If you’re looking for an Old San Juan self-guided walking tour itinerary, you’ve come to the right place! Old San Juan is one of the most interesting cities in the USA.
Many cities in the United States have old towns. These can loosely be defined as colonial era towns that have kept their historical charm. There are quite a few scattered around the US. But perhaps the most spectacular of these old towns can be found in the US territory of Puerto Rico.
Old San Juan is the oldest – and in my opinion most beautiful – of all the historic old cities in the US. Founded by the Spanish in 1521, it’s a walking museum. Here we will cover a full day’s self guided walking tour of Old San Juan!
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Old San Juan – What You Need to Know
Where is Old San Juan?
San Juan is the capital of Puerto Rico and located on the central north coast of the island. Old San Juan is the historic part of town, on a peninsula that juts out into the Caribbean Sea. Puerto Rico is an island between the Dominican Republic and The Virgin Islands and it’s about a 2 hour flight to the nearest spot of the mainland US.
How to get there
There are a lot of domestic flights into San Juan and a few international flights. Most major US cities on the east coast fly to San Juan. If your city doesn’t have a direct flight you’ll likely layover in Miami or elsewhere on the east coast. From the airport you can take a bus, taxi, Uber, or rental car to the Old Town, which is about 12km (7.5 miles) from the airport.
If you’re combining a visit to Old San Juan with other destinations around Puerto Rico, it’s beneficial to have a car. You can use the search bar below to find a great deal on a rental in San Juan.
Parking in Old San Juan
If you’ve got your own wheels then I suggest parking in La Puntilla Parking lot. It’s right outside the old city walls and only $3 per day. It’s closed at night but there is free street parking at night nearby. It’s the perfect place to start your self guided walking tour of Old San Juan.
If you’re staying in the Old Town, though, your hotel might have parking included so be sure to check with your accommodation for parking options.
Language
Puerto Rico speaks Spanish, but in Old San Juan just about everyone will be bilingual and speak English too. If you get outside of San Juan then you start running into places where the locals don’t speak English.
Puerto Rican Food
Puerto Rico has its own unique cuisine. See the section below on Eat Like a Local.
Money
Puerto Rico is part of the United States and uses the US dollar. Cards are accepted just about everywhere and it’s really not necessary to carry any cash, other than for parking lots and street vendors. San Juan is more expensive than you’d expect. It’s on par with smaller US cities in terms of the cost of everything.
You’d think with the GDP of Puerto Rico being lower than US states that things would be a bit cheaper but that’s not the case. It’s not as expensive as New York or Washington DC, but expect similar prices to midwestern cities.
Since you’re still in the US tipping is still a thing. You will be expected to tip at restaurants in San Juan.
Government
Puerto Rico operates sort of like a state, but it’s not. It is a US territory instead, which means that US federal laws still apply, such as federal minimum wage and social security taxes, but citizens who live in Puerto Rico have no representation in the federal government.
They can join the army and go to war and die for the country, yet can’t vote for president. In 2020 Puerto Ricans voted by a slim majority to become a state, but it remains to be seen if that will ever happen.
Weather in Old San Juan
Puerto Rico has a tropical climate and it’s hot and humid year-round. Summers are a bit hotter and rainier. San Juan is usually clear while the interior mountains are cloudy. You can reasonably expect San Juan to be hot, humid and sunny.
You can also reasonably expect to get some rain if you’re there for more than a few days, so be sure to bring an umbrella with you on your trip.
Where to stay
There aren’t really any major hotel brands in Old San Juan. You’ll find a Sheraton on the south coast, but that’s really it. Old San Juan is full of small boutique hotels and holiday rentals instead, which adds to the charm.
They won’t be that much more expensive than staying outside the Old Town in one of the major brand hotels, but there are definitely more options and larger hotels outside. We stayed at Aloft San Juan but don’t recommend it due to loud music from the mall next door till well after midnight.
Within the old town consider the 352 Guest House Hotel Boutique or the Casa Sol bed and Breakfast. Outside of the old town I like the Hyatt House or the Hyatt Place. They are right next to each other and It’s easy to get to the old town from there. Or check out all the listings on booking.com to find another great option!
Time of year to go
The peak tourist season runs from December to May. The weather is a bit cooler and drier. The summer months are the hottest and wettest but offer an experience with fewer tourists. The ideal time might be late spring to early summer.
Just be mindful of when cruise ships stop in the port, because if you can avoid a cruise day that would be best. I explain how to avoid cruise days in a section below.
How long to stay in Old San Juan
It’s easy to see Old San Juan in one day. This self guided walking tour is structured around one day in the old town. A trip to San Juan should be combined with a beach vacation to Puerto Rico or a hike through the jungles of El Yunque National Forest, the only tropical rainforest in the US National Forest system.
A Brief History of Old San Juan, Puerto Rico
Puerto Rico – “rich port” – was first settled in 1508 by the Spanish in a location outside San Juan’s city limits. A year later the settlement was moved to what is now San Juan and the name was officially added in 1521, which is the year the city is considered to be founded. Fortifications were built over the years and helped fend off numerous attacks, especially from the Dutch, French and English.
For centuries it remained a small Spanish port city, never expanding beyond the original city walls. In 1898 the United States did what the Dutch never could and took Puerto Rico, thus ending the Spanish-American war. However, Puerto Rico did not become a territory until 19 years later. It has remained an American territory now for over 100 years.
Over the years the colonial houses and buildings in Old San Juan degraded into a state of disarray. What you see today is the result of painstaking restoration of the old buildings that has taken place over the last 80 years. And they’ve done a hell of a job restoring the city to its original charm. These days Old San Juan is mainly a tourist destination. No more fending off invaders!
If you’re curious what San Juan would have turned into had the Dutch taken over, then be sure to check out my complete guide to Amsterdam!
Your Self-Guided Walking Tour of Old San Juan
The Old Town is not large but there is a lot to see and do. Hitting all these spots will log 8-10 miles on your Fitbit. You can choose your own order of precedence, but hitting them in the order I have given below will make for happy feet. Check out the map below for the points of interest you’ll need to hit on this self guided walking tour of Old San Juan.
The Colorful Streets
Perhaps the main draw of Old San Juan is not one particular location, but the architecture of the city itself. The buildings are nearly all colonial-era Spanish architecture. The Caribbean has all sorts of old colonial-era cities, like the Zona Colonial in Santo Domingo or the Pietermaai district of Willemstad in Curaçao. But when it comes to colonial architecture, nothing beats San Juan.
This means cute balconies and colorful facades. All the streets are lined with charming houses of eclectic, bright colors. The old city itself is a UNESCO World Heritage Site. There is no single street to go for the best views. It depends on how many cars are parked and how crowded the city is. Rest assured there will be no shortage of photo ops on the streets of Old San Juan.
Castillo San Felipe del Moro
Old San Juan’s most notable attraction is almost certainly Castillo San Felipe del Moro, the city’s original fort. This Spanish fortress was built over the centuries, starting in 1539. It’s an impressive structure and was used to fend off attacks, most notably from the Dutch in 1625.
These days the fort is part of San Juan National Historic Site, managed by the National Park Service. It was last used for military purposes during WW2 and since then has been solely a tourist site. It’s $10 per person to enter unless you have the NPS Interagency Pass or another yearly pass.
The fort itself is an impressive structure. It rises seven stories from the water below and includes multiple fortifications and lookouts. It really reminded me of the beautiful ancient forts in Malta.
Allow at a bare minimum of an hour to visit the fort, but more if you want to walk along the coast along the promenade back to the Puerto de San Juan, the old city’s main entrance station.
Castillo de San Cristóbal
On the other side of Old San Juan lies another Spanish fort, Castillo de San Cristóbal. While not as well known, this fort is actually larger, the largest of its kind in the New World, i.e. the Western Hemisphere.
It was built about 100 years after San Felipe and meant to protect San Juan from land attacks. The two forts are connected by the old city wall that runs between them.
Entrance to San Cristóbal is included with admission to San Felipe (and vice versa), so be sure to keep your receipt. It’s similar to San Felipe but has more viewpoints over land. This way the Puerto Ricans could see if the Dutch were gonna attack by landing somewhere else on the island and approaching on foot.
The two fortresses worked like a charm and Spain held on to Puerto Rico until it was surrendered to the United States in 1898.
Catedral Basilica Menor de San Juan Bautista
The Catedral Basilica Menor de San Juan Bautista is the oldest church in the United States and the second oldest church in the Americas. While that might pale in comparison to some of the European gothic cathedrals, it’s still nearly 500 years old, dating back to 1540. I only admired it from the outside, but you’re free to walk in and have a look around. It’s not big and will only take a few minutes.
Casa Blanca
Casa Blanca is now a museum, but centuries ago this house belonged to famed Spanish explorer Ponce de Leon. It’s San Juan’s oldest house and contains many artifacts from the colonial days of the city. The house has some odd hours so consult the website linked above for the latest information.
Puerta de San Juan
Old San Juan’s original entry gate is found at Puerta de San Juan. It’s just an entryway in the city wall, but you can imagine old aristocrats arriving here hundreds of years ago. From here there is a lovely walk along the coast on the promenade. This takes you outside the city wall and eventually to the base of Castillo San Felipe de Moro.
La Perla
Situated outside the ancient city wall, La Perla is a former shantytown. Many years ago the slaves and lower class were forced to live outside the walls, thus La Perla was born. It’s full of colorful houses and right on the water, but you can tell the residents are not quite as rich as those inside the wall by one walk through the village.
It was also seriously damaged by hurricane Maria in 2017. Still cool to walk through though and your self guided walking tour of Old San Juan should definitely include a detour here. Just be careful at night, as there have been recent reports of violent crime aimed at tourists.
Musea de las Americas
If you’re into museums, or trying to beat the heat for a bit, pop into Musea de las Americas to learn a little bit about colonial life in Puerto Rico and see some artifacts from those days.
Guided Tours
If you’d prefer to have a guide walk you around the city and add a bit of historic context onto your day in Old San Juan, then there are numerous short tours available with GetYourGuide, including walking tours as well as sunset cruises and sailing. You can even add on food tours, ziplining and all sorts of other adventurous activities.
Avoiding the Crowds in Old San Juan
Make no mistake, Old San Juan can get pretty crowded. It’s not a huge area but it is an extremely popular place for American tourists. This is especially true on days when cruise ships dock at the port. The largest cruise ships can hold thousands of people. Now imagine all those people getting off at the same time and walking around Old San Juan.
If you’re not a part of one of these cruises then I highly recommend planning your trip to San Juan on a day where no cruise ships dock at the port. You can see which days have cruises using this link. About 500 cruise ships visit San Juan every year, and the vast majority visit between November and March.
In those months it’s very possible to have a day where three cruises stop at San Juan. And you absolutely do not want to be in town when three cruise ships are docked. So do yourself a favor and plan around the cruises. We were there on a summer day with no cruises and felt like we had the city to ourselves!
Eat Like a Local
For a small island, Puerto Rico has its own culinary culture. This isn’t intended to be a full rundown of Puerto Rican food but a quick synopsis on some of the main things to try.
- Mofongo: the most Puerto Rican dish of them all. It’s essentially mashed fried plantains served with some sort of meat. I’ve never seen it anywhere else in the world. It’s delicious.
- Empanadas: Puerto Rican empanadas are fried and scrumptious. Don’t have too many though, as they are super unhealthy.
- Tostones and amarillos: deep fried green plantains and ripe plantains, respectively.
- Arroz y habichuelas: red beans and white rice, served as a side with many meals.
- Lechón asado: Puerto Rican succulent pig
- Pastelon: Puerto Rican lasagna, made with plantains
- Paella: this Spanish staple is found nearly everywhere in Puerto Rico
- Flan: a vanilla custard cake. Simply amazing.
Restaurants
There are tons of great restaurants in Old San Juan. Prices are in line with any large American city, and tipping is expected like anywhere else in the US. Most restaurants are indoors, as the narrow old streets don’t allow for much of a patio presence. You can find some rooftop bars and cafes though.
To eat like a local, head to Cafe Manolin, a no frills ‘50s diner style restaurant with a huge menu. We had lunch there and dinner at Raices, which was recommended by the bartender at our hotel. It’s very popular and we waited over an hour for a table. But the stuffed avocado was excellent and worth the wait. The flan was also to die for.
Some other restaurants that were recommended to us were Cayo Caribe, Cafe El Punto, and El Patio de Sam. Lastly, if you want to try the original pina colada, head over to Barrachina, where the drink was invented by bartender Ramon Portas Mingot in 1963.
Outside Old San Juan
If you have longer in San Juan there are some more areas of the city that are worth checking out. Though I would say that I don’t recommend a beach vacation in San Juan city – even though there are plenty of beach resorts – due to the possibility of smoggy skies. It’s a big, dense city and you’re likely to get more beautiful skies further outside the city.
Condado is the main beach area for San Juan. It’s lined with hotels and restaurants and worth a stop if you have a few days in San Juan. Pinky’s is a great spot for breakfast if you are in Condado.
In the Isla Grande region you will find a lot of new hotels (this is where we stayed) and a huge mall that has DJs every night in a common courtyard. Parque Isla Verde contains the airport and a long stretch of beach, as well as many 4 and 5-star hotels.
The best beaches in Puerto Rico are well outside of San Juan. If you really want to see some amazing sand and water, take a day cruise to Icacos Beach on Cayo Icacos, a small island northwest of mainland Puerto Rico.
To get there you have to drive out of town quite a bit and take a boat to the island. There are tons of organized tours – like this one – so it’s not an issue getting there.
Old San Juan – FAQs
How long does it take to walk around Old San Juan?
Depending on your pace and how long you want to stop at the various sites, it could take anywhere from a few hours (no stops) to a few days if you stop to see everything.
Do you need a tour guide for Old San Juan?
No, you don’t need a tour guide for Old San Juan. This article explains how to do a self-guided walking tour of Old San Juan. If you want additional information on history and a knowledgeable local, having a tour guide can be beneficial though.
Is one day in Old San Juan enough?
Yes, one day in Old San Juan is sufficient to see the highlights of the beautiful old city.
Is it safe to walk around Old San Juan at night?
Yes, it’s perfectly safe to walk around Old San Juan at night. It’s a happening place and there are people all over. Just see the next section about places to avoid.
Where to avoid in Old San Juan?
After dark it’s best to avoid the La Perla neighborhood. Tourists have been known to get mugged and stabbed there in the wee hours of the morning.
What is the difference between Old San Juan and San Juan?
Old San Juan is a neighborhood of San Juan, a large city in Puerto Rico. “Old” comes from the fact that it was built in the Spanish colonial era. It’s the original San Juan. Since those days a sprawling metropolis has emerged from the old city, while the old city still retains all its colonial charm.
Where do I park to access Old San Juan,
As discussed in the introduction, I suggest parking in the La Puntilla Parking lot when visiting Old San Juan. Cheap and right outside the city walls.
Final Word
Old San Juan is one of the most picturesque cities in the Americas. Walking the old cobblestone streets makes you think you’re in some historic European city. And if that wasn’t enough, the beautiful Spanish forts that protected the city for centuries really make you feel like you’ve landed in Europe. You’ll have a great time if you follow this Old San Juan self guided walking tour!
