Once the glamorous offshore getaway for scores of jet-setters, Cuba is again piquing the interest of its neighbors. Steal away with Spirit Quest Tours on a week-long Cuban sojourn that will ferry you from Havana, a capitol whose varied façades recount its eclectic history, to the storied Cuban town Trinidad, a UNESCO World Heritage site that bottles the essence of the island’s bygone sugar industry in pastel-colored manor houses and expansive plantations.

Spirit Quest Tours’s knowledgeable guides reveal Havana by way of a driving tour; cruising around in vintage American automobiles most likely powered by Russian-made engines, see the city as its natives do. A lively walk about the city’s older precinct lets you try your hand at haggling in famed flea markets. Taking leave of the city, you’ll egress to south shore town Trinidad, to peer back on the island’s colonial past via quaint cobblestone streets and manor houses that recall a time when Cuba’s sugar industry held court. From this unadulterated 19th century city, you’ll daytrip to pass a sun-kissed outing at some of the Santi Spiritus region’s natural gems, like the meandering Guarabo River and the halcyon waters of the south shore.

Your return to Havana brings the renewed opportunity to discover the city’s nooks and, on the eve of your return stateside, a concert by the internationally renowned musical group, the Buena Vista Social Club. Named after a former club in Havana’s Marianao neighborhood, The Buena Vista Social Club has brought its brand of revived Cuban music to audiences across the globe; warbling horns and fast-picked guitar riffs of this vacation’s grand finale provide the enduring soundtrack to Cuban memories.

• Welcome dinner at five-star Hotel Parque Central in Havana
• Driving tour in vintage cars
• Lunch at Cafe Del Oriente
• Nighttime visit to Castle Moro
• Lunch at Don Antonio Restaurant in Trinidad
• See full itinerary.