Vacation to San Juan, Puerto Rico – Travel Diary

Detailed travel notes, including dining, lodging, and activity recommendations for adults from a six-day summer vacation to San Juan, Puerto Rico. First published August 2019. Last updated December 2021.

Earlier this month, five friends and I traveled to Puerto Rico for my 30th birthday. None of us had been to the island before but, after our San Juan vacation, each of us plans to return. Puerto Rico is so culturally rich, accessible, and beautiful that I feel like I need to make up for lost time and start planning my next visit ASAP. Below are all the fun details of our trip from Puerto Rican restaurants you should try to things to do in San Juan, beautiful beaches in Puerto Rico, and helpful travel tips so you can plan your vacation like a pro. Let’s get into it!

If you enjoy tropical destinations, check out these sunny trips, too.

Table of Contents

bienvenidos sign on street on Old San Juan, Puerto Rico

Day One – Cabana Vibes y La Placita

We landed in San Juan on a Friday afternoon and headed to our accommodations for the duration of our stay: Serafina Beach Hotel. It is a super chic, boutique hotel on Condado Beach that we enjoyed and recommend. Everyone on staff was extremely courteous and helpful and the vibes were on point. The only thing I didn’t like was that the walls seemed to be a little thin. We checked into ocean view suites with beautiful blue color schemes that perfectly complement the floor-to-ceiling views of Condado Beach. I never got sick of the view. Seeing the ocean every time I returned to the room was grounding and calming. Something about being near the water makes me feel so at peace.

View of Condado Beach from Serafina Beach Hotel window

Our rooms were well appointed and I was perhaps most excited about the powerful garment steamer that was ready to go in our closet without me even having to ask. It came in SO handy to get my all of my vacation looks together. We quickly changed for the pool and headed down to meet up with the rest of our group. The Serafina pool scene is pretty lit. We made friends with the bartenders and found out I share a birthday with one named Angel. He took even better care of us after that. We drank rum punch, tequila shots, and who knows what else poolside and ordered a mix of appetizers and main dishes from the cabana bar.

Serafina has direct access to Condado Beach and the beautiful infinity pool overlooks the ocean. At night, it’s gently heated, lights up, and changes colors. The strip of beach behind the hotel is rockier close to the shore so we didn’t really dive into the water but it was so beautiful.

mojito in cabana in San Juan Puerto Rico

Dash of Jazz on Condado Beach


burger and truffle fries at Serafina Beach Hotel pool

Dash of Jazz in Serafina Beach Hotel infinity pool

Sunglasses | Hoops

In the evening, we got ready for a night out. La Placita was originally on the itinerary for later on in our trip but a few people we had met, including Angel, said Friday was absolutely the best night to go so we hopped in an Uber and went. They we so right! We had a great time bar-hopping. There are bars, restaurants, lounges, and clubs of all kinds right next door and around the corner from each other with dancing and partying spilling out into the streets on the most popping nights. I’d describe La Placita as the San Juan equivalent to Austin’s 6th Street or New Orleans’ Bourbon Street (By the way, get into our girls’ trip to NOLA). We went from place to place and there was a vibe for whatever you might be in the mood–hip hop and reggae, local hits, reggaeton or strictly Spanish tunes.

Dash of Jazz en La Placita, Santurce, Puerto Rico

Slip Dress | Sneakers

Some bars are more heavily visited by locals and other cater to tourists. We started at Maui, which is right near the Uber pick-up/drop-off point for La Placita and enjoyed Medalla (local beer) and rum cocktails to the sound of Spanish-only music. Then we ran into a group of girls vacationing from Chicago at Aguardiente (hip-hop club) and bonded over Megan Thee Stallion. From there, we walked over to Cafe Ruben for late night (around 2 am) eats then headed back to the hotel because we had to be up in just a few hours for an excursion.

Day Two – Culebra y Playa Flamenco

On Saturday, we rose early for a 7am pickup time on an excursion to the beautiful island of Culebra. The departure point was in Fajardo, which is a 45-minute ride from San Juan. From there, we took a choppy boat ride to a crystal clear point for a bit of snorkeling before our ultimate destination, Playa Flamenco. This beach is consistently ranked in the top 10 (sometimes top five) beaches in the world. The water is a beautiful sparkling turquoise and the sand is fine and quite clean. This was not my favorite beach in Puerto Rico (we’ll get to it in a little bit) but is truly gorgeous definitely worth your time to visit.

Playa Flamenco, Culebra, Puerto Rico

playing in water on Playa Flamenco


The island of Culebra is sparsely populated but there are shops set up selling fresh coconuts and other food and drinks. We spent a couple of hours playing in the crystal blue-green water and exploring the beach. We booked our excursion here and definitely recommend the option with transportation simply to avoid the hassle of arranging transport and being able to comfortably sleep both ways. That was clutch since we had been out turning up into the wee hours of the morning. The tour includes unlimited rum punch, mojitos, piña coladas, and lunch.

garlic shrimp, salad, and plantain soup at Waiter's Restaurant in San Juan, Puerto Rico

After getting back to our hotel, we freshened up and napped. Then I made a pharmacy run for bottled water and a few other essentials. This is normally a day one activity but we got right to turning up upon arrival. I also stopped into a souvenir shop and Piña Loka for a piña colada before dinner. That night, we ate at Waiter’s where I had the plantain soup, garlic shrimp, and salad. The service was a little slow but the food was yummy. We meant to check out Club Brava later on that night but passed out (getting old). On the bright side, this made it easy to get up early the next day.

Day Three – Isla Verde y Condado Strip

smoothie at Crush Juice Bar in Condado, Puerto Rico

We got up bright and early on Sunday, dressed for the beach, then walked to Crush Juice Bar on Condado for smoothies then on to Isla Verde Beach, which is SO beautiful. It rained quite heavily while we were inside the juice bar but cleared up beautifully during the Uber ride to Isla Verde. Our driver said it often rains like the sky is going to fall down for just a few moments then opens up to beautiful breezy sunshine, which was exactly what happened.

Isla Verde Beach, Puerto Rico

Dash of Jazz on Isla Verde Beach

Beach Bag | Coverup | Bikini

Isla Verde was my favorite beach of the trip, hands down. It is shrouded by a strip of luxury resorts so the beach is well-trafficked but there were very few people when we arrived that morning. There are vendors for beach massages, parasailing, and all kinds of other activities. One thing to note is there are no showers or public facilities on Isla Verde Beach so, if you aren’t staying in one of the nearby hotels, you’re out of luck.

holding coconut on Isla Verde Beach

Isla Verde Beach

Isla Verde is a family-friendly beach but it isn’t cheesy at all. We felt perfectly comfortable as a group of adults with no children. And the water was a beautiful blue green. We spent a few hours playing in the sea and sand, jet skiing, and drinking fresh coconut water before heading back tot he hotel to get ready for brunch, which was further down the Condado strip from us. Side note: The Condado resort strip has a similar vibe to Ocean Drive in Miami.

brunch spread at Oceano in San Juan

view from rooftop of Oceano Restaurant in San Juan, Puerto Rico

I highly recommend the Sunday brunch at Oceano if you want beautiful ocean views of a more popping part of Condado Beach and a generous eclectic brunch buffet. I’m not usually a buffet fan but this place came highly recommended and was worth the hype. The best beach views are on the third floor, which wasn’t open while we dined but since we were celebrating birthdays and had made friends with some of the Oceano staff, we got to check it out.

holding mojito

Sandals | Romper

Piña Loka was along our walk back to Serafina so we grabbed a round of piña coladas. Later, we went back to La Placita in Santurce just before sunset and enjoyed delicious margaritas and mojitos, live music, singing, and dancing in the streets until nightfall. After dark, we grabbed empanadillas and medalla beer while listening to Bad Bunny at Captain Rum then brought in my 30th birthday with Texas tunes and Afro beats at Aguardiente.

birthday dessert at Serafina Beach Hotel

Day Four – Old San Juan

Monday was my birthday and we packed quite a bit of activity into the day! We met up at La Fortaleza in Old San Juan to explore a bit. A few areas were barricaded and patrolled by police in response to protests that had concluded a couple of weeks prior, so our routes to get to landmarks sometimes took longer than necessary. This was particularly annoying because the heat was brutal that day–around 100 degrees.

Each day we spent in San Juan was hot with a breeze and very comfortable at night. We stopped in a few shops before heading to Chocobar Cortes for breakfast. This restaurant incorporates chocolate into every dish, including the avocado toast! Service was slow. Very slow. The food was good, though. I had a tamarind mimosa, chocolate grilled cheese sandwich, and the chocolate brulee.

barricades in Old San Juan in response to political protests

chocolate grilled cheese at Chocobar Cortes in Old San Juan

Next, we wandered over to Exodo Caribbean Art Gallery, which was full of beautiful modern black art. No pictures were allowed inside the gallery. Outside, we noticed that there are lots of cats roaming around Old San Juan. They haven’t taken over or anything but you’ll definitely notice them down most every street. Old San Juan is more commercialized than we had expected but there’s history at most every turn. The buildings are so colorful, architecture is distinctively Spanish, and it reminded us of the French Quarter in New Orleans.

building in Old San Juan, Puerto Rico

hotel archway in Old San Juan, Puerto Rico

entrace to Puerto de San Juan

We walked over to Puerta de San Juan to look out at the water before taking an Uber to Escambron Beach. Our driver, Santiago, gave us a brief driving tour of the government area along the way, including the Senate house, police station, and Capitol building. Escambron Beach is more urban than say Isla Verde or even Condado and more heavily visited by locals. There were families cooking out and relaxing on a Monday afternoon. This beach is rockier in places and the sand is not as pristine in the park area but the water was still very clear and we saw a lot of colorful plant and fish life while playing in it.

Playa Escambron in San Juan, Puerto Rico

Beach Hat

Playa Escambron has restrooms and rinsing areas to get the sand off your feet as well as a kind of food court. After a couple of hours there, we went back to Old San Juan to get mofongo and the best piña coladas of the whole trip at Raices (Spanish for roots). My brother and sister-in-law had recommended this place as did a number of Puerto Ricans we met so we knew we had to make our way. I had the chicken mofongo with creole sauce. Service here rivaled Chocobar Cortes for lack of speed but the food was great and we loved the history of Raices so I recommend you stop in. Just don’t be in a hurry.

chicken mofongo at Raices in Old San Juan

holding pina colada at Raices San Juan, Puerto Rico

From there, we went back to Serafina and freshened up quickly for salsa lessons. The one-hour class flew by. Here is where we book the lesson. After salsa, we recharged at the hotel with complimentary prosecco and got ready for a late dinner at Marmalade, which is an upscale restaurant back in Old San Juan. The dining experience at Marmalade involves a multi-course meal where you select four, five, or six menu items to come out over the course of the night. The food was delicious and service was perfect.

aMare bar at Serafina Beach Hotel

Everyone on staff seemed to know it was my birthday and stopped by during the meal to wish me a happy 30th. That might be because our table was covered in rose petals. 🙂 It was also our waiter, Louie’s, birthday. I sipped on the global warming cocktail, which is a margarita with an ancho chile-infused ice sphere. This means the cocktail gets hotter the longer you wait. Very clever. Pretty much every cocktail on the menu poked fun at our current orange head of state, his lifestyle, and his policies. We loved it.

global warming cocktail at Marmalade restaurant in Old San Juan, Puerto Rico

My meal consisted of heirloom golden beets, lobster risotto, sea bass, and paradisio for dessert, which I took to-go and enjoyed on the beach the next day. The chef, Peter Schintler, came out to talk us through menu options and we wound up chatting about recovery after Maria as well as Puerto Rican politics. He later sent over his favorite white bean soup for us to sip between courses, which is very rich and comes out in a teacup.

4 course dinner at Marmalade Restaurant in Old San Juan, Puerto Rico

An interesting detail to note about Old San Juan is the old blue cobblestone roads. They make for a bumpy ride when passing through in a car but be sure to look down once you step out into the street. The stones are a beautiful blue, which is more apparent in some places than others.

Dash of Jazz walking in Old San Juan, Puerto Rico

blue cobblestone in Old San Juan, Puerto Rico

Day Five – Santurce

On Tuesday, I slept in until nine then took my time getting ready. We went to Ocean Park Beach,  laid out, and ate food from a beachside restaurant along with my birthday dessert (delicious, by the way), and champagne. Solid Tuesday morning. It was much windier that day and the current was stronger. Sand was blowing everywhere! Our uber driver had described Ocean Park Beach as the most beautiful and the water was a beautiful blue turquoise. The weather made it difficult to truly appreciate, though, so we didn’t spend a lot of time there.

outdoor mural in Santurce

Dash of Jazz on street in Santurce

Linen Pants | Linen Top | Sunglasses

street art in Santurce, Puerto Rico

Next, we explored Santurce, starting with Museo Arte Contemperaneo, which is three stories of artwork and installations. Passes for the museum were $5. From there we walked over to La Placita to visit La Plaza del Mercardo in the daytime and have pineapple mango batidas.

Plaza del Mercado en Santurce, San Juan, Puerto Rico

holding batida in La Placita, San Juan

produce inside Plaza del Mercado, San Juan, Puerto Rico

After walking around Santurce, we went back to the Condado area and hit up Señor Paleta for dulce de leche and fresa mojito paletas (popsicles). We relaxed at the Serafina pool for the rest of the afternoon then had dinner at aMare, which is a Mediterranean restaurant on the Serafina property.

champagne toast against Condado Beach backdrop

dinner options at aMare Restaurant in San Juan, Puerto Rico
Green Tea Killah and Isla Boriquen Fizz cocktails at La Penultima in Santurce, Puerto Rico

We ordered sea bass, mahi mahi, lobster tacos, and salads and dinner highlights include gorgeous ocean views, more prosecco, and celebratory ice cream with sparklers. Leos celebrate our birthdays for more than just a day, in case you didn’t know. 🙂 To top off our last night in town, we ventured back to Santurce to grab cocktails at La Penultima for cocktails. I enjoyed and recommend the green tea killah, which is gin based with matcha.

Day Six – Loiza

sunrise on Condado Beach in San Juan Puerto Rico

I rose early on our last morning in order to watch the sunrise on Condado beach behind the hotel pool deck. I had been waking up around sunrise the entire trip but would typically just peek out my window then go back to sleep for a couple more hours. It was beautiful to see the ocean light up and the beach start to come alive. Afterward, I packed, tidied up the room, and checked out. I was able to stow my luggage with the front desk staff and grab a portable breakfast at a nearby store before getting picked up for an Afro Puerto Rican Heritage Tour of Loiza.

Isla Verde beach along road into Loiza

Heading from Condado, streets and highways eventually slipped away into the single, two-lane road that goes in and out of Loiza. Our first stop was the home and workshop of artist, Samuel Lind and we got a personal tour of his works, which were stunning and distinctively black. I was able to purchase a couple of gorgeous prints for my sister and myself.

Studio de Arte de Samuel Lind en Loiza, Puerto Rico
inside Cueva Parque Histórico María de la Cruzead
Cueva Parque Histórico María de la Cruzead

The next stop was to visit Parque Histórico María de la Cruzead for a traditional head-tie demonstration with fabrics that look just like ankara to me, a tour of the historic cave monument, and a Bomba y Plena dance and drum workshop. Mosquitoes were present throughout the Loiza trip but especially fierce in and around the cave so I recommend you bring bug spray or lavender essential oil to help keep them away. My friends had gotten mosquito bites earlier on during our San Juan vacation but this was the first time I’d been bitten the whole trip.

Vacia Talega Beach in Puerto Rico

After the park, we stopped by Vacia Talega beach then a local restaurant for authentic eats. I had the grouper in creole sauce with vegetables and sweet plantain. The grouper was scrumptious and the other highlights of  lunch were a beautiful beach breeze and open ocean view of Isla Verde. Our tour guide, Ari, was excellent and recently launched independent yoga tours of Old San Juan. After Ari dropped me back off at the hotel, I freshened up and headed to the airport.

grouper in creole sauce with sweet plantains
view of isla verde from restaurant patio

Helpful Tips for Visiting San Juan, Puerto Rico

  • Because Puerto Rico is a U.S. territory, you don’t need a passport coming from the United States.
  • Despite the shiny veneer of tourist areas like Old San Juan and Condado, recovery from hurricane Maria is not complete in Puerto Rico. Flying in, we noticed a number of blue tarps still covering the roofs of homes impacted nearly two years after it hit.
  • Uber cannot pick up from the airport but can drop off. We took a minivan taxi, which came out to a very reasonable $24 for four people and luggage.
  • No currency conversion is necessary because, again, Puerto Rico is a U.S. Territory. Puerto Ricans use US dollars.
  • The time zone is the same as Eastern Standard Time so no jet lag issues coming from the U.S.
  • English is very commonly spoken and many signs are in both English and Spanish. My best friend and I speak enough Spanish that we could hold conversation even when chatting with folks who spoke very little or no English.
  • When leaving, your checked bags have to be scanned by USDA before being dropped. It takes just a couple of minutes and is identical to the process when returning to the U.S. mainland from Hawaii.

condado beach at sunset

I greatly enjoyed my time in San Juan, Puerto Rico and definitely plan to return and see more of this beautiful Caribbean island. If you have any questions about our San Juan vacation, feel free to ask in the comments below or shoot me an email. Thanks for reading!

More from this trip:

rainbow over Condado Beach in San Juan, Puerto Rico
Dash of Jazz at Serafina Beach Hotel, San Juan, Puerto Rico
truck full of plantains outside Puerto Rican restaurant
plantains in bed of truck
Jazzmine on beach with text overlay "san juan puerto rico vacation guide"
Jazzmine at Isla Verde beach with text overlay "plan a trip to San Juan"
hotel room with ocean view and floppy hat on bed with text overlay "san juan, puerto rico travel diary"
bowl of mofongo with text overlay "restaurants to try in San Juan"

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  1. I love your blog so much good information! Saving it:)))So I’ll going solo in December, any recommendations? For a female who loves dancing Reggaeton and yummy drinks + food

    Thank you so much

    1. Hi Joanna! For reggaeton, you definitely want to go to Maui, which is the first bar you’ll encounter to your left coming from the La Placita Uber drop-off point. For cocktails, there are three places I’d recommend to get really good Pina Coladas: La Barrachina, Pina Loka, and Raices. The food at Raices is very good, too. Hope you have a blast!

  2. Just stumbled on your blog! So thankful I found it! I’m taking my baby for her 1st birthday and been nervous about traveling but this helped settled my spirits. Minus the ongoing earthquake after shocks -I’m excited for our trip in 2 weeks!

    1. So glad you found helpful information here! Wishing you two an amazing trip and Puerto Rico a strong recovery from the earthquake.

  3. I have read this post so many times to plan my trip to Puerto Rico. You seem like the kinda lady I’d love to travel with! Thank you!!

  4. Thank you so much for this!!! I’m going to Puerto Rico in July and this helps with my planning. You showcased your trip so perfectly. Following you on IG now!

  5. Wow!! This is EXACTLY what I was looking for was a blog about visiting Puerto Rico. Thanks so much for this!

  6. Is it possible to post approximately how much this trip would cost, Different tours, transportation etc..?

    1. Hi, Lindsay! As this trip was a few years ago, I don’t think the prices would be particularly relevant or helpful but did link to where I booked each activity so that you can see currently available rates and options!

  7. I really enjoyed this guide (and I’m Puerto Rican, ha!) – I have never thought of doing the drum workshop or hair tying tutorial at Loiza -thank you for the creative and original ideas. Your fits were incredible as well. Love your use of color and your fashion sense.

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