Classic Cuba

With striking landscapes, crumbling Spanish architecture and vibrant Caribbean culture, Classic Cuba has it all.

This 12-day itinerary covers everything that this magical Caribbean paradise has to offer: a charming stay in Cuba’s traditional countryside, immersive experiences of the island’s booming food and art scene, and expert tours of some of Cuba’s UNESCO World Heritage protected colonial towns. Beginning with a luxury stay in the capital, you will be able to appreciate the faded opulence of Havana’s architectural grandeur before moving on to the rolling hills of Viñales where much of the island’s world-famous tobacco is grown using traditional methods. Travelling south, you will pass by the French-influenced mansions of Cienfuegos before arriving in Trinidad where your three-night stay will offer ample opportunity to enjoy the region’s nature and culture. Finally, no trip to Cuba is complete without a couple of nights’ relaxation on a glorious white-sand beach. Three nights on the stunning Cayo Santa Maria conclude this luxury trip.

Trip highlights

  • 3 nights in Havana at the Hotel Gran Manzana Kempinski with two full days of activities.

  • 2 nights at Villa Secreta in Viñales with a full day trekking tour of the region.

  • Private tours of the cities of Cienfuegos and Santa Clara

  • 3 nights in Trinidad at the Iberostar Grand Hotel Trinidad with a walking tour of the city.

  • Snorkelling tour of the Cayo Macho and an exhilarating jeep safari of the Topes de Collantes.

  • 3 nights on Cayo Santa Maria at the Iberostar Ensenachos Grand Village with time at leisure.

Map of your holiday

Day by Day itinerary


Hotel Kempinski Gran Manzana, Havana, Cuba

Arrive into Cuba

Arrive into Havana and transfer to your luxury hotel in the city centre for the next three nights.

Pin Suggested accommodation – Gran Hotel Manzana Kempinski


Cuban Varadero car


Today you will enjoy a panoramic tour of Havana in an open-top vintage car with your local guide. Your tour itinerary will be entirely tailored to your particular interests.


Luxury holidays to Cuba

Culture and cuisine in Havana

This morning you will set off on a tour of local markets to learn more about Cuban produce. Enjoy lunch and a gastronomy lesson at Jibaro in Havana, one of the city’s best kept secrets. In the afternoon, explore Cuba’s art scene, visiting two artists’ studios and the Museum of Fine Arts.


Cuban Cigar, Vinales, Cuba


Leaving the city behind, you will set off for Viñales in the Cuban countryside. Check in to your cosy country lodge and enjoy a private tour of a tobacco plantation in the afternoon.

Pin Suggested accommodation – Villa Secreta


Luxury holidays to Cuba

Trekking tour in Viñales

Enjoy a 4km trekking tour through the striking landscapes of rural Cuba made up of rolling hills, patchwork tobacco fields and picturesque country houses.


Cuban Man Portrait


You will drive from Viñales to Cienfuegos and enjoy a private tour of this city’s grand architecture before continuing to Trinidad where you will spend the next three nights.

Pin Suggested accommodation –  Iberostar Grand Hotel Trinidad


The Osa Peninsula

Snorkelling in Cayo Macho

Enjoy a day trip to Cayo Macho by Playa Ancón and spend the morning snorkelling in this area. A fresh seafood lunch is included, and the remainder of the day will be at your leisure.


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Jeep Safari to Topes de Collantes

Today you will enjoy more of Cuba’s wild natural beauty with an exciting jeep safari through the Topes de Collantes in the Escambray mountains. Soak up the stunning vistas and enjoy a traditional lunch.


Che Guevara Memorial, Santa Clara, Cuba

Travel to Cayo Santa Maria via Santa Clara

Today your guide will transfer you to the Cayes, with a tour of the revolutionary city of Santa Clara en-route. Upon arrival in Cayo Santa Maria, you will check in to your hotel for the next three nights.

Pin Suggested accommodation – Iberostar Ensenachos Grand Village

DAYS 10 & 11

Luxury holidays to Cuba

Days at leisure

You can now spend the next two days relaxing at Cayo Santa Maria alone the stunning beaches and swimming in the crystal clear water.

DAY 12

Aeroplane home

Transfer back to Havana

Transfer to the airport in Havana for your onward flight home.

The price for this itinerary is GBP £5,460. (US Dollar pricing also available)

This is a per person price, based on 2 people travelling and sharing a room.

What’s included

  • 11 nights in luxury accommodation as listed above

  • Private transfers and tours with an English speaking guide and driver

  • All internal flights in economy class seating

What’s not included

  • International flights (discuss your specific requirements with us)

  • Travel insurance

  • Any visas you may require

This is a guide price. Please enquire and we will provide a full personalised quote for you.  All our itineraries are tailor-made to your own requirements so can be modified however you wish.



Hotel Kempinski Gran Manzana, Havana, Cuba


The Kempinski Hotel is a chic hotel offering elegant rooms, restaurants & bars, plus a posh spa and a rooftop pool in the heart of Havana near all the best restaurants, bars and live music venues.

Bedroom at Villa Secreta Guest House - Luxury Hotels in Vinales, Cuba

Villa Secreta

Villa Secreta offers rustic elegance set amidst one of the most beautiful sceneries in all of Cuba. Enjoy a stay in a private cabin in total seclusion surrounded by nature. The decor is upcycling chic, and the atmosphere is pure tranquility.

Outside view from the Iberostar, Tinidad, in Cuba

Iberostar Grand Hotel Trinidad

In the heart of Cuba, amid the perfectly preserved Spanish colonial settlement of Trinidad, old-world charm and wonder meet comfort and tranquility in the Iberostar Grand Trinidad’s refurbished 16th-century World Heritage building.

Iberostar, Ensenachos, Cuba

Iberostar Ensenachos Grand Village

The Iberostar Ensenachos hotel is a luxury resort on Caye Ensenachos where you’ll find some of the most exclusive beaches in Cuba, as well as wellness & spa, all-inclusive accommodations, dream villas and unique excursions.