Old San Juan, the oldest settlement in Puerto Rico, occupies a small island off the coast of the main island. Get there by driving across one of three bridges, and you’ll find yourself in a world dating back to 1508. 

This historic city is a stunning example of colonial heritage in Central America and features over 400 restored buildings from the 16th and 17th centuries. A great way to discover the quaint beauty of the walled city is on foot. The cobblestone streets of Old San Juan are lovely to explore and the distance between attractions isn’t far. Be forewarned, though: the afternoon heat can be taxing. Luckily, there’s some shade to be found and cafes to stop in for a cool drink. 

The San Juan National Historical Site houses all of the major historical attractions in the city. See the Castillo San Cristobal, an enormous fortress built by the Spanish in the 18th century. Make your way to the Institute of Puerto Rican Culture for a great education in the customs, traditions and culture of the diverse local people and their shared history. 

Old San Juan is home to many traditional Caribbean restaurants and bars where you can sample the local cuisine and cocktails. Whether you’re looking for a romantic evening for two or a family-style meal, this is a great evening destination. 

Old San Juan is located approximately 35 miles (55 kilometers) from the main island’s eastern tip. No public transportation services the walled city, so come by rental car or taxi. Be aware that the cobblestone streets are narrow and often one way, so  the best way to sightsee is on foot. Old San Juan can be visited daily, and the shops and restaurants are open during normal business hours.