Touch down in Havana and enjoy VIP assistance through customs before meeting your private guide and driver, who take you into the city by vintage car; beginning your Cuba vacation in style. A private concierge then greets you at your luxury hotel or boutique apartment to go through the itinerary and ensure you have everything you need. After settling in, step out for a guided city tour of Old Havana and get your first introduction to this extraordinary UNESCO World Heritage Site, over the course of two insightful hours. Then, spend the rest of your first day in Havana however you please; maybe sipping drinks at the boho El Dandy bar in the Old Town, sampling creole cuisine at Doña Eutimia, or perhaps catching a dazzling cabaret show at the Tropicana—a quintessential Cuban experience.

This morning, glimpse the artistic side of Havana by exploring two local studios, going behind the scenes with the artists themselves. Whether you’re most interested in photography, painting or sculpture, established or new artists, this experience is tailored to your tastes and is then followed by a visit to the Fine Art Museum. In the afternoon, a cycling tour packs in many of Havana’s highlights as you pedal through the city with a guide. Best of all, the e-bikes help you along the way; particularly up any hills! Later, a perfect way to conclude the day is by savoring cocktails at the iconic Hotel Nacional, before dinner at another excellent restaurant such as La Guarida. Relish a meal in this classic parador then do as the locals do and join a Jazz night in town—Havana has plenty to choose from.

Cuba is renowned for its cigar industry, so this morning take a closer look at how they are rolled at one of the Casas de Habanos in Old Town. Learn from the masters when it comes to forming the perfect cigar, then head on for a guided foodie tour of Havana. Browse the colorful produce on display at a local market, then stop by a typical store to glimpse the daily routines of everyday Cubans. Sit down for lunch at Grados, choosing from a menu filled with family favorites of the owner and chef, Raulito, who talks warmly with his patrons while whipping up dishes like slow-cooked lamb and ‘farm-style eggs’ with corn. Fully sated, it’s then time to let your vintage car take the strain while you sit back and admire more Havana highlights during the drive, including the Havana Almendares Forest, Cristobal Colon Cemetery, Hotel Nacional and Riviera, to name a few. Later on, dine at another fantastic restaurant such as Tierra in the Cuban Art Factory, then stay for music and dancing—perhaps a film or art exhibition—in the same location.

As the cars of Cuba are so old—dating back to the mid-20th century—maintaining them is crucial. Today, see how the experts restore these vintage vehicles at a private workshop, perhaps picking up a few tips along the way! In the afternoon, delve deeper into the music scene of Havana by visiting a famous local artist, Brenda, who welcomes you into her home. Take a seat on the leafy terrace as Brenda demonstrates how to play one of Cuba’s most distinctive musical instruments, the Bata, and also how best to dance to it! Following this music-filled afternoon, enjoy your last dinner in Havana at a celebrated seafood restaurant, Cinco Sentidos, and maybe finish up at a local bar for more dancing (now you known the moves) before heading home tomorrow.

After breakfast, your driver transfers you to the airport by vintage car, in plenty of time for your flight home.