Soon after arriving in Cuba in 1511, conquistador Diego Velázquez de Cuellar set about founding seven pioneering villas (towns) in the new colony with the aim of subjugating the Taíno natives. Four of Velázquez’s villas – Trinidad, Sancti Spíritus, Camagüey, and Santiago de Cuba – were given major facelifts over the past few years to coincide with their quincentennials.

Revitalized and ready for visitors, each city offers travelers a unique opportunity to experience a bit of Cuban history.

Santiago de Cuba

Anyone planning to visit Cuba should contemplate braving the itchy eastern heat and decamping to Santiago de Cuba, the country’s second largest city, which was founded on 25th July 1515 and named after St. James the Apostle. Improvements to Santiago’s infrastructure, part of the initiatives to prepare the city for its 500th anniversary festivities, focused on two main areas. Central Parque Céspedes underwent a much-needed makeover following damage done by Hurricane Sandy in 2012, and the exterior of the imposing cathedral designed by Carlos Segrera in 1922 was given new life with substantial work carried out on its dome and handsome bell-towers. Across the square, similar architectural precision was applied to another Segrera creation, the magnificently eclectic Club San Carlos, which is now a decorative arts museum. Similarly, Hotel Imperial is now a radical rethink of a grandiose but long disused hotel; its renovated façade sparkles and rooms are available for booking. The hotel sits on Santiago’s main shopping street, Calle Saco, a proper pedestrianized boulevard.

Cespedes Park and Town Hall in Santiago de Cuba. Image by Paul Thompson / Photolibrary / Getty
Cespedes Park and Town Hall in Santiago de Cuba © Paul Thompson / Getty Images

The second part of Santiago’s 500 project involved the renovation of the neglected harbor. The city’s waterfront had long been a semi-abandoned dead zone grossly unbefitting of a metropolis of its size. Fighting bureaucracy and building delays, planners pushed through an urban renaissance spearheaded by an elegant malecón (pier) beautified with palm trees, restaurants, a playground and a new park. There is even talk of re-establishing the city’s tram line, unused since the 1950s.

Trinidad

One of the best-preserved Spanish colonial settlements in the Americas, Trinidad feels as if it slipped into a deep slumber in 1860 and has only just woken up. Renovation efforts in conjunction with the city’s 500th anniversary in 2014, along with Cuba’s ongoing economic reforms, have given visitors to this Unesco World Heritage Site plenty of reasons to stay awake, particularly on the gastronomic front.

Before 2011, Trinidad sported just three private restaurants. Today, there are over ninety, many housed in the opulent colonial mansions for which the city is famous. Among the front-runners are Sol Ananda, which stands out for its exquisite furnishings and adventurous international cuisine, and Vista Gourmet, memorable for its romantic rooftop terrace where you can enjoy surf and turf dishes with a fine accompanying buffet.

Brunet Palace and San Francisco Church on the Plaza Mayor in Trinidad, Cuba. Image by Education Images / Universal Images Group / Getty
Brunet Palace and San Francisco Church on the Plaza Mayor in Trinidad, Cuba © Education Images / Getty Images

Trinidad is experiencing a surge of new casas particulares (private homestays) and is anxiously awaiting the end of two slow but meticulous hotel-building projects. One aims to incorporate the ruins of an old hilltop chapel (La Popa) into a boutique five-star accommodation. Another, a block from the main square, will convert the magnificent but long mildewed Palacio Iznaga into a hotel befitting of the sugar baron who once lived there.

The centerpiece of Trinidad’s 2014 anniversary celebrations was the opening of the beautifully restored Casa Frias, a cultural center that exhibits an incredibly detailed scale-model of Trinidad’s historic core on its ground floor.

Sancti Spíritus

Sancti Spíritus is Cuba’s underdog city, the least known and least visited of Velázquez’s seven founding villas. Gritty and light on tourists, its grid of hard-bitten streets were given a comprehensive makeover in 2014. A brief walkabout will reveal scrubbed cobbled lanes and colonial edifices repainted in a rainbow of brilliant Caribbean colors. The centerpiece of the renovations is Calle Independencia, the city’s bulevar (pedestrianized shopping street) freshly embellished with potted palms, benches and statues of local personalities, and capped with an attractive new boutique hotel, Don Florencio, that occupies restored colonial digs.

Serafin Sanchez Park in Sancti Spiritus. Image by Brodie Computes Inc. / Moment Mobile / Getty
Serafin Sanchez Park in Sancti Spiritus © Brodie Computes Inc. / Getty Images

With the explosive growth of Cuba’s private sector, new state-run restaurants tend to get short shrift, but exceptions can be made for Taberna La Ribera Yayabo. Enjoying a pretty riverside location overlooking Sancti Spíritus’ emblematic humpbacked bridge, this retro bodega serves Cuban food with a Spanish influence cooked on an open grill in full view of the dining room. Meals are complemented by fine wines plucked from one of Cuba’s best wine cellars (in a cavernous room downstairs) and recommended by a resident sommelier, an endangered species in Cuba until recently.

Nearby you can detour to the Casa de la Guayabera, a mini-museum that revives the long-held belief that Sancti Spíritus is the birthplace of the pleated guayabera ‘wedding shirt’. To add validity to the claim, a small onsite museum displays glass cases of erstwhile guayaberas worn by the likes of Fidel Castro and Gabriel García Márquez, while a workshop next door demonstrates the skill involved in making them.

Camagüey

Founded as Santa María del Puerto del Príncipe in February 1514, Camagüey has long been a regional contrarian counterbalancing the confidence of Havana with the brooding sedition of Santiago. The city’s modern renaissance began in 2008 when the old colonial center, notable for its unusual labyrinthine street layout and generous slew of baroque churches, was listed as a Unesco World Heritage site. With a 500th birthday to celebrate, Camagüey’s rehabilitation rocketed.

A bartender prepares a drink at the Casablanca bar in Camaguey. Image by Adalberto Roque / AFP / Getty
A bartender prepares a drink at the Casablanca bar in Camaguey © Adalberto Roque / Getty Images

Since 2013 the city has opened several elegant restaurants, the quirky Bar Yesterday dedicated to The Beatles, and four new colonial-style hotels, from the regal Hotel Santa María to the railway-themed Hotel Camino de Hierro. However, perhaps the most inspired of its 500 anniversary creations is the ‘Calle de los Cines’, a stretch of arterial Calle Agramonte that has been given over to a movie theme. Camagüey’s key role in Cuban cinema history is cataloged with a multiplex cinema, a video-art gallery, a film studies center, a restaurant with movie director seating, and a bar themed for the film Casablanca.

This article was refreshed in July 2017.

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