The best places to go in Cuba on a first time visit

updated 1/14/2021

Sitting just 160 km off Florida’s coast, Cuba is the largest of the Caribbean islands. From its bigger cities to its rural utopias, each area of Cuba has its own specific history and unique atmosphere. But at 109,884 km², the island is bigger than most people realise and you might just have to make some hard choices when it comes to your itinerary.

To give you a hand, we’ve put together a list of five of the best places to go in Cuba on a first-time visit.

Related tailor-made travel itineraries for Cuba

Havana

Most trips to Cuba start and end in Havana. But Cuba’s capital deserves to be first on the list for many more reasons than its convenience as a transport hub. Full of free spirit, crumbling buildings and classic American cars, Havana is a heady mixture of the run-down and the sophisticated, charged with an under-current of excitement and vigour.

La Habana Vieja, Havana’s old town, is where most of the action takes place. Wander past colourful facades to check out grandiose monuments like El Capitolio (the National Capitol Building). Next, check out the baroque 16th century Catedral de San Cristobal. Then break for a cocktail at the Plaza de Armas, the city’s longstanding social hub.

Before delving headfirst into Havana’s legendary nightlife, spend the rest of the afternoon people watching at the Malecón. The seawall’s coastal views and carefree atmosphere make it one of the best places to go in Cuba.

What to do

A ride in an American classic car is a must when in Cuba. Take this 2-hour ride through the streets of Centro Habana, Vedado and Miramar before heading to the famous Hotel Nacional for a sunset cocktail. Cuba in style!

Our favourite tailor-made trip

Spend 4 nights in Cuba's capital Havana before heading to the white sandy beaches of Varadero: The Culture and Beaches of Cuba trip is the ideal sample for those wanting to taste Cuban life in the capital before relaxing on the beach.

View of Viñales Valley, Cuba © Zaruba Ondrej/Shutterstock

Viñales Valley

It’s been said that Castro’s favourite place on the whole of the island was the Viñales Valley. It’s not hard to see why. Interspersed with rocky karst outcrops, its fertile plains run against mountains to breath-taking effect. Most importantly, the Viñales Valley is also where the country’s finest tobacco is grown – likely another reason for the cigar-loving leader’s adoration. A few days in Viñales will give you a perfect snapshot into rural Cuban life. And while the town is certainly tiny, there’s a dance club if you feel like letting off steam in the evening.

What to do

Explore the region on an e-bike: discover tobacco plantations, stop en-route to chat with the ever-friendly locals and visit a cave that has since turned into a night club.

Our favourite tailor-made trip

Discover Western Cuba in depth with this sample trip. After two nights in Havana you set out to explore Soroa and Vinales before returning for a final two nights in Havana again. And as with all of these sample trips - they're 100% customisable to your preferences, no matter if you want to change the route, activities or accommodation or just book it as it is - simply click 'modify this itinerary' to receive your quote.

Jardines del Rey

Some time on the beach is definitely next on the cards. And where better than the archipelago where Hemingway was said to have sailed his yacht looking for German submarines? Connected to the mainland by a series of beaches, Jardines del Rey is a chain of idyllic islands. Tourism arrived late to Jardines del Rey with the result that it’s pleasingly underdeveloped. In fact, the entire area is a UNESCO Biosphere Reserve with no permanent residents allowed on the islands. One of the archipelago’s best beaches is the sublime Playa Pilar. Pilar sits pretty on the Cayo Coco, and its 21-kilometre stretch of white sand is framed by mangroves. Add a huge flamingo colony to Jardines del Rey’s list of attributes, and we think you’ll agree it’s definitely one of the best places to go in Cuba.

Our favourite tailor-made trip

Complete Cuba - Nature, Tradition and Sights of the Revolution. Arrive in Havana and make your way all throughout the island with stops in Cienfuegos, Trinidad, Cayo Coco, Camaguey and Santiago before returning to Havana.

Jardines del Rey beach, Cuba © Lena Wurm/Shutterstock

Trinidad

Trinidad is Cuba’s colonial treasure. Its Old Town boasts UNESCO heritage listing and to protect its narrow cobbled streets, it’s only accessible by foot or horse-drawn cart. The city is known for its iconic coloured buildings and the neo-baroque architecture at Plaza Mayor, the main square. Explore the fascinating Museum of the War Against the Bandits and then watch the sunset on nearby Playa Ancon. Finish with a night of salsa and canchánchara rum cocktails at Casa de la Música.

What to do

Take an e-bike ride along the coastline and the Valley of Sugar Mills to explore Trinidad's countryside. Afterwards, return to the city to learn more about Trinidad's history and culture.

Our favourite tailor-made trip

If the idea of taking an e-bike for longer than a day excites you, take a look at our Western and Central Cuba by e-bike trip: 13 days of exploration and adventure await.

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Baracoa

Baracoa sits on the spot where Christopher Colombus first made landfall in 1492. Diego Velazquez founded Cuba’s first capital here at the eastern tip of the island some 20 years later. The colonial history of this first city is captured in the lofty architecture of monuments such as the Catedral de Nuestra Senora de la Asuncion. In more modern times, Baracoa has attracted a host of legendary characters, including the magic realist writer Alejo Carpentier. For those after active adventure, there’s the El Yunque mountain’s pristine rainforest to hike in.