Self-Guided Walking Tour of Old San Juan | Historical Sites & Landmarks
Ready to explore the sites that Old San Juan has to offer? This stunning, historic town on the island of Puerto Rico has something for everyone and is SO easy to explore on foot.
If cobblestone streets, colorful buildings, exquisite food, and age-old forts excite you, then you are in the right place. Get your camera ready to capture some beautiful photos for the gram!
For this self-guided walking tour, plan on budgeting around 2-4 hours of your day. Each of these popular stops is relatively close to one another, so the amount of time it takes will depend on how much time you want to invest in each stop. If you simply walked from one stop to the next, it would most likely only take you an hour. However, I highly recommend that you give yourself plenty of time to take in the sights and grab some local cuisine along the way!
Where to Start:
During my time in Puerto Rico, I stayed in a condo in Isla Verde. To tour Old San Juan, I called an Uber to drop me off at the first destination: Castillo San Cristóbal. Even if you rent a car, I would still recommend using Uber to make your self-guided walking tour through Old San Juan as seamless as possible. From there, I made the following stops:
- Stop #1: Castillo San Cristóbal
- Stop #2: Calle Imperial
- Stop #3: Castillo Felipe del Morrow
- Stop #5: Calle de la Fortaleza
- Stop #5: Plaza Colon
Items to Bring Along:
- GPS: This may be the most important item you’ll need. Your phone will do the trick! Make sure you’ve got plenty of juice to get you from place to place throughout the tour.
- Comfortable shoes: Hills and cobblestone streets are around every corner. Wear the comfy shoes and you’ll thank yourself in the end.
- Camera: You won’t capture those Insta-worthy photos without a camera. If you plan to use the camera on your phone, make sure it’s charged!
- Water: Hydration is key! If you don’t want to carry a water bottle around, you can count on the gift shop at both forts to have cold drinks for purchase.
- Sunscreen: Your trip won’t be as enjoyable if you’re burnt. Don’t forget to put on some sunscreen before you begin the tour. Bring it with you just in case you need to reapply throughout the day!
- Umbrella: Rain is unpredictable, so it’s best to keep an umbrella with you during adventures throughout Puerto Rico. Plus, an umbrella can double as sun protection! Win-win. Pack it!
Stop #1: Castillo San Cristóbal
Castillo San Cristóbal is a masterpiece of 18th-century military engineering and innovation that took 150 years to complete. The photographic setting and the stunning architecture are enough to lure us, tourists, in! The entrance fee is just $10, providing you with access to visit both Castillo San Cristóbal and its sister fort, Castillo San Felipe del Morrow.
This stop on the self-guided walking tour is coined as the largest fortress built in the Americas. Built by the Spaniards with a duty to protect San Juan from attack by land from the east, you will find all twenty-seven acres of Castillo San Cristóbal to be eerie, charming, and beautiful all at once. The fortification consists of three levels, and an extensive series of outer defenses.
For my fellow Instagrammers, be sure to check out the Devil’s Sentry Box, also known as Garita del Diablo, located on the second level of the fortification. This is one of the most iconic photo locations on the property!
Stop #2: Calle Imperial
Another photography hot spot on this list is Calle Imperial. Just a short walk down the road from Castillo San Cristóbal, you’ll find this photogenic street with a painting of the Puerto Rican Flag at the end. Iconic, isn’t it?
Stop #3: Castillo Felipe del Morrow
Sitting atop the hill to the west of Castillo San Cristóbal is another fort known as Castillo San Felipe del Morrow, or El Morrow. This fort is one of the largest and oldest in the Caribbean! Nearly 250 years passed as Spain built this six-level fortification, with construction spanning from 1539 until it was considered complete in 1787. Located at the entrance to the San Juan Bay, El Morrow stood strong, remaining undefeated through several attacks from the English and the Dutch throughout the years.
Again, the entrance fee is just $10, providing you with access to visit both Castillo San Cristóbal and Castillo San Felipe del Morrow.
Map to Castillo Felipe del Morrow
Stop #4: Calle de la Fortaleza
This is the oldest street in San Juan’s historic quarter! This bustling area is full of boutiques and shops, starting at Columbus Square and running down into Avenue Juan Ponce de León in the east. Walking down this street is a must. The gorgeous cobblestone streets and the vibrantly painted buildings make it feel like something out of a storybook. If the tourist in you is burning to grab some souvenirs to signify your time in Puerto Rico, this is a great place to do so!
Stop #5: Plaza Colon
The final stop on the sightseeing adventure on foot through Old San Juan is Plaza Colon, which is located at the end of Calle de la Fortaleza, and at the beginning of the entrance to Old San Juan. It is also located just down the hill from where the walking tour started at Castillo San Cristóbal. Right in the center of this plaza is a monument of Christopher Columbus, standing tall to commemorate the fourth centenary of the arrival of the Spanish. Also in this area is a classic I <3 SJ sign if you’d like to snap another touristy photo here.
If this is where you’d like to end your adventure through Old San Juan, this is a great location to call an Uber or take a taxi to your next stop in Puerto Rico!
