Old San Juan, Puerto Rico

The second oldest city in America, Old San Juan is an array of pastel hued Spanish colonial architecture combined with vibrant squares where a stroll up and down its cobbled streets offers a window into this Caribbean island’s past — and present.

The Small List

  1. Punto de Vista - Located on the rooftop of the Hotel Milano this lively restaurant serves up authentic Puerto Rican fare and cocktails. The views of the old city are stunning!

  2. Oceano - The modern architecture, stylish design, relaxed and seductive ambiance draws a hip crowd and offers a standout nightlife experience. Posh and impressive, Oceano is the trendiest venue in the Condado beach area.

  3. Castillo San Cristóbal - Named after the saint patron of land travelers, Saint Christopher, Castillo San Cristóbal, is considered the largest fortress built in the Americas. It was built for the purpose of protecting the city of San Juan from attack by land from the east. It is a fortification with three levels and an extensive series of outer defenses and it took over 150 years to complete.

  4. Condado Vanderbilt Hotel - The festive city of San Juan is the perfect place to experience true Puerto Rican culture, and Condado Vanderbilt is the perfect jumping off point. The Vanderbilt Hotel is the perfect oasis for exploring the sights and sounds of this vibrant city. This hotel is where luxury, elegance and style began in San Juan, Puerto Rico.

  5. Cafe Cuatro Sombras - Sit in this rustic coffeehouse where they roast, grind, pack and serve their specialty coffees every day. Enjoy the ambience and a cup of 100% Puerto Rican coffee.

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