Narrow cobblestone streets, cute little squares with spraying fountains and huge trees, enormous Spanish-built forts and restaurants serving spicy Mexican and Cuban fare are not normal in most U.S. cities.
But then little about San Juan, Puerto Rico is normal. It is far from what we expected. My scant knowledge of Puerto Rico was strongly influenced by the musical West Side Story where white and Puerto Rican gangs battle for the streets of a section of New York.
What my wife and I found were colourful buildings, delightful architecture, friendly people, and a love for an island that has a unique relationship with the U.S.
Puerto Rico is technically part of the United States. Puerto Ricans are U.S. citizens, and make up about 1.3 per cent of the total population of the country. They enjoy all the benefits of citizenship, except one: Puerto Ricans who live in Puerto Rico cannot vote for the U.S. president.
But it is not this straight forward. In the Olympic Games, Puerto Rico fields its own athletic team, separate from the U.S. Puerto Ricans don't file federal income tax returns, unless they work for the U.S. government. Bookstores in the U.S. put travel guides to Puerto Rico in their "International Travel" section rather than "Domestic Travel," where they belong. No wonder we were confused!
Nearly two million people live in, or near, San Juan and many of them rarely set foot in Old San Juan. For tourists it is entirely different. Many visitors see nothing of the wider city except for the drive from the airport to the old city.
Old San Juan lies within a 500-year-old walled citadel that has been declared a UNESCO World Heritage Site. Medieval masonry and cantilevered balconies seem to float above the narrow cobblestone streets below. The streets are perfect for wandering and seem to insist you explore all their secret nooks and crannies.
They are lined with antique iron lampposts, arty shops and souvenir stores. There are pavement cafes in the squares and beautiful old buildings and churches look out to wide views of the ocean.
Cool courtyards done with European flair hide behind the shops and pavement cafés, inviting you to enter. It is more Spanish than many areas of Spain.
In 1493, Christopher Columbus "discovered" Puerto Rico and claimed it for Spain. Some years later the Spanish started their colonization. Puerto Rico's geographic position at the western edge of the Caribbean made San Juan one of the key frontier outposts of Spain's West Indies Empire.
The Spanish built a small fort here in 1540 and then constructed the walls that encircled the city in 1634. The work continued into the mid-1700s when the King of Spain decided to make San Juan virtually unconquerable.
The walls, and two massive forts, are some of the major attractions today. No visit would be complete without spending time exploring the fortifications and marvelling at the impressive structures. Guided tours are available for those who want them.
Elsewhere in the city, the Cathedral, which was commenced in 1521, is worth seeing and there are several museums. The Museum of the Americas is in a wonderfully restored building while the Museum of Art has local works displayed in a building, which itself is a work of art. The Casa Blanca Museum showcases life in the 16th and 17th centuries.
Old San Juan is reasonably compact but it is hilly and usually hot. If you are not comfortable with a lot of walking, there are free trolleys that will take you around the old city.
The area has some excellent restaurants, fast food outlets, markets, shops and several small hotels. The Hotel El Convento is generally considered the best (and most expensive) accommodation, but there are several others in charming old buildings with Spanish ambience.
Souvenir shopping in San Juan is a treat, or a nightmare, depending on your point of view. The Old City could be one of the most souvenir-clogged areas on the planet but there are some interesting buys amongst the "junk." Iconic vejigante masks are found at numerous shops, hand-carved wooden figurines of saints called santos are unusual buys, and hand-made Panama hats are useful and a great keepsake.
Outside the Old City, Condado hugs the beach to the east, and has many similarities to Miami Beach. Here's where expensive hotels, and the casinos inside many of them, attract nightlife-seeking locals and tourists alike.
A final suggestion is to visit the slick Casa Bacardi Visitor Center across San Juan Bay in Cataño. You'll pass through seven different zones covering both the history of the company and the rum-making process and have a taste of some of the brew. The best part is that it's all free.
Getting There: The major U.S. airlines fly from Canada to San Juan via mainland USA.
Visas: Puerto Rico is technically part of the U.S., so the same entry requirements apply.
When to Visit: Puerto Rico is hot between June and September and warm at other times of the year. January to March receives less rain than other months.