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San Juan Itinerary: Plan The Perfect 3-Day Trip

san juan itinerary banner buildings and ocean at condado beach

Being the capital of Puerto Rico, San Juan is one of the best places to vacation on this wonderful Caribbean island. Apart from its beautiful beaches and paradisiac nature, the city is known for its instagrammable streets with colorful colonial buildings, its fascinating culture, and plenty of fun things to do – and you can see most of it in 3 days with the right San Juan Itinerary!

In this post, I’ll be sharing the best things to do and places to visit for an incredible 3-day trip on the island, whether you’re looking for a relaxing getaway or a thrilling adventure.

How To Spend 3 Days In San Juan, PR

Although you can easily spend a whole week exploring the island without getting tired, staying in San Juan will allow you to visit countless museums, historical landmarks, eye-catching landscapes, and so much more in a short time without having to spend hours on the road.

Best Time To Visit San Juan

Puerto Rico is a tropical island and has summer-like weather all year round. Even in winter, temperatures remain between 21° and 29°. On the other hand, the best time for you to visit might depend on other factors like your budget or the overall atmosphere you want for your trip.


Interested in summer destinations? Here’s my guide for an awesome weekend in Orlando, FL.

Still not sure which neighborhood to stay in in San Juan? Check these neighborhoods here!


Dry Season For The Best Weather

Puerto Rico has fairly warm weather all year round, so it all depends on what you’re looking for. If you go during the dry season, between December and April, you can enjoy milder temperatures with little rain. However, this is the peak season for tourists, so the city will be more crowded.

Rainy Season For A Less Busy City

If you want to avoid busy streets and beaches, you can go between April and June and still get amazing weather. Although this is the rainy season, this doesn’t mean it will rain the whole day.

Low Season For Lower Prices

Visiting Puerto Rico during the low season, between August and November, is best for when you’re traveling on a budget. This is when you’ll find the lowest prices for hotels, restaurants, and activities. It will also be easier to plan your San Juan itinerary without having to worry about peak hours and heavy traffic.

Just keep in mind that this is also hurricane season, and although there aren’t hurricanes every year, it’s good to keep an eye on the weather before and during your trip.

Where To Stay In San Juanbuildings and streets in old san juan colonial arquitechture san juan itinerary

Deciding where to stay in San Juan can be a difficult choice. There are 18 official neighborhoods in the city and they all have something unique to offer. If you’d like to go deeper into these different areas to find your perfect hotel, make sure to check out the best San Juan neighborhoods for your stay – including the best hotels and things to do in each one of them.

Otherwise, here’s a quick guide with my top picks for accommodation.

Best Hotels In San Juan

Day 1: Exploring Old San Juan

Start the first day of your San Juan itinerary by checking in early at your hotel and preparing for a day outdoors. Drive to Old San Juan and take a self-paced tour visiting historic places and museums, walking the most Instagram-worthy streets, buying souvenirs, and tasting local food.

If you’re already staying in the neighborhood, you can easily get to know the whole area by walking since most attractions and activities are close enough to go on foot. 

Must-Do Tours In Old San Juan

If you’re short on time and want to see all the best spots and explore like a real local, these guided tours are ideal for first-time visitors. It’s also perfect for small groups and you can personalize it according to your interests.

Historical Places

What better way to start your trip than getting familiar with San Juan’s culture? You’ll quickly realize what a fascinating city this is once you start walking its cobblestone streets full of museums, historical buildings, and landmarks.

castillo el morro with vews of the ocean san juan itinerarySan Cristóbal Castle

Castillo San Cristobal is the perfect place to start your tour of the city’s old center. This is one of two forts located in San Juan built to defend the area from naval invaders during the Spanish-American war.

As you walk among impressive architecture, you’ll find numerous artillery stations, sleeping quarters where soldiers used to spend the night, and the control installations used during World War II.

San Felipe del Morro Castle

The second fort is San Felipe del Morro (also known as El Morro), which also played an essential part during the war, and you’ll get great insight into how the Spanish protected San Juan from attacks – the place is massive and you’ll be walking a lot, but it’s so worth it!

By getting the $10 admission ticket, you have access to both Castillo San Cristobal and El Morro. It’s a self-paced tour, so you can really take your time to see everything.

La Fortaleza Street

Once you’re done with the tour, head to Fortaleza Street, one of the most instagrammable places in San Juan. Along this cobblestone street, you’ll find lots of restaurants, shops, colorful houses, and the iconic canopy of umbrellas hanging in the air, so don’t forget to look up and take many pictures!

La Fortaleza (Mansion)

At the end of the street, there is the mansion called La Fortaleza, a former fortress that is now the official residence of Puerto Rico’s governor. Tourists can take a tour of the mansion and marvel at its flawless architecture, elegantly furnished rooms, and beautiful gardens.

This tour will not disappoint and is totally free! So it should be a MUST on your San Juan itinerary.

Lunch Time!

After all that walking, look for a place to eat in the area and recharge for the second part of your day. Whether you’re looking for a casual atmosphere or upscale gastronomy, Old San Juan is the place to go for a delightful experience

Best Restaurants In Old San Juan

Being the #1 tourist destination in Puerto Rico, Old San Juan has a huge variety of restaurants, bars, and cafes offering local dishes as well as international cuisine. Here are my top suggestions for a delicious meal:

Marmalade – a great option if you’re already on Fortaleza Street. Dishes are made with local produce and fresh ingredients. If you’re looking for the best quality, service, and overall experience, Marmalade will not disappoint. Fun fact: the owner is also the chef and you can see he puts his heart into every detail.

Santisimo – if you’re into fine dining, Santisimo is an excellent choice in El Convento Hotel. Come here for authentic Puerto Rican meals, great-quality seafood, and a varied cocktail menu. You’re also guaranteed outstanding service and a relaxing atmosphere.

Princesa – Cocina Cultura – great food, cocktails, and ambiance. Its beautiful patio surrounded by tropical plants and decorative lights makes it a perfect place to go on a warm summer night.

Cafe Don Ruiz – an absolute go-to for breakfasts, brunches, and probably the best coffee in Old San Juan. 

San Juan Gate & Paseo de la Princesaumbrellas and ornaments hanging at fortaleza street san juan itinerary

Now that you’re stomach is full, you’re ready to continue with this San Juan itinerary by heading to the San Juan Gate, the only gate remaining from the colonial period that used to protect the city, which is now a popular historical landmark. 

After taking awesome pictures, the gate will lead you to Paseo de La Princesa, a beautiful pedestrian promenade and a must for a relaxing afternoon stroll or to rest in front of the majestic Fuente Raices. Besides enjoying the best sights of San Juan Bay, you’ll find lots of artisan stalls and street vendors selling handicrafts and local food. On weekends, the area usually hosts festivals and fairs with live music.

Take A Food Tour

Finish your day diving into Puerto Rican food culture on a guided tour of Old San Juan’s restaurants. This is such a fun activity to do in small groups to taste many local recipes and learn about the island’s culinary influences and history. It’s also a great opportunity to try new dishes and look around the city.

Wanna book your tour? Here are two excellent options:

Day 2: A Day Trip

The second day of your San Juan itinerary involves a lot of adventure! Start your day early with a day trip to El Yunque Rainforest, a marvelous reserve for endangered species, tropical nature, and plenty of activities to keep yourself entertained the whole morning. In the afternoon, drive to Fajardo and stay until sunset to have a magical experience kayaking in a bioluminescent bay.

Book a Rainforest & Bio Bay Tour here!

Hike In El Yunque Rainforest

El Yunque National is the only tropical rainforest in the U.S. and is very popular for being home to unique flora and fauna, natural pools, and waterfalls you can explore through multiple hiking trails of varying difficulties. Getting deeper and deeper into the rainforest is a wonderful experience and you can easily spend the entire day walking and swimming among beautiful nature – so make sure to bring your swimsuit.

The entry ticket to the park is $2 per vehicle and you must make a reservation in advance since there are limited spots.

El Portal Visitors Center

Something you can’t miss in El Yunque is El Portal Visitors Center, placed before the forest entrance. This is a place where you can learn all about El Yunque and its history. Here you’ll find lots of interesting things from information booths and educational displays to in-site restaurants and a few gift shops.

There is an extra $10 fee per person to enter the Portal, but it will make your visit so worth it!

Tours In El Yunque

If this is your first time in El Yunque, I suggest taking a guided tour to make things easier. Your guide will take you along a half-day journey through the forest’s many activities and trails, including transport from designated meeting points to the park. Here are some great tours for first-time visitors:

Kayak In Laguna Grande Bioluminiscent Bay

After lunch, continue with your San Juan itinerary by driving to Fajardo. This town in the eastern area of the island is a great place to enjoy sunny days at some of the top beaches in Puerto Rico, such as Seven Seas Beach, Playa Escondida, and Playa Colorá.

However, the true highlight of Fajardo is kayaking in Laguna Grande, one of the three bioluminescent bays in Puerto Rico. Bio bays are characterized by microscopic organisms that grow in the water producing a unique effect of sparkles glowing in the dark. 

By booking a Rainforest & Bio Bay Tour, you get to explore El Yunque Rainforest during the day, and after a break for a delicious dinner at a local restaurant, the tour takes you to Laguna Grande’s blue waters for a magical kayak adventure.

Other kayaking tours in Laguna Grande:

Day 3: Beach Day & Night Out

No San Juan itinerary is complete without spending a day in Condado, an ocean-front district with a great variety of activities and amenities to offer its visitors. But don’t take too long, head back to your hotel to prepare for one last tasty dinner in Isla Verde and a fun night out in this party neighborhood.

condado beach san juan itinerary

Condado

Condado has the perfect laid-back atmosphere to spend your last day relaxing on stunning beaches, enjoying outdoor recreation, and strolling down its many shopping areas – everything within walking distance.

From outdoor activities like paddleboard at Condado Lagoon and dancing classes to upscale hotels, restaurants, shops, and entertainment at the popular Ashford Avenue, Condado is the ideal place to have the luxurious vacation you’ve always dreamed of.

Tip: If you missed the chance to kayak in Fajardo’s Bio Bay, you can still have an exciting nighttime experience taking a Guided LED Night Kayak Excursion in Condado Lagoon.

Where To Eat In Condado

By midday, look for a nice restaurant on Ashford Avenue and treat yourself to a good cocktail and an outstanding selection of world-class flavors. These are some top suggestions:

Isla Verde

Go back to your hotel to have some rest and prepare to spend the rest of your day at Isla Verde, one of the most visited destinations in Puerto Rico. Not only is it popular for its trendy beachfront resorts but also for its lively atmosphere and exciting nightlife.

With numerous bars, casinos, and nightclubs, Isla Verde is sure to be the best location to enjoy the last night of your San Juan itinerary to the fullest.

If you’re looking for good music and good drinks, check out Club Brava. This well-known, 2-floor club combines an energetic dancing atmosphere with a more chill-out lounge to enjoy both extremes in the same place. It also offers weekly concerts and themed parties – and entry is free if you’re staying at Fairmont El San Juan Hotel!

Tip: if nightclubs are not your style, visit La Placita! This market comes to life at night with live music, restaurants and bars with outdoor seating, and lots of dancing, becoming a great party spot.

Bonus Day: San Juan Landmarks

If you have some time to spare before heading to the airport, make a few quick stops at some of the most iconic San Juan landmarks – In case you didn’t take too many pictures the previous days, this is your chance!

Santa María Magdalena de Pazzi Cemetery

Situated outside El Morro in Old San Juan, is Santa Maria Magdalena de Pazzi Cemetery. This colonial-era cemetery is the final resting place of many of Puerto Rico’s most prominent natives and is recognized as one of the most beautiful memorial parks in the world. 

Residents and tourists are welcome to enter to see the ornate tombs and ocean sights, which make this historical landmark a very calm but enjoyable spot for a quick visit. 

Capilla del Santo Cristo de la Salud

Capilla del Cristo is a small chapel located at the end of Calle del Cristo. The church was built in the 18th century and you can find many objects and paintings from that time inside.

San Juan Cathedral

San Juan Cathedral is an ancient but imposing building right on the other side of the San Juan Gate. Whether or not you’re a religious person, this cathedral is worth a visit to admire its stained glass windows and tall ceilings.

decorative flowers san juan itinerary

How To Get Around San Juan

There are a few ways you can get around San Juan. All of them have their pros and cons, but it will ultimately depend on where you’re staying, the places you want to visit, your budget, and your own preference.

Rent A Car

Renting a car is one of the easiest transportation options for tourists in Puerto Rico. It will give you a lot of freedom to explore your San Juan itinerary at your own pace and it’s cheaper than a private shuttle.

Uber or Taxi

Hopping on a taxi or Uber is another fast and trustworthy way to get around the island. It’s especially comfortable with Ubers since you can easily get one using the app. On the other hand, it can be more expensive for longer routes.

Private Shuttle

Although private shuttles can be significantly more expensive than taxis, they’re excellent for larger groups since the vehicles are usually bigger and more comfortable. 

Walking

If you’re staying in Old San Juan, you can easily explore all areas and attractions within the neighborhood by walking. This way you’ll save money and hate the freedom to move around without worrying about schedules or peak traffic hours. However, you will need a vehicle if you want to visit other places outside of San Juan.

What To Pack

What to pack might depend on the type of trip and activities you have in mind and the time of the year you’re staying. But, to save you some time, here are the essential items I think every traveler should bring when visiting San Juan, Puerto Rico.

Check All Travel Necessities Here!

Cable Organizer
Cable Organizer
Hydration Packets
Hydration Packets
Sleeping Bag Sheets
Sleeping Bag Sheets
Underarm Deodorant Wipe
Underarm Deodorant Wipe
Hand Sanitizer
Hand Sanitizer
Adjustable Door Stopper
Adjustable Door Stopper
Portable Lock
Portable Lock
Sun Protective Swimming Leggings
Sun Protective Swimming Leggings
Satin Robe
Satin Robe
Reusable Water Bottle
Reusable Water Bottle
Eye Mask
Eye Mask
Ear Plugs
Ear Plugs
Electronics Organizer
Electronics Organizer
2 in 1 Travel Blanket and Pillow
2 in 1 Travel Blanket and Pillow
Shoe Bags
Shoe Bags
Jewelry Organizer
Jewelry Organizer
Mini Perfume Atomizer
Mini Perfume Atomizer
Collapsible Travel Sized Bottles
Collapsible Travel Sized Bottles
Pill Organizer
Pill Organizer
Toiletries Organizer
Toiletries Organizer
Clear Toiletry Bags
Clear Toiletry Bags
Passport Holder
Passport Holder
Check Luggage
Check Luggage
Travel Backpack
Travel Backpack
The Best Backpack You Will Ever Have
The Best Backpack You Will Ever Have
Time Caps
Time Caps
Microfiber Lens Cleaner
Microfiber Lens Cleaner
Binoculars
Binoculars
Mobile HotSpot
Mobile HotSpot
Wireless Headphones
Wireless Headphones
Wall Plug Adapter
Wall Plug Adapter
Travel Tripod
Travel Tripod
Basesus Portable Charger
Basesus Portable Charger
Dry Bags
Dry Bags
SuperGoop Sunscreen
SuperGoop Sunscreen
Water Shoes
Water Shoes
Cali Case
Cali Case
Underwater Camera
Underwater Camera
Snorkel Gear
Snorkel Gear

Reusable Water Bottle

Consider taking a reusable water bottle with you if you’re going to be walking a lot or hiking in places without any shops nearby.

Sunscreen

Needless to say, sunscreen is extremely important to protect your skin from UV rays, especially if you’re going to a country like Puerto Rico, where the sun is stronger. You’ll be using this every day of your San Juan itinerary.

Insect Repellent

Due to Puerto Rico’s tropical weather, it might be a good idea to include an insect repellent in your travel bag. You’ll definitely enjoy your day out in nature a lot more without those uncomfortable mosquito bites.

Travel Umbrella

A travel umbrella is another excellent addition to your packing list. It will come in handy on unexpectedly rainy days or if you’re traveling during the rainy season.

Light Clothing

One of the best things about a destination like San Juan, Puerto Rico is that you don’t need to pack a lot of clothes. Even during the winter, the temperature is warm so you’ll mostly be wearing light clothes and swimsuits – also, don’t forget a hat and comfortable hiking shoes for your adventurous days!

Last Thoughts

I hope this San Juan itinerary was helpful and that now you feel more confident in planning your next trip to Puerto Rico.

With so many things to see and do around every corner, no wonder it can be overwhelming trying to fit everything in such a short period of time, but now you can use this itinerary as a great starting point and customize it to your liking. Have fun and safe travels!

XO,

Anna

P.S. Still unsure about where to stay? Find out which of these popular San Juan neighborhoods is the best for you.

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I may collect a small commission from the links on this page if you decide to book a stay, it helps me keep the blog up :) Listed prices are accurate as of time of publication.
Anna
Anna

Anna is a traveler, blogger, and entrepreneur who can’t keep herself still. She’s always on the move, whether working hard on a new passion project or exploring a new city as a part-time digital nomad. Dare to keep up? Check out The Tatted Nomad for everything digital nomad, social media marketing, mental health, and travel (and to see her latest addition, Novah, her service dog and travel companion). As a psychotherapist (to be) she also offers insights about your mental health related questions – anything you see that isn’t covered but you have questions about? Let her know!

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