San Juan: southern sophistication

By Craille Maguire Gillies

This chic Caribbean city has both striking colonial architecture and some of the best shopping south of Miami. Here are five must-see spots in Old San Juan.

1. Retail therapy

Wandering Old San Juan's cobblestone streets will lead you delightfully astray to designer outlets that include Coach and Polo Ralph Lauren.

Start on Calle San Francisco and Calle del Cristo

2. Good booking

Around each corner, you'll stumble across cultural gems such as Casa del Libro, a rare book museum in an 18th-century house. It's kitty-corner to a beautiful, almost forgotten stone chapel.

At the end of Calle Cristo, 787-723-0354

El Morro

3. Strong suit

Known as El Morro, this 16th-century Spanish citadel (a World Heritage Site), is perched 138 feet above foamy San Juan Bay and the ocean. Local families pack picnics and fly kites in the grassy hills surrounding the fort.

Castillo de San Felipe del Morro (El Morro), Norzagaray St., 787-729-6960

Catedral de San Juan

4. Celebrity spotting

Marc Anthony renewed his wedding vows with his first wife (pre J. Lo) at the medieval Catedral de San Juan (Cathedral of San Juan). You probably won't run into him, but one celeb who will definitely be in attendance is Ponce de León, whose marble tomb is housed here. After your visit, cross the street for a pre-dinner cocktail on the terrace at the venerable Hotel El Convento.

Catedral de San Juan, Calle del Cristo 153, 787-722-0861

Hotel El Convento, Calle del Cristo 100, 1-800-468-2779 (in San Juan), 787-723-9020

5. Light fantastic

A short cab ride from Old San Juan, Plaza de Las Luces (Plaza of Lights) is in the upscale Condado neighborhood. The lit-up five-fountain water sculpture (designed by the creators of the Fountains of Bellagio in Las Vegas) is best viewed at dusk. Then enjoy a low-key dinner at nearby Ajili-mójili, a favorite with locals (reservations required).

Ajili-mójili Restaurant, Av. Ashford 1052, Condado, 787-725-9195

(When not working as an editor at enRoute, Craille Maguire Gillies occasionally spends an afternoon admiring striking colonial architecture in Montreal, where she's based.)

Getting There

This November, we're recommencing our weekend flights from Toronto to San Juan, with convenient connections to other Canadian gateways. Book now. And don't miss our great deals on hotels (nightly rates starting as low as $89 USD).

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