Cuba's colonial cities are some of the best-preserved and architecturally intact examples to be found anywhere in the hemisphere. From the remarkable restored grandeur of Old Havana to the rugged realism of Trinidad to tiny Baracoa -- one of the oldest colonial cities in the Americas -- there's a wealth of history, culture, and overall beauty to be found in the country's colonial treasures.
Day 1: Arrive & Settle into Havana
Arrive and settle in to your hotel. Spend the afternoon walking along the Malecón and have a sunset cocktail at the Hotel Nacional. After sunset, head over for dinner at Los Doce Apóstoles in the Parque Histórico Morro y Cabaña. Stick around for the cañonazo (cannon-firing) ceremony.
Day 2: Step Back in Time
Start the morning off in La Habana Vieja. Visit the Plaza de la Catedral, the Plaza de Armas, Plaza Vieja, and Plaza de San Francisco. Be sure to tour the Museo de la Ciudad, the Castillo de la Real Fuerza, and any other attractions that catch your attention. Have lunch at La Bodeguita del Medio. After lunch, head toward Parque Central and visit El Capitolio, then either the Museo Nacional de las Bellas Artes, or the Museo de la Revolución. Finish up your afternoon strolling along the outdoor art exhibit that is Callejón de Hammel, but if your second day is a Sunday, arrive here earlier for the Sunday rumba sessions. If you have a spare half-hour, drive by the Plaza de la Revolución to see the José Martí memorial and the iconic iron sculpture of the face of Che Guevara on the Ministry of the Interior building. In the evening, head to the Tropicana for dinner and a show.
Day 3: Cienfuegos
Pick up a rental car and head for Cienfuegos, a bustling port city on the southern coast, with a compact, yet very attractive, colonial-era core. Get to know the old center around Parque José Martí, visiting the Catedral de la Purísima Concepción and the Teatro Tomás Terry. In the afternoon, head out to the Punta Gorda district and have a sunset drink at the Cienfuegos Yacht Club. For dinner, head to the historic old Palacio del Valle.
Day 4: Trinidad
From Cienfuegos, it's a short hop to Trinidad, with some beautiful scenery along the coast. Stay in one of the many glorious casas particulares right in the colonial center of this classic little city. Spend the afternoon touring Trinidad's colonial-era landmarks, including the Plaza Mayor, the Plazuela El Jigüe, the Iglesia de la Santísima Trinidad, and the Museo Romántico. For dinner, make a reservation at Paladar Estela or Sol y Son. After dinner, stroll around the Plaza Mayor and listen for where the action is. It might be a salsa or son band playing on the steps below the Casa de la Música, or it might be in any one of several clubs nearby including the excellent Palenque de los Congos Reales.
Day 5: Sancti Spíritus
While its colonial center is modest in size and level of restoration, Sancti Spíritus nonetheless retains a wonderful sense of its former glory and receives far less tourist traffic than any other city on this tour. You'll definitely want to walk along Calle Llano, a narrow cobblestone alleyway of pastel-colored and tile-roof houses. You'll also want to have lunch or dinner at one of the outdoor patio tables overlooking the old stone Puente Yayabo (Yayabo bridge), which was built in 1825. Be sure to book a room at the Hostal del Rijo, a comfortable hotel in a restored old mansion set on a quiet little plaza.
Days 6 & 7: Camagüey
Although far less celebrated -- or visited -- than Trinidad, Camagüey just may be Cuba's richest colonial-era city, outside of Old Havana, in terms of art, architecture, and general ambience. The city's colonial core retains its highly irregular layout and an unequaled collection of impressive 16th-, 17th-, and 18th-century churches. The city's Plaza del Carmen and Plaza San Juan de Dios are two impeccable and evocative city squares. Sitting right near the center of all the ancient action, the old Gran Hotel should be your first choice.
Day 8: Bayamo
Even though most of this city was deliberately torched in 1869 as an act of civil disobedience, it still makes a wonderful stop on a route taking in Cuba's principal colonial cities. Stay at the new refurbished boutique Hotel Royalton, which sits right on the central Parque Céspedes or stay in one of the centre's friendly casas particulares. You'll also want to visit the Casa Natal de Céspedes, the birthplace of the "father of the Cuban nation," and the only house on the square that escaped destruction from the fire.
Days 9 & 10: Santiago de Cuba
This is a colonial highlights tour, so you'll want to stay in the heart of downtown; choose either the Hotel Casa Granda, the Hostal Basilio, or the private Casa Maruchi. You'll need 2 days to fully explore this beautiful colonial-era port city, with its host of historical and architectural attractions. Be sure to schedule at least 1 night at Santiago's fabulous Casa de la Trova or its even better Casa de los Tradiciones. Turn in your rental car here in Santiago.
Day 11: Baracoa
From Santiago, take a Víazul bus or private taxi to Baracoa, the oldest and arguably most beautiful city in Cuba. It's fitting to finish off this tour in the oldest city on the island. You'll definitely want to stay in the Hotel El Castillo, with its commanding setting on a hillside over the city. Spend your time here exploring the architecture and old-world charms of the city. Despite its diminutive size, Baracoa is also a bustling little city with excellent nightlife.
Day 12: Heading Home
From Baracoa, take a flight back to Havana in time for your international connection. If you have extra time, head to the Almacenes San José market to do some last-minute shopping before you go.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.