Begin in Havana. Rent a chauffeured 1950s convertible on Parque Central and enjoy a wind-in-your-hair sightseeing tour of the city, taking in the Malecón, Hotel Nacional, Monumento a las Víctimas del Maine, Hotel Riviera and Plaza de la Revolución. Don’t miss Fusterlandia, an enclave of surreal community art. After lunch at Italian Corte del Principe, stop by the Museo Ernest Hemingway and the coastal fishing village of Cojímar, before exploring Castillo El Morro. Dine at Mama Inés and close the evening with cocktails atop Gran Hotel Manzana Kempinski.

After a leisurely breakfast at Dulcería Bianchini, drive east out of the city to the Península de Zapata, then turn south for Playa Larga. Lunch beside the bay at Restaurante Tiki ((54) 715 922) and spend the afternoon relaxing on the beach or kitesurfing, with time perhaps for scuba diving, bird-watching or a guided nature excursion in search of crocodiles. End the day relaxing at Hostal Enrique, a casa particular in Playa Larga.

Follow the coast road to Playa Girón, the key site in the Bay of Pigs invasion. Visit the museum before continuing inland to Cienfuegos, arriving in time for lunch at Finca del Mar. Focus your afternoon walking tour on Parque Martí before joining the locals for sunset on the Malecón (waterfront). Cienfuegos has plenty of nightlife options; look out for music events or catch a baseball game.

Head east to the El Nicho waterfall, then follow the road through the Sierra Escambray for a stunning mountain drive. Your destination is Topes de Collantes, where criolla lunches are served at Restaurante Gran Nena (Carretera Principal; (41) 540 338). There’ll be time for a hike in the pine forests before descending to the lovely colonial city of Trinidad. Enjoy an open-air buffet dinner at Vista Gourmet, before checking out the lively evening entertainment.

Spend the day exploring Trinidad. Start at the Plaza Mayor and take in the beautiful colonial houses; don’t miss the 19th-century Palacio Cantero and the elegant Iglesia y Convento de San Francisco. After lunch at Restaurante Plaza Mayor, walk to the Cabildo de los Congos Reales de San Antonio. In the evening, make a beeline for the Casa de la Trova, where live bands always ensure a riotous evening.

Journey through the Valle de los Ingenios, stopping at Hacienda Manaca Iznaga and Sitio Histórico Guaimiro to admire the restored plantation homes. The scenery is spectacular as you continue to Sancti Spíritus, where the colonial core is worth exploring on foot. Taberna Yayabo is the perfect place for a riverside lunch. Continue along the Carretera Central via Ciego de Ávila, before arriving in the city of Camagüey in the late afternoon. Savour the city’s romance with an alfresco dinner at Restaurante 1800.

Begin your exploration of Camagüey on the main plaza, Parque Ignacio Agramonte. Set aside half a day to wander the cobblestone streets, including the Plaza del Carmén and Plaza de los Trabajadores. After lunch – try Meson del Principe (Calle Astilleros No 7, e/ San Ramón y Lugareño; (32) 274 210) – travel southeast through rural villages to enjoy horseback riding and eco-activities at Finca La Belén, in the Sierra del Chorrillo. You can stay overnight at the finca.

Rise early for a guided bird-watching walk in the forest – it’s well worth it. After, drive northeast to return to the Carretera Central, continuing via Las Tunas to Holguín. Restaurante Los Almendros is known for its lobster and its farmstead-like decor is hard to beat. For a sensational panoramic vista over town, climb the 450-plus staircase to the top of Loma de la Cruz. Holguín’s atmospheric Casa de la Trova is a good place to savour the nightlife.

Head east into the heartland of sugarcane production, stopping at the Museo Conjunto Histórico Birán. Follow the road south to Palma Soriana, where the scenic Carretera Central leads past the Basílica del Cobre, Cuba’s most important Catholic shrine. Have a late lunch on the rooftop at Roy’s Terrace Inn in Santiago de Cuba. After learning about the Cuban quest for independence at Museo de La Lucha Clandestina, walk to the waterfront for live music at Cervecería Puerto del Rey.

With just one full day to explore Santiago de Cuba, concentrate on the highlights: Parque Céspedes, the Moncada Barracks, San Juan Hill and Cementerio Santa Ifigenia. For lunch, Paladar La Canasta serves up seafood dishes in a beautiful garden. Head out to Castillo del Morro to enjoy the cañonazo (cannon-firing) ceremony at sunset before ending your day absorbing the music at the Casa de la Trova.

Today begins with a winding drive through sugar cane country to Guantánamo city, with its quirky Museo Zoológica Piedra (“Stone Zoo”) in the mountains beyond town. Break for lunch at Mirador La Gobernadora, with a view over Guantánamo bay. Today’s highlight, however, is the scenic coastal drive along the Caribbean, before a snaking climb on the La Farola highway that ascends the Sierra Cristal and sweeps down to Baracoa. Sample the local cuisine with dinner at Restaurante Calalú.

Baracoa’s stunning setting entices visitors to immerse themselves in the natural world. Take a guided excursion that combines an early morning hike to the summit of El Yunque with a visit to a cacao farm, where lunch is served. Spend the afternoon walking through the historic core of Cuba’s oldest city, then close the day by enjoying traditional regional music in the tiny yet ever-lively Casa de la Trova.

From Baracoa, follow the coastal road east beyond the Río Yumurí towards Punta Maisí, pausing to enjoy the views of the Caribbean from the top of the lighthouse at Cuba’s easternmost point. Then drive into coffee country following the beautiful narrow road through a semi-arid region studded with cacti. Continue through Guantánamo and turn north to Mayarí Arriba for a lesson in revolutionary history at the impressive Conjunto Histórico de Museos del Segundo Frente. Returning to Santiago de Cuba, enjoy a final night on the town.

Spend your morning exploring Santiago de Cuba’s Tivoli district and Calle Heredia, which house a plethora of quirky sights and museums. Not-to-be-missed highlights include the fascinating Museo Emilio Bacardi and the colourful Museo del Carnaval. Enjoy lunch at St. Pauli before departing Cuba’s second city for home.