You have a three day San Juan itinerary in your hand but is that enough time to get a true feel of this historic city? Absolutely! As a matter of fact if you only have the chance to spend one day in San Juan you should jump at that opportunity. San Juan is the capital city of Puerto Rico and is the beating heart of the island. It’s also one of the most unique cities in the Caribbean. On one hand you have a city that’s loaded with old world charm, and on the other, you have a city that offers up all the modern amenities that you’d need.
The island of Puerto Rico is known as the “Island Of Enchantment” and for good reason. With its vibrant culture, lush rainforests, and pristine beaches, there’s always something to discover on the island.
In San Juan you can spend your time eating delicious Latin-Caribbean cuisine, dancing the night away, and so much more. There’s no shortage of things to do in this lively city. Read on for some of the best things to add to your three day San Juan itinerary.
San Juan, Puerto Rico. Photo credit: Diego F. Parra
How To Travel To San Juan, Puerto Rico
There are two ways to get to Puerto Rico and it’s either by plane or boat.
Flying To San Juan, Puerto Rico
Luis Muñoz Marín International Airport is the main airport on the island and is only about 13km away from the city center. Getting to and from the airport is very easy as visitors can get there by taxi or shuttle. You can also schedule an Uber or get a rental car from the airport.
If you’re coming from Canada unfortunately there aren’t many options for getting to San Juan. Currently Air Transat is the only airline who’s flying direct from Toronto. Air Canada also flies to Puerto Rico but after spending some time on their website we couldn’t find any non-stop flights. Almost all made at least one stop.
From the U.S. though the number of flights options are higher (and prices much lower) as many direct flights come in from airports all over the country. Visitors would find the cheapest flights are those that originate from either New York or Miami.
Flying from the U.S. is definitely the way to go if you want to savor every minute of your three day San Juan, Puerto Rico itinerary.
Ferries to San Juan, Puerto Rico
As for getting to the island by boat, visitors have two choices. The first being a cruise as almost all major cruise lines have some of their cruises either starting from, or making a stop in San Juan. The other option is via a ferry but the only one available is one that goes between San Juan and Santo Domingo in the Dominican Republic.
Is San Juan Worth Visiting?
If you like history, stunning architecture, a vibrant food scene, beautiful beaches, and people who are deeply proud of their heritage, then you should definitely be thinking about spending some time in San Juan.
San Juan is one of the oldest cities in the Americas which means that there’s history around almost every corner. The historic district of Old San Juan is a UNESCO World Heritage Site with many buildings still standing from the Spanish colonial days. Exploring Old San Juan on foot is the best way to see the sights in this part of the city. You have to stroll down the colorful streets to take in all the colonial-era Spanish architecture.
The biggest attraction in Old San Juan is Castillo San Felipe del Moro, the Spanish fort that was started in 1539 and finally finished in 1790.
Castillo San Felipe del Morro. Photo credit: Malcolm Garret
Getting Around In San Juan, Puerto Rico
Now that you have your three day San Juan itinerary all set, the next thing you need to figure out is how to get to all the cool spots. The great thing is that getting around San Juan is quite easy and visitors have a number of options.
Getting around San Juan By Foot
San Juan, like most cities, is made up of different neighborhoods each with it’s own unique charm. Old San Juan is the historic part of the city and is located within San Juan itself. There’s a lot to see and experience in this neighborhood and is best explored by foot. You can easily see all the sights and do some shopping in just a few hours. Don’t forget to explore the culinary scene as there are some great restaurants in Old San Juan. Like a lot of other islands, the Caribbean is known for some delicious food and Puerto Rico is no different.
Outside of Old San Juan can also be explored by foot, but obviously it’s a much bigger area to cover. A lot of the popular hotels are located close to the beach and again, it’s quite easy to walk to wherever you need to go for all your shopping and dining needs.
Getting Around San Juan By Car
There are a number of ways to get around San Juan by car. First up are taxis. These can be easily hailed and are always outside popular tourist spots like attractions, malls, cruise ships, and hotels. Taxis are very safe and reliable. Uber is also available in San Juan but not in other parts of the island.
If you’d like to do your own driving then there are a number of car rental companies in San Juan. With a rental car you’re not tied to a schedule so you can explore at your own pace. On the other hand, you’d need to learn about routes and road rules. Another downside of renting a car in San Juan is that last minute bookings can be very pricey so it would be best to book early as possible, even before you have your three day San Juan, Puerto Rico, itinerary finalized.
Getting Around San Juan By A Free Trolley
A free trolley service? Yes, you read that right. Basically it’s a hop on/hop off service that stops at all the popular spots in Old San Juan.
Your Three Day San Juan Itinerary
Day 1: Old San Juan
Old San Juan, or Viejo San Juan as it’s known to its residential Spanish speakers, is listed on the United States National Register of Historic Places. With origins dating back to 1521 when it was first settled by colonizers from Spain, it’s the oldest city in the U.S.
The history is felt around every corner as you walk down the cobblestone streets lined with colorful buildings. The architecture is more reminiscent of Europe than anything you would find in most parts of the continental United States. There are many old hotels and unique vacation rentals offering comfortable accommodations.
Calle de la Fortaleza. Photo credit: Reynaldo Brigantty
Castillo de San Cristóbal
There are several must-see sites within this walled city. Castillo de San Cristóbal is the largest fortification built by the Spanish in the New World and is one of the most-visited attractions on the island. Some of the best views of Old San Juan and the surrounding ocean are seen from on top of this fort. For any history buff, Castillo San Felipe del Morro and La Fortaleza are also worth checking out.
La Perla Neighborhood
The neighborhood of La Perla is also worth a visit. This barrio is going to give you the best example of true Puerto Rican culture in Old San Juan. A decade ago, this would not be a very safe area for tourists, but it has seen a revitalization in recent years with new artwork and small businesses making a name for themselves. Lending a hand with this resurgence is the music video for the international megahit “Despacito,” which was filmed in La Perla. This is a great area for a quick but delicious lunch in the form of traditional street food.
La Perla
Visit The Birthplace Of The Piña Colada
The national drink of Puerto Rico is the piña colada, which is said to have been invented on the island. While this is widely accepted as truth, there are two bars in Old San Juan that both claim to have served the first-ever piña colada. You may want to pay a visit to both, just to be sure.
First, head to Barrachina, a traditional Puerto Rican restaurant that offers indoor and outdoor seating. Right next to the front door, you will find a plaque commemorating the birthplace of the tropical cocktail. Next, head over to the Caribar in Caribe Hilton. The hotel also takes credit for inventing the coconut and pineapple-flavored drink.
Dinner at Marmalade
When it comes time for dinner, check out Marmalade, one of the highest-rated restaurants in all of Puerto Rico. Here, Chef Peter Schintler combines international flavors with a Caribbean influence. This award-winning restaurant has become famous for its five-course tasting menu and wine pairings.
Go Salsa Dancing
When the sun goes down, just follow the music to find a place to do some salsa dancing. La Factoria has become a favorite among tourists and locals alike. This bar never seems to end as you walk through its secret passageways that lead to different rooms, each with its own unique ambiance. With carefully-curated live music and drink options, it’s easy to see why La Factoria has been named one of the World’s 50 Best Bars for five years in a row.
For better or for worse, Old San Juan is the tourist capital of Puerto Rico. It’s common for cruise ships to stop here and unload huge crowds into the city. Due to this, there are a number of boutique stores and souvenir shops can be found along the historic streets. If you want to buy a memento from your trip to San Juan, this is a great place to do it.
Day 2: Beach Day
One of the best things about San Juan is being able to access stunning beaches directly from the city. The only difficult part is deciding which one to choose. You can claim the perfect spot at one beach for the day, or go “beach hopping” to enjoy several different areas along the coastline. A beach day is the one must-do thing you HAVE to add to your three day San Juan, Puerto Rico itinerary.
Escambron Beach
Located between Old San Juan and Condado (new San Juan), you will find Escambron Beach. When most people picture a beach in the Caribbean, they might imagine something like this. Fine sand, crystal-clear water, and palm trees swaying in the gentle breeze. Swimming, snorkeling, and scuba diving are popular activities at this beach.
Escambron Beach also boasts convenient facilities such as bathrooms and showers. If you find yourself wandering away from the beach, there are several parks and historic sites in the immediate area. The fort of Escambrón, Sixto Escobar Stadium, and Polvorín San Gerónimo de Boquerón are all landmarks worth seeing just off of Escambron Beach.
Condado Beach
Condado Beach is located in the heart of the city, so there are plenty of food and drink options nearby. This beach can be a party on the weekends, but never overly crowded or obnoxious. If you aren’t staying at one of the nearby hotels, you can rent an umbrella or beach chair for a small fee.
Condado Beach
Playa Ocean Park
Playa Ocean Park is another solid beach option within the city. This beach is located next to a large park with athletic fields and a track just in case you’d like to work off some of the fantastic food you’ve eaten. This beach also tends to be less crowded than Condado Beach but still has plenty of soft sand and palm trees for shade.
Isla Verde Beach
Isla Verde Beach is a great place to mingle with groups of young people. Due to the popular bars and clubs nearby, this beach tends to attract a younger crowd but is certainly welcoming to people of all ages. Isla Verde is also a hotspot for water sports. It’s quite common to see people engaging in activities such as surfing, kiteboarding, and windsurfing.
La Playita del Condado
If the tides are too strong at other beaches, head to La Playita del Condado. The water around this smaller stretch of beach is enclosed by large rocks, creating a natural pool. This results in some very calm waters with no strong currents. This is a wonderful place to rent a lounge chair and relax. There are also kiosks near this beach selling hot food and cold cocktails.
For a different kind of experience, simply head across the street from La Playita del Condado to Condado Lagoon. The still water in the lagoon makes it the perfect spot for kayaking or stand-up paddleboarding. Manatees, sea turtles, and other tropical fish have been known to swim in these clear waters.
Day 3: Explore Condado and Greater San Juan
Condado
After crossing the bridge from Old San Juan, you’ll find yourself in the upscale beachfront neighborhood of Condado. While Old San Juan is all about the historic look and feel, Condado is quite the opposite. Condado is full of modern highrises, luxury hotels, and plenty of entertainment. Condado is the ideal destination for trendy bars and restaurants. There’s even a casino on the main strip.
A fun and convenient way to explore this area is by renting a bike or scooter. Bike lanes are well-marked throughout Condado so it’s quite safe for those on two wheels. And since the weather is nice and warm year-round in San Juan, you don’t have to worry about it being too cold for a bike ride.
Museum Of Contemporary Art
One of the top museums in San Juan is the Museum of Contemporary Art of Puerto Rico. The museum houses over 1,200 unique pieces from around Latin American and the Caribbean. Even if modern art isn’t your thing, the building itself is deserving of a visit. The museum is located in a building with large white columns that was originally a school constructed in the early 20th century.
Miramar District
Next, take a walk around the Miramar district. This area might make you feel like you are in Miami as you marvel at the shimmering buildings along the waterfront. There are some cute cafes around here, such as La Isla, where you can find a delicious cup of Puerto Rican coffee,
Food Truck Eats
For lunch, there are two food truck parks serving up a wide variety of cuisine. Miramar Food Truck Park is the more “local” option, with trucks serving vegan, Asian, Mexican, and other types of food. The other option is the Lote 23 food truck park, which stays open late and attracts more tourists. For traditional Puerto Rican food, try the El Cuchifrito food truck. They serve some of the best mofongo, the classic Puerto Rican dish consisting of mashed plantains and other ingredients.
Street Art And Shopping In Santurce
The neighborhood of Santurce is a great place to spend the afternoon. Santurce hosts a festival every year that invites artists to create murals on the walls of the neighborhood. The murals remain on the buildings all year, so you can walk through the streets and admire the creativity around every corner. Santurce is also a great place to do some shopping.
Dinner At La Placita
End your three day San Juan, Puerto Rico itinerary with dinner and drinks in La Placita. A local market during the day, La Placita turns into Puerto Rico’s premier nightlife destination when the sun sets. A trip to San Juan is not complete without visiting this lively square of open-air restaurants, live music, and dancing.
Conclusion
San Juan, Puerto Rico is a fascinating city that offers up a great blend of history, culture and natural beauty. Spend some time exploring Old San Juan with its cobblestone streets, colonial architecture and iconic forts that’ll take you back in time. Relax on some of the Caribbean’s best beaches or get out onto the water for some water sports. As the sun goes down the Condado neighborhood offers up a whole lot of activities to keep the fun going. There’s also a lot for art enthusiasts such as the Museum of Contemporary Art and vibrant street art in Santurce. As you can see, creating a three day San Juan itinerary is very easy as this city offers something for everyone.
Huge thanks to Steven Geist from Bro On The Go for this guest post. Steven is a digital nomad who shares all that he has learned on his site to help others with their travel dreams.
