Puerto Rico 2019: Travel Diary

December 2019                                    NJ —> San Juan, PR

This Holiday break we decided to trade in cold and snow for sunnier climes.  After a week on a Caribbean cruise (post coming soon), we decided to spend some time in San Juan and soak up the sun, flavor and history of San Juan.

Getting There/Getting Around

From NY, it was a fairly short flight to San Juan.  Most major airlines have flights daily from the east coast to San Juan.  If you are staying in San Juan/Old San Juan, flying into San Juan Luis Munoz Marin Airport (SJU), is your best bet.  It was a quick 20 minute uber ride from the airport to the pier to catch our cruise and our hotel in City Center was likewise 20 minutes to the airport.

If you are staying in Old San Juan, the city is extremely walkable.  Since we were staying just outside of Old San Juan, we opted to Uber into the main part of Old San Juan and then hoof it from there.  NOTE:  Do NOT rent a car to get around the city.  The streets in Old San Juan are narrow and crowded.  It seemed that 80% of the cars in Old San Juan were Ubers, so you never have to worry about waiting to long to get a ride.  The traffic getting in and out of Old San Juan got a little congested in the evenings so it was honestly nice to let the Uber driver deal with it while we just sat back and relaxed.  Even for the two trips we took to areas outside of Old San Juan, Uber worked great.  There are mass transit options as well, but honestly as someone who commutes every day to and from work, that is not something I wanted to deal with on our vacation.

Where to Stay

Since we were there during the holidays, finding affordable lodgings was tough.  We decided to stay at the Hyatt Place-San Juan City Center.  If you don’t need to be in the middle of Old San Juan or want a hotel that is centrally located to local attractions outside the old city, this is a great option.  It is very kid friendly, the rooms are spacious, their outdoor pool is great for kids and the staff were super hospitable.  Located across the road is the Hyatt House San Juan which is another great option.  Both hotels are located walking distance to the Convention Center and are a quick uber/cab ride to Old San Juan, The Condado beaches, or downtown San Juan. 

If you are looking to stay in Old San Juan and you have some $$ to burn, a stay at the Hotel El Convento is a must.  The building was originally a convent in the 17th Century and throughout the rooms and grounds much of that history has been preserved and honored.  While we didn’t stay here this time, we are definitely looking to come back and rest our heads amongst the luxury and history of this beautiful hotel.  

Another great option in Old San Juan is AirBnB.  For a weekend in Jan, you can get a great AirBnb in the heart of Old San Juan ranging from $115 to $300 a night!  Honestly we probably would have done an AirBnB to cut down on all the ubering but since we were there with my parents, as well as my brother and his wife, it was easier to just stay in a traditional hotel.  

Exploring Old San Juan

Since our cruise docked in San Juan at 6 a.m. on a Saturday, we disembarked as early as possible and took a quick (seriously 15 minutes) cab ride to our hotel to drop off our luggage.  Ready to hit the ground running, we grabbed our ubers and went straight to the Castillo San Felipe del Morro in Old San Juan.  This 16th century Spanish fort is at the farthest tip of the island of Old San Juan and was a great starting point to get our geographical as well as historical bearings.  The Castillo is a National Park (so don’t forget your membership card if you have it), and admission to the Castillo will also get you admission to the Castillo de San Cristobal down the road.  In addition to providing breathtaking views, the Castillo del Morro has a number of historical exhibits providing information about San Juan and Puerto Rican History as well as the significant role the Castillo played to the various forces that battled to control Puerto Rico’s advantageous position in the Caribbean.  After you have thoroughly explored the ramparts and structures within the Castillo (and sufficiently crisped your skin in the persistent sun), be sure to check out the documentary they play in one of the cooler alcoves of the fort to get a great cliff notes recap of San Juan’s history.

*We had Asher in the stroller the whole time, there are plenty of ramps (for moving cannons) that make it possible to explore without hindrance but there are parts that are only accessible by narrow and winding stairs that are definitely not stroller or claustrophobe-friendly.

While it is entirely possible to walk from Castillo del Morro to Castillo de San Cristobal, we decided to take the quick uber ride down to escape the heat.  Where Del Morro stands guard to protect Old San Juan from the sea, Castillo de San Cristobal stands guard to the land entrance to the walls of Old San Juan.  While the Castillo del Morro is more well known, I think both are equally worth a visit.  I am happy we spent our first morning exploring both to get a great foundational understanding of the history of San Juan.

From the Castillo de San Cristobal it is an easy stroll past the Antiguo Casino de San Juan (now an elegant event space), past Plaza Colón, to the heart of Old San Juan.  Be sure to reserve some time to just stroll the pastel colored streets and take in the beautiful European/Spanish architecture that has been so well preserved.  While meandering the streets keep your eyes peeled for some really interesting shops (once you look past ALL the gemstone/jewelery stores and tacky tourist shops).  Some of my favorites include Ole Puerto Rico which specializes in authentic hand-fitted Panama Hats; Poet’s Passage which is part poetry museum, coffee bar and local art gallery; and Mi Pequeño San Juan which specializes in beautiful hand painted tiles meant to look like the beautiful doors of Old San Juan.

After you have satisfied your shopping urges, be sure to make your way up to the San Juan Bautista Cathedral just across the road from Hotel El Convento.  Even if you are not a guest at the Hotel, you are still able to explore the ground floor common spaces and even sip a piña colada in their covered inner courtyard bar.

Next to the Hotel El Convento is the Plaza de la Catedral which is really a small green space but provides welcome shade from the heat and is a great place to sit and rest your feet while watching local life pass before you.  After you have rested a bit, you can make your way down Caleta de San Juan to the Puerta de San Juan which served as the welcoming gate for dignitaries and visitors to the Old City.  From there you can stroll along the waterfront on the Paseo del Morro towards La Fortaleza. Farther along the walkway you will reach the Raices Fountain and the start of the Paseo de la Princessa which is a European Style tree-lined Promenade featuring shops, outdoor cafes and parks for children.  If you have time, or are feeling a little peckish be sure to stop at the Cafe La Princesa for some drinks and snacks while enjoying some live music.  If you find yourself itching to do more shopping, then Paseo de la Princessa is a great peruse local handicrafts and artisanal souveniers. 

 If you are like us and find that strolling these vibrant and colorful streets leaves you wanting to know more about the history, I highly recommend on or both of the following walking tours:  Old San Juan Best Kept Secrets Tour or Old San Juan Walking Tour.  Both are approximately 2 hours and take along the very streets and sights I just described.  The Best Kept Secrets Tour fills up fast probably because it is so good.  You get an insider look at the history and architecture of old San Juan and get taken into private residences and places of limited access with a local architect as your guide.  If architecture is less of an interest to your, the Old San Juan Walking Tour is another great option.  The tour is led by a local writer who delves into the history, culture and Puerto Rican experience while showing you some of the most beautiful San Juan sights.  My favorite part of the tour was the San Juan Bautista Cathedral, the inside look and history of the Hotel El Convento and the catacombs of Igelsia San Francisco. 

Where to Eat

No trip to Puerto Rico would be complete without sampling the local delicacies.  Our first stop was lunch at Barrachina.  As the birth place of the original Piña Colada, let me tell you, those suckers were STRONG!  Be sure to fill your belly with some Mofongo and Arroz Mamposteao otherwise those Piña Coladas will knock you on your butt.

At the risk of turning this post into a Hotel El Convento stan account, I HIGHLY recommend making some time to have a meal at Patio Del Nispero inside the Hotel.  Words cannot even begin to describe how delicious and unexpected each and every dish was.  Even Asher’s simple truffle fries and Arroz Mamposteao was beyond delicious, I could have honestly had that as a meal for myself!  From appetizers to dessert, each dish had us oohing and aahing at how exquisite the flavors were. Not to mention the amazing cocktail list.  Though it felt almost sinful to not have a Piña Colada at every meal, deviating to try out some of their signature cocktails was totally worth it!

Another unexpected gem was Pirilo. It is near blasphemy to leave NY and seek out a pizzeria anywhere else by Italy.  And yet, we found ourselves waiting with the hoard of hungry patrons outside its very tiny doors hoping to get a chance to worship at their wood fired alter.  Pirilo was packed EVERY time we walked by it.  It seems the crowd never seemed to diminish outside its door, and they DO NOT take reservations.  It seems like a no-brainer that we should have just walked away but I can tell you, it was worth every minute of waiting, shoving and elbowing our way to a seat.  I can say without reservation it was one of the best pizzas I have ever tasted.  If you find yourself in Old San Juan, do yourself a favor and make the pilgrimage to Pirilo.

I’m almost embarassed to include the next two suggestions because it seems counter to everything I believe. But both these restaurants had some of the best Mexican (more like Tex Mex) food I have had outside of the Southwest.  The first, Greengos, we encountered by total chance.  Thoroughly exhausted from walking the cobblestone streets we just could not make ourselves brave the hoards outside Pirilo, so we resolved to find elsewhere.  Just down the street and out of sheer hunger desperation, we ducked into the only restaurant that did not seem to suffer from a Saturday night deluge.  I will be honest, I was skeptical.  The look and smell of the place looked like a bootleg version of Señor Frogs.  I have no doubt this establishment has presided over many a wet t-shirt competition.  But from the minute we dipped our first chips into the salsa, all our doubts disappeared.  This food was…really good.  Even my father, the greatest of Mexican food skeptics, proclaimed that he would be happy to eat here the following night for dinner. There truly is no greater endorsement I can give.  

Likewise, we stumbled onto Don Tako, by sheer happenstance.  Our walking tour was schedule to meet at the Starbucks around the corner and we figured it would be a good idea to grab a quick bite to bolster our energies for more walking.  We randomly chose a table and chairs at the various outdoor cafes and it so happened to be owned by Don Tako.  We were even more wary as it could seem possible that lightening would strike twice and we would encounter quality Mexican food in one trip.  But, boom clap, lightening had indeed struck again.  The food was so good it had me reminiscing about my favorite hometown Tex Mex establishment (may it rest in peace).  

Raices Fountain
Raices Fountain
Old San Juan
Old San Juan

San Juan Day Trips

We only had two and half days in Puerto Rico before we headed home but we wanted to make some time to get outside the city and explore.

What trip to the Caribbean would be complete without some quality time on the beach?  We asked our hotel concierge for their recommendations since we only really had half a day for the beach.  They recommended Playa Alhambique in Isla Verde.  It was about a 25 minute Uber ride to the entrance to the beach.   Along the beach were plenty of stalls to rent chairs and umbrellas and the beach at not crowded at all.  We were able to pick some chairs and umbrellas a little away form the “crowds” so it felt like we had out own private beach.  Considering it is a public beach, it was pretty surprising how clean the beach was.  Maybe I’m just so used to the obstacles of litter and debris that are so prevalent in NYC public beaches but it felt like we were on a resort beach.  The water was a little chilly (but as they say, your body gets used to it).  Since the beach is on the north side of the wind side of the island, the water was definitely active.  This is definitely not a snorkeling beach.  But the waves mellowed out by late morning and it was perfect for boogie boarding or body surfing.  Or if you are brave like me, you can battle the wave breaks to make it out to the calmer water just deep enough you can float along with the swells with your toes barely skimming the floor.  

I will however warn the area where we picked to park ourselves seemed to be at the outer edge of the beach so there was A LOT of seaweed on the beach and in the water.  It was literally impossible to go in the water and not come out picking pieces of kelp and algae out of every seam in my swim suit.  We discovered that just 5 minutes farther down the beach the seaweed as non-existent.  Also I will note, since most of the buildings on the edge of the beach are private condos/residences and not commercial hotels or buildings, there were NO BATHROOMS on the beach.  Plan accordingly.  Also there were a few random vendors selling grilled fish, meat and snacks but once they ran out, they ran out.  So again, plan accordingly. 

A trip to Puerto Rico wouldn’t be complete without a stop to Casa Bacardi.  We almost skipped this because it was definitely out of the way, but I am so glad we made the time to go and check it out.  It was roughly a 40 minute Uber ride to the Bacardi Factory.  We pre-booked our tour tickets, and after quickly checking in at the tourist office, we were handed our free drink tokens and souvenir cups to enjoy a signature drink on their patio.  Since our tour was at 10 in the morning we decided to wait and redeem our free drink after the tour was done.  The tour takes you on a trolley ride around the grounds, where you are told about the various buildings and their role in the rum distilling process.  Then we got let out at the Museum and Visitor Center where our tour guide took us through the history of the Bacardi family and their libatious legacy.  After walking through a replica of the old Barcardi distillery and factory there were several exhibits about the different types of Rums and their uses.  This was probably the most fascinating part of the tour.  Then we were taken to the gift shop where of course you could purchase whichever rum struck your fancy.  After the tour it was nice to just lounge on their outdoor patio as we enjoyed our complimentary Mojitos and Cuba Libres.  What better way to close out our holiday in the sun!


We hope you enjoyed our travel diary for San Juan and stay tuned for our next adventure!

If you have any questions about this trip in particular or have suggestions on where we should go next, please leave them in the comments below! And be sure to follow us on instagram (we have even more photos from the trip saved in our story highlights).


M&T (and Asher too!)


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