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Luxury Cuba Holidays: an Overview

Cuba is the largest island in the Caribbean and without a doubt the most fascinating. Few countries conjure up as many mental images as Cuba - Castro, cars, cigars - the list is endless and not all of them begin with 'c', either.

Travel to Cuba is becoming increasingly popular and so it is becoming harder to confirm our preferred accommodation options. In order to offer the best chance of securing our favourite hotels and casas, we strongly recommend planning your holiday at least nine months in advance of travel. Should you wish to get away with a little less notice then we suggest discussing alternative destinations in Central or South America, or the Caribbean with our specialists.

As part of your tailor made itinerary Havana is a must visit, in fact it's a destination worth a trip in its own right, and our guides are excellent at bringing this already vivacious place to life, which makes for a hugely memorable visit. Wander down el Prado avenue, past Spanish colonial buildings with paint that has been peeling for a couple of decades and the fine 18th century opera house, which stages both ballet and opera. Havana is Cuba's historical hub, with museums and stunning architecture aplenty. The UNESCO-sponsored Havana Vieja is a must - explore the old city by horse and carriage and see the Capitolo building, the Gran Teatro, the Plaza Cathedral and the Plaza de Armas. Despite the constant reminders of the 1960 revolution - namely in the crumbling plaster and peeling paint of the colonial buildings - it is certainly a city on the up. Havana is also one of the best places to learn two of Cuba's most sacred arts - cigars and rum, and there are plenty of bars and cigar shops around that make a suitable classroom.

In a country where the food is communistically bland, Original Travel's Latin America team can also recommend and book the few excellent restaurants, or a visit to a cigar factory - a cut and dried 'must do'. Aside from the charismatic capital, beautiful beaches frame the island, and there's history and culture aplenty to be explore while in holiday in Cuba in towns such as the UNESCO World Heritage Site of Trinidad.

Touring is easy, and mostly on good roads with bad sign posts. On the south coast there is excellent snorkelling and diving, and Original Travel can book a fishing trip so you can make like Hemingway and go after bonefish, tarpon, trevalley, sailfish and marlin.

A couple hours west of Havana lies Viñales, a fertile region famous for its tobacco (the education continues) and bananas. The landscape is stunning and diverse, with mogotes - otherwise known as steep, round hills - providing a stark contrast to the flat landscape they sit on. Further contrasts lie in the day to day life of the Viñales inhabitants. Old fashioned farming methods are still in practice, with oxen and wooden carts dotting the countryside. Los Jazmines is one of our favourite hotels in the region, perched high on a hill all of the rooms have fantastic views over the tobacco plantations.

Away from the countryside and onto the coast, Cuba boasts stunning beaches and bays to rival any other Caribbean island (in fact, Cuba is the largest of the Caribbean islands), such as those of Varadero, Cayo las Brujas and the Island of Cayo Largo.

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A Note on Price

All of our holidays are completely tailor-made and prices will vary based on things like when in the year you will be travelling, how far in advance you book and the level of accommodation you choose. The guide prices shown across this website are designed to provide you with a broad indication of how much to budget for your trip.

Itinerary Suggestions

Classic Cuba

From $4,300pp