Dan and I flew to San Juan, Puerto Rico at the end of August to celebrate our 7th wedding anniversary(!). This was our 5th trip to San Juan and it was as fun and delicious as always. In light of the recent comments about Puerto Rico, now is a better time than ever to write about how much fun we had (and always have) in San Juan! This post details how we spent our long weekend, including what we did, where we stayed and what we ate and drank.
Colorful buildings of Old San Juan at night.
DAY 1: POOLING & A SUNSET CRUISE AROUND OLD SAN JUAN
Our anniversary is August 31st, so we traveled over Labor Day weekend. We flew in to San Juan direct from Newark very early this morning (like 1:00 AM on Friday morning), so we booked the prior night at our hotel and checked into our room around 2:00 AM. We went right to bed. When we woke up, since it was technically a work day, we enjoyed complimentary breakfast at Choices Urban Bistro due to our Marriott status (generously, they gave us either a continental breakfast or the money equivalent to use on anything on the menu!) and worked for a few hours by the pool. Luckily, work was not too busy.
Had to start with a Mallorca, or a sweet Puerto Rican bread topped with powdered sugar for our first breakfast.
The roof deck pool at the Sheraton.
Once the work day ended, we walked a few minutes to the San Juan Bay Marina to board a sunset cruise around Old San Juan. While several companies offer a similar tour, we went with Rico Sun Tours because they had availability when I booked last minute, ha. Basically, this tour is on a pontoon boat and it drives from the San Juan Bay Marina to Castillo San Felipe del Morro and back. We stopped for close ups of points of interest such as the US Customs House, Puerta de San Juan, Goat Island and Castillo San Felipe del Morro. The tour also offered Medalla beer and a box of snacks per person. It was a good tour.
Goat Island, which I find so picturesque.
Old San Juan from our boat.
My handsome husband on our sunset boat cruise.
Our evening ended with dinner out near Isla Verde. And while we normally would not drive that far for dinner, but our favorite chef, Jose Enrique, closed his namesake restaurant in Condado (SO SAD) and is now running dinner service at Cana inside the Fairmount hotel. We booked as soon as I found out that Jose Enrique was doing the dinner menu, despite the drive. Cana was quite good and I am happy that we went, but it absolutely did NOT compare to Jose Enrique! Go if you are in Isla Verde, but I really hope Jose Enrique somehow reopens.
Cocktails at Jose Enrique.
Sweet corn beignets with Ron del Barrilito sauce. This was so good!
Fried red snapper. It was no swordfish schnitzel, but it was very tasty.
DAY 2: A RUM DISTILLERY TOUR, COCKTAILS IN OLD SAN JUAN AND THE BEST DINNER OF OUR TRIP
After a solid breakfast, our second day began with a 15 minute Uber ride to Ron del Barrilito. Ron del Barrilito is a rum distillery started by a real Puerto Rican family all the way back in 1880 (well, they started making the rum then!). We toured Ron del Barrilito, including the old house on site, which was my favorite part. We ended our tour with a tasting of rums and a cocktail of our choosing. The cocktails were really, really great!
A rum tasting at Ron del Barrilito.
A Ron del Barrilito cocktail.
This day was our 7 year wedding anniversary so after a rest, we went into Old San Juan for dinner and drinks. We began our evening at yet another Puerto Rican rum distillery, this one much smaller called Scryer Rum & Barrelhouse. We both ordered cocktails and drank them on the roof. The cocktails and the rooftop area were unfortunately juuuust ok. Too bad – a missed opportunity. To even things out, we also stopped by one of our FAVORITE Puerto Rican bars, La Fattoría! We enjoyed Dan’s favorite drink, a Fernet Daiquari, which was just as delicious as ever.
Walking around Old San Juan.
Scryer Rum and Barrel House.
La Fattoría bar.
Dinner this evening was at the absolutely fantastic Celeste. We walked from La Factoría, and this dinner was incredible. You can read all about it here. If you are in San Juan, please, please eat at Celeste. You won’t regret it. It is one of the best meals that we have had in years.
Celeste menu in late August 2024.
Fried swordfish.
DAY 3: PASEO DEL MORRO, CASTILLO SAN JUAN, OLD SAN JUAN AND A PUERTO RICAN DINNER
Day 3 was “Old San Juan Day,” meaning that I had a host of activities planned for us in Old San Juan. And while we had done some of these activities in the past, I always enjoy repeating fun adventures! After our complimentary breakfast at Choices, we Ubered to Caleta (a tasty restaurant without AC (!)) in Old San Juan. This only took about 10 minutes. The reason for this destination is it is incredibly close to the Puerta San Juan, which also happens to be the entrance to Paseo del Morro. Puerta San Juan is a large gate dating back to 1635 that was, at the time, the main entrance to the walled city of San Juan during the Spanish Colonial time period. This door (i.e., puerta in Spanish) is free to visit and very cool for photos.
The walk from Caleta to Puerta de San Juan.
Puerta de San Juan – it’s more impressive from the other side.
Puerta de San Juan from Paseo del Morro.
We snapped a few photos at Puerta San Juan and then did the 20 minute stroll from Puerta San Juan to Castillo San Felipe del Morro along the water. The entire walk is flat until you reach the Castillo San Felipe del Morro, at which time you must climb stairs to access Castillo San Felipe del Morro. The walk is very pretty and easy. We unfortunately encountered some rain but it passed quickly.
Paseo del Morro.
Made it to Castillo San Felipe del Morro.
Dan going strong after the rain.
After our walk, we toured around Old San Juan a bit more and swung by Casa de Montecristo for a cigar for Dan and a cocktail for me in the cold air conditioning! Casa de Montecristo is one of the coolest, literally, places in Old San Juan and also a great place for cocktails and cigars.
Old San Juan.
One of the famous Puerto Rican flags.
We then lunched at La Casita des Rones before waiting in line for ice cream at the famous Anita Gelato. It’s well worth the wait if you need ice cream in San Juan!
The drinks at La Casita del Rones.
La Casita del Rones.
Anita Gelato.
This evening we dined at another Puerto Rican restaurant, Casita Miramar. Casita Miramar was located close-ish to our hotel inside an old mansion. We enjoyed chicken schnitzel and a fried pumpkin risotto. The food was excellent but the service was not the best.
Pumpkin Risotto.
A Puerto Rican schnitzel.
DAY 4: A POOL DAY AND THE AIRPORT LOUNGE
We spent our final day lounging at our hotel pool before leaving around 2:30 PM. We had great weather and it was nice to get in some Caribbean sun before flying back to New York.
Palm trees on the rooftop pool deck.
WHERE WE STAYED: SHERATON PUERTO RICO HOTEL & CASINO
We stayed at the Sheraton Puerto Rico Hotel & Casino in the “T-Mobile District”. Honestly, this is neither my favorite hotel nor location, but we used points so that was that. This was our second time stay at the Sheraton Puerto Rico Hotel & Casino (both on points).
The rooftop pool at the Sheraton.
The Sheraton Puerto Rico Hotel & Casino is a large hotel offering guests casino access on site, a pool, a hot tub (which was being renovated as of September 2024), 2 restaurants, a nice gym and a spa (that was booked when I tried to visit). We only used the pool and breakfast restaurant, Choices, where we received complimentary breakfast due to my Marriott Platinum status. The hotel is fine, particularly on points, but its in an odd area of San Juan. ‘
Breakfast tater tots at Choices.
TIPS AND TRICKS FOR VISITING SAN JUAN
- Puerto Rico is part of the US, meaning no passport is needed if you are from the US and Puerto Rico uses USD.
- Puerto Rico uses the same electricity and electric outlets as the US.
- While neighborhoods are walkable, San Juan is large and you will need a taxi or a car to fully explore it.
- Knowing some Spanish is helpful, but everyone in the tourist industry speaks English.
- If at all possible, explore Old San Juan when cruise ships are not in port.
- San Juan is a great jumping off point for the rest of the Caribbean, as its one of the largest and most well connected airports there.
- The best beaches in Puerto Rico are not in the Old San Juan area. Head to the islands or Isla Verde for better beaches.
- If you want to be able to walk around Old San Juan from your hotel, stay in Old San Juan.
- Given the size of Puerto Rico, if you are staying for longer than a long weekend, I suggest spending a few days in the Old San Juan area and the rest of the time elsewhere.
- Uber works well to get around the San Juan area.
STEAL OUR TRIP
Sheraton Puerto Rico Hotel and Casino: 200 Convention Blvd, San Juan, 00907, Puerto Rico.
Rico Sun Tours: We took the sunset cruise and booked via Get Your Guide. The tour leaves from San Juan Marina and includes Medalla beer and a decent snack box per passenger.
Cana: Located inside the Fairmont El San Juan Hotel in Isla Verde.
Ron del Barrilito: Open Monday – Saturday 9:00 – 18:30.
Scryer Rum & Barrelhouse: 259 C. Tetuán, San Juan, 00901, Puerto Rico. Open daily.
La Fatoría: 148 C. de San Sebastián, San Juan, 00901, Puerto Rico. Open 11:00 – 01:00 (02:00 Friday and Saturday). The “secret” portion doesn’t open until around 17:00 daily.
Celeste: 100 C. Pelayo, San Juan, 00901, Puerto Rico. Open for lunch Monday – Friday 11:30 – 14:00, dinner Friday – Monday 17:00 – 10:00 all day. Reservations suggested and can be made here.
Casa di Montecristo: 201 Calle del Cristo, San Juan, 00901, Puerto Rico. Open daily 12:00 – 01:00.
La Casita de Rones: C. Comercio, San Juan, 00901, Puerto Rico. Open daily 10:00 – 22:00 (00:00 on Friday and Saturday). Reservations recommended but not required.
Anita Gelato: 65 C. de la Fortaleza, San Juan, 00901, Puerto Rico. Open daily 8 AM – Midnight.
Casita Miramar: 605 Av. Miramar, San Juan, 00907, Puerto Rico. Open Wednesday – Monday 4 PM – 10 PM. Closed Tuesday. Reservations mandatory and can be made on the website.