If you came to work on your tan—and you came to do it on a big, beautiful Caribbean beach—consider staying in Isla Verde, home to the nicest beach in the metropolitan area. The main commercial strip is not especially attractive: it's filled with fast-food restaurants and other businesses. You'll also need a car or taxi to get anywhere. That said, the resort-style hotels (many of them beachfront) offer so many amenities and so many restaurants on-site, you may not want—or need—to leave very often.
South of Condado is Miramar, home to a few hotels and a handful of the city's top restaurants. Seedy in spots, thriving in others, it's worth a visit if only to see what the innovative chefs are doing. From there you can venture into Santurce, a mostly commercial district with a growing artistic community, thanks to the Museo de Arte de Puerto Rico and the Museo de Arte Contemporáneo. You'll also find a thriving nightlife scene there on weekends. Hato Rey is a busy financial district, where you'll find the large Plaza las Américas Mall. The mostly residential Río Piedras area is home to the Universidad de Puerto Rico.
If You Have 1 Day
Many people find themselves with a single day—or even less—to explore San Juan. There should be no question about your destination—head to Old San Juan. Spend the entire day rambling around the cobblestone streets and ducking into the many shops, being sure to save plenty of time for exploring the turrets, towers, and dungeons of Castillo San Felipe del Morro, the original fortress on a rocky promontory at the Old City's northwestern tip.
If You Have 3 Days
It's only fitting that you spend the first day enjoying a walking tour of Old San Juan. What to see? Castillo San Felipe del Morro is at the top of the list. You might want to explore the equally enthralling Castillo San Cristóbal, which has underground tunnels and hidden passages, plus cannons and a more impressive museum than San Felipe del Morro. The city's original fortress, the Fortaleza, wasn't much protection from marauding pirates, but it does a great job at sheltering the governor and can be toured. And Casa Blanca, a home built for Juan Ponce de León, is a wonderful place to explore how the Spanish lived in the colonial days, though at this writing, it was undergoing a lengthy renovation. Day two should be for lazing on a playa (beach). Choose from the city's finest at Condado, Ocean Park, or Isla Verde, and park yourself in a rented chair with a good book, a cold drink, and plenty of sunscreen. In the evening, make sure you enjoy the warm weather by dining alfresco. On your third day, hop the ferry across the bay to Cataño for a tour of the Casa Bacardí Visitor Center. Return in time for some shopping in the high-end shops and delightful arts-and-crafts galleries along Calle Cristo, then dinner in one of the trendy eateries on Calle Fortaleza.
If You Have 5 Days
Follow the itinerary above for your first three days in San Juan. On Day 4 head for the Santurce district. You can immerse yourself in island art at the Museo de Arte de Puerto Rico and, nearby, the Museo de Arte Contemporáneo de Puerto Rico. Afterward, wander through the produce stalls at the Plaza del Mercado in Santurce, with a fresh papaya or soursop shake in hand, and have your palm read. Be sure to note the giant bronze sculptures of avocados by artist Annex Burgos. On the morning of Day 5, hit the beach once more; then head to Avenida Ashford in Condado for an afternoon of shopping in its ritzy boutiques.
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