How To Spend 4 Days In Puerto Rico: Travel Itinerary & Tips

Puerto Rico is one of my favorite destinations in the Caribbean! Maybe it’s  because of how much it reminds me of my home city of Havana, but I think you’ll love Puerto Rico even if you’ve never been to Cuba. It’s a great destination to unwind and relax all year round, especially if you are traveling from North or South America: you’re right next to the Caribbean, so you’ll have a quick and cheap flight! There’s always something exciting to do and a new place to explore on the island, especially if you have enough time to spend 4 days in Puerto Rico. From one of the incredible National Forests to dreamy clear-water beaches and smaller islands off the main coast, you’ll find it all in Puerto Rico. It’s a country that’s rich in natural resources, has plenty of delicious food, and is full of welcoming people. 

To share all my secret spots, the advice of my local friends, some of my favorite restaurants, and the best things to do, I have put together this “4 days in Puerto Rico Itinerary”. If you’re visiting the island for just the weekend, you can still use our travel guide and simply choose your favorite activities and places to add onto your own itinerary. 

They say Cuba and Puerto Rico are “two wings of the same bird” so read on to find out a little more about this beautiful island that reminds me so much of my home!

Travel Itinerary: 4 Days in Puerto Rico

Day 1: Old San Juan

Old San Juan is without a doubt one of my favorite parts of Puerto Rico, and going there is the best possible way to dive right into the local culture of the island at the start of your 4 days in Puerto Rico. Since most flights will go into San Juan anyway, it’s the perfect way to start your trip!

 There are many things to do around the Old San Juan: tons of restaurants and historical places to visit, plenty of great local shopping opportunities, and some amazing photograph locations. My top recommendations are: 

Stop 1: El Morro Fort, San Cristobal Castle and Fortaleza Street 

El Morro Fort dates from the 16th century, when it was built to protect San Juan Bay and the city from the threat of pirates and hostile foreign nations. El Morro has remained a fixture of the city throughout the years, so it's an amazing place to visit, see the old cannons, and learn about some of the iconic historical events that involved the fort.

Less than 5 minutes away by foot from El Morro Fortress, you’ll find San Cristobal Castle. San Cristobal Castle was also built by the Spanish to protect the island from enemies. It was the largest defensive structure built by the Spanish in all the Americas, and has its own unique history to learn about. Both places are definitely worth a visit! 

Just nearby San Cristobal Castle, you’ll find Fortaleza Street. This street is well known for its iconic display of hanging umbrellas, colorful rows of houses, and picturesque colonial restaurants and hotels. The umbrellas might not be on display all the time, but there’s plenty more to make you fall in love with this little street.

Stop 2: Lunch

Restaurant Recommendations in Old San Juan:

 Once you’ve explored the Old Town for a while, it’s time to stop for lunch. You’ll be ready to relax and recharge a bit before heading to your next set of destinations. There are many restaurants in Old San Juan serving delicious criolla food, but my top two restaurants are El Jibarito and Marmalade Restaurant and Wine Bar. 

For lunch, I recommend El Jibarito. The restaurant has a very homey feel, the service is incredible, and the food is definitely very authentic Puerto Rican. The restaurant owner's wife is the head chef, so you know you’re in the right place to have an incredible meal! Some of my favorite dishes are the Bistec encebollado (steak with onion) and the flan (of course!). Don’t be afraid to ask for recommendations if you’re not sure what to order. 

 Marmalade Restaurant and Wine Bar opens at 5pm, so if you had a late breakfast/brunch and you are heading to an early dinner this might be the place for you! The restaurant offers different tasting menus without the crazy prices that normally come with this kind of experience, so I definitely recommend checking them out if that’s your thing. It’s also a fun place to stop for a quick late afternoon drink!

Stop 3: The Black Puerto Rican Flag Mural, Casa Blanca & Beyond

There are so many historical places, museums and landmarks in Old San Juan, but the Black Puerto Rican Flag Mural is one you definitely won't want to skip during your 4 days in Puerto Rico Travel Itinerary! 

This mural was originally painted on a door in Old San Juan by a local artist, and was at first just a normal depiction of the red, white, and blue flag of Puerto Rico. But in 2016, the flag was repainted in black and white to symbolize social resistance. It has since then become an even more iconic image throughout the world. It’s a great way to get a bit more in touch with the local sentiments on the island, and from a lighter point of view it is also a very insta-famous spot in Puerto Rico. When you’re done, head a few blocks over to grab an amazing coffee at Finca Cialitos! 

 Another location I think is worth visiting in this area is Casa Blanca. This house was built in 1512 as a residence for the Spanish conqueror Ponce De Leon and his family. While Ponce De Leon died without ever actually occupying the premises, the house today is a museum that helps visitors understand the history of the colonization of Puerto Rico and the relationship between the Spaniards and the indigenous Taino people. The Taino were the original people living in many parts of the New World before Europeans arrived, and were actually the ones first encountered by Christopher Columbus. The Casa Blanca museum is a great place to learn more about the history of an amazing culture that sadly is mostly forgotten today.

Stop 4: Cathedral

Whether you are spending one day in Puerto Rico or four, The Metropolitan Cathedral Basilica of Saint John the Baptist or Catedral Basílica Metropolitana de San Juan Bautista is one of the top places in Old San Juan that history lovers won’t want to skip. The Cathedral is among the oldest cathedrals in North and South America, and was the one of the first of its kind built in the U.S. The church itself was the second worship structure built in the region, constructed in 1521 after the Cathedral of Santa María la Menor in Santo Domingo, Dominican Republic. The church has actually been reconstructed and renovated several times through the years after a few hurricanes caused damage to the structure and several other instances of robbery and theft, but the three most important highlights inside the cathedral have passed the test of time: The tomb of Ponce de León (a Spanish explorer), the mummy of St. Pio (a Christian martyr persecuted and killed for his faith)  and the incredible stained glass windows all remain on display for visitors to appreciate!

 Stop 5: The Santa María Magdalena de Pazzis Cemetery

Latin American cemeteries are well known around the world for their unique historical designs and architectural details. A few of the most culturally and historically rich cemeteries in the region are the Recoleta Cemetery in Argentina, the Colon in my hometown Havana, and of course the Santa María Magdalena de Pazzis Cemetery in Puerto Rico. Although I don’t usually recommend visiting a cemetery as part of a regular itinerary, the Santa María Magdalena de Pazzis Cemetery (or the Old San Juan Cemetery, as the locals call it) is such a beautiful historical destination in the city that it's well worth the visit. The cemetery was built in a colonial style, and has the Atlantic Ocean and the San Cristobal Castle and the Fortaleza as a backdrop. 

Stop 6: Paseo de La Princesa

Paseo de La Princesa is a tree lined promenade in Old San Juan dating back to 1853. Around the year 1837, the area housed a famous prison: La Princesa Prison.  And later on, it served the Spanish military as a vital area in the defense of the city. 

The promenade was completely restored in 1989, and today visitors can experience some of the famous Old San Juan Landmarks while walking by! Don’t miss the Americas Heritage Fountain, the La Concepción Bastion and the San Justo y Pastor Bastion. 

After walking through the area, sit down at an open air café serving traditional Puerto Rican food and drinks, or grab a quick bite from one of the many street vendors. If you're visiting during the weekend, enjoy some of the live jazz that Puerto Rican artists play in the Paseo on Fridays and Saturdays, and the salsa on Saturdays and Sundays. 

 These are some of my favorite sites in the Old San Juan, but there are so many others! My advice is to not only visit these places, but also walk around the many streets and wander off the beaten path a bit while you’re there. Old San Juan has tons to see and discover, but the area itself is quite small and is easy to explore in a day or less.

Stop 7: Take a salsa class

A super fun thing to do while spending 4 days in Puerto Rico is to take a salsa class. Visitors will learn the basic steps with a local expert and will dance with a partner to the compass of the intoxicating caribbean rhythm. Most classes will take place in a private space, but many of the instructors will later take you for a night out to some of the local establishments to practice your new moves with the locals. Super fun!

Stop 8: Sunset on a Rooftop ( La Verguenza or San Juan Water & Beach Club Hotel, Mist Rooftop)

If dancing salsa is not really your thing then we recommend spending your first night watching the sun set and making friends at a local rooftop bar.  

There are several restaurant-bars with great views of San Juan, the San Juan Bay and the Atlantic Ocean. Yet if I had to pick one to spend a great night in San Juan, it would be the Mist Rooftop in the San Juan Water & Beach Club Hotel.  The rooftop hotel is located in Isla Verde overlooking the beach, and it provides a super fun atmosphere with a mix of locals and tourists on its terrace, great rum based drinks, and the latest musical hits playing in the background. 

Day 2: el Yunque or Bosque Estatal de Piñones

EL YUNQUE

Approximately 45 minutes away from San Juan is El Yunque National Rainforest.  

El Yunque National Forest is the only tropical rainforest in the United States, and one of the best in the Caribbean. El Yunque extends for an amazing 28,000 acres, and its highest peak rises up to approximately 3,494 feet above sea level. The forest is one of the most well-known destinations in Puerto Rico, and it’s believed to be a place of high importance for Taino and indigenous people. And in some areas even today, you’ll be able to see some incredible Taíno petroglyphs!

This is definitely one of the must-visit places during your 4 days in Puerto Rico. The forest is truly one-of-a-kind in North America, and is a dream destination for nature lovers and eco-tourists. It has several walking trails of varying degrees of difficulty, so everyone can have the chance to go hiking, exploring, and kayaking. 

Some useful things to bring with you when heading to the rainforest are a natural bug repellent and some water non-slippery shoes.

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There are several companies offering transportation to El Yunque directly from your hotel and some really fun tours.

BOSQUE ESTATAL DE PINONES

Another famous forest area to visit in the island is the Bosque Estatal de Piñones or Piñones State Forest. The forest is not only a great destination in and of itself, but it is located near the famous beach Playa Aviones. There’s a wooden boardwalk where visitors can go on a walk or bike ride, all while admiring the mangroves, flora and fauna of the area

Day 3:  The Islands: Culebra (Flamenco), Culebrita & Vieques 

There are several smaller islands off the main coast of Puerto Rico, and many of them offer turquoise waters, white sand, picture-perfect landscapes. If you’ve been dreaming of that postcard beach getaway, this is the time to do it!  There are several options: 

 Flamenco is a beach on the main Culebra island. It’s often recognized as one of the best beaches in the world, and it’s the perfect place to dive into the water and snorkel. 

Culebrita is an even smaller island found  right next to Culebra. Culebrita has six beautiful beaches that you can visit, giving you plenty of options to choose from. The island itself is uninhabited, making it the perfect destination to head to if you want to avoid the big crowds. 

Vieques has a small local population and several popular beaches to choose from. If you want a nice balance of less crowded but not totally undeveloped, this might be the place for you.  A highlight in Vieques that you won't want to miss during your visit is the Puerto Mosquito Bioluminescent Bay, or Bahía Bioluminiscente. The bay is famous for the blue color and natural glow that comes through the water when the resident dinoflagellate Pyrodinium bahamense gets agitated. The phytoplankton species are endemic to Caribbean islands like The Bahamas, Puerto Rico and the Virgin Islands.

 There are three ways to get to these islands from mainland Puerto Rico. One is by air: you can take a very quick flight from either San Juan or the town of Fajardo. This is definitely the quickest option, though you’ll spend more money than with the other two. 

The other two ways are by sea: you can either take a ferry from Fajardo, or book a smaller boat excursion. The ferry ride costs approximately $2 each way, so if you’re on a budget this is definitely the way to go! Many of the small boat trips will also include lunch and snorkeling or diving activities, so if you’re planning on that as well you can get a good deal. We did just that and had a blast!

 Note: If you are staying in San Juan, be aware that it takes approximately an hour to get to the adjacent town of Fajardo, which is where the ferries depart. In most boat excursions, transportation to and from Fajardo is included.

 Day 4:  Casa Bacardi, Isla Verde Beach & more entertainment

For your last day in Puerto Rico, I recommend spending half of the day exploring and the other half just relaxing. After all, you’re probably traveling to Puerto Rico to enjoy the magic of the Caribbean, so make sure you schedule some time to simply unwind and enjoy yourself. So for the first stop of the day, I recommend…

  Stop 1: The Bacardi House

Here, you’ll learn about the interesting history behind the iconic rum brand: how it all started in Cuba, then moved to different parts of the Caribbean and the rest of the world over time. A Caribbean vacation is definitely synonymous with mojitos, so this is a great opportunity to get a really good classic one or learn how to make one!

To get to the Bacardi House (distillery), you can either take a ferry from Pier 2 in Old San Juan, or just drive if you rented a car for the trip. If you decide to take the ferry, the boats depart every thirty minutes and the ride costs approximately 50 cents (!!). You’ll arrive at the Cataño pier, and from there the Bacardi House is two miles away.  You can find taxis right by the pier, or walk if you prefer some fresh air. 

Note: Another great option is to visit the Bacardi House late in the afternoon and wait to catch the ferry back during the sun set hours. This way, you’ll get to sail during sunset without paying extra for an expensive tourist ride.

Stop 2: La Vergüenza & La Perla

A great destination for lunch, tapas, and drinks is a local rooftop restaurant called La Verguenza. The establishment is on the corner of one of the less busy streets of Old San Juan, overlooking the ocean and the famous neighborhood of La Perla. Talk about picturesque!

La Perla is one of the most well known neighborhoods of Puerto Rico. For years it was referred to as a dangerous and not very friendly area of San Juan, but for more than a decade now it has been a place praised in songs and literature for its ties to the local culture and for being very authentically Puerto Rican. Although there’s much to see or do in the neighborhood itself, you can always go on a self walking tour of the neighborhood and stop by La Garita restaurant.  Just be mindful, respectful of the neighbors, and aware of your surroundings like you would anywhere else in the world. More recently the streets of La Perla have been seen in the pop culture world as the set for the famous Despacito song’s hit music video.

 Stop 3: Isla Verde

Isla Verde is one of the most beautiful and fun areas in San Juan. Not only is the beach itself gorgeous, but there are plenty of exciting things to do: jet skiing, parasailing, banana boat rides, and more! 

Isla Verde is one of my favorite places to stay in San Juan, as there are plenty of resorts and boutique hotels to choose from. If you are planning to Airbnb while in San Juan, this is also a great area to do so: there are tons of condos and high rise buildings overlooking the beach, so you should find plenty of options to book. As with any popular destination, the earlier you book the better!

Note: Isla Verde is just 15 minutes away by car from Old San Juan, making it a super easy drive. And if you decide to stay in the area, there are tons of beachside restaurants, smoothie and juice bars, and regular bars. You’ll probably want to check them all out at some point! 

Stop 4: Water sports

A few minutes away from Isla Verde is Condado Beach and the Condado Lagoon, two popular summer destinations in the area among beach lovers and practitioners of sports like kayaking and paddle boarding. Some of our favorites things to do in the Lagoon include Guided LED Night Kayak Excursion.

 Stop 5: Asere Cubano and La Placita

For your last night in Puerto Rico, I recommend going out and enjoying some Caribbean food and music. Asere Cubano is one of my favorite restaurants in Puerto Rico. It’s actually a Cuban restaurant, with a great atmosphere and some delicious food. Cuban food is very similar to Puerto Rican, so you’ll definitely still get the Caribbean culinary experience if you decide to eat here. And the best part is that you’ll be just right next to La Placita, which is the place to be on the weekends to enjoy a true Puerto Rican night out with the locals. 

La Placita is a farmer’s market during the day and a cultural epicenter at night. You’ll find the whole family having fun here: listening to local music, eating delicious food, and hanging out with friends. No matter who you ask in Puerto Rico, they’ll tell you La Placita is a place you won’t want to miss!   

Additional Travel Tips for your 4 Days in Puerto Rico

 With 4 days in Puerto Rico, you’ll have plenty of time to explore the island. If some of the recommendations above aren’t for you, these other areas are also among my favorites on the island: 

 Rincon: This small town is located in the northwest part of Puerto Rico, and is well known as a true surfer’s paradise with especially beautiful sunsets. If you’re looking to get a bit more off-the-grid, Rincon is the place you should definitely check out. 

 Isabela: Also in the northwest of Puerto Rico, Isabela is a popular vacation spot for the locals. You’ll find everything from underground rivers to lakes, forests, mountains, and delicious Puerto Rican restaurants (check out El Platanal and try the traditional Puerto Rican dish Mofongo). You can’t really go wrong here!

 Aguadilla: Another popular local spot, Aguadilla is known for its lively beach atmosphere, especially on the weekends. Expect to find barbecues and restaurants on the beach, music and dancing, and other fun activities like jet skiing. 

Cabo Rojo: In this municipality, you’ll find some of the most breathtaking landscapes in Puerto Rico. You can head to  Las Salinas (gorgeous unique pink salt flats), visit the Los Morrillos lighthouse, or stop by the fishing village of Joyuda for some amazing seafood. 

Ponce: This is the second-largest city in Puerto Rico, so you’ll find tons of things to do and places to visit. Among my favorites are Parque de Bombas (a historic fire station) and La Guancha boardwalk. If you want to spend the night, there are lots of hotels and other options as well! 

Cayo Icacos: A white sand crystal clear water uninhabited island off the coast of Fajardo, Puerto Rico. It's the perfect destination to do some snorkeling or exploring on a day trip.   

Languages

Puerto Rico's official languages are Spanish and English, so you can easily communicate on the island if you know either of these. Most people on the island are bilingual!

 Airport and Transportation Tips

Unless you have a yacht (I wish!), the best way to get to Puerto Rico is to fly in. You’ll likely fly to San Juan. From the airport to the city center takes approximately 15 to 20 minutes, and the cost will vary depending on how you choose to go. Taxis are available, though you can always rent a car. 

 If you are spending most of your trip in San Juan or doing a guided tour with a company, I recommend against renting a car. The roads in Puerto Rico are a bit rough, and you won’t need the car while in the city. Please note that driving to Old San Juan is definitely not advisable, as the streets are very crowded and narrow and parking spaces are almost non-existent. You’ll spend more time stuck in traffic and looking for a place to park than you will enjoying the old city!

 However, if you are venturing outside the capital for several days during your 4 days in Puerto Rico, I do recommend renting a car. You might want to look a bit outside the airport, as most rental companies will have steeper prices if you get your car at the airport. Check all of the options! 

Another transportation tip is that you won’t be able to take an Uber directly from the airport. While you can definitely use Uber to get around the island, the company is currently only allowed to drop off passengers at the airport, not pick up.

Best Time to Visit Puerto Rico?

Let’s start by saying that for me, there’s never a wrong time to visit Puerto Rico! Most people, however, recommend going from April to June. This is right after the peak of the winter season and just before the start of hurricane season and the high temperatures of the summer.  Spring weather in Puerto Rico is perfect for going to the beach, hiking and exploring: it will be in the high 70’s or lower 80s almost all of the time. 

Note: The high/busy season in Puerto Rico starts at the end of November and runs through the end of March. 

 Hotel Recommendations

If you want to splurge on your stay, El Dorado Beach, The St. Regis Bahia Beach Resort, or La Concha Renaissance San Juan are probably the best options. You’ll definitely find luxurious accommodation here! 

 A more moderate hotel with great amenities and amazing views from its rooftop is the San Juan Water Beach Club Hotel. This is a perfect place to stay if you want a good balance of affordable and nice. 

If you are skipping a beachfront hotel and instead want to enjoy the charm of a city hotel in Old San Juan, I recommend Hotel El Convento. This iconic hotel was originally built as a convent, and boasts amazing city views and stunning Colonial Spanish architecture. 

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 For travelers heading to other North America or Caribbean destinations, head to our North America travel section to discover some other amazing cities and towns. We have awesome travel guides to places like New Orleans, New York, and so much more. Don’t miss our one of a kind Cuba Travel Guides, which have all the insight you need for your future trips.

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 For those who have already visited Puerto Rico, let us know in the comments what you think about the island! What were the highlights of your trip?

 Besitos from San Juan,

Laura

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