Why go

San Juan is a vibrant cocktail of Taíno Indian, African and European heritage. Its Spanish-era, UNESCO-listed Old Town just turned 500, and is rich with Boricua character, architecture and laid-back places to eat and drink. There’s also Calle Loiza, a working-class, predominantly Afro-Boricua area that’s forging a cultural renaissance with an influx of new businesses and eye-catching street art. El Distrito, a five-acre entertainment complex right in the heart of the city, will open this spring, and in December, Steven Spielberg’s remake of West Side Story will bring the tale of Puerto Rican migrants back onto the silver screen. Whatever your reason for going, there’s never been a better time to get to know this heady Latin American capital and its distinct neighbourhoods.

What to do

Wander the cobbled streets of Viejo San Juan (old town), a historic district that’s a kaleidoscope of candy-coloured buildings and home to cultural treasures like San Juan Cathedral and the colonial-era Castillo San Felipe del Morro fortress. It’s easy to explore on foot and there’s lots to do; have a drink in one of its many cool cocktail bars, like Barrachina where bartender Don Ramon Portas Mingot invented the piña colada back in 1963; walk along the El Paseo de la Princesa, a promenade made up of restaurants, street vendors and views of the city’s historic bay; and pick up some unique creations by local artists in and around the lively Calle de la Fortaleza area.

Where to eat

Puerto Ricans love to eat out, and the Calle Sol area in Old San Juan is a good place to start for authentic Puerto Rican/Caribbean cuisine. On the corner is Deaverdura, a hole-in-the-wall style cafe run by Virna Brull, where the menu includes local favourites like mofongo, a wooden pestle and mortar filled with mashed fried plantains with pork and garlic; tostones de pana, breadfruit fritters; and arroz con gandules, locally-grown rice with pigeon peas, which is the island’s national dish. If unsure, opt for the ‘Puerto Rican sampler’ option, which serves up a taste of each, and wash it all down with one of the fresh juices like tamarindo or sour Caribbean cherry.

Don’t miss

Calle Loíza, in the mural-laden, once ‘seedy’ sub-barrio of Santurce, is a culturally and historically important street that connects San Juan with Loíza, a coastal city home to the island’s biggest Afro-Boricua population. In the 16th century, African slaves started to settle around here, and today, the traditionally working-class area is lined with lively bars, restaurants and the most striking street art in town. For the best café con leche in the area, stop off at Tostado, a favourite brunch spot among locals. Outside, the stone walls are graffitied with the words of Luis Palés Matos, the Puerto Rican poet known for creating the Afro-Antillano genre.

After hours

To party like a true Boricua, head to the bars around the buzzy Calle San Sebastian in Old San Juan, where the sounds of salsa and reggaeton, the genre native to Puerto Rico, ring through until the early hours. If you only shake your bon bons in one place, make it La Factoria, a dimly lit, speakeasy-esque joint that doesn’t look like much from the outside (in fact, it almost looks derelict), but inside is an eclectic maze with seven bars where locals dance salsa until the small hours. In late 2017, part of the Despacito music video by Puerto Rican singers Luis Fonsi and Daddy Yankee was filmed here; which, at 6.6 billion views, is still YouTube’s most-watched video of all time.

Where to stay

There’s a bit of everything in San Juan, from hotel giants to humble hostels — but Old San Juan is where you’ll find the character. Hotel El Convento, a charming convent-turned-hotel housed inside a 1651 building, faces the historic Plaza de las Monjas and San Juan Cathedral, and is yards away from most landmarks and nightlife. Inspired by the island’s Spanish colonial era, the yellow-hued hotel has a rooftop terrace overlooking the walled city and five floors of cosy rooms in which to bed down. For the best bit, order a cocktail at the bar in the courtyard, and listen out for the distinctive croaks of the coquí, Puerto Rico’s native frog.