San Juan, Puerto Rico: Historical Architecture, Dynamic Nightlife, and Relaxing Beaches

El Morro in Old San Juan is a massive stone fortress built by the Spanish in the 16th century to guard the coast of Puerto Rico from invasions. Today, the grounds surrounding the fortification are used for a much more benign purpose: kite-flying. Families converge on the spot on weekends, taking advantage of the coastal breezes to send their colorful creations soaring over the ramparts. Surrounded by a 20-foot-thick stone wall, Old San Juan boasts distinctive blue cobblestone streets lined with colonial-era churches and theaters alongside open-air taquerias and hip nightclubs that stay open into the wee hours. This historic center of the island’s capital city is just one stop on Beyond Boundaries Travel’s Puerto Rico tour spotlighting modern and historical culture. Conrad San Juan Condado Plaza hotel serves as a posh home base.

Click here to view the full itinerary.

Day 1 : After settling in at the trendy Conrad San Juan Condado Plaza, you can spend your first day exploring the bistros and museums of nearby Old San Juan. For dinner, sample entrees such as petit duck magret and North Atlantic swordfish at the hotel's posh Pikayo Restaurant, which draws from African and Asian influences. When it’s time for bed, you’ll retire to a stylish city-view room overlooking Old San Juan and San Juan Bay.

Day 2: An English-speaking guide leads you along the famous blue cobblestone streets of the historic district, located just minutes from the hotel. Along the Paseo de la Princesa, you can hear live salsa tunes, find local artisans selling handmade wares, and take in views of the ocean.

At the Bacardi Rum Factory, you'll delve into the world-famous distillery’s 150-year history. Exhibits trace Puerto Rico’s role as a leading exporter of rum, from the Spanish colonial days through Bacardi's founding in 1862 to today. You can see a collection of vintage ads and tour a life-size replica of the company's first distillery. A nosing station lets you sniff various spirits, and the tour concludes with a sampling of Bacardi drinks.

After a day packed with tours, spend the evening relaxing at the hotel or try your luck at the 24-hour casino, which is equipped with 350 slot machines.

Days 3–4: On these free days, you can take advantage of the resort's natural surroundings or explore Condado's boutiques and restaurants. With Condado Lagoon on one side and the Atlantic Ocean on the other, the resort is ideally situated for water fun. You can rent a standup paddleboard or a kayak onsite. The resort's three swimming pools include one with saltwater and another with a slide.

For an additional cost, you can check out optional excursions ranging from a hike through El Yunque rainforest (the only tropical rainforest in the United States) to a boat ride through Bioluminescent Bay, where hundreds of thousands of micro-organisms give the water an eerie, blue-green glow.

Day 5: As the trip comes to a close, you'll head back to San Juan's airport for the return flight home.

Read the Fine Print for important info on travel dates and other restrictions.