Cayo guillermo resort
Luxury Travel Tips and Advice Twin-centre Holidays

Havana and Cayo Guillermo Luxury Itinerary

Havana, 3 nights/ Cayo Guillermo, 4 nights

Get to know the fantastic city of Havana with its centuries of faded beauty, music, dance, art, architecture… fill your eyes and your soul with its energy. And then, like Hemingway used to, find your way to Cayo Guillermo, Playa Pilar. Hemingway’s favorite spot whenever he sailed in that area of the northern shores of the island. Enjoy Kempinski’s hospitality all along the way. We offer a complete luxury itinerary tailored to your needs.


  • Accommodation
  • Private Transfer IN/OUT(regular taxi)
  • A personal guide.
  • Internal flight from Havana-Cayo Coco-Havana
  • Custom guide tours and Activities.
  • Restaurant Reservations and entry fees according to the itinerary.
  • VIP arrival
  • Concierge services
  • Visas

Note: FOR US CITIZENS, we provide a fully legal itinerary checked by our legal team in the USA; who are experts in OFAC travel related regulations. Additionally, our guides will school you in Cuba so that the trip is correctly documented should you ever be audited.

Snapshot of Your Journey

Day 1

Upon leaving the plane, you will be met by an airport rep that will take you through customs into the VIP lounge. Our airport representative will meet you after going through Customs and will lead you to your guide. Once in the city, you will check in at Kempinski, rebuilt on a building originally constructed between 1894 and 1917 as the first European style shopping arcade in Cuba; Gran Hotel Manzana Kempinski is located in the heart of Old Havana. Your private concierge/contact person on land will welcome you at the Hotel; and go through your itinerary with you and make suggestions of places to see and things to do. Later you will enjoy dinner at Más Habana restaurant, an excellent new addition to the Havana Food Scene, centrally located in the Old City.

Day 2

Firstly walk in the footsteps of Havanas colonial past visiting the four key squares of Old Havana, a UNESCO World Heritage site, with our expert guide offering insights into the history and present of the city and the country. Then take lunch at La Vitrola, considered one of the most typical bars/restaurants in Old Havana, has lively live music in the afternoons. In the afternoon, Hemingway tour visiting the Ambos Mundos Hotel in Old Havana. His Finca Vigia in San Francisco de Paula, south of Havana, and, by the end, the Floridita Bar, the cradle of the Daiquiri, the writer’s favorite cocktail. For the evening, fine dining at La Guarida, the Cuban most celebrated paladar since 1996, when the government allowed to open private restaurants.

Day 3

Your driver will pick you up and take you to the airport. You will board an internal flight from Havana to Cayo Coco. A private driver will take you from Cayo Coco to Cayo Guillermo, where you will enjoy 4 days by the beach.

Check in at Cayo Guillermo Resort Kempinski. Designed as a contemporary hideaway, Cayo Guillermo Resort Kempinski is a one-of-a-kind resort nestled in the tranquillity of Cayo Guillermo in Cuba and the first Non-All-Inclusive Beach Hotel in Cuba. It certainly offers a refreshing and authentic Caribbean experience, inspired by Ernest Hemingway’s legendary love for the Cayes and intended to be the most exclusive Cuban resort on the pristine shores of Playa Pilar, ideal for relaxing by being surrounded by turquoise waters and virgin white sands chic accommodations, irresistible culinary highlights, healing spa traditions, and precious beachfront moments of peace. For more information about Kempinski hotels in Cuba, read our blog Luxury holidays in Cuba, Havana and the beach with the Kempinski connection.

Day 7

Your driver will take you from Cayo Guillermo to Cayo Coco airport to board an internal flight from Cayo Coco to Havana. You will arrive in Havana on time for lunch at Cinco Sentidos. From the quality of the food to the exceptional service … another of the best new restaurants in town. Discover more of Cuban music in the afternoon as part of our experience Cuban Music at Brenda’s Terrace; Brenda Navarrete, indeed one of Cuba’s most talented female musicians, opens her house for those interested in learning about our oldest rhythms. After, check in at Gran Hotel Manzana Kempinski in Old Havana. For the evening, we suggest dinner at Jibaro, a funky, small new restaurant in Old Havana, with attractive decor. There you will find delicious small menu, combining old Cuban standards with Greek and Middle Eastern dishes.

Day 8

Enjoy a morning at leisure in Havana before departure

Here you are some advice about things to know before a trip to Cuba.

To book this itinerary please email us at