Beyond the casinos and resort-studded beaches, a rainbow of possibilities beckons.
Writer: Heather Chadduck
1 of 16Photo: David Hillegas
Flora and Fauna
Old San Juan's quirky Gallery Inn, a cluster of buildings dating from the 18th century, is almost as colorful as the flock of avian inhabitants that perch and chatter on its overgrown walls.
2 of 16Photo: David Hillegas
Signs of the Past
Old San Juan, the historic section of Puerto Rico's capital city, is brimming with colorful signage. Local activist Ricardo Alegría is credited with saving the area's Spanish Colonial architecture from demolition.
3 of 16Photo: David Hillegas
The 500-year-old cobblestone streets of Old San Juan are chockablock with colorful examples of Spanish Colonial architecture—from the trademark tile roofs and ornate balconies to the heavy wooden doors guarding secret courtyards. Calle San Francisco, lined with antiques shops and cafes, is a particularly beautiful street; for a stunning view of the sea, walk to the corner of Calle San Justo and Calle Norzagaray.
Left: Cafícultura, a charming spot to take five in Old San Juan
4 of 16Photo: David Hillegas
In the surfer haven of Rincón, on Puerto Rico's western coast, the Horned Dorset Primavera's Restaurant Aaron serves French cuisine with a Caribbean flair, in a lavishly painted dining room. In Old San Juan, head to Calle Fortaleza, the de facto restaurant row, for late-night spots specializing in Spanish-Caribbean fusion food.
Left: Restaurant Aaron at the Horned Dorset Primavera in Rincón
5 of 16Photo: David Hillegas
The docks near the San Juan Gates in Old San Juan recall an old-time fishing hangout. You can see the picturesque El Morro fort in the distance as you chat with friendly fishermen bringing in their catch. The people-watching is fabulous no mater where you go, especially among the hipsters set behind the island's bustling restaurants and shops.
Left: A fisherman near El Morro, Old San Juan's 500-year-old fort
6 of 16Photo: David Hillegas
Rooms and common areas at the Gallery Inn exude old-world patina, from Spanish tiles and peeling walls to paintings and pottery made by both the owners and their guests.
7 of 16Photo: David Hillegas
Whether you're on the Atlantic or the Caribbean side of Puerto Rico, the water views are always inspiring. The surfing town of Rincón, two hours west of San Juan, is famous for its spectacular sunsets and has been drawing surfers since it hosted the World Surfing Championships in 1968.
Left: A fisherman casts his net on the western tip of the island, near Rincón.
8 of 16Photo: David Hillegas
Nothing beats mornings in Puerto Rico, where the sunrises are always staggering and church bells ring in every town, from metropolitan San Juan to the tiniest beachside hamlets. Breakfast is always a treat, given the island's abundant fresh fruit and famous locally grown coffee.
Left: Fresh fruit and yogurt at the Horned Dorset Primavera
9 of 16Photo: David Hillegas
Whether your tipple of choice is a cocktail or coffee, you can't go wrong in Puerto Rico's countless bars, quirky cafes, and coffee shops. As early as 3:00 in the afternoon, expect to see both locals and tourists stopping everything for a social sipping break.
Left: Cocktails and Spanish tapas at El Picoteo in Old San Juan
10 of 16Photo: David Hillegas
The upscale seafood restaurant Perla is located in the whimsically shell-shaped newly reopened La Concha hotel in Condado, a district of San Juan along the Atlantic Coast. The 1950s folly survived numerous calls to tear it down and was restored by a local architect.
11 of 16Photo: David Hillegas
Spectacular views surround the restored—and still working—1882 Faro de los Morillos de Cabo Rojo, which guides ships through the passage where the Caribbean sea and the Atlantic Ocean meet. An easy 10-minute hike gets you to the lighthouse, which stands at the top of a 200-foot limestone cliffs and has views of the stunning blue Caribbean. Stop off at nearby La Playuela Beach, a sandy cove in a nature preserve. For more information call 939/630-5180.
12 of 16Photo: David Hillegas
Fly to San Juan International Airport—there is direct service from several U.S. cities—and rent a car in San Juan to get to areas outside the city. (Avoid driving in Old San Juan.)
Left: A dog peeks out of his streetside living room.
Left: Coffee and homemade guava cookies at Cafícultura
15 of 16Photo: David Hillegas
Where To Drink
El Batey Bar in Old San Juan features dim lighting and graffiti-covered walls; 101 Cristo (no phone). El Picoteo at El Convento serves festive cocktails and tapas; 787/723-9020 or elconvento.com. In Rincón, go to Banana Dang for a java fix; 787/823-0963 or bananadang.com. Sip cocktails and eat sushi with surfers at the Pool Bar; 787/823-8135.
Left: Grab a snack at the Pool Bar in Rincón, founded by Yuri Palchevsky (pictured) and Allison West.
16 of 16Photo: David Hillegas
Where To Shop
Old San Juan is a shopper’s paradise. Try Concalma (207 Calle San Francisco; 787/729-0800) for handbags and totes manufactured by a women’s cooperative in the mountains of Puerto Rico; El Alcazar (103 Calle San José; 787/723-1229) for colorful art, furniture, and antiques; Frankys (363 Calle San Francisco; 787/722-6691) for accessories from the 1940s, ’50s, and ’60s; and Cappalli Store (206 Calle O’Donnell; 787/289-6565) for fashion designs by Lisa Cappalli, K. Jacques sandals, and other chic accessories.
Left: Zaidy Santoni models a funky tote at Concalma