In addition to traveling the globe like the Sahara dust, I am a firm believer in a good Stay-Cation. A stay-cation is defined by the Oxford Dictionary as, “A vacation spent in one’s home country rather than abroad, or one spent at home and involving day trips to local attractions.” A good stay-cation is not just hanging out at home on your off days, nor is it simply enjoying local entertainment. A stay-cation is a mindset. You purposefully don on the mantle of a tourist in your hometown. You act like a tourist, you look like a tourist, you think like a tourist, you speak like a tourist, you spend like a tourist- you become a tourist. This is much harder than people realize, to be a tourist as a local, but when you do the city reveals a charm you do not appreciate in the day-to-day living of life.
Old San Juan is charming! The Fort itself is over 500 years old. The buildings are brightly colored. And the party is never contained in the establishment, always spilling onto the streets. There is always something to do and the hospitality of the people of Puerto Rico is well known.
The city itself was originally called Puerto Rico, meaning Rich Port, and the Island called San Juan, but a cartographer made a mistake and switched the names and it stuck. You will see both Spanish and American influences as the island has been a part of both cultures. That is also evident in the duality of both Spanish and English being spoken in OSJ; Spanish being the native language and English the learned one. However, if you are playing tourist, speaking English is the way to go.
First let us talk logistics. You will not find the best accommodations in Old San Juan on Expedia. The best things in San Juan often go without advertising simply because they do not need to, word of mouth keeps them fully booked. The best places to stay are generally boutique hotels that have around 20 rooms that are immaculately designed and well maintained. Among my top 5 favorites are The Gallery Inn and Casablanca. Both are hotels that have been lovingly restored to give an understated elegance to their spaces.
When I am being a tourist in OSJ I always take an Uber into the city and have it drop me off at Plaza Colon. I am of the opinion that this is the beginning of Old San Juan. This is where the old fort began and in the center of the Plaza is a statue of Christopher Columbus as a tribute to the arrival in the city in the 4th century. From this point in Old San Juan everything is walkable and having a car is a liability.
A stay-cation is a mindset. You purposefully don on the mantle of a tourist in your hometown.
From Plaza Colon and after check in at my hotel I make my way over to Plaza de Armas, named so because it was in this square that the soldiers used to practice their drills. At the end of the Plaza is a fountain representing the four seasons. Fun fact- often at night you will find a fifth, live statue, who recites poetry and Shakespeare in Spanish for tips. Behind the fountain is one of the best places for coffee and empanadas in the city. They are also open late, which is a plus. And they only take cash, which is good to know. At the other corner of the Plaza you will find Poet’s Passage, home to local poet Lady Lee Andrews, a gifted poet who hosts an open mic poetry set every Tuesday night that begins at 7 pm sharp.
Another great thing to do is visit Castillo San Felipe del Morro or El Morro as it is locally called. I am not a National Monument kind of person and the idea of visiting historical war sites is not my definition of fun. That being said, I take all of my guests, and my person, to El Morro when I am in Old San Juan. I go at night because the magnificence of the fort is breathtaking, and I go during the day to envision life 500 years ago. I will not try to describe it for you. All I can do is tell you if you go you will not be disappointed.
But Amy, what about the beach? On my stay-cations I beach like a tourist. My favorite beach in the area is Isla Verde (technically it is 3 beaches in one but no one knows them by their real names). After you take an Uber to the Alambique Lounge you can enjoy literally anything on the menu for lunch. Then walk across the street to the beach and you will find insta-worthy aqua blue water both shallow and calm enough to play in. When I am living like a local, I will hoist my chair and cooler and paraphernalia to the beach and try to find a tree to park under. When I am playing tourist, I rent an umbrella and beach chair for $15 and $5 respectively and have a whole unique experience as I buy from locals selling food and drink on the beach.
For the high brow, there are plenty of museums, antique bookstores, and theaters in Old San Juan. My favorite is Teatro Tapia, across from Plaza Colon. Teatro is the oldest free-standing theater in use in the United States, having opened its doors in 1832. Like most of the best things in Puerto Rico, you will not find a website advertising the events at the Teatro. The best way to find out the upcoming plays is to check for posters around the area or search for the theater events on Eventbrite.
And then the nightlife- the nightlife in Old San Juan is a funny thing. It is funny because Puerto Ricans can turn any event into an impromptu party. One moment you are having a quiet dinner and the next a band is playing, and the dancing has erupted into the streets. Most of the best nightlife spots are spots where local musicians have set up randomly and people start dancing- which takes a sense of adventure to find. However if you are looking for a little more direction La Factoria has been the go to place for the nightlife scene. It is actually six bars in one all connected by mazes and the location itself is unmarked. However, if you follow the laughter and bass, you will know you are in the right spot. Personally I like the outdoor patio between Anam Spa and Cocktail Lounge and T-tuan. Every weekend there is live outdoor music and dancing in the pedestrian street. The night is not complete until you have had Gelato at Anita la Mamma del Gelato, which is simply referred to as the Gelato place. There will be a line bet embrace it. When you have amazing ice cream dripping down your chin in the middle of the night you will find it is well worth it.
There are so many more things I could recommend doing in Old San Juan, but part of the fun is the Discovery. Old San Juan will not show you her treasures easily. Like any good treasure they have to be hunted for or wandered upon to be discovered. Which is what life being about, is it not, the Discovery of things?
Be you an actual tourist or a local having a tourist experience- enjoy the treasure hunt.
Photos by the author.