17 Colorful Things to Do in Old San Juan (Plus Day Trips)
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Colorful! If there’s one word to describe Old San Juan, it’s that.
From its pastel-painted buildings to its lively food and people, the city bursts with vibrancy.
But the Caribbean capital of Puerto Rico is more than eye candy – it’s steeped in history and culture.
Founded by Spanish colonists in 1521, San Juan is the oldest city under U.S. sovereignty and the second oldest European-established capital in the Americas.
There are enough things to do in Old San Juan to fill an entire week!
But if you’re a cruise visitor, like we’ve been several times, and only have one day, don’t worry.
Partially encircled by ancient walls, the old town is delightfully compact – just seven square blocks – so you can see a lot in few hours.
And the Old San Juan cruise port is in the heart of the action. Step off your ship, and the city’s historic landmarks are just a short walk away.
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Contents: Must-do Old San Juan activities
17 Activities and places to see in Old San Juan
Pssst! Also see comments and questions from readers at the end of this post.
Map of Old San Juan
Here’s a good map of of Old San Juan (Viejo San Juan in Spanish) that you can print off as a PDF from your computer (courtesy Moon Travel Guides).
17 Best things to do in Old San Juan, Puerto Rico
1) Explore the colorful streets of Old San Juan
One of the greatest pleasures in Old San Juan is simple. Just walk – and gawk.
The cobblestone streets, lined by colonial churches and centuries-old buildings, are a treat for the eyes. Indeed, the Old Town is filled with more than 400 restored Spanish colonial buildings, all dating back to the 16th and 17th centuries.
Plaza de Armas, the main square with the city hall on its north side, is a great starting point.
Soak in the charm of wrought iron balconies, the profusion of flowers and the facades painted in shades of lemon, mint green, peach and baby blue.
We joined an Old San Juan walking tour (similar to this top-notch author-guided tour), which helped us discover the city’s fascinating history.
But honestly, with or without a map, strolling these streets is a joy all on its own.
Authentic Old San Juan food tour
If you’d like to try some of Puerto Rico’s local food while exploring on foot with a guide, here’s a winning 3-hour small-group food tour.
Sample local cuisine like plantains, fresh ceviche and mofongo (see #15) at don’t-miss restaurants – and learn about San Juan’s history too! It’s a great combination.
2) Stroll along Fortaleza Street
Wandering through the historic district, you’ll come across Fortaleza Street – easily one of Old San Juan’s prettiest streets.
Look up! When we visited, a canopy of pink, purple and blue umbrellas floated above.
The art installation, originally known as the Umbrella Sky Project, was intended to bring color back into the lives of the people after two devastating hurricanes in 2017.
Over time, the umbrellas were swapped out for pink kites, but the umbrellas remain a local favorite. So don’t be surprised if they make a comeback – restoring “Umbrella Street” to its whimsical glory!
3) Take a peek at the governor’s house (La Fortaleza)
At the end of Fortaleza Street, you reach the governor’s mansion known as La Fortaleza (Palacio de Santa Catalina). It’s a building you must see in Old San Juan.
Originally built in the 16th century as part of a huge fortress structure to defend the island, it was remodeled in 1846 and turned into the official residence for the sitting governors.
The frothy blue-and-white confection, with its tiled roof and lots of wrought iron curlicues, has housed every Puerto Rican governor since then.
Free tour of La Fortaleza
Free guided walking tours are available by appointment Monday through Friday.
Call the Tourist Guides Office La Fortaleza at 787-721-7000 to book up to one week in advance. English tours are offered, and you’ll need a government-issued ID to pass security.
The 30-minute tour includes the gardens and look inside the mansion when the government isn’t in session.
4) Admire the cobblestone streets of Old San Juan
As well as looking up, you must look down – at the cobblestones on the streets themselves.
Do you notice that they’re blue?
Called adoquines, these cobblestones were the blocks of ballast (made from the waste of iron smelting) placed in the early ships that sailed over from Spain.
When the ships reached San Juan, the ballast was dumped and replaced with gold, which was taken back to Spain.
And the streets of Old San Juan were paved with the ballast.
5) Sip a pina colada
Did you know that San Juan is the birthplace of pina coladas?
In 1954, a bartender at the Caribe Hilton blended a mix of rum, coconut cream and pineapple juice – and the refreshing frothy pina colada was created. Or so the story goes…
Whatever. Today, the pina colada is the official cocktail of Puerto Rico.
You can sip one at the iconic Caribe Hilton (located between Old San Juan and Condado beach) or at Barrachina (another spot claiming to be the place where the cocktail was invented).
But many other bars in Old San Juan also serve stellar pina coladas. Try La Factoria – voted one of the top 50 bars in the world for several years running. You can even join a fun bar crawl!
Tip: Make pineapple cocktails at home – see these 15 margarita recipes, including a pineapple jalapeno margarita (#5) and frozen pineapple margarita cocktail (#13).
6) Wander about El Morro
Castillo San Felipe del Morro (El Morro) is probably the most famous attraction in Old San Juan.
Perched at the northwestern tip of the Old Town, it was constructed to guard against attacks from the sea.
Dating back to 1539, it’s the older of the city’s two impressive forts. (The other is Castillo de San Cristobal, covered under #9 below.)
Together with San Cristobal Castle, La Fortaleza (#3 above) and a large part of the old city walls – it’s now a UNESCO World Heritage Site
A $10 USD ticket covers entry to both forts.
Tip: For a unique experience, try this guided sunset walking tour, which includes a stop at El Morro during the golden hour.
7) Walk the Paseo del Morro
The Paseo del Morro is a flat scenic seaside path skirting the city’s outer walls, leading to El Morro (#6).
On one side, towering stone walls rise dramatically – imagine the enormity of the task to build such mammoth fortifications centuries ago!
On the other side, you’re treated to stunning views of San Juan Bay and the blue sea.
The trail runs for about ¾ mile from the San Juan Gate to its end, where you’ll need to turn back – but the views look different on the return.
We walked it late in the afternoon, enjoying the sea breeze and cooler temps.
Tip: There’s no shade, so if you walk this path in the heat of the day, wear a hat and bring water.
8) Photograph the kitties
One curious sight we noticed on the Paseo del Morro? All the wild stray kitties sunbathing on the rocks!
We read on a plaque that the fur balls are cared for by a non-government cat rescue group, which helps to neuter and feed them. (Volunteers leave kibble piles for the cats to eat.)
But, we discovered after getting hissed at, the kitties don’t like to be petted. They’re feral. Fair warning!
9) Visit Castillo de San Cristobal
We’ve already covered El Morro (#6), but its “younger sibling” – Castillo de San Cristobal (Saint Christopher’s Castle) – is also one of the most interesting places to visit in Old San Juan (whether or not you’re interested in military history).
Built between 1765 and 1785, it was designed to protect the city from a land invasion.
The castle fortress is operated today by the U.S. National Park Service. (Castillo San Cristobal, El Morro, most of the city walls, the San Juan Gate and Fort San Juan de la Cruz across the bay are together known as the San Juan National Historic Site.)
Walk the parapets, squeeze through dark tunnels burrowing below the fort (one even leads to a dungeon!) and hold a bayonet in the soldier’s barracks.
You get sweeping views too from Castillo de San Cristobal.
Can you see your cruise ship in the distance?
10) View the sculpture at Rogativa Plaza
Plazuela de la Rogativa (Rogativa Plaza) is a small corner of the city near the San Juan Gate. In the plaza, a large weathered bronze sculpture overlooks the Bay of San Juan.
The sculpture shows several women, led by a priest, holding torches up high in their hands.
The story goes that in 1797, the British were planning to invade San Juan.
However, they abandoned their attack when they thought women walking through the streets in a religious procession were actually reinforcements of soldiers who’d arrived to help defend the city.
11) Pop into the historic San Juan Cathedral
The oldest cathedral in the United States is actually in Old San Juan on Puerto Rican soil (a U.S. territory).
Built from wood in 1521, then refashioned over the years, the Cathedral of San Juan Bautista (Cathedral-Basilica of Saint John the Baptist) is where the Spanish explorer and former governor Juan Ponce de Leon is buried.
It’s free to visit, so step inside and admire the cathedral’s vaulted ceiling and beautiful stained glass windows.
12) Browse the shops in Old San Juan
Old San Juan has some lovely independent boutique shops.
Jewelry, souvenirs, clothing, arts and crafts. You name it. You’ll find it.
Needless to say, one of the top things to do in Old San Juan is to browse the many interesting stores.
Keep an eye out for a good guayabera, the traditional Cuban linen shirt with four pockets for men.
We poked our heads into several shops. But without room in our suitcases, we resisted the urge to buy, deciding to collect only memories.
13) Eat at a food truck
The food in Puerto Rico is a real treat. The local food trucks, especially, serve up some tasty traditional dishes that are fun to try.
Check out the food trucks and vendors lining the waterfront off Plaza Darsena (near the cruise ship dock) and on Paseo de la Princesa (#14 below).
Pick up pinchos (kebabs), alcapurrillas (plantain fritters stuffed with ground meat), empanadas and tostones (deep fried plantain slices). Quench your thirst with fresh lemonade.
When your stomach is growling, but you don’t feel like a proper sit-down meal at a restaurant, Puerto Rican street food is the perfect answer.
14) Enjoy the Paseo de la Princesa
The Paseo de la Princesa is a lovely tree-lined promenade sprinkled with fountains, sculptures and often street vendors and food trucks too.
Tip: If you’re visiting Old San Juan on a cruise and looking for some exercise, make your way from the cruise ship dock to Paseo de la Princesa, which then turns into Paseo del Morro (#7). You can go for a great run or walk along this combined path.
15) Eat mofongo
You can’t go to Puerto Rico and not try mofongo.
This popular savory dish – one of Puerto Rico’s most-loved dishes – consists of green plantains, mashed with garlic and crispy pork rind.
The mixture is then formed into balls and fried. It’s often topped with pork, beef, chicken or seafood.
Tip: Some of the best mofongo in Old San Juan can be had at El Jibarito (known for its local Puerto Rican fare) and Café Manolin (a simple cafeteria-style Old San Juan institution).
16) Listen to live music
Fancy a free sunset concert?
One of the most fun things to do in Old San Juan at night is to listen to some live music outside.
On Sunday evenings, locals and visitors alike gather at the Plaza de la Marina (Plaza Darsena) between 5:30 and 8:00 pm to listen to local bands playing a mix of traditional and modern music.
And if you get into the groove, don’t be shy. Shake those hips and join the locals dancing in the plaza.
17) Soak in the serenity at the beautiful San Juan cemetery
It might sound odd, but adding the St. Mary Magdalene of Pazzis Cemetery to your old San Juan itinerary is totally worth it for the history and breathtaking views.
Nestled right by the ocean near El Morro, this 19th-century cemetery is both poignant and peaceful. Its white tombstones pop against the blue sea and sky, honoring many notable Puerto Ricans.
Sure, some parts are a bit neglected, but it’s still a strikingly unique spot – especially with the roosters and iguanas roaming around.
Tip: If visiting on a cruise, take a short Uber or taxi ride to the cemetery then walk back to the cruise pier, enjoying all the sights along the way.
Day trips from San Juan
Staying in Old San Juan for a few days? You may want to do a day trip or two! Here’s what we recommend:
Chilling on the beach at Isla Verde
We’re telling you about Isla Verde (Green Island) because it would be a shame to miss this gorgeous stretch of sand – one of the best beaches in San Juan!
It’s just 7 miles away from Old San Juan (a quick 15-minute Uber or taxi ride).
With calm waters perfect for swimming, shady trees and plenty of restaurants and bars, it’s ideal for a beach day. Rent chairs and an umbrella to make the most of it. After all, you are on a Caribbean island!
El Yunque hiking and swimming
El Yunque National Forest isn’t just any rainforest. It’s the only one in the U.S. National Forest Service, and visiting it is hands down one of the best things to do in Puerto Rico, period!
Just 45 minutes from San Juan (traffic willing), this 29,000-acre paradise is packed with waterfalls, rivers and 240 tree species. Keep your eyes peeled for lizards, singing coqui frogs and even scarlet-crowned Puerto Rican parrots.
Several hiking trails lead to waterfalls and natural freshwater rock pools, where you can cool off with a swim.
Don’t miss climbing the 98 steps up to the top of the Yokahu Observation Tower. Perched at an elevation of 1,575 feet, it looks a bit like a Scottish castle, with killer views of the surrounding green hills and blue ocean beyond.
Uber works to get there, but service can be spotty for a return trip. If you don’t have a rental car, you can book a guided tour from San Juan with hotel transfers for a hassle-free adventure.
Guided El Yunque rainforest tours
- Full-day hiking and waterfall adventure – This exhilarating 5-star-rated adventure (under $70 USD p.p. too!) has you hiking to watering holes, scooting down rocky waterslides, rope swinging and cliff jumping.
- Half-day scenic excursion – For something shorter and more relaxing, this small-group experience takes you to scenic spots in El Yunque’s lush rainforest, with time for a refreshing swim.
Bioluminescent kayaking in Laguna Grande
Fancy kayaking through a shimmering watery wonderland? Laguna Grande makes it happen!
This magical bio-bay is one of the world’s rare spots to witness bioluminescence. Tiny organisms in the water called “dinoflagellates” light up when disturbed.
Several companies offer sunset and night-time kayaking tours of the bay from the town of Fajardo (about an hour’s drive from San Juan). Paddle through the mangroves and watch the water sparkle! (You’ll get wet, so wear quick-drying shorts and T-shirt.)
Guided bio-bay kayaking tours
- Marine biologist-guided adventure – This amazing 2-hour sunset tour comes with a side of cool science facts. (To get to and from Fajardo, you can book this roundtrip taxi service.)
- Night kayaking (with transfers) – This tour includes roundtrip transfers from San Juan.
Where to stay in San Juan?
The following are our picks for the two best luxury hotels in San Juan if you’re staying overnight in the city.
(And if you’re wondering whether you should tack on a few days in the city before or after a Caribbean cruise, wonder no more – just do it!)
El Convento
El Convento is a 350-year-old Carmelite convent that’s been turned into a lovely boutique hotel.
Smack-dab in the old city, it’s perfect if staying for just one night before or after a cruise.
El Convento: Check rates and availability
Condado Vanderbilt
For two or more nights, we’d probably prefer to stay in a hotel by the sea, with a large pool too.
Originally built in 1919, the uber-luxurious Condado Vanderbilt looks gorgeous!
Condado Vanderbilt: Check rates and availability
Now you know how to experience the best of Old San Juan!
Hopefully you’re no longer wondering what to do in Old San Juan.
There’s something for everyone to experience – whether you’re spending just one day in Old San Juan on a cruise or staying here on a longer vacation.
For more Puerto Rico travel information, see the official Puerto Rico tourism website.
Thanks for reading, and have fun on your Old San Juan visit!
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Hotels: Booking.com is perfect for scoring a “wow” hotel – or at least a decent one – at lower rates than the hotel’s own website. We especially like Booking’s flexible cancellation policy!
Vacation homes, condos and rentals: We prefer and use Vrbo (Vacation Rentals by Owner).
Cruises: CruiseDirect offers amazing deals on cruises (including Holland America, Viking Ocean Cruises, Seabourn and other lines we’ve reviewed).
Flights: To book the cheapest flights, search on Google Flights or Expedia. (Just be aware Expedia tickets may be non-refundable.)
Airport lounge access: We love (and have) Priority Pass for comfy lounge seats, free snacks and drinks, complimentary WiFi and sometimes even showers and spa services!
Tours: For the best local food, walking and other guided tours, plus skip-the-line tickets to attractions, check out Viator (a TripAdvisor company) and GetYourGuide.
Car rental: Renting a car is often a great way to explore off the beaten path. Discover Cars searches car rental companies so you get the lowest rates.
eSIMS: Stay connected affordably with Airalo eSIMS covering 200+ countries and trusted by 10 million+ users, including us! (No more huge roaming bills!)
Travel insurance: SafetyWing is designed for frequent travelers, long-term adventurers and digital nomads. It covers medical expenses, lost checked luggage, trip interruption and more. We also have and recommend Medjet for global air medical transportation.
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Photo credits: Hotel photos courtesy of the two respective Old San Juan hotels
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