Day 1: Welcome to Havana! After clearing immigrations and customs, our airport representative lead you to your driver who will transfer you to Hotel Nacional de Cuba in the heart of the country's capital. *Light lunch and meet and greet with your concierge. *Get your feet wet with an afternoon orientation walk. Later that evening, celebrate your arrival with a welcome dinner at a private restaurant. (*For morning arrivals)

Day 2:Meet with our local expert guide and walk in the footsteps of Havana's colonial past visiting the four key squares of Old Havana. Lunch at a private paladar in the heart of the historic center. Then you will have the opportunity to see masterpieces of the Cuban architecture before and after 1959 with our architecture expert guide. Finish this day having a dinner at a 1950s penthouse with a fabulous terrace overlooking the US Embassy and the Malecon. Night cuban musical show inspired by the Son music of the famous Buena Vista Social Club.

Day 3: Start your day with a rendezvous with the Mob by an open top classic american vintage car. Your guide will bring you closer to the history of Havana during the first 60 years of the 20th century and will take you or pass by the former haunts and highlights of the mafia bosses in Havana (Meyer Lansky, Lucky Luciano, Al Capone to name but a few), including visits to the Havana Libre, the Capri, the Riviera and Copacabana hotels. After lunch in a local paladar our sommelier will join you at hotel Nacional for a pre paid rum and cigar testing. He will pair your cigar with a good rum and explain how cigars are made and smoked. Then visit Casa del Habano, a cigar house and experience a cigar roller works showing how the best cigars in the world are rolled. Dine in a high-ceilinged room inside, or al fresco under the canopy beneath the 80ft chimney stack. Great seafood and delicious, modern Cuban cuisine with a twist. To finish your night enjoy live music, dance, film, art and shows under the same roof.

Day 4: This morning our expert guide will share with you interesting insights into the life of Hemingway and into that period in Cuban history. You will visit the Hemingway Museum. Gertrude Stein, the celebrated American writer, once said that Hemingway had a good nose for finding good places to live and eat. She wasn't wrong as Hemingway's villa on the outskirts of Havana proves. On the way back your guide will bring you to see Cojimar fishing village, a small picturesque town that inspired Hemingway to write the novel 'The Old Man and the Sea'. Visit Hotel Ambos Mundos where Hemingway lived for a time, this old world hotel has a beautifully located roof terrace, perfect for a lunch and cocktails. Continue your day stopping at Floridita Bar. Mixologist Constantino Ribalaigua served up the classic daiquiri in this Old Havana haunt until the early 50s. After a cocktail in the 'cradle of the daiquiri', favoured by writer Ernest Hemingway, wander the bar-lined streets of the old town to another Hemingway haunt, La Bodeguita del Medio. This small drinking hole, close to the cathedral, opened its doors to the drinking public in 1951, and it's where the author would drink his mojitos. Early dine in a newish paladar that certainly doing things another and a better way. This sleek restaurant in a converted 1950s mansion which opens out towards the garden offers some of Havana's top food and the attention to detail both in the food and in the service make this a boon to the restaurant scene in Havana. Enjoy your last night in Havana at Tropicana Cabaret show.

Day 5: After breakfast, bid farewell to Cuba and board your departure flight.

IMPORTANT NOTE: Many of the places we visit are not tourist destinations and are thus not always available. Therefore, this program should be considered as a sample only – please keep in mind that your bespoke travel plan is designed with our staff according to the specific interests that you would want to highlight in your trip. Final itineraries and quotes are sent 24hrs after we receive your request to our contact email: enquiries@bespoketriptocuba.com