Two-Week Best of Cuba Itinerary

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

A deep purple chevy parked on the street amidst colorful buildings in Havana.
A chevy on the streets of Havana. Photo © Christopher P. Baker.

Day 1

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

Day 2

Take a self-guided walking tour of Habana Vieja, including the Plaza de Armas, Plaza de la Catedral, and Plaza Vieja,, as well as the key 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

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.

Derelict building on the Malecon. Photo © Christopher P. Baker.
Havana’s Malecón. Photo © Christopher P. Baker.

Day 4

Travel map of Centro Vedado, Cuba
Centro Vedado
Spend the morning exploring the streets of Vedado, being sure to call in at the Hotel Nacional, the Hotel Habana Libre Tryp, and Universidad de la Habana. After cooling off with an ice cream at Coppelia (with pesos in hand, stand in line with the Cubans), hail a taxi to take you to Cementerio Colón and Plaza de la Revolución.

Day 5

Rent a car and tour suburban Havana, calling in at the Museo Ernest Hemingway. Then head west along the Autopista Habana-Pinar 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 Moka.

Day 6

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

Day 7

This morning, head to the town of Pinar del Río and Finca El Pinar San Luis, then 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.

Days 8-9

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 midafternoon. On day 9 spend an entire day relaxing on the beach and enjoying water sports.

Day 10

Depart Cayo Coco and head south via the provincial capital, Ciego de Ávila, and then turn west and follow the Carretera Central for Sancti Spíritus. After strolling downtown, continue through the Valle de los Ingenios, stopping at Hacienda Iznaga. Arriving in Trinidad, spend the rest of the afternoon perambulating the ancient plazas.

palm trees stand in a plaza in Trinidad Cuba
Plaza Mayor in Trinidad. Photo © ArtMarie/iStock.

Day 11

After further walking the cobbled colonial heart of Trinidad, visit the studio of artist Lázaro Niebla, then check in with “horse-whisperer” Julio Muñoz and go horseback riding in the countryside. Tonight, check out an Afro-Cuban performance before heading to the Disco Ayala, set in a cave.

Day 12

Get up early again to follow the long and winding road over the Sierra Escambray to Gran Parque Natural Topes de Collantes. Descend to El Nicho to bathe in mineral pools at the base of the waterfall before continuing to the lovely bayside city of Cienfuegos, with time to stroll the pedestrian boulevard and explore Parque Martí.

Days 13-14

Drive west to Playa Girón, the landing site for the 1961 Bay of Pigs invasion. Visit the museum before continuing west to Cueva de los Peces to snorkel in the blue hole and turquoise Caribbean. At La Boca de Guamá stop to visit the crocodile farm. Head back to Havana via the Autopista. This evening, visit the Tropicana cabaret, being sure to have made reservations. On day 14, fly home.


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