Looking Inside Old San Juan

Looking Inside Old San Juan

SAN JUAN, PUERTO RICO - It seems visitors only flirt with this Caribbean beauty — no long-term relationships, thank you.

That’s because the average stay in this lovely walled city that juts out into the Atlantic Ocean is just a few hours, about the time it takes to get from San Juan’s international airport to its cruise terminal, where hundreds of thousands of tourists pile onto ships and leave town quickly.

I refused to be one of them.

So, I arrive in San Juan a few days before my ship sets sail on a six-day Caribbean cruise because I want to learn all I can about this place, where the piña colada, the unofficial drink of the cruise-ship set, was first poured.

It doesn’t take me long to fall madly in love with San Juan thanks to its:

• Pastel-coloured homes that line the narrow blue cobblestone streets of its Old City.

• Grand churches and stately buildings that remind me that San Juan, the second-oldest city in the Americas, was once the seat of power in Spain’s New World.

• Great squares, like Plaza Colon, Plaza de Armes and Plaza San Jose, which come filled with ornate fountains and dramatic statues of historic figures like Columbus.

• And its gorgeous bayside promenade, which looks out on a seascape that is breathtakingly beautiful.

I’m told the best place to start a tour of the Old City is at San Juan Cathedral, the final resting place of Ponce de Leon (he founded the city in 1508), and the second-oldest cathedral in the Western Hemisphere. Life-like statues of saints and religious figures adorn the great church and the marvelous paintings that hang on its weathered walls are museum-worthy.


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Left: Old cars on old streets.  Right: A view of the city's famed cemetary.

Across the street, I find the city’s oldest hotel, El Convento, which started out as the Monastery of Our Lady of Carmen of San Jose in 1646. It was transformed into the city’s chicest hotel in 1962, but relics from its earliest days are still scattered about the charming property and in its 58 elegant rooms

The area around the cathedral and hotel is teeming with history and great shopping — high-end American and Spanish designers have set up “outlet” stores here and the bargains are as hot as the weather most days.

A walk along the promenade brings me to the San Juan Gate, which has been welcoming visitors to the New World since the early 1700s. The Wedgewood-blue governor’s mansion, La Fortaleza, perched above the promenade (Puerto Rico is an American “unincorporated territory” ruled by an elected governor) affords its occupants stunning sea views and is one of the most charming buildings I’ve ever seen.

When I stop to ask directions, a Puerto Rican woman who has just returned home after living in New York City for 20 years, suggests I take a “Night Tales in Old San Juan” tour ($35 per person) to get some “real insight into Old San Juan.”

“Did you know that San Juan was the first city in the Western Hemisphere to get regular phone service back in 1897?” the woman asks. “That’s the kind of interesting tidbits you’ll be told on the Night Tales tour.”

Other stately structures I see on my walk around the Old City include El Capitolio, the domed capitol building, the handsome Supreme Court building, and City Hall, all classic examples of neo-colonial architecture.

The city wall, constructed to guard San Juan after it was first settled, is almost 10-metres thick in places and leads me to San Felipe del Morro, the massive fort that rises above the Atlantic at the western end of the Old City.

San Cristobal, perched on granite cliffs that rise more than 30 metres above the sea, is another of the imposing fortresses constructed by the Spanish to protect their New World treasure. The Old City cemetery, where many of the founding fathers were laid to rest, sits at the foot of San Felipe del Morro.

Tunnels and staircases snake through the old forts and they’re fun to explore; they’re are now under the protection of the U.S. National Park Service. The UNESCO World Heritage fortresses are remarkable examples of the marvelous work carried out by Spanish military engineers more than 400 years ago using primitive equipment.

As I pass La Princesa, the city’s former penitentiary, I’m reminded that San Juan was once home to cutthroats and real-life pirates of the Caribbean, many of whom met their demise within the walls of the old jail, which now houses Puerto Rico’s Tourism Company.



Left: Homes in the Old Town are colorful and historic.

A stroll down Calle Cristo (Cristo Street) leads me to the 18th-century ruins of Capilla del Cristo, the old chapel, which was built to commemorate a “miracle” said to have been performed on the street back in 1753. Capilla del Cristo now stands as one of the Old City’s most treasured and photographed landmarks and from it you get great views of the cruise terminal area and the gigantic passenger ships that slowly sail into this historic port city.

San Juan is also one of the Caribbean’s most festive cities; the annual four-day San Sebastian Street Festival is reputed to be the best party in the Caribbean. But locals party every night in San Juan and some of the most popular hangouts include El Batey on Calle Cristo, a favourite watering hole of visitors for many years, or Hijos del Borinquen, where you can dance to the sultry sounds of rumba music, and of course Barrachina, not far from the cruise terminal, where legend has it a bartender named Ramon Portas Mingot invented the piña colada.

Restaurants in San Juan reflect the city’s diversity — there’s a distinct mix of Spanish, Mediterranean and local Creole cultures blended into the cuisine and the spicy results produce wonderful results for diners.

The colourful art scene here has few equals but the country’s best art is reserved for the walls of the Puerto Rico National Gallery in Plaza San Jose.

The best shopping is found on lower Cristo and San Francisco streets but art lovers will find great original works on Calle Fortaleza in the Old City.

Despite arriving early, I’ve still not seen all historic San Juan and tiny Puerto Rico have to offer, but my ship is about to sail. That just means I’ll have to plan a return trip and a longer stay because San Juan is just too lovely to ignore.




Puerto Rico


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