Vintage Havana: El Capitolio and a classic ride

Cuba is one vibrant island, combining a trip down memory lane with beautiful beaches, Colonial architecture, friendly people, and “La Habana,” one of the most atmospheric cities in the Americas. Rent a classic Chevy for a few hours and cruise past the Capitolio, often compared to the U.S. Capitol, but in fact taller, wider, and far more detailed.

“La Habana” at its classic finest

Having reopened to tourism, Havana entices with a mix of crumbling Colonial and Neoclassical architecture, streets mostly devoid of traffic other than the 1950s vintage cars and an aura of days gone by. Many Americans are under the impression that visits here are not allowed, but this is not true.

While regular tourism technically isn’t sanctioned, you can still come to the Caribbean island if you travel under one of twelve categories, the easiest of which to satisfy being “Support of the Cuban People.” You are not allowed to spend money in Cuban government hotels or in state-run businesses or restaurants, but AirBnB stays, private restaurants (called paladares) and privately-run tours all qualify under this category.

Just make sure to keep your AirBnB receipts or other proof that qualify you for the exception.

Surf’s up along the Malecón

The Malecón is Havana’s famed esplanade that runs along the ocean. You can tour here in a classic car, but it’s even better to walk, especially in the late afternoon when thousands of Havana residents come out to talk, promenade and relax. It’s a great place to make local acquaintances, enjoy the beautiful cityscapes and watch the sunset.

Often called the “world’s longest sofa” for its social atmosphere, the Malecón also serves as a seawall against the massive waves that beat up against the city.

Relax at a casa particular

“Casa particular” is the term for private family accommodation, which tourists stay in not only to satisfy the “Support of the Cuban People” requirement, but also to experience a local slice of life. You can pretty much get off a bus anywhere on the island and find a house with a casa particular sign, but there are also now plenty of dedicated websites where you can book them in advance.

Often they are in lovely old palatial homes, complete with high ceilings, balconies and almost always a rocking chair, the staple of Cuban life, where you can sit back with your mojito and cigar and contemplate why you didn’t get here years ago.

Endless tobacco fields in Viñales

Cuba is not only about Havana and Colonial architecture. Head out west to Viñales, a sleepy town surrounded by mountains, and home to Cuba’s tobacco plantations (where all those famed cigars come from). You can tour the plantations here and even stay on working farms, and the verdant valleys boast some of the island’s most picturesque scenery.

Viñales shows off rural Cuba at its best

Horse and ox carts are king here, with charming dirt roads and paths connecting small hamlets. Lots of tourists come out here for day tours, as Havana is only three hours away, but it’s best to stay a few days and soak up the atmosphere.

Viñales has probably the greatest number of casa particulares on the entire island, so you’re sure to find somewhere you like. It also has a burgeoning paladar scene, as the government has allowed private enterprise to spring up. There’s even some cutting edge cuisine that has taken off, with local chefs returning from overseas to show off their skills. 

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A delight for walkers and photographers

Walkers and hikers will love Viñales, as it’s easy to escape the crowds, find your own routes and wander amongst the magnificent karst formations, red soil plantations and pastoral scenes. Viñales is also home to a pretty dramatic rock climbing scene, which isn’t overtly advertised, but come here and ask around. You’ll find some of the Caribbean’s most challenging routes, along with a community of avid climbers.

Even those who prefer more sedentary vacations may enjoy it as well, as you can take an oxcart or horse riding tour and not have to leave your feet to enjoy the gorgeous surroundings. 

Cayo Jutías boasts some of the Caribbean’s most beautiful sand and sea

Cuba’s beaches are some of the best in the Caribbean, featuring amazing turquoise water and blinding white sand. While the fancy all-inclusive resort beaches are off limits to American travelers (due to being connected to or owned by the government), there are plenty of local spots to enjoy a beach holiday.

Cayo Jutias is a small island connected to the mainland by a causeway, and located just a short drive from Viñales. It’s easy to come over here for a day trip, enjoy fresh seafood, a few mojitos, soak up some sun and then return after sunset. If you time it right, you may have this gem of a beach all to yourself. 

Turquoise paradise dreams

Caleta Buena is located just outside of Playa Girón and by the famed site of the Bay of Pigs. It’s a private club set on the Caribbean where you can pay a $15 entry, which includes buffet lunch and all-you-can-drink alcohol. Plus, make use of the palapa huts, beach chairs and wonderful swimming holes and cenotes that dot the coastline.

It’s yet another tranquil bit of tropical paradise that you won’t want to leave.

St. Francis of Assisi Convent at blue hour

Architecture buffs will love Trinidad, a UNESCO World Heritage Site and one of the best-preserved cities in the entire Caribbean, with lots of colorful Colonial buildings gracing the atmospheric old town center. Cobblestone streets, horse carts for traffic and lovely old churches such as the St. Francis of Assisi Convent are part of the allure.

After Havana, this is Cuba’s second-most-visited city and should be a must on any agenda. You can get here in about seven hours by bus from Havana, or several hours less if you charter one of those classic old cars.

Horse and carriage taxi on the streets of Trinidad

Taking a ride on a horse carriage is a great way to see Trinidad. Horse carriages serve as taxis in several Cuban cities, and are not only a good form of transportation and sightseeing, but also an excellent way to connect with the locals. Our driver gave us tips on where to find the best mojitos in town and showed off a few hidden spots we never would have found on our own. 

Street musicians in Trinidad

While the days of the Buena Vista Social Club may have come and gone, their wildly popularized music is still played throughout Cuba, and you’ll find plenty of street musicians gathered in shaded plazas everywhere. If you have a chance in Havana, make a beeline for the narrow alley of Callejon de Hamel, where the Santería community holds Afro-Cuban dance parties throughout the week.

Don’t be shy here; Cuba is a vibrant and very lively country with not a wallflower to be found!

Cuban cigars: Not just a great souvenir

Cuban cigars are world-famous, and one great bargain here in their place of origin. If you are out in Viñales, you’ll be able to buy them in the countryside right at the tobacco plantations. Havana also has cigar factories and museums, not to mention plenty of smiling old women who ham it up for the camera with their cigars, trying to make a few coins from passing photographers.

Walking streets and plenty of social interaction and community life are a Havana staple.

Neoclassical Colonial architecture in Cienfuegos

Whether you’re coming here for the city charm, the vintage rides, to stop by Hemingway’s La Bodeguita for a mojito or to tour any of the famed Che Guevara or Fidel Castro historical sites, you will come away with a treasure trove of memories.

Driftwood and solitude in beautiful Cayo Jutías

And if you’re coming for some social distancing, silence, solitude or just to see one beautiful island, the hills of Viñales, the mountains of the Sierra Maestra or the endless empty beaches with warm tropical water, you most definitely won’t be disappointed.

Just make sure to keep your receipts so that you can prove you’ve satisfied one of the twelve categories required by American visitors to go check out this happening place. Put Cuba at the top of your post-COVID travel list now.

10Best is a part of the USA TODAY Network, providing an authentically local point of view on destinations around the world, in addition to travel and lifestyle advice.

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