The Classic

  • 18 Days

It’s your first time in Cuba and you want to see as many eye-opening sights as possible countrywide. Even better, you don’t mind a bit of road travel. This itinerary ferries you between the rival cities of Havana and Santiago, bagging most of the nation’s historical highlights on the way. Víazul buses link all of the following destinations.

Fall in love with classic Cuba in Havana, with its museums, forts, theaters and rum. Three days is the bare minimum here to get to grips with the main neighborhoods of Habana Vieja, Centro Habana and Vedado.

Head west next to the bucolic bliss of Viñales for a couple of days of hiking, caving and relaxing on a rocking chair on a sun-kissed colonial porch. Daily buses connect Viñales with French-flavored Cienfuegos, an architectural monument to 19th-century neoclassicism. After a night of Gallic style and Cuban music, travel a couple of hours down the road to colonial Trinidad, with more museums per head than anywhere else in Cuba. The casas particulares (homestays) resemble historical monuments here, so stay three nights. On the second day you can break from the history and choose between the beach (Playa Ancón) or the natural world (Topes de Collantes).

Santa Clara is a rite of passage for Che Guevara pilgrims visiting his mausoleum but also a great place for luxurious private rooms and an upbeat nightlife. Check out Club Mejunje and have a drink in dive-bar La Marquesina. Further east, Camagüey invites further investigation with its maze of Catholic churches and giant tinajones (clay pots).

Laid-back Bayamo is where the revolution was ignited, and it has an equally sparky street festival should you be lucky enough to be there on a Saturday. Allow plenty of time for the cultural nexus of Santiago de Cuba, where seditious plans for rebellion have been routinely hatched. The Cuartel Moncada, Cementerio Santa Ifigenia and Morro Castle will fill a busy two days. Save the best till last with a long, but by no means arduous, journey over the hills and far away to Baracoa for two days relaxing with the coconuts, chocolate and other tropical treats.

Escape from Varadero

  • 1 Week

Varadero has some cheap packages and is a popular gateway into Cuba, but once you've pacified your partner/kids and had your fill of the beach, what else is there for a curious Cuban adventurer to do? Plenty. Víazul or Conectando buses link the following places.

Take a bus west, stopping off for lunch in Matanzas, where Cuban reality will hit you like a sharp slap to the face. Investigate the Museo Farmaceútico, take a peep inside the Teatro Sauto and buy a unique handmade book in Ediciones Vigía. For a slow approach to Havana, get on the Hershey train and watch as the lush fields of Mayabeque Province glide by. Book a night in a fine colonial hotel in Havana and spend the next day admiring the copious sights of the old quarter, Habana Vieja. Essential stops include the cathedral, the Museo de la Revolución and a stroll along the Malecón.

The next day, head west to Las Terrazas, an eco-resort that seems a million miles from the clamorous capital (it's actually only 55km). You can bathe and birdwatch at the same time in the Baños del San Juan and recuperate with a night in the Hotel Moka. An optional two-day extension of this itinerary lies further west in Viñales, a resplendent yet bucolic Unesco World Heritage Site where you can decamp to a casa particular, eat some of the best roast pork in Cuba (the world?), go for a hike and then slump into a rocking chair on a rustic colonial porch.

Going back east, keep on the green theme in Boca de Guamá, a reconstructed Taíno village and crocodile farm with boat trips to and around a tranquil lake. Procure a night or two of accommodations at a homestay in Playa Girón, where you can either dive or plan wildlife forays into the Ciénaga de Zapata. A couple of hours east lies the city of Cienfuegos, an elegant last stopover with fine boutique hotels and sunset cruises on the bay.

On the leg back to Varadero you can uncover a dustier, time-warped Cuba in half-ruined San Miguel de los Baños back in Matanzas Province, an erstwhile spa that harbors a grand abandoned hotel. Last stop before returning to your Varadero sunbed is Cárdenas, home to three superb museums.

Around the Oriente

  • 12 Days

The Oriente is like another country; they do things differently here, or so they'll tell you in Havana. This circuit allows you to bypass the Cuban capital and focus exclusively on the culturally rich, fiercely independent eastern region. With poor transport links, a hire car is useful here.

Make your base in Santiago de Cuba, city of revolutionaries, culture and folklórico dance troupes. There's tons to do here pertaining to history (Morro Castle), music (Cuba's original Casa de la Trova) and religion (Basílica de Nuestra Señora del Cobre). On the second day, reserve time to explore east into the Parque Bacanao and the ruined coffee farms around Gran Piedra.

Regular buses travel east into the mountains of Guantánamo Province. Pass a night in Guantánamo to suss out the changüí music before climbing the spectacular road La Farola into Baracoa, where three days will bag you the highlights – beach time at Playa Maguana, a sortie into the Parque Nacional Alejandro de Humboldt and a day absorbing the psychedelic rhythms of the town itself.

Heading north via Moa is a tough jaunt, with taxis or rental cars required to get you to Cayo Saetia, an isolated key with an on-site hotel where lonesome beaches embellish a former hunting reserve.

Pinares del Mayarí sits in the pine-clad mountains of the Sierra Crystal amid huge waterfalls and rare flora. Hiking married with some rural relaxation seal the deal at the region's eponymous hotel. If you have half a day to spare, consider a side trip to Museo Conjunto Histórico de Birán to see the surprisingly affluent farming community that spawned Fidel Castro.

Take a day off in hassle-free Bayamo with its smattering of small-town museums before tackling Manzanillo, where Saturday night in the main square can get feisty. More-adventurous transport options will lead you down to Niquero and within striking distance of the largely deserted Parque Nacional Desembarco del Granma, famous for uplifted marine terraces and aboriginal remains. Linger in one of Marea del Portillo's low-key resorts before attempting the spectacular but potholed coast road back to Santiago.