An Enchanting One Day in San Juan, Puerto Rico Itinerary

Visiting Puerto Rico and only have one day in San Juan? Here’s how to plan the perfect San Juan itinerary, with all the best things to do and tips for planning the best day!

San Juan, Puerto Rico is a special place.

The city is steeped in history, dating back 500 years. Founded in 1521 by Spanish colonists, San Juan is the oldest city under US jurisdiction (and one of the oldest in the Western Hemisphere).

Walking through the streets here is like taking a step back in time. You’ll see the city’s history come alive in the charming cobblestone streets, the colorful colonial facades, and fascinating historic attractions.

Spending one day in San Juan will let you see these wonders for yourself, and give you a taste of what makes Puerto Rico such a unique destination. It’s the perfect starting point for your Puerto Rico itinerary.

There’s plenty of things to do in San Juan, from discovering the Old Town, checking out some of its beautiful beaches, eating delicious traditional Puerto Rican cuisine, partaking in the nightlife – and much more.

I’ve curated this San Juan, Puerto Rico itinerary so that you can see some of the best of the city in only one day! Keep on reading to see how to plan the perfect day in San Juan, along with helpful tips for visiting.

This post contains affiliate links. This means that if you make a purchase or booking, I may receive a small commission at no additional cost to you.Pictures & Words is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to amazon.com and affiliated sites at no cost to you.

A few things to know before your one day in San Juan…

• Wear comfortable shoes: You’ll do tons of walking during your 24 hours in San Juan, so wear comfortable shoes! The streets of Old San Juan are made of cobblestone, so you’ll want to leave those heels at home. Also note that Old San Juan is pretty hilly.

• It gets HOT: Puerto Rico experiences tropical weather and is pretty hot all year round. I was covered in sweat within an hour of walking around! Bring plenty of water, and slather on that SPF!

• Get an early start: This will allow you to avoid that midday sun, and the crowds that show up later in the day.

• Be prepared for rain: It can rain suddenly, so bring an umbrella or light rain jacket! This is especially true if you’re visiting during the rainy season (May-October). Luckily, it doesn’t last very long, but it’s good to be prepared. 

• Ditch the rental car: While it’s nice to have a car to get around the island, you don’t need one while in San Juan. It can be super annoying to drive around San Juan, especially with the narrow, hilly streets of Old San Juan. Traffic and parking are a pain as well. If you plan to drive around Puerto Rico, wait to rent a car until your way out of San Juan.

• Most people speak English: While the official language of Puerto Rico is Spanish, I found that most people in San Juan spoke English, especially in tourist frequented areas. 

• You don’t need a passport if you’re traveling from the US: Puerto Rico is a US territory, so those travelling from the United States don’t need a passport. Likewise, if you’re arriving from an international destination, you’ll follow US customs and immigration procedures.

• The official currency is the US dollar: Also note that credit cards are widely accepted, but it’s good to have some cash on hand.

• The legal drinking age is 18: However, many clubs are still 21+ only.

The Perfect One Day San Juan, Puerto Rico Itinerary

Get ready for a full day of exploring San Juan! I recommend getting an early start so that you can see and do as much as possible (and to avoid the heat and crowds)!

On this San Juan, Puerto Rico itinerary, you’ll start off the morning in the colorful Old Town, wandering the charming streets and visiting some of its top historic attractions. After enjoying some Puerto Rican food for lunch, you’ll visit a few more attractions in the Old Town.

After this, I’ll let you choose your own adventure. If you want to stay near Old San Juan, I’ll give you some ideas for dinner and post-dinner activities. Otherwise, if you want to venture out into other areas of San Juan, I’ve got a few options for those as well.

Now, let’s get to it!

Start the day with some Puerto Rican coffee

Fuel up for your full day exploring San Juan with some coffee! Puerto Rico is known for their coffee, so the perfect way to start the day is with a cup of local brew.

While there are plenty of coffee shops around San Juan, I recommend stopping at  Café Cuatro Sombras. Located in the heart of Old San Juan, they serve some amazing coffee, along with pastries (try the guava roll!), sandwiches, and other light breakfast items. 

It’s also got a super lovely patio out back, with some pretty patterned tiles and plenty of green plants. It’s the perfect setting to enjoy your coffee and relax before embarking on your busy day!

Wander the charming streets of Old San Juan

Walking through the picturesque streets of Old San Juan is like taking a step back in time. The charming cobblestone streets are filled with colorful colonial buildings, each with a story to tell. Spending some time wandering the streets is a must-do on your one day in San Juan.

The colorful facades of Old San Juan are painted in a rainbow of bright pastel colors, each carefully selected as part of historical preservation efforts that date back to the 1950s. See if you can also spot the blue cobblestone, which are the original stones brought over by the Spanish all those centuries ago.

The best time to explore the streets of Old San Juan is in the morning, before the cruise ships arrive. It’s much quieter in the mornings; later on, it gets BUSY.

To learn more about the unique history of Old San Juan (and Puerto Rico itself), take this Old San Juan walking tour. You’ll walk through the charming streets in San Juan, see its top sights, and learn more about the stories behind them.

While you’ll encounter many pretty spots just walking up and down the streets, here are some of my favorite spots in Old San Juan:

• Caleta de las Monjas
• Calle Imperial (this is where you’ll find the orange Puerto Rican flag mural, but the surrounding streets were some of my favorites as well)
• Calle de la Luna 
• Calle San Jose (this is where you’ll find the black and white Puerto Rican flag door)
• Calle del Cristo 
• Paseo de la Princesa (the tree-lined pedestrian promenade, known as one of the most beautiful walks in the world)
• Paseo del Morro (the seaside path that skirts the outside of the city walls, connecting the original gate of the city to El Morro, the next stop on this San Juan itinerary)

Looking for more things to do in Old San Juan? Check out my Old San Juan guide, with the best activities and tips for visiting!

Explore the Castillo San Felipe del Morro monument

The Castillo San Felipe del Morro monument, also known simply as “El Morro,” is one of the top attractions in Old San Juan. It’s a must visit on any San Juan, Puerto Rico itinerary!

El Morro was built in 1539, but was not completed until 1790. The historic fort stands on top of a 140 foot promontory at the westernmost edge of San Juan. It was designed to protect the city from enemy ships.

It’s a UNESCO World Heritage Site, and a fascinating place to explore and learn about the history of Puerto Rico. At one point in time, it was the most feared of all the forts built by the Spanish in the Americas. At the conclusion of the Spanish-American War, the United States took control of El Morro (and Puerto Rico). It also played a role in both WWI and WWII.

I recommend coming in the morning, as it tends to get super hot here and there’s no shade. You’ll also beat the crowds!

We only had about an hour here, but I really wish we had more time. There’s 6 levels, so there’s plenty to see! Some of the things to check out  include the original cannons used to fire at enemy ships, the barracks, walking around its walls and dry moat, and more. And, don’t miss the views of the water – that alone makes it worth a visit!

Pro tip: If you have an America the Beautiful Pass, bring it with you! It costs $10 to visit El Morro, but admission is included as part of the pass. And if you don’t have the pass but plan to visit at least 3 National Parks or NPS managed sites in a year, I highly recommend purchasing it!

If you have extra time…The Castillo San Cristobal sits on the eastern end of Old San Juan, and also makes up the San Juan Historic Site. The 17th century fortress was constructed to protect the city from land attacks, and is another fascinating place to explore. However, if you only have limited time (you’re trying to see San Juan in a day!), I’d head to El Morro. 

If you do decide to visit both, keep your receipt as one admission fee will get you into both.

Cementerio Santa María Magdalena de Pazzis

As you walk out of El Morro, look out towards the ocean. Behind the grassy fields, you’ll see a circular yellow building with a peach colored dome, with a cluster of white gravestones around it.

This is the Santa María Magdalena de Pazzis Cemetery, known as one of the most beautiful cemeteries in the world. The cemetery is the home of some of Puerto Rico’s most famous residents, including Jose Celso Barbosa, the founder of Puerto Rico’s statehood movement, composer Rafael Hernandez, and actor Jose Ferrer. 

There is a collection of ornate marble tombstones, set against the gorgeous blue backdrop of the Atlantic Ocean. This is a symbol of a person’s spirit crossing over into the afterlife.

Even if you don’t get to visit the cemetery itself, I recommend at least admiring it from above, as it is such a unique sight. It sort of reminded me of the cemeteries of New Orleans! You can also catch a glimpse of the colorful La Perla neighborhood peeking out from behind.

Stop for a traditional Puerto Rican lunch

After a morning of exploring, you’ll probably start getting hungry, so it’s time to stop for lunch! I recommend sitting down and trying some traditional Puerto Rican food at El Jibarito. 

This popular restaurant serves homestyle Puerto Rican cuisine, and has a variety of meat and seafood dishes. Each entree comes with a side, and this is the perfect chance to try some mofongo, which is sort of like the national dish of Puerto Rico, made with mashed plantains fried with garlic and other seasonings.

Otherwise, if you want to try all of the top eateries in Old San Juan while learning more about the area, you can book the Old San Juan Walk & Taste Tour from Spoon Experiences. While I didn’t get to go on the tour, several of my friends did and absolutely raved about it! 

Visit a museum

Old San Juan has a number of interesting museums, where you can learn more about the unique history of the city and Puerto Rico. After lunch, take some time on your San Juan itinerary to pop into one of them. 

Here are a few of the museums you can visit:

• Museo de San Juan: Housed at where the city’s marketplace used to be, this small museum exhibits fine art in the context of the island’s history. Best of all, admission is free – and the building is quite photogenic as well! 
  
• La Casa Blanca: Built in 1521, La Casa Blanca is the oldest occupied residence in the Western Hemisphere. It was the home of the family of Juan Ponce de Leon, the Spanish explorer who became Puerto Rico’s first governor. Today, it’s a museum exhibiting artifacts and furniture from the 16th and 17th century. You can also check out the gardens, which are free to visit.

• Museo de las Americas: Located on the second floor of Cuartel de Ballaja, an eye-catching structure that once housed military barracks, this museum is dedicated to traditions, objects, and stories of the Americas.  

Admire the San Juan Bautista Cathedral

Next, head over to the Catedral Basilica Menor de San Juan Bautista, which is the oldest church built on US soil (it’s also the second oldest in the Western Hemisphere). 

Built in 1521, it has a distinctive Gothic facade, with stunning stained glass windows. It’s best known for being the final resting place for Juan Ponce de Leon.

Take some time to admire the church, and check out the beautiful architectural details. Also spend some time strolling through the small square right in front of it, as well as the side streets, which were some of my favorites.

Hang out in Plaza de Armas

Plaza de Armas is the city’s main square, dating back to the 16th century. It’s got the look of classic Spanish plazas, reminiscent of those seen anywhere from Spain to Mexico.

There’s always plenty going on here, with a variety of street vendors and street performers. Throughout the year, a number of festivals and events take place here as well. It’s a great spot to grab coffee and a pastry and just sit and do some people watching.

The centerpiece of the square is the Four Seasons Fountain, with a statue representing each season at each corner. There’s also a statue of Tite Curet Alonso, a Puerto Rican salsa composer. If you visit during the holiday season, there’s also a beautiful Christmas tree here as well.

Snap a photo under the umbrella street (and catch a glimpse of La Fortaleza)

Next, head over to Calle Fortaleza, which is also known as “the umbrella street.” Here, you’ll find a canopy of umbrellas in various colors. It’s one of the city’s most popular sights, and definitely worth a stop on your one day in San Juan itinerary!

The colors of the umbrellas change from time to time. When I was there, there were multi-colored umbrellas, but I’ve also seen pink ones and white ones as well. Depending on the time of year, there might not even be umbrellas – you may see a giant Puerto Rican flag or holiday decorations instead!

There is a barricade in front of the street, so you can’t actually go stand under the umbrellas, but it’s a fun photo op nonetheless. You can get an awesome shot if you get creative with angles!

The street leads to La Fortaleza, which is a UNESCO World Heritage Site and the Governor’s Mansion. Built in 1540, it was originally built as a fort, but has served a number of purposes. 

You can’t freely go into La Fortaleza, 30-minute tours offered on weekdays between 8:15am-3:30pm, as long as the government is not in session. 

Try the original piña colada at Barrachina

San Juan is the birthplace of the piña colada. Obviously, trying the fruity cocktail where it was invented is a must-do on your San Juan, Puerto Rico itinerary!

It’s said that the piña colada was invented in 1963 at Barrachina, located just down the street from the umbrella street. It was here that Ramón Portas Mignot blended together rum, pineapple juice, and coconut cream to create the tasty concoction that’s become the ultimate vacation cocktail! 

It can get quite busy at Barrachina, and the wait for a table might be long. However, since you’re stopping in just for a piña colada, you can also sit at the bar, which is what we did. They have machines mixing piña coladas constantly, so they’re always ready to go! They even have non-alcoholic versions too if you don’t drink.

FUN FACT: Barrachina isn’t the only bar that claims to have invented the piña colada – the Caribe Hilton, just outside of Old San Juan, makes that claim as well. If you have extra time during your 1 day in San Juan, it’s worth trying both versions, as they are quite different! But if you only have time for one, I recommend Barrachina, as I preferred theirs (it has a stronger pineapple flavor).

Visit a local beach

Next up – some beach time! Puerto Rico is known for its beaches, so why not dedicate part of your San Juan one day itinerary to some time on the beach? 

The city’s beaches are actually outside of Old San Juan, so you’ll have to travel outside of it to one. Luckily, you won’t have to go very far!

Here are some of the best beaches in San Juan:

• Playa El Escambrón: If you want to stay near Old San Juan, this is your best bet, as it sits on the edge of where it meets Condado, near the Caribe Hilton. It’s protected by coral reefs, which makes it an ideal place to go snorkeling.
• Playa Condado: The most popular beach in the area, thanks to its accessibility. Playa Condado  is surrounded by high-end resorts, restaurants, rooftop bars, and more. If you’re looking for calmer waters, head to Playita de Condado, located at the western end.
• Condado Lagoon: Condado Lagoon is the place to go for water activities. Kayaking or paddleboarding are some popular things to do – you can even go on a glass-bottom kayaking tour or a LED night kayaking tour.
• Isla Verde: This top-rated beach is located in neighboring Carolina, near the airport. Isla Verde has a long, wide beach with soft golden sand flanked by tall palm trees, which many refer to as a paradise.

Alternate activity – Go on a sunset cruise! If you don’t want to hang out on the beach, or just want to stay in Old San Juan, consider  booking this sunset cruise! On the 2 hour cruise, you’ll board a catamaran and sail by some of the most iconic monuments in Old San Juan, and see them in a new perspective!

Sit down for a delicious dinner

And now – time for dinner! You’ll find plenty of amazing dinner spots all around town, whether you’re looking for more traditional Puerto Rican food, or something else. Here are a few recommendations:

• La Madre: We really enjoyed this spot, located right in the heart of Old Town. La Madre serves delicious Mexican dishes with a modern twist. They also have some amazing margaritas, made with freshly squeezed fruit juices, to wash it all down.
• Orozcos: This restaurant is located in Orozcos, and serves traditional Puerto Rican food. It’s famous because it was featured on an episode of Diners, Drive-Ins, and Dives. I ordered the roast pork mofongo, and I think it was my favorite of all the mofongos I had on my Puerto Rico trip!
• Ocean Lab Brewing Co.: This brewery/restaurant is located near Isla Verde, and has locally brewed craft beers, with delicious pub fare like burgers, fish tacos, sausages, and more. It’s got some amazing views as well!

Experience San Juan’s nightlife

End your San Juan itinerary by partaking in the city’s nightlife! San Juan is famous for its nightlife, and you definitely need to go for a fun night out. Whether you’re looking to enjoy some craft cocktails, or go salsa dancing all night, there’s something for you.

Here are some places to go to experience San Juan’s nightlife:

• La Factoria: Known as one of the 50 Best Bars in the World (and #1 in the Caribbean), La Factoria is located in a grungy, unassuming building in Old San Juan. Behind the front bar (which has some awesome craft cocktails), you’ll find secret passageways that lead into 6 other rooms, each with its own theme and vibe. There’s a wine bar, a Cuban cocktail bar, and a salsa dancing club, among other things.
• Distrito T-Mobile: We had the opening party for our conference here, and it was so fun! There’s a collection of fun restaurants and bars, with a lively and exciting atmosphere. We had such a great time enjoying the live music and dancing – when they say Puerto Ricans love to party, they mean it!
• La Placita: During the day, La Placita serves at a marketplace, selling produce, meat, and more. At night, it transforms into a vibrant nightlife district. If you want to party, you definitely need to come here! The street is lined with tons of bars and thumping music, with plenty of people dancing the night away and having an awesome time! It’s not the place where you go for a cocktail bar, but even this old lady enjoyed her night out here. 

Spending more time in Puerto Rico? Check out my 4 day Puerto Rico itinerary to plan the perfect trip!

Where to Stay in San Juan

San Juan is the perfect place to base yourself during your time in Puerto Rico, as it’s the island’s main tourist hub. You’ll find no shortage of shops, restaurants, and activities. Many tours leave from San Juan, and you’ll be close to the airport as well.

There’s a ton of accommodation options, to suit any budget and preference. I recommend staying in either Old San Juan or Condado, both of which have tons of places to stay, and lots of dining options.

Staying in Old San Juan

As the main tourist hub of Puerto Rico, there’s plenty going on in Old San Juan. The charming cobblestone streets are lined with historic boutique hotels, shops, and restaurants. There’s plenty to do, making it an ideal place to base yourself.

However, do note that it’s always super busy in Old San Juan, so it might not be the place for you if you’re looking for some peace and quiet. Another con is that there’s no direct beach access. The properties are also located in old historic buildings.

Here are some of recommendations for places to stay in Old San Juan:

• Hotel El Convento: This historic boutique hotel is one of the most beautiful hotels in Old San Juan. It’s housed in a yellow building that used to be a Carmelite convent, dating back to 1646. Inside, you’ll find colonial architecture and elegant Spanish design details.
• Palacio Provincial: Housed in a 19th century building in the heart of Old San Juan, this adults only hotel has a beautiful courtyard, comfortable rooms, and a rooftop pool that overlooks the ocean and the historic buildings in the neighborhood.
• CasaBlanca Hotel: This eclectic boutique hotel has a beautifully decorated lobby and bar area, comfortable rooms, and rooftop terrace with beautiful views of Old San Juan and the water.

Staying in Condado

Another option is to stay in the Condado neighborhood, which borders Old San Juan and is known for tree-lined streets, beachside restaurants, and easy access to the water. If you want more upscale accommodation options and want to stay right next to you, Condado is your best option.

The one downside of Condado is that I found it lacks charm and personality, especially in comparison to Old San Juan. 

Here are some options for where to stay in Condado:

• Caribe Hilton: This is where our conference was hosted, and honestly, I really wished I stayed here instead of in an Airbnb. The location is at the edge of Condado, so you’ll be located right in between Condado and Old San Juan. The historic Caribe Hilton was the first Hilton property built outside of the US mainland back in 1949 and still retains signs of its glam past. It’s got rooms with ocean views, and a beautiful pool area.
• O:Live Boutique Hotel: This laid-back boutique hotel has a Mediterranean style, with stylish decor, spacious rooms, and a rooftop infinity pool overlooking Condado Lagoon. Its vibe manages to be luxurious yet relaxed at the same time.
• Condado Vanderbilt: This luxury beachfront hotel is located steps from the Condado Lagoon, with rooms overlooking the ocean. There’s also a stunning infinity pool, a beautiful bar and lobby area, and acclaimed on-site dining at Ola Oceanfront.

More things to know for your San Juan itinerary…

Traveling to San Juan, Puerto Rico

Arriving by Air

If arriving via plane, you’ll arrive at Luis Muñoz Marín International Airport (SJU) in San Juan, the island’s main international airport. The airport serves 30 airlines, connecting the island to many domestic and international destinations. 

Puerto Rico is a popular destination for American travelers, as a passport isn’t necessary if traveling from the United States. If you are arriving from an international destination, you will follow US customs and immigration procedures.

While there are many direct flights from all over the US, they aren’t as common from the West Coast (which is part of the reason it took me so long to get to Puerto Rico). Coming from Orange County CA, I flew a redeye from San Diego with a layover in Philadelphia, and the trip took almost 12 hours. On the way back, I flew through Chicago (with a 6 hour layover), back to LAX.

Getting from the airport to your accommodations: Once you arrive at the airport, it’s very easy to get to your accommodations! The airport is only 3 miles outside of the city, so it’s very accessible.

The best way to get from the airport to your accommodations is via Uber. The trip usually takes around 15 minutes, and costs under $16. However, note that this may be higher when surge pricing is in effect, and take longer during rush hour. 

You can also rent a car, although it’s not necessary to have a car while in San Juan. For the best rates on cars, I recommend booking on rentalcars.com, which allows you to compare prices from the top car rental companies and offers a price match guarantee. 

Arriving by Cruise Ship

San Juan is a popular port stop for Caribbean cruises, and is a departure port for some routes as well. If you are spending one day in San Juan as part of a cruise, then you will arrive in one of two ports:

Old San Juan Piers: This is the largest port in San Juan, located within walking distance of Old San Juan. It serves a number of cruise lines, including Carnival, Royal Caribbean, Norwegian MSC, Virgin Voyages, and Holland America.  

Pan American Pier: This cruise port is located southeast of Old San Juan, and serves Princess, Celebrity, and Disney cruises. It’s about 10-15 minutes out of Old San Juan, so if you arrive here, you’ll need to take an Uber/taxi, or the cruise line shuttle (if provided).

Getting around during your San Juan, Puerto Rico itinerary

Walking: Old San Juan, where the majority of your day will be spent, is *very* walkable. The charming cobblestone streets are a joy to explore on foot.

Uber: Uber service is readily available in San Juan, and super easy to use. It’s the best way to travel between other areas of San Juan. I was able to find a car easily, and rides were pretty affordable (usually around $7-10). 

Driving: While a rental car may be the best way to reach other areas of the island outside of San Juan, I do not recommend having one while in San Juan itself. The streets of Old San Juan are busy, narrow, and hilly. Traffic and parking can be a pain as well.

If you plan to rent a car for the rest of your Puerto Rico itinerary, I recommend renting it on the way out of San Juan. For the best deals, book on rentalcars.com, which allows you to compare prices from the top car rental companies and offers a price match guarantee. 

Best time to visit San Juan

There isn’t really a “bad” time to visit Puerto Rico – it’s a beautiful place to visit at any time of year. It’s quite warm all throughout the year, with highs ranging from 83-89 degrees Fahrenheit.

November through April is the dry season, which is considered to be the best time to visit. This is when it’s cooler, and it’s not as humid. However, do note that it’s the most popular time to visit, so flight and accommodation prices may be higher (especially during the holiday season and spring break).

May and June are considered the island’s shoulder season, and you’ll encounter fewer crowds and lower rates. However, it gets pretty hot during these months – the warmest month of the year is actually in June.

I visited in mid-May and it was pretty hot and humid! There was also a torrential downpour at some point every day, although it didn’t last very long. 

July through October is the low season, and Puerto Rico’s hurricane season. It’s not necessarily a bad time to visit, as prices are low and crowds dissipate quite a bit. However, you will have to keep an eye on the weather forecast to keep informed of any upcoming storms. If there’s a hurricane in the forecast, you may have to reschedule your trip.

What to bring for your one day in San Juan

• Light, breathable clothing: Clothing made from light, breathable fabrics such as cotton and linen are ideal for the hot weather in San Juan
• Comfortable shoes or sandals: You’ll do a ton of walking, and note that the streets of Old San Juan are uneven cobblestone. Wear comfy shoes – leave the heels at home! I relied on my trusty Crocs sandals, which are super cute (I swear!) and very comfortable. 
• Reef-safe sunscreen: The sun is strong here, so be sure to slather on that SPF! Choosing a mineral based sunscreen will also help protect the marine life in the area. 
• Hat: Great for sun protection, and also cute in photos. Grab a straw hat, which is also perfect for the beach. 
• Bathing suit: If you plan to hang out at the beach and/or do water activities.
• Sunglasses: The sun is very bright here, so pack a pair of shades. Goodr makes my favorite affordable polarized sunglasses.
• Light rain jacket or poncho: It can pour without any warning, so bring a light, packable rain jacket or poncho.
• Water bottle: It gets hot, so be sure to stay hydrated! I like to carry around a reusable water bottle at all times.
• Power bank: Keep your devices charged as you explore San Juan. 

Have you ever been to Puerto Rico? What would you include on your San Juan itinerary?

More Puerto Rico content you may enjoy:

• The Perfect 4 Day Puerto Rico Itinerary
• 30 Charming Things to Do in Old San Juan

Liked this post? Save this San Juan, Puerto Rico itinerary to Pinterest for later!