicana outdoor cabaret, or explore Museo Ernest Hemingway, in the author's home outside the city.
A three-hour drive west of Havana, the Valle de Viñales boasts Cuba's most spectacular scenery. The valley, in the heart of the Sierra de Los Órganos, is surrounded by mogotes, free-standing limestone formations rising sheer from the valley floor. If that weren't enough, this is also the heartland of tobacco farming. Ox-drawn plows till the ruddy fields framed by royal palms. Thatched tobacco drying sheds and a quiet calm add to the visitor's sense of having been transported back in time more than a century.
This area has recently evolved as a center for active adventures as well, from ATV tours to ziplining. Three hotels cater mostly to tour groups, but hundreds of casas particulares (private B&Bs) offer more intimate accommodations.
#3 Península de Zapata
Head east for two hours along the autopista - Cuba's only freeway - and you'll find this boot-shaped peninsula renowned as the setting for the infamous 1961 Bay of Pigs invasion by a CIA-trained and supplied Cuban-American exile army. The tale is told at an excellent museum beside the beach at Playa Girón (the main battle site), and by roadside monuments commemorating the Cubans who were killed.
Most of the peninsula is now protected within Parque Nacional Cienaga de Zapata, Cuba's largest national park. A mosaic of swamps and wetlands, it harbors a fabulous variety of wildlife, from flamingos and zunzuncitos (the "bee hummingbird," the world's smallest bird) to manatees and two species of crocodile. It's a popular venue for birding, hiking, sport-fishing, and scuba diving. The two beach zones, Playa Larga and Playa Girón, have boomed in recent years with heaps of casas particulares and paladares, so you'll have plenty of lodging and meal options to choose from.
This peaceful city, three hours southeast of Havana, is a great place to slow down and mingle with Cubans. The youngest city in Cuba, Cienfuegos was founded in 1819 by French settlers from Louisiana. It's laid out on the east side of a massive bay and has a distinctly Gallic architectural style in the historic core.
Many key sites to explore are located on the Parque Martí (the main square), including the cathedral, neoclassical Teatro Tomás Terry, and Museo Histórico Provincial. Stroll the Malecón and Punta Gorda peninsula to admire the Palacio del Valle, a former sugar baron's home in Mughal style. Architecture and history buffs might also enjoy the Necropolis Tomás Acea and the Museo Histórico Naval.
Out of town sites not to miss include the Castillo de Jagua (take the funky ferry with the locals), the Jardín Botánico, and - if you have extra time - the beach at Rancho Luna.
#5 Santa Clara
This industrial university city will forever be associated with Ernesto 'Che' Guevara. It was here, four hours east of Havana, that in late December 1958 the revolutionary hero led his troops out of the Sierra Escambray and captured the city, causing dictator Fulgencio Batista to flee. Although it also has a lovely historic quarter, most of the sites of interest in this town relate to revolutionary events.
The must-not-miss site in Santa Clara is Complejo Monumental Comandante Ernesto Che Guevara, a massive monument of Che dominating the Plaza de la Revolución. Beneath, explore the superb museum and mausoleum where Che's remains are interred. And check out the Monumento a la Toma del Tren Blindado, where carriages were strewn haphazardly after his troops derailed a train carrying soldiers and armaments.
There are some really cool places just a quick drive from Santa Clara, including the colonial city of Remedios (a UNESCO World Heritage Site) and the Cayos de Villa Clara, with some of the best beaches and resort hotels in Cuba.
Cuba's most perfectly preserved colonial city is a UNESCO World Heritage Site, and justifiably so. Founded in 1514, it enjoys a superb location on a breeze-swept mountain slope with views towards the Caribbean Sea and the rugged Sierra Escambray.
Most buildings in the cobbled, traffic-free historic core date from the 18th century. The most important sites of interest cluster around Plaza Mayor, with its beautiful cathedral and three museums including the Museo de Arquitectura Colonial. Expect to come across quinceañeras (15-year-old girls) in flouncy dresses, weathered señores on donkeys, and rugged cowboys trotting through town on horseback.
Trinidad's art scene impresses with dozens of studio-galleries. The music and dance scene is abuzz, from Afro-Cuban rhythms at the Casa de los Congos Reales to a happenin' disco inside a cave. And you'll also find heaps to do outside town, from lazing on a beach and scuba diving at Playa Ancón, or hiking in the Sierra Escambray, to horseback rides into the Valle de los Ingenios (once Cuba's most important sugar-producing valley), replete with historic colonial-era sugar mills.
The only downside? Immediately upon arriving you'll understand why this is Cuba's foremost visited attraction beyond Havana - it can get overly crowded with tourists in peak season. Luckily, more than 1,000 homes have rooms for rent!
In the very center of the island, Camagüey - Cuba's third-largest city - is deservedly another UNESCO World Heritage Site. Its haphazard historic core is a warren of cobbled colonial plazas, for which it's known as the "City of Squares." The town is distinguished by unique architecture, and tinajones: giant earthenware jars used since colonial times to store water. It got a face-lift for the 2014 quincentennial, when several lovely boutique hotels opened their doors. Combine these four main plazas on a walking tour: Parque Agramonte, the main square named for local War of Independence hero Ignacio Agramonte; Plaza del Carmen, with its life-size figures of real locals; Plaza San Juan de Dios, perhaps the most scenic square; and Plaza de los Trabajadores.
The town straddles the Carretera Central, the central highway, and is surrounded by cattle ranches and sugarcane plantations. South of town, nature lovers are drawn to Finca La Belén, a wilderness area in the Sierra del Chorrillo. To the north, Playa Santa Lucía is a second-rate beach resort with world-class scuba diving, while Cayo Romano and Cayo Sabinal are newly emerging as resorts with sensational beaches.
#8 Santiago de Cuba
At the far east of the island, Santiago de Cuba - Cuba's second-largest city - was founded in 1515 as Cuba's original capital. Surrounded by mountains and sloping gently down to a bay, this hilltop city has a mood all its own. Following the Haitian Revolution in 1791, French settlers (and the enslaved people they brought with them) infused the city with their own architectural, musical, and dance styles. The city is steeped in Afro-Cuban culture and has a wicked nightlife, from son at the island's top Casa de la Trova to red-hot Carnaval in July.
Its other call to fame is that the Cuban Revolution was birthed here on July 26, 1953, when Fidel Castro's revolutionaries attacked the Cuartel Moncada barracks: today, it houses a school and a museum about the event. There are plenty of other historic sites that recall the city's key role in the Revolution. You'll want at least one hour to explore Cementerio de Santa Ifigenia, where Fidel Castro and National Hero José Martí top a long list of important figures buried here.
Meanwhile, conquistador Diego Velázquez's house still stands over Parque Céspedes, the always-bustling main square, lorded over by the Basilica Metropolitana Santa Ifigenia. While exploring the narrow, hilly streets of the Reparto Tivoli and Reparto Los Hoyos historic zones, don't miss the eclectic Museo Municipal Emilio Bacardí Moreau. History buffs should also head to the city outskirts where you'll find Parque Histórico La Loma San Juan, the infamous San Juan Hill of Spanish-American War fame, and Parque Histórico El Morro, a castle at the mouth of the bay with a museum on piracy and a nightly firing of a cannon at sunset.
Draws further afield include the Basilica El Cobre, Cuba's foremost pilgrimage site - and Cayo Granma, in the midst of the bay, is a great place to chill with local fishermen.
#9 Sierra Maestra
This massive mountain zone runs more or less the length of southeast Cuba and seems to rise vertically from the Caribbean Sea. Most of it has never been trod by foreigners, which makes it all the more alluring. There's also a historical draw: these mountains were home to the base of Fidel Castro and his Rebel Army from 1956-1958 during the fight to topple Batista.
The two principal reasons to visit are to hike to the summit of Pico Turquino, Cuba's highest peak at 6,576 feet (1,974 m), and to hike to La Comandancia de la Plata, Fidel's former guerrilla headquarters, maintained as they were six decades ago high amid the forested mountains.
Cuba's oldest city, founded in 1511, is surrounded by rainforest-clad mountains that include El Yunque, a flat-topped mesa that can be hiked. Reached by a twisting mountain road, the compact town fronts the Atlantic seashore and the Bahía de Miel (Bay of Honey). It appeals primarily for its time-worn wooden buildings and a sense of remove from the rest of the country.
Baracoans claim, unconvincingly, that Christopher Columbus first set foot in Cuba here and left a cross behind, which can be seen in the Catedral Nuestra Señora on Plaza Independencia. Cacao is grown locally (you can visit the plantations), and Baracoa is renowned as Cuba's center for chocolate production. Most of the surrounding mountains are protected with a series of national parks, tremendous for hiking, and traces of indigenous pre-Columbian culture linger on in Taíno archaeological sites.