A Historic Path

Days 1 & 2: Havana

Follow the itinerary as laid out above in "In 2 Weeks."

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 either in the new Gran Hotel Iberostar Trinidad, or one of the many 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. 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.

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 very comfortable hotel in a restored old mansion set right 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 wonderful 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. You'll definitely want to stay at the Hotel Royalton, which sits right on the central Parque Céspedes. 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 Leonardo y Rosa. 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. Turn in your rental car here in Santiago.

Day 11: Baracoa

From Santiago, take a Víazul bus, private taxi, or short commuter flight 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 art galleries, bars, and 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 Calle Tacón street market to do some last minute shopping before you go.