Having landed at Santiago de Cuba Airport, your driver-guide meets you and whisks you off to your accommodation in the city: La Hiedra. This ivy-clad casa particular is among Cuba’s best, bedecked with a patio, garden, roof terrace and just four tastefully decorated rooms. After checking in and meeting your friendly hosts, head for the city’s famous El Morro fortress to watch the sunset over the bay and get a grasp of Santiago’s past. This UNESCO World Heritage Site, built during the days of Spanish Empire, was crucial for defending the city against threatening pirates, today standing as a real-life testament to the past. In the evening, sample some local cuisine at restaurants such as La Brassa, then perhaps soak up some live music at Casa de la Trova, watching (or joining) the dancers.

Your first full day in Santiago de Cuba is a great time to go under the skin of the city on a guided tour, getting a closer look at important sites such as the Moncada Barracks (where Fidel Castro led the guerrillas’ first armed attack against the government), Revolution Square and Cespedes Park, among others. Following lunch, venture to the outskirts of Santiago to discover the Church of La Virgen de la Caridad del Cobre, a treasured religious site that’s dedicated to the patron saint of Cuba. After your guide explains all about this iconic figure, continue to the Cimarron monument and learn more about what this beautiful bronze and iron statue stands for: the 17th century slave revolt, and the fight against oppression in Cuba. Set high up on the hills of Cobre, it’s also a wonderful place to take in sweeping views of the sea. Return to Santiago for dinner in town, perhaps at the highly acclaimed St. Pauli, serving creative dishes with a distinct Cuban flavor.

Today, head out of the city again, this time to Gran Piedra in the Sierra Maestra Mountain Range, at 1,200 m above sea level. This lush place is home to intriguing native plants and wildlife, as well as superlative coffee estates, a botanical garden and La Isabelica Museum, not to mention the ‘Big Rock’ that the region is named after. Returning to Santiago de Cuba in the afternoon, prepare for an insightful few hours learning about the city’s revolutionary heritage. Expert guides explain the role Santiago played in the Cuban Revolution as you visit important sites like Villa Blanca, and the legacy this has left on the country as a whole. In the evening, relish your final night here with a delicious meal; we recommend Palenquito, specializing in BBQ delights and flavorful desserts.

After breakfast, a private transfer takes you from La Hiedra to the airport, for your return flight home, or continue your journey to Havana with our Insider’s Havana Escape program.