Yes, like much of the Caribbean, Cuba has long been attractive to the sun-seeking quickie vacationer—but in the last decade, as Fidel Castro’s authority waned with age and time (and now his death), increasing numbers of people have ventured to the Caribbean island nation to seek out and experience its culture, rich history and natural tropical beauty.

This six-day tour takes in the country’s west, and uniquely includes homestays as well as hotels, for as true a taste of the real Cuba as you could get—well, for now anyway: Raul Castro has succeeded his brother, and freedom and human rights are not exactly priorities. Be that as it may, the Cuban people are beautiful—I’ve been there enough to say it!—and I highly recommended any opportunity to get to know them and their country better.

Cuba tour

The culture, the people, the beaches! (Credit: Laughan Raven)

This trip does that. You begin with an exploration of the capital Havana, with its faded glory, its revolutionary monuments, its colour and its vibrancy. Visit its most famous sites, including the sweeping Plaza de la Revolucion that is overlooked by the famed giant mural of Che Guevara, or perhaps stroll the vast El Malecon sea wall.

Cuba, Havana

The stunning capital of Havana

Before hitting the road to head to the countryside communities of Las Terrazas, you stop at a few community projects in Havanna, where artists work and children learn to follow in their footsteps. One of these is in the little seaside neighbourhood of Jaimanitas, where Jose Fuster—known as the Cuban Gaudi or Cuban Picasso—lives and works.

Later, outside of Havanna, you spend the night at the UNESCO Biosphere Reserve of Las Terrazas, which is also famed for its art, woodwork and pottery. And visit a waterfall and an orchid garden, as well as enjoy a spectacular lookout on the way to the mountain resort of Soroa. In Viñales, you visit the home of a local tobacco farmer to learn how to roll the perfect Cuban cigar, which rests amid the area’s rich, fertile groves of avocados, mangoes, pineapples and papayas. Before arriving back in Havana, you will explore caves, hike valleys, visit an organic farm or head to the beach for some relaxation away from the island’s famed resorts.

Although options like in-home restaurants and homestay accommodation are welcome developments for travellers, they are also indicative of a gradual and subtle change to the entire country. Cuba has a long way to go before it’s politically and economically sound—but any opportunity to witness what I call the real revolutionary Cuba should be grasped while it’s still available.

Booking Info

Great Expeditions

  • Phone: 800.663.3364
  • Length/Departs:  6 days / year-round
  • Accommodation: Hotels, homestays
  • Starting Price: $300 to $500 USD (plus local payment)
  • Difficulty: Easy

To learn more about this trip or to book it now, click here.

  • By Simon Vaughan, Senior Editor/Special Travel Advisor for Outpost Travel Media

Want more awesome trips hand-picked by the editors at Outpost? You can buy our 2018 Global Travel Guide here

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