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Want to head to Cuba but avoid the tourist trail? AllTheRooms has spoken with locals and we have put together an epic 2-week Cuba holiday itinerary that will take you off-the-beaten-track. From rebellious cities to Ernest Hemingway’s favorite beach, your 2-week itinerary begins here.

Day 1: Havana

2 weeks in Havana
Photo by Bryan Ledgard

No trip to Cuba is complete without visiting Havana, the island’s electric capital city. Most international flights land in Havana, so it makes sense to start your two-week itinerary here. While the city is becoming increasingly touristy, we recommend you spend 24-hours in Havana to get a flavor of the city before heading towards the south of the island.

Day 2 – 3: Santa Clara

2 weeks in Cuba
Photo by Stephen Colebourne

The next stop is Santa Clara, a city known for its explosive, youthful energy. Santa Clara’s rebellious youths have been pushing against government policies for years and because of this, the city has loads of cool bars, cafes and hang-out spots. If you really want to get to know the history of the Revolution, Santa Clara is a great place to start. The city has several monuments to Che Guevara, who liberated the city from the Batista dictatorship in 1958. Be sure to visit the Che Guevara Mausoleum and the Che Guevara Museum to feel closer to the country’s history.

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Day 4 – 6: Trinidad

2 weeks in Cuba
Photo by Stephen Colebourne

While Trinidad is on the tourist trail, it is a good stopping point between Santa Clara and Morón. Trinidad is a beautiful, historic city, which is easy to explore on foot. If you want to get away from the tourist spots, we have alternative ideas for you to enjoy:

To get a flavor of the country’s history, visit a nearby former sugar plantation – its chilling history will send shivers down your spine as you imagine what life must have been like for the workers. Slave owners used to stand atop the watchtowers whose 360-degree views of the plantations made it near impossible for slaves to escape.

In the evening, head to one of the world’s most unusual clubs – Disco Ayala, which is a club in a natural cave. The club – which occupies three floors – draws thousands of people on the weekend.

Day 7 – 9: Morón and Playa Pilar

2 weeks in Cuba
Photo by Kyle Taylor

Next stop is Morón, a city that is really off-the-beaten-track. Moron is a smaller, more dilapidated version of Havana and there are barely any tourists. Nearby Playa Pilar is considered the most beautiful beach in Cuba. Ernest Hemingway loved Playa Pilar so much he even named his boat after it. With sugar-white sand and crystal-clear water, you will really feel like you’ve stepped into paradise.

Day 10: Camagüey

2 weeks in Cuba
Photo by Marika Bortolami

The sophisticated city of Camagüey is our next destination. Camagüey is a less time-worn city, with clean roads and well-kept houses. Spend the night in Camagüey before continuing your journey South the following morning.

Day 11 – 14: Santiago de Cuba

2 weeks in Cuba
Photo by Matteo Artizzu

We’ve saved the best city for last! Santiago de Cuba bursts with energy and Caribbean flavor. It’s known for its large Afro-Caribbean community and its streets are filled with music and a slower, more enjoyable way of life. Better still? There are fewer tourists here, as it is on the opposite side of the island from the usual tourist trail. Dedicate three or four days to explore the city and the surrounding area.

A two-hour drive away from the city is the Pico Turquino mountain range. Che Guevara and Fidel Castro plotted the Revolution from these mountains, training their guerrilla army here.

If you have a spare day, we recommend stopping at La Mula, a gorgeous Caribbean beach which is only a 15-minute drive away from Pico Turquino.

2 weeks in Cuba
Photo by Geoffroy Magnan

Getting home

If you’re flying home from Havana, there are daily flights back to Havana from Santiago de Cuba’s airport (Antonio Maceo Aeropuerto). The airport also has some international flights to Fort Lauderdale (Florida), Madrid (Spain) and Kingston (Jamaica).

The route

We recommend hiring a car for this 2-week Cuba holiday itinerary. You can pick up a car in Havana through rental agencies such as Havana Car Hire. You can also travel the island by taxi, which is relatively cheap.

2 weeks in Cuba
Photo by Google Maps
Off The Beaten Path Adventures in Cuba 2-week Cuba - Travel
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