San Juan in Two Days: The Ultimate Weekend Trip

If you are worried that you can’t see the best of San Juan in two days, I’m here to tell you that you absolutely can. This historic port city is bursting with vibrant colors and flavors – and that’s not just the food I’m talking about. But with just two days in San Juan, you’ll want to hit the ground running and waste no time, so that’s where I’m here to help!

I myself spent a total of 5 days in San Juan, and have compiled the highlights and must dos for the perfect San Juan itinerary. And yes, you totally can see everything in just two days! Let’s dive in!

Have more than 2 days? Check out: How to See the Best of Puerto Rico in 4 Days

Things to Know Before You Go

1. Puerto Rico Uses US Dollars

Americans won’t need to worry about exchanging any cash here since the official currency of Puerto Rico is US dollars. I was also happy with how widely accepted card payments seemed to be in San Juan, so I didn’t have to deal with taking out huge amounts of cash from the ATM.

2. San Juan is Insanely Hot

Puerto Rico, specifically the San Juan area, is the hottest place I’ve ever traveled to date. And that’s saying something considering that I’ve been to Africa and the Middle East.

The heat here just hits differently, and can feel 100% relentless at times. My guess is that the humidity is a huge factor in this plus the fact that you are so close to the equator.

From the morning, to late at night, or even in the shade – you will always feel hot and sticky here. This should not deter you from coming, but it should give you an idea of what type of clothes to bring.

3. COVID Regulations

Update: As of February 2023, there are no longer any COVID related restrictions for entering Puerto Rico from the USA. If you are flying in from abroad, you may still be asked to show your vaccination card (source: Discover Puerto Rico)

At the time of writing (in 2021), Puerto Rico has some pretty strict COVID rules.

You can expect them to thoroughly check your COVID test results or vaccination card when you land, and you will be asked to present either of these almost everywhere you go in San Juan. That includes restaurant, bars, and most public spaces.

If you aren’t vaccinated, you’ll need to get tested every few days throughout your trip. Depending when you go, there may be a curfew as well.

When I was in San Juan, the curfew started at 9 PM each night, but supermarkets and some restaurants closed way earlier. On the upside, it made me feel safer knowing they follow health and safety protocols.

4. Uber is Best

For getting around San Juan, Uber is best. The prices are much lower than a standard taxi fare, and you don’t need to pay with cash. In San Juan you’ll never have to wait more than a few minutes to get an Uber and they are both safe and reliable.

5. No Wifi at the Airport

Just a minor inconvenience, but I was surprised to find that the airport doesn’t have wifi. This made it impossible to call an Uber, and I had to take a pricier taxi into the city.

Keep this in mind, and have all your documents readily saved on your phone before checking in for flights since you won’t have internet access. Of course, depending on your phone plan, you may have service in Puerto Rico, in which case this won’t be an issue.

6. Bring or Withdraw Cash

Although I mentioned that card payments are widely accepted, you’ll still want to take out some cash. Cash will be necessary for tipping, street food stalls, taxis, and some of the food places.

Plus, it’s best to have some cash on hand for emergencies.

7. Tipping

In Puerto Rico, tipping is required. When dining in a restaurant, be prepared to tip as you normally would in the US. This means a tip of 15% or more for a sit down restaurant, and perhaps 10% on drinks and other services.

When to Go

The best time of year to visit San Juan is likely in spring, during the dry season, but right after the busy holiday season.

This means visiting between Mid-April to right before June. The weather stays in the mid 80s Fahrenheit (about 27 Celsius), which is entirely bearable compared to the summer months.

Visiting in December to March is the peak of winter, which means the coolest and driest weather, but far more tourists. Depending what type of experience you’re after, this may not be a bad thing, but I’m sure some would love to avoid peak season.

Hurricane Season

Visiting in summer and autumn (from June to October) means visiting during hurricane season. While most locals and experts would advise against visiting during this time, it’s possible to go and still have a great trip.

Just keep in mind that the potential for hurricanes or bad weather is higher during this time, and when it doesn’t rain, it will be insanely hot.

Where to Stay: Old San Juan

If you only have two days in San Juan, I wholeheartedly recommend staying in the Old San Juan area.

Not only is this the area with the most historic value, but you have a ton of restaurants, bars, cafes, museums and points of interest within walking distance.

Not to mention the vibe in Old San Juan are one of nostalgia and vibrance – you’ll totally feel transported back in time while here.

The Best Hotel in Old San Juan

We spent 5 nights at the Decanter Hotel in Old San Juan and loved it!

I can definitely recommend it for the location, comfort, and instagram worthiness. The picture above (and below) are taken from the Decanter Hotel balcony in our room, with the colorful old town buildings as the background.

Ready to Book? Book the Decanter Hotel Here!

Top Hotels in Old San Juan

If you like options, here are more beautiful hotels I saw in Old San Juan worth checking out:

El Colonial: This is by far the most luxurious hotel in Old San Juan, for those on a honeymoon or just looking for the best of the best. It’s for adults only, and features stylish rooms, a rooftop terrace and onsite cocktail bar.

Fortaleza Suites: A great mid-range option in the dead center of Old San Juan, on the famous Fortaleza Street. You have a ton of cafes and boutiques at your doorstep, plus great balcony views of the colorful old town building.

Fortel Hostel: This is a good pick for solo travelers and budget travelers. Modern, clean and with it’s own onsite restaurant. Definitely on the nicer end as far as hostels go.

Alternative Neighbhoorhood: Condado

This is another popular area for tourists in San Juan. Instead of colorful historic buildings, it’s an area comprised of more modern buildings, luxurious hotels, and high-end restaurants.

It’s also idyllically located right next to the beaches, making it a prime vacation spot. If you are more interested in relaxation and luxury, Condado makes a good base for your stay in San Juan.

Best Hotels in Condado, San Juan

Casa Isbael B&B: If you prefer a more intimate, homely feel rather than a resort. This B&B features modern fixtures meets old world decor and charm, and flowery garden views. Feels like you’re in someone’s home.

Condado Vanderbilt Hotel: If you love resorts, this is as good as they come. Located right on the beach with a fabulous pool and pool area offering dreamy sunset views. Not to mention a few onsite bars, spas, and wellness centers to make your stay unforgettable.

Live Boutique Hotel: If you want luxury, look no further. This hotel is smaller than a resort but pulls all the stops to make for a bucket-list worthy stay. Featuring a Mediterranean style interior decor, and top-notch amenities including a rooftop terrace and infinity pool.

What To Pack

San Juan, and Puerto Rico in general, is a hot destination year round.

Unless you are acclimated to intense sun and humidity, you’ll want to pack carefully to make sure you’re comfortable, as the excited of hearing a Bad Bunny song coupled with intense heat can lead to a heatstroke.

Here’s what I’d recommend for women vacation in San Juan:

San Juan Women’s Packing List

• loose, breathable tops
• synthetic fibers or cotton, that won’t show sweat as much
• 1 maxi skirt
• a pair of jean shorts
• cute dresses for day or night
• A wide brimmed hat – you won’t survive the midday sun without it! I love a wide, straw hat for the tropics. They match most outfits and quickly elevate your outfit and instagram pics
• sunglasses
• sandals
• bikinis
• At least 1 set of athletic clothes – I like this set that comes in soo many colors, for only $30
• 1 or 2 large silk scarves – versatile for sun protection, and a great outfit accessory for island vibes photos

In most cases I would never advise overpacking, but for San Juan? Feel free to pack an extra couple of tops or a dress or two. It was so hot when we visited, that we frequently had to change outfits every couple hours or so to have fresh clothes.

San Juan in Two Days

If you actually do plan to make it to San Juan for a weekend, aim to fly into San Juan Friday night if possible.

There are pretty late departure flights coming in from New York or Miami, so you should have plenty of time to make it to the airport after clocking out for work if you happen to live in these cities.

Regardless of when you are arriving in Puerto Rico or how long you will actually stay, I wouldn’t recommend anything less than two full days in San Juan.

Day One: Historic and Cultural Day

On your first day in San Juan, you’ll want to wake up early. You’ll be discovering a lot of the historic and cultural aspects of the city on foot, and believe me, you’ll want to do as much of this as you can before that midday heat settles in.

To ease your early start, grab a coffee in Old San Juan. Puerto Rico after all, is known for its coffee!

For something a bit less traditional, head to Café Cuatro Estaciones, a little kiosk stand in the Plaza de Armas Square in the old town of San Juan.

According to Google, they should be open from 6 AM. Here you can choose from all types of caffeinated drinks. I’d recommend getting an iced coffee, which you can infuse with another flavor if you choose. A unique one I’d recommend is the lavender iced coffee.

Stop By La Fortaleza

Walk down Calle de la Fortaleza, and admire the colorful historic buildings of the old town. This is the main draw of the old town of San Juan.

This street is home to many fashion boutiques, souvenir shops, craft shops and restaurants which you can browse later. For now, make your way to La Fortaleza for a quick peek.

La Fortaleza is the residing place of the governor of Puerto Rico. You obviously can’t go in, but it’s a significant landmark of the San Juan old town, dating back to 1533 during the founding of San Juan by the Spanish.

Walk to Paseo de la Princesa (promenade)

Not far from La Fortaleza, you’ll find the La Princesa Promenade. This is a beautiful place to start your walking tour for the day. You are now face to face with the sea, and a gorgeous tree-lined pedestrian area. Here, there is a famous fountain popular for photos.

The promenade here leads you directly into the next point of interest.

Puerta de San Juan

The Puerta de San Juan is a 40 foot tall gate, that once was the only entrance into the historic walls of the city. It’s from here that you can join the Paseo del Morro, and walk along the sea and the old town’s historic walls until you reach the fortresses.

Walk along the Paseo del Morro (historic city walls)

The Paseo del Morro is an easy walk on a flat, well-paved sidewalk, albeit a very hot and roasty one.

The day time heat in San Juan, coupled with the lack of shade on this walk, make this a sweat inducing activity. This is also why I advise starting the day as early as possible, to avoid the brunt force of the sun.

This walk takes you around the outer parameter of the city wall. You have the option of walking along the sea, or just inside the city wall. The first option has better views since you’re right next to the water, but the latter is better for photo spots.

You’ll pass the iconic pink mansion known as Casa Rosa, along the way. At a leisurely pace this walk may take 20 minutes at most until you reach a big grassy hilled area known as the Historic Park of San Juan.

Here is were you’ll find many historic forts from the colonial era. If you walk to the end of the bay, you’ll reach Castilla San Felipe de Morro.

Castillo San Felipe de Morro

Castillo San Felipe de Morro will be a major highlight and must-see during your two days in San Juan.

This historic fortress was built by the Spanish in order to protect San Juan from invaders coming by sea. It was used for military purposes even in WW1 and WW2 until as recent as 1961. Today, it’s a UNESCO site which you can pay to enter.

Side Note: if you choose to visit the fort, keep the ticket because you can also use it later to visit Castilla San Cristobal for free

Cementerio Santa María Magdalena de Pazzi

I’d imagine that this is one of the most beautiful cemeteries in the world. It’s just a short walk across the grass from Castillo San Felipe where you’ll have a great overhead view of this grand cemetery.

The Santa María Magdalena de Pazzis Cemetery was built in colonial times, and is the resting place of many famous and influential people throughout Puerto Rico’s history.

You can also walk down to the gate and visit the cemetery. It’s a very serene and peaceful place, with pure silence aside from the sound of the waves.

Lunch: Caribbean Food or Puerto Rican Food

As your first day in San Juan and likely the first in Puerto Rico, you should waste no time and get right into the regional cuisine. Around San Juan Historical Park, you are a short walk from plenty of lunch options.

If you want to try some Caribbean Food, head to Deaverdura. It’s a chill restaurant with a laidback vibe, and authentic Caribeean style cuisine. That means, the prices are fair too. Around San Juan you have options to eat at those overpriced touristy places, but honestly, when it comes to Puerto Rican food I feel like the basics are best.

Other similar options around to choose from are Las Palmas or El Jibarito, both of which serve exclusively Puerto Rican food in humble, no-frills restaurants.

You can also try Ajo Del País, which only opens after 2 pm, which is a restaurant and also a bar. Depending on your plans for the day, this may be too late.

Optional Places for the Afternoon

For the afternoon, choose from either options below depending on your interests.

Option 1: Museo de las Americas

If you are a lover of the arts and culture, head back towards Museo de las Americas, located right along the edge of the Historic Park.

The museum itself is located inside a historic building that served as an army barracks in the 1800s. Here you’ll find an impressive collection of both permanent and temporary art exhibits that highlight the history and cultural aspects of the American continent.

It’s both a rich experience for artistic value as well as educational, since the exhibits all highlight the culture and past of Puerto Rico.

The museum is open only until 4 PM, so time your visit accordingly. Entrance is $6.00 USD.

For more information on the museum click here.

Option 2: La Perla

La Perla is a historic shanty town located just along the northern edge of Old San Juan. It’s known for its colorful boxy homes which look very aesthetic sitting just at the edge of the sea. Its most recent claim to fame however was being the filming location for the music video “Despacito”.

A visit here will show you another side of San Juan in a historically underserved community. But today, you’ll find murals, colorful buildings, cool dive bars called chinchorros, and beautiful ocean views along the Malecon walk.

As charming as it may look, you do have to keep in mind this neigborhood is historically known to be rough. Murders do happen here, and it has happened in the past that the victims were tourists.

If you want to visit La Perla, try to go with a local. You can do this by taking a tour or making friends via couchsurfing or elsewhere. If you want to visit on your own, that’s probably fine but you should be cautious.

At the very least try not to visit alone or at night. Also, when visiting remain respectful and vigilant, and try not to do anything that could be seen as confrontational or offensive. Lots of people visit this area and have a great experience, it just takes some street smarts and precautions.

Evening: Drinks at La Factoria

When happy hour hits, head to La Factoria for some drinks. On top of being rated as one of the top 50 bars in the world, it’s by far the most popular one in Old San Juan and definitely has one of the best vibes.

From the outside the bar is unmarked, so you’ll need to rely on Google Maps to find it. Once here, you’ll find a rustic looking bar that’s probably full of people. What makes this bar special aside from the excellent cocktails, is that it’s actually the entry point to 5 other bars.

La Factoria has a number of secret doors that lead to several entirely different bars serving up their own ambience and drink menus. From a salsa dance hall, to an eclectic music dive type bar, to a candlelit cozy bar, try every single door while here.

I’d honestly recommend starting in La Factoria, and coming back after dinner to check out the rooms you’ve missed.

Alternative: If this is too early for you to start drinking, opt to go shopping in Old San Juan instead. Check out the boutique and craft shops and find something special to bring home as a gift or for yourself.

T•tuan Old San Juan dinner

T•tuan is an outdoor restaurant is located in the cutest little corridor of San Juan with a view over the bay. You have fairy lights and the fresh ocean breeze plus live music to set the mood for an amazing dinner.

This restaurant serves food tapas style, perfect for you to sample many flavors in bite sized and shareable servings. I’d recommend the ceviche, mofongo bites, and pulpo (octopus). Also, I highly recommend the passionfruit mojito.

Cigar Bar at Casa de Montecristo

After a light dinner and hopefully more drinks at T•tuan, head to Casa de Montecristo for cigars and more cocktails.

Here you can check out their collection of both Puerto Rican cigars and others from around the Carribean. As a country and region notorious for their cigars, it’s definitely worth a visit even if you don’t smoke. Ask questions, learn about what makes each cigar unique, and maybe even buy one for the night.

I am honestly not a huge fan of cigars at all, but it makes a good once in a lifetime experience when in San Juan.

Even if you don’t buy a cigar, you can enjoy the sophisticated ambience of the bar and order a signature cocktail instead.

Nightcap at La Cubanita

If you haven’t had enough drinks yet, head to la Cubanita for another round before calling it for the evening. This is one of the bars connected to La Factoria via hidden doorway, but only became part of La Factoria recently.

It’s a Cuban inspired bar built into what used to be a corner store. It has an ambience very reminiscent of the bars in Havana and really capture those Cuban vibes, and of course they serve bomb ass mojitos to fit the bill.

See More: Why You Should Visit Vinales Valley, Cuba

If you prefer a more lively night, head instead to Shing A’ling for a more upbeat atmosphere with a full on dance floor. You can find it through one of the secret entrances in La Factoria.

Day Two: Beach and Food Day

Morning: Take in The Colors of Old San Juan

On this day feel free to have a later start to accommodate lasts nights mojito marathon. Wake up whenever, and have a leisurely stroll around Old San Juan itself. You don’t need a destination to enjoy the colorful and historic buildings that line each street. But if you prefer to have a destination check out the Cathedral de San Juan Bautista, Puerto Rico’s grandest church, or Plaza Colon, another square with historic significance.

You may also choose to check out Castillo San Cristobal, the fortress that was used to protect San Juan from land attacks. If you visited Castillo San Philipe del Morro the day before, the same ticket will get you in free.

Coffee at Filtrado

My only complaint about this place is that it doesn’t open until noon. But it’s worth the wait as the coffee really is exceptional. This cafe exclusively serves coffee along with a select few sweet treats to go with your morning brew.

Filtrado has a cozy patio seating area, although rather hard to get a seat. If you love their coffee, you can even buy some to bring home as a gift.

Eat Cheap Local Food at Cafe Manolin

The original Cafe Manolin was established over 70 years ago. Their offerings remains true to their roots: great food in a family atmosphere, at reasonable prices.

The cuisine on offer is creole style food. Honestly, the hardest part is choosing just one dish off the menu. You can’t go wrong with ordering mofongo or one of the fish dishes.

If you are a breakfast person, they do great breakfasts here too.

Have a Pina Colada at it’s Birthplace

Did you know San Juan is the birthplace of the pina colada? Now you do. While I usually don’t like this sugar bomb of a drink, there is a ring to saying you’ve had a pina colada straight from it’s source.

For some reason, many locals tried to talk me out of buying a pina colada during my stay. Perhaps they are suffering from their own success at having invented one of the most famous drinks, who knows.

You can find pina coladas at basically any place with a drinks menu, but head to Barrachina if you want to have it in the place it was originally concocted.

As an alternative, head to Senor Paleta, a quirky popsicle shop where you have dozens of options to choose from for a fresh fruit popsicle, including a pina colada option.

Head to Isla Verde for the Afternoon

Isla Verde is the best beach located around San Juan. It’s located fairly close to the airport so you’ll regularly see planes arriving and departing from here. Don’t worry, they don’t come close enough to disturb you.

This beach is characterized by stunningly bright turquoise waters, which are warm and inviting year round. The beach is pretty calm and shallow, perfect for wading and swimming. The sand is soft and the beach is wide, making it an amazing place to chill out for an entire afternoon.

You can rent an umbrella and chair from the Marriott Hotel located around the center of the beach. Unless you plan to eat at the hotel, there aren’t really many food establishments nearby. So plan accordingly and bring snacks if needed.

This beach does also get pretty nice sunsets, so plan to stick around for that if you have time.

La Placita Marketplace

After the beach (and heading back to your hotel to freshen up) head into another part of San Juan for the night. La Placita is a local favorite hang out spot located in the Santurce neighborhood. While the market itself closes in the afternoon, it’s the restaurants and bars around it that you really want to check out.

On weekends, this area is the place to be for nightlife for visitors and locals. It starts off as a dinner spot, to a full on block party of dancing in the street.

You should plan to start your evening off with dinner in one of the many restaurants in the area. There are so many to choose from, that I can’t really recommend just one.

To help you navigate the restaurants here, check this article.

After dinner, stick around this area for bar hopping, dance clubs, and a lot of partying.

If You Have More Time

If you have more than two days in San Juan, you should definitely plan to venture out of the city and see some of the natural beauty around the island. Some highlights in Puerto Rico that make good 1 or 2 day trips from San Juan are:

• Flamenco Beach – pristine white sand beach with war history
• El Yunque National Rainforest – tropical rainforest with waterfalls and wildlife
• Camuy Caves – one of the largest cave systems in the world
• Mosquito Bay – the world’s brightest bioluminescent bay

Other Things to Know

San Juan Safety

San Juan is not entirely safe nor unsafe, but it’s probably a lot safer than the majority of cities in the Caribbean. And while there is definitely some crime, it’s still safer than most US cities in comparison. If you’re staying mostly in Old San Juan, you’ll feel very safe as it’s heavily under surveillance by the police and you’ll mostly just encounter other tourists.

Outside of Old San Juan and in more local areas such as La Placita, it’s still pretty safe. Just stick to places you know, don’t wander into unknown alleyways, or get too drunk at night, and you should be fine.

Every year a few horror stories pop up about tourists that were murdered in San Juan, but the truth is these incidents are far and few between. Plus, they were usually the result of poor judgement on the tourists behalf.

When looking at the crime rate in Puerto Rico, you may also be uncomfortable about the high homicide rate. These types of crimes are usually condensed in certain areas where most tourists won’t go, and are related to gang or drug related activities. Steer clear from both and you should be ok.

San Juan Solo Travel

I spent the last day in San Juan by myself. Based on my experience, I can see it being a good destination for solo travelers. There are plenty of things to do to keep you occupied, from museums, to food, to exploring historical sites. I never felt that my safety was compromised because I was traveling alone.

With that said, many of the best things to do in San Juan are things we would consider social activities ie. bar hopping, dining out, going to the beach, etc. If you are traveling alone, it’s possible to enjoy these things solo if you enjoy your own company, and are used to traveling as a party of one.

For those hoping to make friends, I found the Couchsurfing app to be somewhat active in San Juan, so you can probably link up with other solo travelers or locals using that.

San Juan FAQ

How many days do you need in San Juan?

2 days is enough to see the highlights in San Juan, before moving onto other destinations within Puerto Rico. Of course, if you have a longer trip, you can easily spend much more time here.

What is the best month to go to San Juan?

April may be the best month to visit San Juan. This is the beginning of the shoulder season, meaning there are less tourists than in winter. But it’s still the tail-end of the dry season so you’ll still have comfortable weather conditions and less chance of rain.

How many days should I visit Puerto Rico?

It’s hard to say, but if you’d like to travel in Puerto Rico beyond just San Juan, you could easily spend 4 – 7 days here. I think for most people visiting for the first time, 4 days in Puerto Rico is perfect.

And that wraps up this guide to spending two days in San Juan. Have you been to Puerto Rico? Share your favorite places below.

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