My first impression of San Juan wasn’t good. Leaving the airport, I thought I’d travelled to an overdeveloped American playground of casinos and high-rises linked by freeways – a Caribbean version of Florida. But as if by magic, everything changed when I crossed the bridge to the historical heart of Puerto Rico’s capital, Old San Juan.

'New' San Juan

‘New’ San Juan

The roads narrow to European width and you’re immersed into a town of tightly packed, balconied, Spanish colonial buildings – housing, shops, bars and restaurants. Every few hundred yards the lanes open out into squares and piazzas, most with a fountain at the centre. It’s the colour you notice first – the buildings are painted like a tube of Smarties!san-juan_street-1 san-juan_street-2 san-juan_street-3 san-juan_street-4 san-juan_street-5

My guide, Javier Ruiz, from Private Tours of Old San Juan explained that planning regulations mean you have to gain approval for painting property in the old town. Adjacent buildings must be different colours even if you own both or they are connected internally.

Javier Ruiz

Javier Ruiz

You can easily spend a day wandering around this beautiful, historic city. Even the cobbled streets are colourful. The early builders used river rocks for road surfacing but they became slippery when wet, so they coated them with furnace slag brought over as ship’s ballast from Spain. The humid environment has turned the stones blue. Later on, during my food walk with Flavors of San Juan Food and Culture Tours, our guide explained the process. “The stones started oxidising over the years because of the humidity from the ocean and Puerto Rico’s 63 inches of rainfall each year. The cobbles have become iconic and there is a fine for removing any loose ones.”san-juan_blue-cobbles

Although Puerto Rico is a US Territory, Old San Juan couldn’t be less American. It’s more like Seville or Sitges in Spain. Spanish is spoken in the street and Latin rhythms fill the air. I was surprised to find a band of eight men dressed like Shakespearean actors in tights and baggy breaches. These students mix traditional Spanish instrumentation with Puerto Rican music. They’re known as Tuna Bardos and many Spanish universities have similar groups who perform as the 15th century troubadours would have. The lads regularly play functions around the old town and member Charles Sanchez told me that dressing up in the Spanish clothing of the era showed their commitment in such high heat!san-juan_tuna-bargos-1

Unlike most US cities, Old San Juan is not designed for cars. It’s single file traffic in the narrow streets. I even saw opportunists standing in the road next to vacant parking spaces, flagging them up to passing motorists for a finders’ fee. Space is tight because this strategically important base for Spain was well fortified.san_juan_space_minder

A thick tall stone city wall ribbons the compact town. On three corners, mighty forts protected the inhabitants. These should be on your itinerary. Javier explained that each fort was built at a higher elevation than the last so if the first defence was taken they could attack from a higher position. “La Fortaleza was built to protect the port. But there was a problem. If the enemy made it all the way to the beach it was too late, so they had to build another fort on the tip of the island and then build the third fort on the other side. The original tower was turned into the governor’s mansion and over 160 governors have lived there since the 1540s.” Legend states that the first governor, Juan Ponce de León had been killed by Indians where the fountain of eternal youth was located. Clearly the water had not worked.san-juan_fort-1

These mighty fortresses helped protect the walled town as a safe haven for galleons carrying gold and silver. Old San Juan used to be locked down at night but only one of the four city gates built into the wall remains.san-juan_fort-gate

In the old days, if you weren’t on the right side of it at 6pm you’d be sleeping out in the mosquito-ridden swamp. “There used to be a wall going all around the city but they demolished part of it because they needed the city to grow. Today, 3,500 people live within the old town but it used to be 40,000, so they had to expand outwards because disease was rife in the poor sanitation caused by cramped conditions. It is a shame they demolished around 30% of the wall but luckily the ocean borders most of it,” explained Javier.

Luis Salva had told me that Old San Juan looks even more impressive from the water, so I met him next to the cruise ship terminal for the 60-minute sunset boat trip he offers as San Juan Water Tours. Soon we were on the water just a few feet off the magnificent Del Morro fort, towering high on the hill with thick walls built into the cliff face. You can tour the fort’s different levels as I did and look at the gunpowder batteries and take in the impressive view.

san-juan_castillo-san-felipe-del-morro-3 san-juan_castillo-san-felipe-del-morro-2san-juan_castillo-san-felipe-del-morro-from-boat-2 san-juan_castillo-san-felipe-del-morro-from-boat-1“Every so often you’ll see a guard post called a garita. In those days there was a guard assigned to each one of those to look out for enemy ships that may try and attack the city,” Luis explained. “You can see how elegant the fort looks from the water. You can appreciate the whole wall at sunset and all the important and historic aspects of this elegant and magnificent city.”


The huge, multi-level fort took 200 years to construct. “When we’re cruising we’re probably 100 feet from land. We try and keep as close as we can to these landmarks so you can appreciate the magnificence of the historic buildings and the whole wall gives you a sense of the age. You can imagine what it must’ve been like to come to Puerto Rico in the mid-1500s. You can still walk through the gate – I remember as a child my dad used to drive through it.”

Javier’s customised tour will take you to places in Old San Juan that most visitors would not find. The city has many tiny museums, often run as labours of love. We called into the Pharmacy Museum, where Yolanda Velazquez showed me around an authentic replica of a 19th century chemists.

Yolanda Velazquez

Yolanda Velazquez

We also called into the Casa del Libro, a museum dedicated to the history of books where you can see one of the first printed bibles. “They have collections of old books that people don’t know about. They even have a page from the original 1450s Gutenberg Bible,” said Javier.san-juan_casa-del-libro

San Juan used to be the seat of Christianity for this region and was the place where the Bishop administering Central America and the Caribbean was based. There’s a lot of religious heritage, because of the town’s role. Over thirty chapels lie within the square mile of the Old Town, which also contains the oldest church and cathedral in the region.san-juan_san-francisco-chapel

Inside the 1700s San Francisco chapel there’s a splinter, which is said to be from Christ’s crucifix. It’s preserved in a glass case. Javier spoke with the priest and it was brought out for me to see. Javier translated as the clergyman explained that it was brought over by the Spaniards and is blessed each Good Friday.san-juan_relic

Despite the forts and walls, which have been granted UN World Heritage Status, locals still felt vulnerable and feared invasion. There’s a rabbit warren of tunnels under the town that locals built as boltholes or emergency escapes. “We keep finding tunnels. Every time you dig something in the town you find another one. They weren’t built as part of the masterplan – every neighbour built their own. If you had a house, you built a tunnel so you could escape in case of invasion or you could put your children in a safe place and fight the enemy,” said Javier. Today, homeowners use blocked off tunnels as wine cellars. The Rosa de Triana restaurant repurposes part of an underground passage as a dining area.san-juan_restaurant-tunnel

I visited the eatery to sample the local food on a guided walk with Flavors of San Juan Food and Culture Tours and it was a ‘hands on’ experience. We were given a mortar and pestle to mash up fried green plantain, roasted garlic and butter. It’s added to rice and beans to make the traditional local dish called Mofongo. It was really hard work mixing the ingredients together and making sure the buttery mixture didn’t splatter your neighbour. Chicken or seafood is added to make a creamy, almost risotto-like dish.

san-juan_pestle-and-mortar san-juan_food-1I learned that Puerto Rican food is considered to be creole. Local dishes have the taste of sofrito – that’s the seasoning created by frying two types of coriander, olives, garlic and chopped peppers in olive oil. Cooks leave that in their fridges and add a couple of spoonfuls to the cooking pan. We also learned about majorcas on the tour. They are sweet bread rolls with powdered sugar on top and locals add savoury or sweet fillings, including egg. They’re a bit like a croissant, but not as flaky, and were introduced from the Balearics.


The many stops of the food tour also included an artisan ice-lolly maker. A local couple have started producing a range of ices with flavours represented by all shades of the colour spectrum. My brownish lolly was deliciously flavoured like Nutella. I’d recommend Senor Paleta’s shop.san-juan_lollies san-juan_lollies-2

You’ll get a good cup of coffee in Puerto Rico too. The island was once the sixth largest exporter in the world although now only 15% of locally consumed coffee is sourced here. Paolo Garcia from the Princesa Gastrobar, another stop on the food tour, told us that the island’s coffee is historically very sweet and is light roasted to avoid bitter tastes. “Locals will tell you the story that the Pope, at the turn of the 19th century, repeatedly requested that the Vatican served Puerto Rican coffee,” Paolo explained. “The Three Angels Plantation coffee is still sold in Italy as a gourmet coffee.”

san-juan_night-2 san-juan_night-1 san-juan_night-3 san-juan_night-4Old San Juan has a relaxed, friendly nightlife with lots of intimate bars, many lit by candles. Some, like the cocktail bar at La Terraza Hotel, only seat a half a dozen people. It’s just an open doorway off the street with six bar stools next to the counter. But you can sample a wealth of cocktails here including Puerto Rico’s Piña Colada. We enjoyed one on the food tour. The origin of the world-famous rum and coconut cream drink is contested. Both the busy and rather touristy Barrachina and the Caribe Hilton claim to have concocted it first.

san-juan_pina-colada-signI’d recommend the food tour to get a real taste of San Juan. The island has its own distinct culture, heritage and tastes. One waitress told me she was fed up of people asking for tortilla chips because they heard Spanish being spoken and ignorantly assumed that food here was the same as in Mexico.

Both Luis and Javier are proud Puerto Ricans and are happy to answer questions about life in the territory – good and bad. Not everyone is content with the way the US administers this area, as you will discover if you ask about it. Puerto Ricans had no say in the presidential election, so they’re in no way responsible for Donald Trump’s success! Yet they pay taxes to the US.

One of Puerto Rico’s biggest income generators must be the Bacardi Distillery. Around 250,000 people take a ten-minute ferry ride across the water from the Old Town to Cataño each year. The ferry ride is cheap, less than 50p, with good views back over the city. On the other side you catch a bus for the ten-minute drive to Bacardi. A $12 ticket gains you entry and you wait for you tour guide in a rather cool, open air pavilion – a huge, white canopy – that’s meant to be in the shape of a bat, Bacardi’s logo, but actually looked more like a nun’s wimple!

san-juan_bat-building san-juan_cathedral-of-rumMy guide was Señor Riveria. He told me his first name. “With a name like Jesus, you know you’re in good hands,” he joked. I suspect he’d used that line before. There’s a restaurant and lots of gift shops. You don’t actually go in the distillery but you get to learn about the company’s heritage and history, how they make rum, smell the product as it goes through production stages then taste the different types. You can opt for a cocktail making mixology course too.

Jesus Riveria

Jesus Riveria


Inside the visitor and tour centre, Jesus gave me an overview of cocktails. Mojitos were originally named the ‘Drake’ after Sir Francis. He had his men drink them for the vitamin C in the lime. Daiquiris are named after a small town near the mineral quarries in Cuba. The name stuck because it was easier than naming all the ingredients when requesting the drink from a bartender.

At the gift shop you can buy their top-of-the-range rum and fill your bottle from a massive barrel. You then seal it or have the bottle engraved with a special message. There’s a lot of theatre involved with that process. Overall, the presentation was slick and well polished but it is a big promotion for the Bacardi brand. Not all locals drink Bacardi either, despite what you’re told on the tour.san-juan_shop san-juan_shop3

On the way back to Old San Juan, make sure your camera lens cap is off. We were crossing the harbour where Luis had shared interesting sealife-spotting stories on the previous evening. “We see dolphins and manatees and green turtles. They come into the harbour to seek refuge. We see impressive fish too, including tarpon,” he told me excitedly.

san-juan-boat-tour-3 san-juan-boat-tour-1

The Atlantic Ocean is just a mile away and Luis says you can often see male stingray leap out of the water. Apparently the higher they jump, the more love action they’ll get. It impresses the lady stingrays.


I spotted pelicans – they were perched on a tree. Luis explained that they eat sardines that swim in the harbour and you see them going under and grabbing the fish. As we spoke parrots, almost fluorescent green in colour, chased each other overhead. “They are from the Dominican Republic,” Luis told me. “We have our own Puerto Rican parrots but they’re down to fifty pairs now. They’ve been raising them in captivity and recently released fifteen into the rainforest.”

Back on dry land, more wings caught my attention in the window of a gallery. The Butterfly People had covered every available space on its white walls with framed butterfly art. The specimens were all in-flight and the displays were incredibly colourful. Cirene Revan’s parents started the business 47 years ago. As a child she had mobiles above her crib that her granddad made with real butterflies. “They don’t kill them – it’s just that they have a short lifespan,” she told me. They import the butterflies from all over the world and some of the works are commissioned by people who want an arrangement in a particular colour.san-juan_the-butterfly-people-1

You can see more bright tropical hues in the flowers at San Juan’s Farmers’ Market. Javier took me to look around and see the abundance of fruit and vegetables grown in the fertile soil. Each Saturday morning the museum courtyard is filled with both music and merchants. A flower vendor’s loud cries cut through the salsa music for a few seconds. Saul Darila has walked the Old Town’s streets selling beautiful blooms for 25 years.

san-juan_market san-juan_flower-sellerSan Juan’s Old Town is safe for tourists but crime can be a problem outside the walls and there’s an infamous ghetto called La Perla just a few hundred metres from the Del Morro Fort. Locals will point out where it is but you’ll probably get a sense that you’re straying into a dodgy area for tourists.

La Perla

La Perla

Craig Lindemann has recently relocated from mainland USA and told me you’re safe within the walls. There’s a high police presence because of the governors’ and government offices and the number of tourists. I noticed cops standing on duty at fixed points well into the night. “I see little old ladies walking home with groceries at midnight and they are perfectly safe,” Craig assured me. “Unless you go down to La Perla, there seems to be an unwritten rule with the state that you don’t interfere with them and they won’t bother the tourists.”

I stayed two nights in Old San Juan and it’s great for a city break or a stopover heading to Central America, the US or Caribbean. You might want to stay longer and explore the rest of the island. There’s 3,500 square miles of it! Be sure to arrange your travel beforehand though – public transport is non-existent. You can hire cars but road surfaces and driving standards are poor.

Norwegian fly the nine-hour route from Gatwick and you can get a return in March for £329.

For More Great Travel Articles Please LIKE US on FACEBOOK