Weekenders: Old is New in Old San Juan

Our guide to soaking up the sun, the trends and the sights in this nearly 500-year-old Caribbean town.

By Jessen O’Brien | Photography by Pamela Ashley Pasco

A flourishing art scene and foodie renaissance have transformed San Juan into a must-see destination—and thanks to Puerto Rico’s commonwealth status, a weekend in San Juan, the capital, offers both the excitement of a foreign locale and the convenience of staying close to home. Leave your passport behind and reserve room in your suitcase for the treasures you’re bound to pick up in this cultural haven.

Explore Old San Juan

The heart of San Juan is the original walled city, founded by the Spanish in 1521 because of its natural defensive position, on a small walkable islet at the northeastern end of San Juan Bay. Old San Juan’s streets are paved with blue cobblestones that once were put into the bottoms of European merchant ships to stabilize them and are lined with restored colonial buildings painted in bold greens, reds, yellows and blues. If you look up you’ll spot twinkling lights strung between buildings, delicate ironwork and rooftop gardens.

To energize yourself for a day of sightseeing, start the morning with a cup of strong traditional Puerto Rican coffee at Café Manolín. Regulars trade newspapers and gossip with servers at U-shaped counters. For an extra kick, try the café’s flavorful homemade hot sauce. Then stroll down the street to La Fortaleza, the oldest executive mansion in continuous use in the western hemisphere. The free tour may not always be punctual, but the carefully landscaped sunken garden alone makes it worth the wait.

La Fortaleza was the first fortress built along San Juan harbor, but it proved too small and too far from the bay’s entrance to defend the city, so the Spanish built the massive Castillo San Felipe del Morro and Castillo San Cristóbal to bookend the islet and provide more protection from English and Dutch naval invasions. The main appeal of both forts is the panoramic views: Turquoise waters surround El Morro, while San Cristóbal overlooks the main city. If you start at El Morro, consider stopping beforehand at the nearby farmers market, Mercado Agrícola Natural Viejo San Juan. On Saturday vendors sell refreshing coconut smoothies and sweet red bananas you can snack on while browsing among the stalls for natural remedies and soaps. Buy a joint-entry pass for the two forts so you can pause for lunch in between. If you walk (about 20 minutes) you can stop at La Fonda El Jibarito while making your way between the forts. This family-run restaurant is known for its hearty cocina criolla—traditional Puerto Rican cooking with Spanish, African and indigenous influences. Or take the free trolley from Castillo San Felipe del Morro straight to Castillo San Cristóbal and afterward walk to Café Puerto Rico for mofongo (a fried dish made from plantains or yucca) filled with spicy chicken.

Caribbean Shopping List

The Lisa Cappalli boutique (next door to Café Puerto Rico) sells fun, flirty high-end sundresses and gingham skirts. From there it’s a short distance to Paseo de la Princesa, a bayside promenade set outside the city walls, where on the weekend, artisans set up stalls selling jewelry and other crafts. The walkway offers sweeping views of the harbor as you wander among sculptures commemorating San Juan’s 500-year history. If you exit through San Juan Gate (once the city’s formal entrance), 3 Mujeres is just up the block. The three women the store is named for sell bold paintings of female figures, hand-stitched and -painted textiles and ceramics that range from wall hangings to pendant necklaces.

Then wander up Calle del Cristo, a street known for its many art galleries and stores. Skip the chain shops and tourist traps in favor of handmade Panama hats at El Galpón or Caribbean hot sauce and Puerto Rican coffee at Spicy Caribbee. Duck into Galería Botello to see oil paintings and bronze sculptures by one of Puerto Rico’s most famous artists, the late Angel Botello. At the southern end of the street stands one more work of art, Capilla del Cristo. Legend says that this small stone chapel was built after a young man lost control of his horse and would have ridden off the cliff if the horse hadn’t miraculously stopped, at the spot where the chapel now stands.

After a day of shopping, relax in the Spanish-style courtyard of Patio del Níspero. There chef Luis Castillo cooks up a lighter take on local fare. Consider starting with the gazpacho, made with herbs from an on-site garden, then trying the red snapper in tangy papaya sauce. If you’re feeling adventurous, opt for the tasting menu at Marmalade, a 10-minute walk away, where chef and owner Peter Schintler serves popcorn shrimp and chicken coated with spicy jalapeño cornbread crumbs.

Hit the Beach

No trip to San Juan is complete without a day at the beach. Ocean Park is a favorite among locals, who bring coolers and play music. There’s only one vendor, On the Beach, a truck from which Raul Rosado sells frozen fruit frappes and ocean gear. Once you’ve had enough sun, cool down in the Museo de Arte de Puerto Rico, a short drive away. This 1920s neoclassical building houses one of the largest art museums in the Caribbean. The museum’s fourth floor houses dramatic must-see installations by artist José Morales. Down the road, you’ll find bold tropical-patterned dresses at the Stella Nolasco clothing boutique.

Or check out Condado Beach, three miles from Old San Juan. White umbrellas line the shore, and the closest road, Avenida Ashford, is known for its shops. The men’s store Root sells polo shirts with not-so-standard details, like patterned collars, while Hecho a Mano offers funky beach wear. For a low-key meal, Solera dishes up Caribbean-Asian fusion dishes, such as grilled skirt steak with shoyu sauce. For an elegant dinner try 1919, where executive chef Juan José Cuevas’s salmon is meltingly good. The restaurant looks out on the shore, so you can watch the sun fade over the royal-blue waters of this colorful historic city.

Capilla del Cristo
Calle del Cristo; 787-722-0861; admission, free
Castillo San Cristóbal
San Cristóbal; 787-729-6960; nps.gov; joint ticket with Castillo San Felipe del Morro, $5*; kids under 15, free
Castillo San Felipe del Morro
Calle Norzagaray; 787-729-6960; nps.gov; joint ticket with Castillo San Cristóbal, $5; kids under 15, free
La Fortaleza
63 Calle Fortaleza; 787-721-7000; fortaleza.gobierno.pr; tour, free
Museo de Arte de Puerto Rico
299 Avda. de Diego; 787-977-6277; mapr.org; tickets, $6
3 Mujeres
63 Caleta de San Juan; 787-509-0282
Galería Botello
208 Calle del Cristo; 787-723-9987; botello.com
El Galpón
154 Calle del Cristo; 787-725-3945; elgalpon.net
Hecho a Mano
1126 Avda. Ashford; 787-722-5322
Lisa Cappalli
206 Calle O’Donnell; 787-289–6565
Mercado Agrícola Natural Viejo San Juan
Museo de San Juan, 150 Calle Norzagaray; open Saturdays only
1129 Avda. Ashford; 787-946-7668
Spicy Caribbee
154 Calle del Cristo; 787-725-4690; spicycaribbee.com
Stella Nolasco
310 Avda. de Diego, Suite 101; 787-723-2897
Condado Vanderbilt Hotel, 1055 Avda. Ashford; 787-724-1919; 1919restaurant.com; dinner for two, $120
Café Manolín
251 San Justo; 787-723-0308; cafemanolinoldsanjuan.com; dinner for two, $20
Café Puerto Rico
280 Calle O’Donnell, Plaza Colón; 787-724-2281; dinner for two, $40
La Fonda El Jibarito
208 Calle Sol; 787-725-8375; dinner for two, $30
317 Calle Fortaleza; 787-724-3969; marmaladepr.com; four-course tasting menu, $65 a person
On the Beach
Yardley Place; 787-409-0069; frozen fruit frappes, $5
Patio del Níspero
Hotel El Convento, 100 Calle del Cristo; 787-723-9020; elconvento.com; dinner for two, $70
La Concha Resort, 1077 Avda. Ashford; 787-721-7500; laconcharesort.com; dinner for two, $50
RCI affiliated resorts in and near San Juan include:
Royal Holiday—Park Royal Club Cala 8843
Villas overlook the Caribbean Sea at this resort. 270 Harbour Dr., Suite 1, Palmas del Mar, Humacao
Member Reviews: “The closest attraction was the beautiful rain forest.”
“Great location if you plan to travel around.”
It’s not too early to start planning your 2015 vacation! Start early for destinations that are popular in all seasons, like Puerto Rico. Did you know that Puerto Rico’s temperatures range from 75 to 85 degrees year-round?
For complete member reviews (as member reviews have been condensed) and additional resort listings, visit RCI.com or call 800-338-7777 (Weeks) or 877-968-7476 (Points). Club Members, please call your specific Club or RCI telephone number.

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Non-RCI affiliated resort:
Da House
An artist-run hotel in the heart of Old San Juan. 312 Calle San Francisco; 787-977-1180; dahousehotel.com; doubles from $100 a night
  • *Estimated meal prices do not include drinks, tax, or tip.
  • *All prices are in USD.
  • NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
  • Published: Spring 2015