Arrive at José Martí International Airport in Havana; transfer to a hotel or casa particular in Habana Vieja or the Vedado district.
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.
Rent a car and set out on a tour of suburban Havana, calling in at 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.
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.
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.
Depart Cayo Coco and head south via the provincial capital, Ciego de Ávila, 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.
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.
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. Now head back to Havana via the Autopista. This evening, visit the Tropicana cabaret, being sure to have made reservations.
Fly home today.