Three days exploring Old San Juan


I have been to Puerto Rico, including Vieques, many times in the past, but this time I only focused on exploring the district of Old San Juan, the oldest settlement within Puerto Rico with a historic colonial section. Read my own travel experience with recommendations on where to stay, where to eat and what to do for a perfect three-day getaway.

Old San Juan is located on a narrow island which lies on the north coast, about fifteen minutes away from the International Airport. Old San Juan is united to the mainland of Puerto Rico by the three bridges, bounded by the Atlantic Ocean to the north and to the south by San Juan Bay.

I arrived at the hotel, a nineteenth century Spanish colonial building, after a short drive from Luis Muñoz Marin International Airport, and the minute I stepped into Old San Juan, a special feeling began filling me. We drove through the charming and colorful narrow cobblestone paved streets, until we reached our destination. We recieved a warm welcome by Beatriz (my host) and her on-duty staff. At check in, I felt like my family were waiting for me to arrive and taking me, after a characteristic cup of local coffee, to my old room where I grew up. You know that feeling.


La Terraza de San Juan

Luxury has many shades, and some of them stand far from the mere and obvious concept of opulence and richness. Travel these days is all about life events and experiences; in one way or the other, while some may be rough around the edges, they leave an unforgettable mark. La Terraza de San Juan is, to me, best described as homemade luxury. A true rustic and colonial take on Puerto Rico, with impeccable charisma and local traditional camaraderie, is delivered by the owners themselves and their casual but professional staff. Located in the heart of Old San Juan over Calle Sol, La Terraza de San Juan was my ideal epicenter to discover this charming district. It unveiled a new face of Puerto Rico, full of traditions and heritage, that I truly enjoyed. Read & See More


Cafeteria Mallorca / Breakfast

I could not help stopping by the old-fashioned, 1950s-style diner, Cafeteria Mallorca, to have my own Mallorca experience; it is located right in the heart of Old San Juan, over Calle San Francisco, across Plaza Salvador Brau. Mallorcas are sweet pastries, buttered, grilled, and then sprinkled with powdered sugar—ham and cheese are optional. I found this cafeteria very charming and iconic, with a mix of locals and tourists. If you are willing to try something more modern, then perhaps you should try Caficultura across Plaza Colon. Both bars are located only steps away from my hotel La Terraza de San Juan. Read & See More

Chef Jose Enrique / Lunch

I found the perfect excuse to come and explore the upcoming and trendy district of Santurce, Puerto Rico, which is located only ten minutes’ walk from Condado and ten minutes by car from my headquarters at La Terraza de San Juan. This restaurant is the classic example of why a book should never be judged by its cover and that first impressions are not always the right ones. Seen from outside, Jose Enrique looks like any other restaurant, but you are in for a gourmet treat if you follow your instincts. My recommendation, weather permitting, is to ask to be seated outside. I did and LOVED it. FYI, each time you visit is a new gourmet experience, since there is not any set menu, and every day has a new selection. Read & See More

The Mezzanine Cocktail Lounge / Before or after dinner

A beautiful and unique cocktail lounge located on the second floor of a colonial building, right upstairs from St. Germain. The menu has a variety of classic and signature cocktails, microbrews, and some select wines—in addition to delicious tapas—all served in a speakeasy-esque environment unique to Puerto Rico’s bar scene. Read & See More

Verde Mesa / Dinner

Without a doubt, this was the best dinner I had during my last visit to Old San Juan. The space, location, atmosphere, food and drinks were just perfect in balance and compliment to Old San Juan. It’s located on Calle Tetuan #107, perched on the wall of the Old San Juan, along the Paseo De La Princesa. Verde Mesa is a fish and vegetarian restaurant featuring great dishes, including traditional Puerto Rican ones, which will even captivate the meat lovers. Read & See More


I arrived in Puerto Rico on the first flight of the morning, checked in at my beautiful suite in the heart of Old San Juan, and got ready to explore the old courts, fortresses, and secrets of this charming district. My hotel made all the arrangements for an expert guide to take me on a private two-day tour of the entire district, including some great lunch and dinner options. 

Day 1: Exploring Old San Juan & Castillo San Felipe del Morro

We headed out of the hotel and walked for over an hour along the colorful quaint cobble-stoned streets of Old San Juan before stopping by the traditional Cafe Puerto Rico, located at Plaza Colon, across from the statue of Cristobal Colon (similar to the one in Barcelona) for a true local lunch. The meal consisted of Yuca Mero Mofongo and Red Sangria (YUMMMM). Afterwards, both heart and stomach were happy and full, ready to continue the Old San Juan experience. 

After lunch and a few strong shots of coffee, but before we carried on to one of the area’s main attractions, the Fort San Felipe del Morro, we took a lovely stroll downhill towards the promenade Paseo de la Princesa, a restored 19th-century esplanade. Stop by Cafe la Princesa, or, like we did, just walk along and enjoy the panoramic bay views. Once we reached the main gates to the intra-muros, we crossed through and uphill once again to head to the fort. Also known as Castillo San Felipe del Morro, the 16th-century citadel encapsulates Puerto Rico’s role as a guardian of the New World. 

When the sun set, after contemplating the stunning views, I headed back to my hotel to chill for an hour, take a shower and get ready for dinner. Read & See More

Day 2: Exploring Old San Juan & Castillo San de San Cristobal

After a deserved rest and early morning breakfast at the rooftop of my hotel, La Terraza de San Juan, I was ready and excited to begin my second day exploring Old San Juan. I was not aware that I would go beyond it to the districts of Santurce and Condado, which I loved, but I was happy to always return to my historic quaint district of Old San Juan.

We headed to the district of Santurce, which is considered the SOHO of Puerto Rico. It is still undergoing some development, but you can see the bohemian side of it with the Fruit Market and some really particular restaurants. Our choice was Chef Jose Enrique, and WOW that was a great choice. After that we walked for over fifteen minutes to the district of Condado, where we enjoyed some lovely views of the beach, and briefly visited the new Condado Vanderbilt Hotel. From there we took a taxi, which dropped us right in front of Fort of San Cristobal. 

Also known as Castillo de San Cristobal, it’s located on Cerro de San Cristobal, literally a ten minute walk across Old San Juan from the Fort of San Felipe. We crossed the gate into the San Juan National Historic Site, and immediately I felt as though I had been transported to 1783. I walked by the underground tunnels, where the dungeons feature some original frescos. I also got a glance at the famous Garita del Diablo or “The Devil’s Guerite.” It is a very interesting site—the largest fortification built by the Spanish in the New World. 

From there we took a walk across Old San Juan where it borders the right bank esplanade by the district of La Perla, with panoramic views of the Atlantic Ocean. On our way I got the chance to meet one of Old San Juan’s celebrities, Mr. Azucenas, who has even been immortalized on the walls of Old San Juan. Then we returned to my hotel, ready for drinks at the terrace, followed by dinner at Perla, in La Concha Hotel & Casino.Read & See More

The following morning, I woke up late, went for my own Mallorca experience at Cafeteria Mallorca, and by the time I made it back to my hotel, my ride was waiting to take me to Luis Muñoz Marin International Airport to fly back home. An easy, relaxing, cute and educational three-day getaway, only a few hours’ flight away from New York. 

Carlos Melia is a travel expert, blogger, niche marketing consultant, jetsetter, and bon vivant, who travels around the world discovering what’s new and cool in luxury travel and hospitality. Also the founder of the Luxury Gay Travel Network (LGTNetwork), his reviews on hotels, restaurants, destinations, and attractions, based on his own experiences as an OUT Gay Traveler can be found at

About The Author

Carlos Melia Travel Agent Luxury Travel Curator & Blogger Wedding Planner Public Relations & Marketing CM by Carlos Melia Haute Experiences MLGTPP Twiitter YouTube Pinterest Shameless BIO Carlos Melia (38) Bespoke and Luxury Gay Travel Expert, Blogger and Tourism/Hospitality Niche Marketing Consultant. For the past 20 years, I have been an independent travel agent with my own company CM by Carlos Melia - - and have travelled and lived extensively all over the world. I have international travel experience, both as a traveler and professional, specializing into Luxury and Bespoke Gay Travel worldwide. Experiential travel perfected is my mojo. My firm commitment to you, and main reason of my following is - Been There Done That. All travel services and products to be offered and featured, have previously been experienced, tested and approved personally by me. At CarlosMeliaBlog - - I speak Gay, but I am also fluent in Straight. Everyone is welcome, everyone. There you will find reviews, tips and information on hotels, restaurants, tours, destinations, among other travel related services and products. Former Mr Gay International 2008, and member of the Board of Directors at Mr Gay World, I work along the main LGBT organizations worldwide, in pro of our rights and to assure everyone, that indeed It will be Better. I have partnered along the leading lifestyle, travel and hospitality PR firms, media groups and corporations, implementing creative and effective targeted outreach to the LGBT community. Narrowing the existing gap in between mainstream travel/hospitality services and the LGBT community worldwide. Been called, awarded and recognized, by peers, press, and customers, as a gay travel guru, jetsetter, influencer, broadcaster and globe trotter, with known as the little Marco Polo. Bachelor degree in Hotel and Restaurant Management, tree times around the world, going for the forth, more destinations, air miles and room nights that I can keep track of and recently have added gay wedding planner to my curriculum. Regardless of your sexual orientation or preference, travel should always be a memorable, unique and unforgettable experience, and not just a destination. For this, I work closely with clients and suppliers to assure that this happens. Hope you enjoy the ride, and look forward hearing your feedback and comments. Sincerely, Carlos Melia (*) Proud and active member of two of the most relevant and influential organizations within the Travel and Hospitality Industry, which are IGLTA – International Gay and Lesbian Travel Association, TZELL Travel Group and Signature Travel Network.

Send this to friend