Tack a couple days on to your Cuban adventure and visit Trinidad or Santiago de Cuba, two cities that reveal a different side of Cuba. Santiago de Cuba is substantial if you want to immerse yourself in the country's history, and Trinidad—a smaller, walkable city—has beautiful colonial architecture.
TRINIDAD – a four-hour drive from Havana
Walking down the streets of Trinidad—a blue pastel colonial house to your left, a pink to your right—the sound of donkey hooves on 19th-century cobblestone echoes around you. Vendors sit on the sidewalk, guarding the entrance to their bodegas, and locals socialize at the windows of private homes turned into specialty shops during the day.
Start with a walk to the Plaza Mayor and visit the Iglesia Parroquial de la Santisima Trinidad, the largest church in Cuba. Then make your way past girls taking pictures in their quinceañera gowns to the Museo de Arquitectura Colonial before heading to lunch at Paladar Cubita. In the afternoon, visit the Palacio Cantero and the beachfront, and don’t forget to do as Cubans do: Take several café (and mojito) breaks. Mimic their pace of life. In the evening, dine at Paladar Sol Ananda. Absolutely not to miss, this beautifully restored Baroque home is a cave of antique treasures, each handpicked by its modest and eclectic owner. Street bands will perform during dinner (and the guitarist will likely have a diploma from Havana’s Music Conservatory), priming your palate for a night at Casa de la Trova, an open-air bar where you’ll dance to live mambo and son with locals. Stay at... the Iberostar Grand Hotel Trinidad.
SANTIAGO DE CUBA – a one-hour, 30-minute flight from Havana
Sipping a café cubano in Parque Cespedes—the heart of Santiago de Cuba, day and night—allow yourself to be transported by the music, the chatter, and the heat. Santiago has a very different vibe compared to Trinidad, and way more people, but it’s the best city to get a true sense of Cuba’s history and cultural diversity. As you walk through the busy streets, you can see the blend of Spanish and Afro-Caribbean influences in the architecture and hear the sounds of son and bolero music.
Start your day with a visit to the Casa de Diego Velazquez—looming over Parque Cespedes, it’s the oldest house on the island—followed by a walk through nearby Catedral de la Asunción. Explore the colonial quarters before having lunch at Zunzún. In the afternoon, drive to the UNESCO World Heritage Site, Castillo de San Pedro de la Roca, an 18th-century fortress built to protect the city from pirates—another important piece of Cuba’s history. After, try to catch a traditional Tumba Francesa performance. In the evening, dine at the romantic Paladar Salón Tropical, followed by a night out with locals at Iris Jazz Club.
If you have time for an additional half-day, take the ferry to Cayo Granma, and walk around the pedestrian-only island before feasting on the catch of the day at El Cayo, a waterfront seafood restaurant. Stay at... Hotel Casa Granda.
