5 Days in Puerto Rico Itinerary

Five friends and I recently traveled to San Juan and beyond for the first time to celebrate my 30th birthday, and each of us plans to return. Use our firsthand recommendations to plan a memorable trip with this Puerto Rico itinerary 5 days guide to beaches, nightlife, food, and excursions!

And if you enjoy this article, you'll love my list of San Juan vacation activities, too!

Is San Juan worth visiting?

In my opinion, absolutely. But I highly recommend venturing out beyond the capital city to experience more, and this itinerary definitely delivers on that! 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 to see more of the island. Here are a few helpful travel tips:

• No currency conversion is necessary because Puerto Rico is a United States 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 widely spoken, and lots of the signage is in both English and Spanish. But it's always a good idea to learn basic phrases in the local language when traveling. My best friend and I do speak Spanish, which was especially helpful outside of the touristy areas.

Best Time to Visit

Puerto Rico's high tourist season is from December to April. This is when the weather is most favorable, but prices for everything from accommodations to attractions will be higher, and everything is more crowded.

I generally like to travel on a budget during the low season (July to November) for the cheapest prices or shoulder season (May and June) for the best of both worlds. The thing to consider most heavily here is the weather, specifically, hurricane season.

Despite the shiny veneer of tourist areas like Old San Juan and Condado, recovery from Hurricane Maria was not complete as of my last visit. Flying in, we noticed many blue tarps still covering the roofs of homes impacted nearly two years after it hit.

Puerto Rico has a tropical climate and is warm year-round. Each day we spent on the island was hot with a breeze and very comfortable at night.

Read my Puerto Rico outfit ideas and vacation packing list!

Getting There

Because Puerto Rico is part of the U.S., American citizens don't need a passport or visa coming from the United States. Several airlines run direct flights from the East Coast. Coming from Houston, Texas, we had a connection in Atlanta.

There are no customs or immigration lines to wait in for American citizens or permanent residents, but when it's time to leave, your checked bags have to be scanned by the USDA before being dropped. It takes just a couple of minutes and is identical to the process when I returned to the mainland after visiting Hawaii.

I actually booked my Puerto Rico flights (on United Airlines) and hotel using credit card points. I recommend the Chase Sapphire Reserve card for travel rewards.

How to Get Around

Do I need a car in Puerto Rico? Not for a San Juan trip itinerary-Uber and excursions with transportation have you covered. However, if you plan to road trip to multiple cities outside of operated tours, renting a car is a must.

Is San Juan walkable? Yes, especially within areas like Condado, Santurce, and Old San Juan. We also found Uber rides to be inexpesive and widely available.

Note that Uber cannot pick up from the SJU airport but can drop off. We took a minivan taxi, which came out to a very reasonable $24 for four people and luggage.

Check out the best car rental options at the San Juan airport!

Where to Stay

We stayed at Serafina Beach Hotel, which is now called Condado Ocean Club, for the duration of our 5-day itinerary in Puerto Rico. It is a super chic, boutique hotel on Condado Beach that we all enjoyed and would recommend. Everyone we encountered 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 stayed in 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.

Here are the top hotel deals in San Juan on Expedia!

What to do in Puerto Rico in 5 Days

Condado, Cabana Vibes, and Clubbing

Condado Beach - We landed in San Juan on a Friday afternoon and spent hours at the Serafina pool scene, which has direct access to Condado Beach. We ate appetizers and burgers and drank probably too many tequila shots and glasses of rum punch from the cabana bar.

At night, the pool is literally lit with changing colored lights. This was a great pregame to our nighttime move, La Placita.

The iconic La Placita was originally on our itinerary for later in the trip, but one of the bartenders, Angel, said Friday was the best night to go, so off we went. And he was so right! There are bars, restaurants, lounges, and clubs of all kinds right next door to and around the corner from each other. The dancing and partying literally spill out into the streets.

There's a vibe for whatever you might be in the mood for, from Hip Hop and Reggae to Reggaeton to strictly Spanish tunes. Note that some bars are more heavily visited by locals, and others 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 to wake up a few hours for an excursion.

Read my list of things to do in San Juan--day or night!

Culebra y Playa Flamenco

Excursion to Culebra - On Saturday, we rose early for a 7am pickup time on an excursion to the beautiful island of Culebra. This tour included transportation to our departure point in Fajardo, a boat ride to crystal clear snorkeling waters, then to the soft sand of one of the top 10 best beaches in the world!

Flamenco Beach - We spent a couple of hours playing the crystal blue-green water and drinking fresh coconut water on the beach. I highly recommend the Culebra excursion we booked as it includes hotel pickup as well as unlimited rum punch, mojitos, piña coladas, and lunch.

Here's our full itinerary from San Juan to Culebra to help you plan your day!

Drinks & Dinner - After getting back to the hotel, we freshened up and napped, then grabbed piña coladas from Piña Loka and dinner at Waiter's. I recommend both, just note that the service was a little slow at Waiter's. We meant to check out Club Brava later that night, but went straight to sleep, which is on brand for celebrating a 30th birthday, am I right?!

Isla Verde y Condado Strip

Crush Juice Bar - We got up bright and early on Sunday and put on our Sunday best...for the beach. Condado is a walkable area, so we strolled over to Crush Juice Bar for a fresh liquid breakfast, then Ubered to Isla Verde Beach as it was raining.

Isla Verde Beach 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. It's kid-friendly but not cheesy and there are vendors for beach massages, parasailing, and all kinds of other activities.

Here are all the beaches I recommend in San Juan!

Oceano came highly recommended for Sunday brunch and we enjoyed the beautiful ocean views as much as the generous eclectic brunch buffet.

Now, I'm not usually a buffet girl but would recommend it. The best views are on the third floor, by the way! This part of the Condado strip has a similar vibe to Ocean Drive in Miami.

La Placita (again) 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 back at Aguardiente.

Old San Juan

Sightseeing in Old San Juan - 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 Old San Juan landmarks sometimes took longer than necessary. This was particularly annoying because the heat was brutal that day--around 100 degrees.

Old San Juan is more commercialized than we had expected, but there's history at every turn. The buildings are so colorful, the architecture is distinctively Spanish, and it reminded us of the French Quarter in New Orleans.

As is the case on many Caribbean islands, there are lots of cats roaming around the historical district. They haven't taken over or anything, but you'll definitely notice them down most every street.

Chocobar Cortes - 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, but the food was good.

Exodo Caribbean Art Gallery - We kind of happened upon this place, which was full of beautiful modern Black art and connected to a pretty courtyard. No pictures are allowed inside the gallery.

Playa Escambron is more urban than, say, Isla Verde or even Condado, and more heavily visited by locals. There were plenty of 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 it's a popular place for snorkeling. We saw a lot of colorful plants and fish while playing in it.

Raices - After a couple of hours at the beach, we went back to Old San Juan to get mofongo and the best piña coladas of our whole trip at Raices (Spanish for roots). 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!

Birthday Dinner at Marmalade - This was our fanciest meal of the trip and provided everything you'd expect from a five-star dining experience. Everyone on staff seemed to know it was my birthday and stopped by during the meal to share well wishes-- it was also our waiter, Louie's, birthday!

I really enjoyed the global warming cocktail--a margarita with an ancho chile-infused ice sphere, which means the cocktail gets hotter the longer you wait. Very clever. Pretty much every cocktail on the menu poked fun at our current Head of State, and the food was all equally delicious and clever. Try the lobster risotto and sea bass!

Read my detailed guide to plan your day in Old San Juan.

Santurce

Ocean Beach Park - On Tuesday, we slept in (til 9am) then ate breakfast on the beach. Our Uber driver had described Ocean Park Beach as the most beautiful, and the water was a beautiful blue turquoise. But the high winds made it difficult to truly appreciate, though, so we didn't spend a lot of time there.

Art - Next, we walked around Santurce, starting with Museo Arte Contemporaneo, which is three stories of artwork and installations. Passes for the museum were just $5.

From there, we checked out all the vibrant street murals and installations on the way to La Placita to visit La Plaza del Mercado in the daytime and have pineapple mango batidas.

Dinner & Dessert - After walking around Santurce, we went back to the Condado area and hit up Señor Paleta for a lil' sweet treat. We took it easy at the Serafina pool for the rest of the afternoon, then had dinner at aMare, which is a Mediterranean restaurant on the Serafina property.

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 their birthdays for more than just a day, in case you didn't know. 🙂

Nightcap - To top off our last night in town, we ventured back to Santurce to grab cocktails at La Penultima. I enjoyed and recommend the green tea killah, which is gin-based with matcha.

Check out my guide to restaurants in San Juan!

Loiza

Beach Sunrise - I rose early on our last morning in order to watch the sunrise on Condado beach behind the hotel pool deck. It was beautiful to see the ocean light up and the beach start to come alive before checking out and setting off on the last adventure to conclude this jam-packed Puerto Rico 5-day trip.

Half-Day Tour of Loíza - Heading from Condado, streets and highways eventually slipped away into the single, two-lane road that goes in and out of Loiza. This Afro-Puerto Rican Heritage Tour included:

• Visiting the home and workshop of artist Samuel Lind, with a personal tour of his works
• Traditional head-tie demonstrations, and a Bomba y Plena dance and drum workshop
• A tour of the historic cave monument at Parque Histórico María de la Cruzead
• Vacia Talega Beach
• Lunch at a local restaurant with ocean views and one of my favorite meals of the whole trip!

You could easily spend a weekend in this beautiful town. Use this Loìza day trip guide to plan your trip!

More Favorite Caribbean Island Destinations

I hope this Puerto Rico itinerary for five days (or more) helps you make the most of your time on the island soon and very soon. And sharing is caring so be sure to pin this post for later and follow me over on Pinterest. Thanks for reading!