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Friday, February 26, 2016

Visitors Guide to Old San Juan

Old San Juan is probably what comes to your mind when you think of Puerto Rico.  Chances are if you cruised the Caribbean, you probably stopped here.  Whether you are on a cruise, or flying to the island for the week, Old San Juan has to be on your "Must See List".  Old San Juan is home to culture, history, and brightly colored buildings.  Forts , food, and cobblestone streets.  To escape the touristy area and prices of Condado and experience some of the history of Puerto Rico, head on over to Old San Juan.

For my first disclaimer....don't get me wrong... Old San Juan is also really touristy. As I mentioned, it is a huge stop for cruises ships and the port can hold 12 cruise ships at once.  Cruise ships dump roughly 3,000 to 5,000 people off (each ship, we checked) at once.  If you venture near the cruise terminal, you will be greeted with overweight cruise going Americans poking in and out of touristy shops.  But don't let this turn you away from Old San Juan.  You can slip into a cafe, or enjoy the sunshine at one of the parks.  You can get lost in one of the cities massive forts.  

But before you do all of that, 
pay attention to my DO's and DONT's of visiting Old San Juan. 

- - - - DO - - - - 

Rent a bike - it's the best way to see Old San Juan. Though do be aware that the roads are cobblestone (very bumpy) and hilly.

Dive into the history of the old city, the forts, and Puerto Rico's past. 

Walk the streets - there are so many awesome shops, bars and restaurants.  Also take in the beautiful colored buildings, the famous historic doors, and cobblestone streets.  

Eat! Some of the best food on the island can be found here. 

Stroll past the capitol - beautiful building on your way to Old San Juan.

Ask a localAfter traveling enough, I learned to always always ask the locals about the best spot in town.  Once again, I asked my dive instructor for some recommendations for dining in Old San Juan.  He said Old San Juan has some of the best food on the island, and pointed me in the direction of his two favorite places.  

Be aware of restaurant wait times - Trying to get into popular restaurants at prime dinner hours can be very difficult (especially if you are in a group). 

Get apps and drinks somewhere else than dinner - We always tried to have appetizers and drinks, then dinner at two different locations. This let us try more of the restaurants, without adding a huge cost.

 - - - - - DON'T - - - - - 

Wear heels .  You will be doing a lot of walking.  And lets be honest, cobblestone streets and tiny sidewalks don't work so well with stilettos.  Wedges if you must. 

Drive - the traffic is awful, especially on the weekends.  On the shuttle Sunday heading to the wedding ceremony, it took us over an hour to get to Old San Juan from Condado (normally a 10 minute drive).  The roads are narrow, often one way, and very confusing.  There's also only one major route in and out of the old city. Like any old city, driving is not for the faint of heart.  Take the free trolley, ride your bike, our walk around. There are also plenty of cabs making their way through the area.

Bring home all the cats - Old San Juan has a large stray cat problem.  Especially at El Morro.  You will see roughly 50 cats sleeping among the rocks at the fort.  I was amazed and stunned by the amount of cats in the streets, and along this walkway where they are fed.   It will be tempting to bring all the fluffies home.  Just don't.  Know that the Save A Gato project is taking care of them.  They are being fed and are part of their Trap Neuter Release program.  Some of the cats also get adopted out in the TNR process. 

Just pick a restaurant - being a large tourist destination, there are a ton of restaurants with a variety of food catering to people who can't get into the popular local places. 
You can get pizza anywhere. Plan ahead!

- - - -  Favorite Food - - - - - 

There will be an entire post dedicated to the food of Puerto Rico.  Because I have so much to say about it and it deserves its own space on KW.  Do know, that OSJ has some of the best food on the island. For now, I am going to recommend two of our favorites in OSJ  (recommended to me from someone who lived his whole life on the island). 

La Cueva Del Mar (amazing affordable seafood) per above picture. 

El Jibarito (cheap delicious local fare, including tons of fried goodies-empanadas anyone?)

- - - - Parks and Statues - - - - - 

The statues, parks and plazas in OSJ deserve your attention and a visit.  From their amazing viewpoints of the Atlantic, and rich historical references, they are a great addition to a trip through Old San Juan.  

Paseo La Princesa (1853)-located on the south side of Old San Juan near Plaza de Hostos and Plaza Darcenas and just along from where the cruise ships dock. It is at the end of a European style promenade with trees, shops, restaurants, and live music. A beautiful spot to walk the promenade and take in the views of the Atlantic. 

Plaza De La Rogativa (1979) - Right by the Old San Juan Gate and Paseo del Morro. Rogativa means “The Procession”, which tells the legend about a Catholic Bishop and his companions who made a procession in faith holding crosses, torches, and chanting during an invasion by the British on the city in 1797. The British thought they were Spanish Army reinforcements and gave up on the attack. “Faith does move mountains”… Source

The history behind this statue was really interesting, and lets be honest, this park/square is just absolutely beautiful.  This is a great place to watch the sunset, or to stop and enjoy a coffee with amazing views.  This was also the location of Jill's wedding ceremony, so I have to stop and thank her for introducing me to the beautiful spot.  A beautiful bride walking towards the water at sunset, and gigantic pelicans flying and nesting in the trees around it (quite magical!)

- - - -  The Capitol- - - - - 

A stop at Puerto Rico's capitol building (1929) is worth the time.  It is on your way to Old San Juan from the Condado area.  Not only will you see the amazing views of the coastline from here (featured above) but the capital building and surrounding promenade are worth oogling over too. The Capitol Building is open to the public Monday- Friday from about 9am to 5pm. Admission is free.

The Capitol Building
San Juan Bautista Plaza at the Capitol Building
- - - -  The Forts - - - - - 

Castillo San Felipe del Morro
Castillo de San Cristobal
Fortin San Juan de la Cruz (closed to public)

San Juan National Historic Site (16+) $5.00 per person
Children 15 and under Free! (Good for one week for both Cristobal and Felipe del Morro)

Castillo San Cristobal & Castillo San Felipe del Morro are open to the public everyday 9:00am to 6:00pm except on Thanksgiving Day, Christmas Day and New Year's Day.

"San Juan Bay was a sheltered harbor that had high political and military value in the days of sailing ships. The easiest course to cross the Atlantic from Europe to the Americas was to go south to the coast of Africa; place your ship in the dependable trade winds and sail due west to the Caribbean. The trade winds, and wealth of the Caribbean islands in colonial times, made this harbor a target. El Morro was built to defend against sea attackers; later San Cristóbal was built to protect against attack on San Juan by land". Source and more facts

The forts were built at Puerto Rico to protect its coastlines from invasion. Due to its location along the trade routs from Europe to the States, Puerto Rico was a very valuable port. "The Spanish-American War of 1898 ended Spain’s colonial empire in the Western Hemisphere and secured the position of the United States as a Pacific power. U.S. victory in the war produced a peace treaty that compelled the Spanish to relinquish claims on Cuba, and to cede sovereignty over Guam, Puerto Rico, and the Philippines to the United States. The United States also annexed the independent state of Hawaii during the conflict. Thus, the war enabled the United States to establish its predominance in the Caribbean region and to pursue its strategic and economic interests in Asia".  Source

-Castillo San Felipe del Morro - 
A National Historic Site.  It is on the northwestern most point of Old San Juan.  It was designed to guard the entrance to San Juan Bay. Oldest section built in 1539. Source Paseo del Moro is the beautiful walk/passage by the fort along the water, and by the Gate to Old San Juan.  

Castillo San Felipe del Morro at sunset 
Castillo San Felipe del Morro 
Santa Maria Magdalena Cemetery at Castillo San Felipe del Morro (1863)
Walls of Castillo San Felipe del Morro 
ridge/lawn by Castillo San Felipe del Morro 
Me posing at the ridge/lawn by Castillo San Felipe del Morro 
Entrance to Paseo del Morro 
Walking along Paseo del Morro 
Past the City Gate and Walking along Paseo del Morro
Gate to Old San Juan

- Castillo de San Cristobal
A National Historic Site- Oldest section built in 1634. San Cristóbal covers 27 acres of ground (110,000 square meters) and is the largest fortification built by the Spanish in the New World. It was built by Spain to protect against land based attacks on the city of San Juan. Source

Entrance to Castillo San Cristobal
Castillo San Cristobal
Flags at Castillo San Cristobal
"At El Morro and San Cristobal alongside the U.S. and Puerto Rican Flags flies the "Cross of Burgundy," a Spanish military flag used from the 16th to the 18th century to identify warships, forts, and regiments of troops loyal to the king of Spain. When the great forts were built, this was the flag flown" NPS.Gov

Flags at Castillo San Cristobal
View of the harbor from Castillo San Cristobal
View of the harbor from Castillo San Cristobal
Inside the Castillo San Cristobal
Castillo San Cristobal (Capitol building in sight)
Castillo San Cristobal
 Castillo San Cristobal
Castillo San Cristobal
Educational signage showing the geographical importance of San Juan 
Castillo San Cristobal

Castillo San Cristobal

-Fortin San Juan de la Cruz.-
 The fort is closed to the public, but you can walk around the ground.  "The square coastal fort has massive sandstone walls that date back to the 1630s. he original fort built on this site in the late 1500s was made of wood and burned to the ground in 1625 during a Dutch attack. However, the Spaniards replaced it with a stone fort between 1630 and 1660. The fort is part of the San Juan National Historic Site" Source


  1. I visited San Juan years ago as part of my friend's destination wedding cruise that sailed around the Eastern Caribbean. We only had 8 hours to explore Old San Juan, but I loved every minute of it because the city is so mesmerizing. My personal highlight from the day was walking past Santa Maria Magdalena Cemetery for its astonishing beauty and unique location by the sea.

    Old San Juan requires at least a good 2 days of exploration if you don't want to feel rushed. I hope to return to Puerto Rico again in the future as OSJ only gives you a little taste of what Puerto Rico has to offer for the intrepid traveler.

  2. That cemetery was absolutely beautiful with its unique location right on the water. I agree, Old San Juan does at least need two days. We stayed nearby in Condado but biked down to Old San Juan on three separate occasions. It is such a great place.

  3. Would you say that Puerto Rico is one of your top favorite places to visit?

    1. Not my top favorite but a beautiful destination that is easy to travel to! Warm weather, same currency and language :)


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