Quick Overview

RATES: From $1,845 USD

DATES: On demand

  • Duration: 5 days
  • Activities: Real Havana, Cigars, Rum, Culture
  • Activity Level: Low
  • Minimum Age: 16

Cuba’s story is like many stories—composed of shadows and light, sombras y luz. A study in chiaroscuro. Repression and revolution. Dilapidated plazas next to opulent palaces. The silhouette of cigar smoke drifting across the luminous shimmer of the Tropicana Cabaret. The beauty is in the contrast; the temptation in the unpredictability.   

Even though it’s been half a decade since the glamourous days when Hollywood flew down in droves for weekends of dissipation and decadence, Cuba retains the air of flash and magnetism. Stepping into Havana can be like stepping into a self-indulgent novel or one of Frank Sinatra’s film sets. We invite you to experience Cuba’s indulgent side, its glamorous side, its uninhibited side. The side that enticed legends to its shores and then created them.

Step into Cuba’s most illustrious bars, drive around in timeless classic cars that take you back to another era, and indulge your senses with Cuba’s puros and libations. Follow in the footsteps of Hemingway, Sinatra, Gary Cooper, and Tennessee Williams. Sit in the Tropicana and imagine Nat “King” Cole singing into the hot Havana night. Sip on a daiquiri and see where Hemingway toiled away at his novels. Wander through tobacco farms where the world’s best cigars are produced and made—and then sit down and enjoy one.

Experience classic, classy Cuba on our new Classic Cars, Rum, and Cigars tour. Don’t just read Cuba’s story—live it. Live it while learning richly from this Educational Exchange program, flooded with the knowledge of our teachers – cigar aficionados, rum connoisseurs and classic car enthusiasts.  Designed for small groups of two to six people, and perfect for a private journey, this tour dives deep into Cuba’s history and pleasures.  

*Note: this tour is available with TWO accommodation options: 1) Hotels, or 2) Casas Particulares.  Casas Particulares are private home accommodations similar to B&Bs in the United States, but typically with more of a family feeling.  Tours staying in Casas Particulares are less expensive and provide even more contact with Cuban people.