With a mix of rich history, unique culture, fascinating Colonial Spanish architecture, and stunning natural beauty, surrounded by a breathtaking coastline, there are so many things to do in San Juan, Puerto Rico, that it’s hard to know where to start. San Juan is just a two-and-a-half-hour flight from southern Florida, making it an easy getaway destination for a long weekend as well as a popular port of call on cruise ship itineraries.
Prior to the arrival of Columbus in 1493, this island paradise was populated by the indigenous Taino, but when the Spanish Conquistadores arrived, their destiny changed forever. Over the following four centuries, despite numerous attempts by English, Dutch, and various French privateers to take over this strategically placed island, Puerto Rico remained in Spanish hands. Then, as a result of the Spanish-American War, it was ceded to the US in 1899.
Today Puerto Rican culture is a fascinating mix of Taino, European (mainly Spanish), American, and African (as a result of the horrific slave trade). Citizens of Puerto Rico are US citizens but don’t have Congressional representation or electoral college votes. Full-time residents, with income only from the island, pay no federal income tax. The questions of statehood, along with other political issues frequently arise accompanied by spirited debate. I think it will be interesting to see how the political future of the island is shaped over the next few decades.
We’ve been to San Juan many times, both on a land vacation and as a port of call on a cruise itinerary. I most recently visited on a Caribbean cruise, and while it’s not enough time to see everything San Juan has to offer, it was a chance to revisit a few favorites.
An island visitor could easily spend months here and not get to see and experience all the delights of this Caribbean wonderland. By no means a complete guide, this is just a small sample of some of the best things to see and do when visiting San Juan, the capital of Puerto Rico.
Let’s get started!
Castillo San Felipe del Morro
Any visitor arriving in San Juan by boat gets their first sight of this imposing fort as they approach the harbor. With its massive stone walls,130 feet tall, and bronze cannons facing the sea, the fort guards the entrance to San Juan Bay. Steeped deeply in history, the construction of this citadel began in 1539 on the orders of King Charles V of Spain. Continual modifications and additions occurred over the next 250 years.
Over the 16th, 17th, and 18th centuries, San Juan successfully repelled numerous attacks from various competing colonial powers. The result was that the island remained in Spanish hands until 1899 when ownership was ceded over to the United States. It also played its part in WWI, when in March 1915, it opened fire on a German ship, preventing it from delivering supplies to German submarines in the Atlantic. These were the first shots fired by the United States in WWI, although the war wasn’t officially declared for another two years. During WWII, the fort kept watch for German U Boats, which were ravaging US supply ships in the Caribbean and Atlantic.
El Morro is a magnet for so many of the island’s visitors and in 1983 it was declared a UNESCO World Heritage Site. Going on a guided or self-guided tour into the dungeons, barracks, and around the immaculately kept grounds, will give you a sense of military life all those years ago. Below the walls on the eastern side of El Morro, the white marble tombstones and statues of the Santa Maria Magdalena de Pazzis Cemetery and the Castillo de San Cristobal in the distance with the colorful houses of La Perla sandwiched in between, make a great place for photographers.
If that history doesn’t feel compelling, the panoramic views of the ocean, San Juan Bay, and the city from the top of this six-story fort, are to die for. Make sure to return after dark when the castle is all lit up, it’s spectacular.
A $10 fee gets you into El Morro as well as the equally impressive Castillo de San Cristobal less than a mile away.
Castillo de San Cristobal
The heavily fortified Castillo San Cristobal is just a few minutes walk from El Morro. It was built during the 18th Century, and is the largest of the Spanish forts in the Americas, housing the infamous Garita del Diablo (Devil’s Sentry Box). Protruding out into the ocean and far from the others, legend has it that a sentry, called Sanchez, mysteriously disappeared from this post one night, leaving only his uniform and rifle behind…and so, the legend was born.
The sentry box is inaccessible from the fort, but you can view it if you’re prepared to approach it from the rough and rocky La Perla shoreline. If you’re a fan of spooky stories, visit after dark. It’s said that you can hear the sound of laughter and Sanchez playing his guitar!
Paseo del Morro
You can begin and end this scenic walk at the Raices Fountain on Paseo de la Princesa. Walking alongside the historic old city wall, you pass the San Juan Gate, through which arriving sailors would walk on their way to the San Juan Cathedral to give thanks to God for the safe passage they endured across the ocean. And, you’ll get stunning views of San Juan Bay every step of the way.
When you reach El Morro, the 18-40 feet thick solid stone walls will also give you a sense of the scale of this structure and the intimidating sight that faced any would-be invader. The path sweeps around the fort where several raised viewing platforms offer views of the Atlantic Ocean and the castle behind you.
Old San Juan City Tour
This historic part of the city is bursting with culture, history, and vibrant colorful architecture dating back to the early Spanish colonial times, Around each corner of these cobblestone streets of San Juan is a feast for the eyes. Cathedrals, art museums, monuments, and the city’s oldest buildings are everywhere, while hotels, local restaurants, bars, and street vendors, offer all the delicious flavors of Puerto Rican cuisine. Come hungry!
In and around the Old Town you will find numerous places of interest. Here are just a few.
La Fortaleza (The Fortress)
Built as a fort during the 16th Century, La Forteleza was later converted to the governor’s house and office. It’s a functioning government mansion. Guided walking tours are available through this historic building and lush gardens when the government is not in session.
Catedral de San Juan Bautista
This is the oldest cathedral in the US and the second oldest in the Western Hemisphere. The original church was built in 1521 during the earliest period of Spanish colonization. It was destroyed in a hurricane some years later. Over the centuries, this cathedral has had its fair share of turmoil and tragedy in the form of hurricanes, robberies, and vandalism. The worst damage was caused when the English ransacked the city and looted the church in 1598, and then again in 1615 when a hurricane blew the roof off.
Although small in comparison to other churches, it is absolutely stunning. The well-trodden marble floor, high beautifully painted ceiling, colorful stained glass windows, artwork, and sculptures, all showcase its 500 years of history. It also contains the tomb of Spanish explorer Juan Ponce de Leon.
Hotel El Convento
Just across the street from the San Juan Cathedral, is the historic Hotel El Convento. Built as a convent in 1646, it was closed in 1903 and restored and converted to a luxury hotel in 1962. This elegant hotel, situated within walking distance of so many historic sites, offers the perfect alternative to the highrise chain hotels on the Condado strip.
With 58 rooms, El Convento gives you the best of both worlds – the opulence of Spanish colonial architecture, each room adorned with vintage antique furnishings, while offering all the modern amenities any guest in the 21st Century would expect. Their restaurant offers Spanish and Puerto Rican cuisine, while the views of San Juan Bay from the plunge pool and heated Jacuzzi on the terrace are lovely.
We stayed at the El Convent on our first visit to Puerto Rico and it has remained a favorite.
Capilla del Santo Cristo de la Salud
Just three blocks down and tucked away in a little corner is a tiny chapel with a big history. Its story begins in 1753 during the San Juan Bautista celebration when a horseman lost control of his horse and plunged down the cliffs to sure death. Watching the drama unfolding before his eyes, the Spanish Government Secretary cried out “Christ of Good Health save him!” The horse was killed, but the rider miraculously survived.
The rider, Baltazar Montanez, built the chapel on the exact spot where he fell over the cliff to celebrate his miracle. Ever since, people have come here to pray for their own miracles. Beautiful oil paintings, various Christian ornaments, and an altar covered in silver and gold leaf decorate this humble chapel. It is maintained by a group of local volunteers called the Sisterhood of the Holy Christ of Health.
Pause at the Plaza
In among all the historic buildings and monuments, pause for a while in any of the six plazas and watch the life and soul of the old town around you. The little cafes, bistros, vendors, street entertainers, and the local Puerto Ricans add life, color, and a festive vibe to the area.
Cool down with a fruity piragua (fruity shaved ice dessert) or grab yourself a tripleta from the nearest food stand. Don’t worry about what it is, just buy one. They are delicious! (It’s a sandwich with steak, pork, and ham.) If you have young children with you, head straight to the Parque de las Palomas (Park of the Pigeons). While the kids go crazy feeding the birds, a great way to let off a little steam, you can soak in the scenery of San Juan Bay and perhaps catch a luxury liner sailing past.
Holocaust Memorial Monument
A few hundred yards southwest of San Cristobal on Constitution Avenue is a monument you may not expect to find in Puerto Rico – a Holocaust Memorial Monument. Although not as elaborate as other monuments, it is simple, moving, and powerful, lest we forget the atrocities committed by human beings against human beings not all that long ago. It’s worth stopping at this beautiful spot to pay your respects and to let it serve as a reminder that such tragedies must never be allowed to happen again. There is no admission fee.
Walkway of the Presidents
There are various memorials on Constitution Avenue, including the Walkway of the Presidents barely 50 yards from the Holocaust Monument. This is a small outdoor park with life-size bronze statues of the nine US presidents who have visited the island.
Puerto Rico Capitol Building
While you’re in this history mode, walk across the road from the Walkway of the Presidents to the grand white-marbled Puerto Rico Capitol. With the American and Puerto Rican flags flying side by side in front, you can’t miss it.
Construction on this neoclassical style building began in 1925, with the dome completed in 1961. Exquisite murals and mosaics depicting the rich history of Puerto Rico adorn the walls and ceiling of this building. Entry is free
Enough culture and history stuff. Let’s hit the beach!
Hit the Beach
If you can’t resist the lure of the ocean, there is no shortage of beautiful beaches on which to spend the day. Here are just a few of the best ways to enjoy the San Juan beaches.
Within walking distance from the old town is arguably one of the best beaches on the island – El Escambron Beach. Protected by a coral reef, with fine white sand and tall palm trees offering relieving shade, Playa 8 (Main beach) is perfect for the whole family to enjoy. It’s one of the best places to swim, snorkel or play. Scuba diving is popular from here (and also at Playa 9 slightly to the east). The water is crystal clear with a wide variety of marine life, including turtles close to the drop-off. It’s hard to believe you are in the middle of a city.
A little to the east you’ll find the famous strip with its long and beautiful Condado Beach. Fringed by numerous high-rise hotels, up-market resorts, beach bars, and eateries, all bustling with people, this is a perfect spot to catch a stunning sunrise.
If you want to escape the madding crowds try Ocean Park Beach, a little to the east. It’s a far less crowded beach, and although the water can get a little rough here, it’s perfect for surfing. An abundance of cafes and bars make this a popular place to stroll after dark.
Isla de Cabras “Goat Island”
For unusual and sweeping views of the El Morro, San Juan Bay, and the city skyline, while enjoying a secluded beach with all the amenities, shoot across the western side of the bay to the Isla de Cabras. In addition to the great views and water activities, there are two forts – similar to but smaller than El Morro – located on either side of the beach. They, too, protected the Bay from invading ships.
Live it up on the Condado Strip
When it comes to wining, dining, and nightlife, San Juan will spoil you with choices. If glitz and glam are your things, drop everything and head for the Condado Strip, where luxury and opulence come standard. The luxurious Vanderbilt Hotel, the La Concha Resort, and the Condado Ocean Club overlook the ocean and are surrounded by trendy bars, coffee shops restaurants, and all the shopping you could ever want.
After dark, though, is when this upmarket side of town comes alive with live music pumping out from the nightclubs, hotels, and rooftop bars located along Ashford Avenue. San Juan parties till the wee hours. Dress up and dance the night away, swaying to the rhythms of the Caribbean and cool down with an array of refreshing cocktails mixed by some of the best mixologists in the islands.
And speaking of cocktails…
Have a Pina Colada
Puerto Rico is the home of the Piña Colada. Although there is no doubt that the Piña Colada was invented in Puerto Rico, there is an ongoing debate as to when and who actually invented it. The Barrachina Restaurant, situated in Old San Juan, claims their Spanish bartender, Don Ramón Portas Mignon, invented the world-famous drink in 1963. But the Caribe Hilton located just a few miles away, claims that their bartender, Ramón “Monchito” Marrero, had already invented it way back in 1954.
Why not visit both establishments and decide for yourself whose Piña Colada is the best? Have a few of each to make sure.
While this debate will continue till kingdom come, let us not forget the undisputed and original inventor, who must surely be turning in his grave listening to this squabble. An early 19th Century Puerto Rican pirate, Roberto Cofresí, started the whole thing off, when he offered a homemade brew, made of pineapple, coconut, and a good dose of the local rum, to boost the morale of his plundering crew. We don’t know whether his brew had red maraschino cherries and little umbrellas, but we do know he did not live too long after that. His concoction, however, was destined to become the national drink of this Caribbean island and even had a song written about it.
Visit the World’s Oldest Rum Distillery
Book a tour through the Bacardi Distillery and learn how they manage to produce so many varieties of rum from just three basic ingredients – molasses, yeast, and water. You can choose the Historical Tour, the Rum Tasting Tour, and the Mixology Class. The only advice we have is for you to arrange transportation to bring you back. No drinking and driving.
Laguna del Condado
Immediately behind the hotels and resorts on the Condado Strip is another gem. The calm waters of this lagoon make for excellent kayaking and paddleboarding, while the national park on the south-eastern end, is the perfect place for a stroll, jog, cycle, skating, or a casual dip. Yes, the water is clean – just ask the manatees that are enjoying their time here. For a special treat, try kayaking under the stars on a glowing kayak.
On the last Sunday of each month there is a local farmer’s market and jazz music, while on the first Saturday of the month, free movies are shown here on a huge inflatable screen. Bring your blanket, chairs, and picnic basket and enjoy an evening on the town.
Take a Bioluminescence Night Tour
Of the five bioluminescent bays on earth, three are found right here in Puerto Rico. Bioluminescent bays have an unusually high level of dinoflagellates, which are microscopic marine organisms that glow bright blue when disturbed. Although pollution and hurricanes are said to negatively affect the numbers of these planktonic organisms, they inexplicably doubled in numbers after the deadly Hurricane Maria supercharged them in 2017.
The best bioluminescent bay in Puerto Rico is found at Mosquito Bay and is regarded as the brightest of all bioluminescent bays in the world. You will have to stay overnight in one of these places to view this marvel of nature, with a new moon being the best time to do it. The darker the night, the brighter the bioluminescence. Kayaking or swimming in these bays could easily be the highlight of your trip to Puerto Rico. You just move through the water and let the magic begin.
Scuba and Snorkel
Since is located between the Atlantic Ocean and the Caribbean Sea, the island of Puerto Rico has been blessed with a rich marine ecosystem that attracts divers from all over the world. Shore or boat dives and snorkel trips can be arranged by several tour operators in the city, and you’ll soon be cruising the reefs in crystal clear water, amongst multi-colored fish and, if you’re lucky, turtles.
Learn More
Islands Under Fire by Kevin McCarey
A portrait of an often overlooked part of America—Puerto Rico and the Spanish Virgin Islands—this is the little-known story of how the U.S. government, in particular the Navy, almost destroyed a pristine coral reef to provide a target for gunners.
Book a Fishing Charter
If fishing is your game, you have come to the right place! The coastal waters off San Juan are teeming with game fish such as tarpon, snook, permit, jacks, barracuda, and billfish while an abundance of freshwater fish like the colorful peacock bass, rainbow bass, and largemouth bass can be found in Carraizo Lake just a few miles south of the city.
There are several charter companies in San Juan to take you straight to the fishing hotspots where you can land yourself the fish of your dreams. Tight lines!
Sail the San Juan Bay at Sunset
Another way to see the beauty of San Juan is a sunset cruise around the bay aboard a yacht or a 19th Century style schooner. Capturing the sights of the El Morro, the Old City wall, and other historic sites from a completely different vantage point is a photographer’s dream. Book well in advance.
Go on a Day Trip to the El Yunque National Forest
Less than 30 miles out of town is a lush tropical rainforest with numerous hiking trails suitable for all fitness and skill levels. The scenery in the El Yunque rainforest is spectacular. At an elevation of 1,575 feet, the view from the Yokahu Observation Tower alone will make your trip worth every step as you gaze at lush velvet green mountain slopes below and the deep blue coastline in the distance.
Along the way you will learn about the unique ecosystem of the island, teeming with rare birds like the mango hummingbird and the Puerto Rico parrot. You can stop and cool off in the numerous pools, waterfalls, and lagoon along the way.
If you’re feeling a little more adventurous take a zipline over the canopy and get a bird’s eye view of this majestic landscape. Bring a towel, a raincoat, and an extra set of clothing as it often rains four times a day here.
Getting to San Juan, Puerto Rico
San Juan (airport code SJU) is served in North America by major carriers – United, Jet Blue, American, Southwest, Delta, and Hawaiian – as well as several low-cost and regional carriers.
For Pinterest
Pin to your favorite Pinterest boards and start planning your trip to San Juan, Puerto Rico
