36 Hours in San Juan, Puerto Rico

(Photo: Laura Magruder for The New York Times)

By Charles Isherwood, New York Times

Trying to sample the pleasures of some cities over a weekend can be a bit like entering a pie-eating contest. Sounds like a madcap lark, but after a while you’re likely to feel overstuffed, foolish and maybe a little sick. Sure, you could do Paris without the Louvre, but why? Even negotiating the fabled museum itself in that time frame would be a challenge.

San Juan, the capital of Puerto Rico, poses no such problems. True, as with any major metropolis, you could pass a week in the city and still not probe all its corners. (As it turned out, I did: planning a weekend visit, I was forced to extend my stay a few days when Hurricane Sandy struck.) But the major highlights of San Juan can be easily accommodated in 36 hours, even accounting for the leisurely pace that seems appropriate to the tropics.

FRIDAY

4 p.m.
Buy a Hat

A walk through the central streets of Old San Juan reveals a city in ferocious competition to become the most souvenir-clogged metropolis on the planet. Perhaps because it’s a popular stop on Caribbean cruise tours, the central city is so chockablock with stores selling tacky gewgaws that you could conceivably furnish an entire apartment with merchandise announcing its provenance in Puerto Rico. (There’s even a shop that calls itself the Tourist Trap.) But since a hat is necessary on a steamy afternoon, visit the tiny, old-fashioned emporium called Olé (105 Fortaleza Street; 787-724-2445), which sells hand-fitted Panama hats that you can customize yourself. I chose one in a color somewhere between mauve and brown, and accessorized it with a nice striped ribbon ($60). The proprietor, Guillermo Cristian Jeffs, will describe the history of the Panama hat in effusive detail, and assure you that none of his hats — in contrast to the piles to be found filling shelves elsewhere — are made in China. Also for sale: an assortment of touristy trifles and a few used books: I picked up a slightly worn copy of E. M. Forster’s “Howards End” for a few bucks.

7 p.m.

Make your way to the famous Hotel El Convento (100 Cristo Street; elconvento.com), an Old San Juan institution. The name derives from the grand building’s history: founded as a convent — the first in Puerto Rico — it housed Carmelite nuns for 250 years before entering a period of tumultuous decay, for a time becoming a flophouse and eventually (Dios mío!) a parking lot for garbage trucks. The structure was rebuilt beginning in 1959 on the foundations of the original, reopening some three years later as a hotel. The bar and restaurant overlooking the grand open-air courtyard is the perfect spot to grab dinner or a drink.

SATURDAY

10 a.m.
Pick-Me-Up

Breakfast is served all day at Caficultura (401 San Francisco Street; 787-723-7731), a bustling coffee house that sits on a corner of the Plaza Colón, near the eastern end of Old San Juan. Black glass chandeliers hang from the high ceilings, and marble floors magnify the convivial sound of locals and tourists lingering over a morning meal. Although sandwiches are on the menu, the range of breakfast options, with local twists like banana pancakes with rum ($12), is most appealing, along with local pastries. A table with a view of the passing scene is recommended, since as with many restaurants in San Juan, the byword here is not necessarily efficiency.

1 p.m.
Explore the City

Old San Juan is justifiably cherished for its beautifully preserved buildings and its sleepy charm. Wander its streets with their distinctive blue-glazed cobblestones: check out the cathedral on Cristo Street, stop for a rest in the slightly seedy central Plaza de Armas on San Francisco Street, stroll along Fortaleza Street until you come to the western end, where the grand governor’s mansion sits. While you walk, tally up all those souvenir shops, and note the occasional anomaly: What’s Dooney & Bourke doing here? I found myself preferring to avoid the sometimes dreary spectacle at street level and cast my eyes upward to the ornate balconies, or let the myriad colors of the buildings collect into a sort of visual kaleidoscope.

5 p.m.
History With a View

Just before dusk is a prime time to visit the Castillo San Felipe del Morro at the north end of Del Morro Street, where it intersects with Norzagaray Street, one of the two historic fortresses that more or less bookend the north side of Old San Juan. The majestic structure takes on a soft glow as the sun falls over the horizon (it’s open daily until 6 p.m.) and offers views of the bay and the ocean that are best savored when pink and orange bands of light begin to settle over the water. Construction on the castle began in 1539, when Spain was in control of San Juan. It’s from here that the Spanish forces fended off various maritime attacks, and you can peek through windows where cannons once stood.