Cuba is a large island, and exploring the isle fully would take at least a month, but the following fast-paced travel itinerary combines a sampling of the top scenery, beaches, and cities for those intent on seeing the best of the island. Rent a car and plan to spend at least four days sampling Havana before heading out to the provinces (don’t underestimate how much there is to see in the capital city).

Day 1

Arrive at José Martí International Airport in Havana; transfer to a hotel or casa particular in the Habana Vieja or Vedado districts.

Day 2

Take a self-guided walking tour of Habana Vieja, including the Plaza de Armas, Plaza de la Catedral, and the museums, galleries, and shops along the surrounding streets. Return at night to savor the plazas lit by traditional gas lanterns. Don’t fail to sip a mojito at La Bodeguita del Medio.

Day 3

Continue exploring Habana Vieja, including the Plaza de San Francisco, Plaza Vieja, and the surrounding area; be sure not to miss the Museo de Ron. In the late afternoon, head to the Parque Histórico Militar Morro-Cabaña, lingering to enjoy the sunset cañonazo ceremony.

Day 4

This morning, concentrate your time around Parque Central and Paseo de Martí. You’ll want to visit the Capitolio Nacional, Fábrica de Tabaco Partagás, the Museo Nacional de Bellas Artes, and the Museo de la Revolución. A daiquiri at El Floridita is a must! At dusk, walk the Malecón.

Day 5

Spend the morning exploring the streets of Vedado, being sure to call in at the Hotel Nacional, the Hotel Habana Libre Tryp, and University of Havana. After cooling off with an ice cream at Coppelia (with pesos in hand, stand in line with the Cubans), walk along Calle 17, calling in at the Museo de Artes Decorativas. Then hail a taxi to take you to Cementerio Colón and Plaza de la Revolución.

Day 6

Rent a car and set out on a tour of suburban Havana, calling in at Iglesia de Santa María del Rosario and Museo Ernest Hemingway. Continue to the village of Cojímar for lunch at La Terraza, then head to Playas del Este for time on the beach. I recommend the Playa Mégano section at Tarará.

Day 7

Head west along the Circuito Norte highway to Las Terrazas, an eco-resort and rural community in the heart of the Sierra del Rosario. Hike the trails and visit the artists’ studios. Overnight at Hotel La Moka.

Day 8

Continue west to Valle de Viñales. Spend the afternoon exploring Viñales village, the Cuevas del Indio, and tobacco fields. Overnight either in a casa particular or at the Horizontes La Ermita.

Day 9

This morning head to the town of Pinar del Río and take the Autopista east to Havana and onward to Santa Clara. Visit the mausoleum and museum of Che Guevara and spend the night in town.

Day 10

Continue east to the historic town of Remedios. During Christmas week, you’ll want to overnight in Remedios to enjoy the local fireworks battles called parrandas. Once done, follow the coast road east via Morón to Cayo Coco, arriving mid-afternoon in time to enjoy the beach and water sports.

Day 11

Follow the Circuito Norte east to Las Tunas, then continue along the Carretera Central to Holguín. I recommend staying at a casa particular.

Day 12

After walking the main plazas, set out for Museo Conjunto Histórico Birán, birthplace of Fidel Castro, before following the coast road east via Moa to Baracoa, arriving in this isolated and charming town in early evening. Overnight at Hotel El Castillo or a casa particular.

Day 13

Stroll the streets of Baracoa, savoring its unique laid-back flavor. In the afternoon head to El Yunque, where you can hike to the summit of this fantastic mountain formation.

Day 14

Continue over La Farola, a switchback mountain road, dropping to the city of Guantánamo. En route, be sure to visit the Zoológica de Piedra. Continue to Santiago de Cuba, arriving early evening. Check into the Hotel Casagranda or a casa particular.

Day 15

After visiting the Cuartel Moncada and Museo de la Revolución, spend the balance of the day exploring the historic quarter of Santiago de Cuba, being sure to include the Cementerio de Santa Ifigenia.

Before dusk, head out to Castillo de San Pedro del Morro to watch the cañonazo ceremony, when soldiers in period costume put a light to an ancient cannon. In the evening, call in at the Casa de la Trova to hear traditional Cuban music at its best.

Day 16

This morning depart Santiago and follow the Carretera Central northwest to the town of Bayamo. En route, call in at El Cobre to visit the shrine of the Virgen de la Caridad. After sightseeing around the main plaza of Bayamo, continue northwest via Yasa to Las Tunas. Overnight at a casa particular.

Day 17

Continue west along the Carretera Central to Camagüey, arriving midday with time to explore the three major colonial plazas. For digs, I recommend the charmingly restored 18th-century Hotel Colón, which also has one of the best restaurants in town.

Day 18

Get an early start today for the drive west via the provincial capitals of Ciego de Ávila and Sancti Spíritus, then through the Valle de los Ingenios, where you should have a late lunch at Hacienda Iznaga. Arriving in Trinidad, spend the rest of the afternoon walking the ancient plazas.

Day 19

After further walking the cobbled colonial heart of Trinidad, drive out to Playa Ancón for beach time and perhaps even some scuba diving. Tonight check out an Afro-Cuban performance, before heading to the Disco Ayala, set in a cave.

Day 20

Get up early again to follow the long and winding road over the Sierra Escambray to Topes de Collantes. Continue north to Santa Clara, then head back to Havana via the Autopista. This evening, visit the Tropicana cabaret, being sure to have made reservations. Fly home the next day.