Carolyn Always Earley

San Juan and Condado Beach – April 2023

My best friend Veronica and I decided to visit Puerto Rico for her birthday. She’s from Ponce (further south on the island), but she wanted to see family in San Juan and do all of the touristy things. We had an amazing time! Here is our 6-day itinerary with personal recommendations of great food and activities.

Days 1-2 (Travel Days):

We flew into the San Juan airport (SJU) from Phoenix, so it was an 8-hour flight with one connection. We chose to take an overnight flight since we would need to connect on the East coast and went through the Philadelphia airport, getting into San Juan around 1 PM local time.

Tip: Since SJU is about 30 minutes away from the hotel area, arriving in the early afternoon is ideal so that you don’t have to wait long to check into your hotel (and you can take a nap before dinner after your long day of travel).

We stayed at the La Concha San Juan Renaissance Resort and it was beautiful! As a Marriott Bonvoy member, I received a free gift upon check-in, which was a bottle of wine. Our room wasn’t quite ready when we arrived, so they held our bags and we used their changing area to put on our swimsuits.

View of Condado Beach from our room

Tip: Avoid planning big activities or making dinner reservations on the day you arrive (in case of travel delays or just plain exhaustion). I suggest checking out the hotel amenities and grabbing dinner either at the hotel restaurant or somewhere within walking distance.

The Hotel

La Concha San Juan Renaissance Resort is located in the Condado area in the northern part of San Juan, right on Condado Beach and next to Old San Juan. We chose this hotel for its location, private beach and multiple bars and restaurants. The hotel had several pools and hot tubs as well, notably including one for adults only and an infinity pool right on the beach (pictured below).

Day 3:

We Ubered to Bahía Viva Cataño, an outdoor waterfront promenade for tourists. We walked around the boardwalk, grabbed coffee and breakfast from a food truck, and made our way up the coast.

We stopped for lunch at Empanadillas El Gordo. It’s the epidemy of a “hole in the wall” restaurant – delicious food, cheap, and very small. We sat outside and ate quickly before continuing on to our destination: Casa BACARDÍ.

We booked the Rum Tasting Tour at Casa BACARDÍ, which includes a welcome drink, 75-minute tour of the facility with history on the family, and a tasting of four different rums. The tour ends at the gift shop, where you can buy souvenirs only available at the facility.

Dinner at Santaella

We had a dinner reservation at Santaella, specifically to try their Pastelón del Dia (it’s like a Puerto Rican version of lasagna) and it did not disappoint. The flavor of the day was corned beef and it was one of the best things I’ve ever eaten.

Tip: I highly recommend making a reservation if you want to dine here. The vibe is classy and intimate. Also, this particular dish, Pastelón del Dia, is for 2 people to eat together so make sure your dining partner is on board if you want to try it!

Don’t forget dessert! The budín de guayaba y queso crema (guava and cream cheese bread pudding) was TO DIE FOR. I’m salivating just thinking about it. (Take me back!)

Day 4:

A trip to San Juan wouldn’t be complete without a tour of “Old San Juan”. The castles, the statues, the food – you don’t want to miss it! You can spend a whole day perusing the sights here.

We started off the day by heading to Castillo San Cristóbal. You can book a tour of the castle, but I’d suggest just walking around to view it on your own. There are plenty of signposts explaining the history of the castle and surrounding area that you can read at your leisure.

The views from the castle were amazing – you could see both the ocean and the city. Plus, it was a great starting off point before heading into the city by foot.

Tip: Buy a $10 pass at one of the castles and you can also visit the other castle (Castillo San Felipe del Morro is pictured above in the distance) within 24 hours for free! (Fun fact: There are also 6 nationally recognized holidays on which the entrance fee is free. Visit their website for details.)

We meandered through Old San Juan, making sure to stop at Plaza Colón, Puerta de San Juan and Los Paraguas de la Fortaleza (pictured below) before reaching the 2nd castle.

If you want to do some shopping, stop into any of the boutiques along the alleyways. The clothing and souvenirs and super cute and well priced. There are also some great museums you can check out: Museo de las Americas and Museo Casa Blanca are the most popular, but there are also a bunch of small museums throughout Old San Juan.

By the time we reached Castillo San Felipe del Morro, the weather had gotten a bit cloudy/rainy. Fortunately, it didn’t last long and we were still able to tour the castle before it closed.

Food & Drinks

We stopped at several places as we walked through Old San Juan to grab a quick drink or snack and briefly enjoy some air conditioning. One of the places that was recommended was La Factoría, a hole in the wall bar that we almost couldn’t find. They had great appetizers and drinks (though the bathroom was a tad sketchy)!

For dinner, we went to Princesa – Cocina Cultura. This is a great place to experience authentic, old-school Puerto Rican food. According to the restaurant’s website, the menu is based on Puerto Rican cookbooks published between in 1859-1950. The vibe is relaxed and earthy.

Day 5:

On Saturday, we met Veronica’s family for lunch at a restaurant known for its Dominican food, El Camarón. This was a casual restaurant with a big menu and big servings.

For dinner, we went to Raya. This was our “splurge” dinner, as the meal prices average $100 per person. We shared several appetizers and small plates so that we could try multiple things. Everything we tasted was incredible!

Tip: Many restaurants in Puerto Rico close on Sunday and Monday, so be sure to research their hours of operation. If you are celebrating a birthday or other special occasion that falls on one of those days, I suggest booking your celebratory meal on Saturday (or Tuesday).

We decided to check out the nightlife at La Plaza del Mercado de Santurce – a farmer’s market by day and club scene at night. All of the bars are open to the street, so you can buy a drink and walk around or just hang out (similar to Las Vegas). Seating was very limited. You could hear music throughout the area and everyone was having a great time! We went into one of the clubs that had air conditioning and danced for a bit until it was time to Uber back to the hotel.

Day 6:

We had Sunday brunch at The Loft Beachfront, which is located upstairs at the resort. They have a great menu you can order from or you can choose the buffet, and the view from the restaurant overlooks the private beach.

We decided to spend the day relaxing on the beach since we had spent most of the trip so far walking and sightseeing, and many places are closed on Sundays.

For dinner, we went to Serafina, an Italian restaurant located at the front of the resort. The food was delicious! The vibe was family-friendly and casual (and we were awkwardly very overdressed as we were heading next door to the Vanderbilt after for cocktails).

The Condado Vanderbilt Hotel has a number of fancy dining options, but we just went to the lounge for wine and dessert. We were no longer overdressed – this place is muy classy and elegant. A five-piece band played at the front of the room and everyone was dressed to impress.

Pro Tip: Since hotels are open 24/7, hotel restaurants tend to be the exception to the rule when it comes to Sunday/Monday closures. If you’ve already checked out the restaurants at your hotel, look into nearby hotels with restaurants to expand your options.

To see more pictures from this trip, visit my Facebook page.