Four Days In San Juan (A Travel Guide)

“San Juan is an excellent destination for a long weekend or for a longer holiday depending on your preference. I do believe that at least three to four days is necessary to enjoy what San Juan has to offer.”

San Juan is an excellent destination for a long weekend or for a longer holiday depending on your preference. I do believe that at least three to four days is necessary to enjoy what San Juan has to offer. Puerto Rico is more than just San Juan, but it is good to just start out with getting to know the capital city of this United States territory. I have various recommendations to focus on during your stay and there are still some places that I would check out for which I was not able to visit personally. Not only is San Juan a fun city but the weather in the Winter and Spring months will make you want to come back in the future.

  • Visit The Beaches – On your 1st day in San Juan, I recommend checking out a beach or two to relax, enjoy the sunshine, go swimming, or even go windsurfing with the help of a guide especially if you had a long flight coming in. There are beaches that cater more to tourists such as Condado Beach, which are close to different resorts and hotels that are right on the beach within walking distance.

Condado Beach can be a bit crowded depending on the time of the year that you visit it, but it is clean, compact, and has enough chairs and umbrellas to go around if you decide to rent one. Personally, I prefer Ocean Park Beach, which is further from Old San Juan and the Condado Neighborhood, but for which is more local, laidback, and is likely to have less tourists. If you decide to split your beach days up, I recommend going to Ocean Park Beach the 1st day if it is closer to where you’re staying and then going over to Condado to explore the neighborhood and to visit that beach on your 3rd day in San Juan.

Other beach options in San Juan include Balneario del Escambron, El Alambique Beach, and Playa (Beach) del Capitolio, one of the great things about San Juan is that the neighborhoods that have a beach are quite walkable and are accessible to the public. While the hotels take up a lot of real estate and have their own areas of the beach for their guests only, each beach is still accessible to the public even if they are not staying nearby, which makes visiting multiple beaches during your four days in San Juan a good way to spend your vacation time there.

  • Enjoy Nearby Nature – El Yunque National Rainforest is the only tropical rainforest in the United States National Forest System. There are hundreds of unique animal, bird, and plant species that call El Yunque home as well, making it must-see. While not in San Juan, it is only a 45 minute to an hour drive away. While I would not recommend an Uber to get there and back, it would be wise to hire a taxi to get to and from the rainforest to avoid paying for parking there. You can also join a tour group, large or small, to get there without splurging. Rental cars are also available that your hotel can arrange for you or that can be given at the San Juan airport. If you visit the rainforest, be sure to leave earlier in the morning so that your hike through El Yunque won’t be delayed by packs of tourists wanting to stop for selfies on the way up to the waterfalls.

However, you choose to get there, you will enjoy the beautiful, quiet, and peaceful nature of the rainforest. It is the largest protected forest in the country and where you can really enjoy hiking, swimming, and even doing rock climbing if you choose to. Parts of El Yunque also have natural pools where you can jump in from meters above or use a rope swing in certain areas. One area that I went to have a naturally formed waterslide with a smooth area of rock formation allowing you to slide down without hurting yourself.

Having a guide there will teach you a lot about the flora and fauna that inhabit El Yunque as well as the kinds of frogs, fish, birds, monkeys, etc. that call the rainforest home there. A trip to El Yunque would not be complete without stopping off for some fresh coffee or some fresh fruits or fried empanadas at a road stand where they wake up at the crack of dawn to start getting the produce ready. In between beach days, I highly recommend spending a full day at El Yunque to enjoy a bit of nature outside San Juan.

  • Eat, Drink, and Dance – I love Salsa dancing and if you enjoy salsa music as I do, going to San Juan will allow you to indulge in some live dancing even on a weeknight! Old San Juan has many salsa bars and clubs along with for bachata and reggaeton if you prefer those music genres instead. My go to place would be La Factoria, which has been ranked among the Top 100 bars in the world. It’s not only known for its old school décor, six unique bars within a main bar, as well as its live Salsa bands playing most nights, but its cocktail drinks are fantastic and reasonably priced.

La Factoria has a very relaxed vibe, and the bartenders are friendly enough to give you their favorite drink recommendation. While the Salsa live music does not start until 10 PM, it doesn’t take long for the dance floor to be filled with people from Puerto Rico and all over the world who enjoy this fun genre of music. Puerto Rico is the home of many famous Salsa musicians including my favorite, Hector Lavoe. If you come to San Juan, I highly recommend this bar to visit and make sure to bring your friends or family with you!

For dancing and drinking good cocktails, San Juan has a lot of options and that is also the case with its food scene. As the capital, there are several good restaurants to check out with not just Puerto Rican cuisine but also seafood, pizza, and burgers available. My recommendations to check out would first be Kasalta, a famous bakery that even former President Barack Obama visited in his trip to San Juan. Kasalta is known for its sandwiches, local cuisine, but especially its desserts including its Tres Leches cake.

Other recommendations for dinner are La Cueva Del Mar, where they are known for their delicious fish tacos, and I would recommend the shrimp arepa as a starter dish. Lastly, while I am a native New Yorker, the best Pizza place in San Juan may be Pirilo Pizza Rustica, where the island’s influence extends to the pizza where you can order a delicious pizza pie with sweet plantains and shredded beef. It’s a good option for having a nice beer to go with your pizza and has outdoor seating as well to enjoy your meal with a cool breeze from the ocean. Lastly, for the coffee drinkers out there, you must go to La Coffeetera, with excellent coffee to stay or to go before hitting the beach with excellent paninis including one with egg, sausage, and cheese. It’s a great way to start one of your days in San Juan without question.

  • Explore Old San Juan – No four days in San Juan is complete without spending some time in old San Juan, which is well preserved with its colorful houses, trendy shops, and beautiful murals that capture your attention. While it is nice to shop around in old San Juan, the main draw for me going there was to check out the famous and historic San Felipe del Morro Castle or Castillo. It’s right on the edge of the old part of the city leading into San Juan Bay, which juts out into the Atlantic Ocean. It is a very strategic point and one that exchange hands for centuries going under the control the Spanish Empire, the Puerto Ricans, and now the United States since the 1500s. It is a massive castle and one that is well worth a few hours with all the information to read and parts of the fort to explore.

San Felipe del Morro Castle is not only great for its history but has some great vantage points to see the coastline of San Juan, to see the bay in its full view, and to see the rest of the old city as well. You can really appreciate how much the island has changed in five hundred years but also see that not much has changed as well. If I had more time during my four days, I would have gone to see Castillo San Cristobal, which while younger than San Felipe del Morro, having been constructed during the late 1700’s, is still the largest of any fort ever built in the Americas including the one in Cartagena, Colombia.

To cap off the four days and to really enjoy old San Juan, I would recommend visiting Scryer Rum Barrelhouse and Rooftop for drinks to end your trip to the city. It has an excellent, spacious rooftop, with a pleasant overview of one of the old San Juan’s most bustling streets. You can get the Scryer rum brand that is only made in San Juan and is not exported currently and it’s good to mix with a cocktail or have a beer after at the impressive three-story bar. You’ll be glad to have a refreshing rum drink after a day of seeing the historic Spanish forts and walking the cobbled streets of the old city.

In terms of four days in San Juan, I hope you will follow the recommendations I have laid out but don’t be afraid to add or subtract other activities to bring to your own itinerary. I believe there are a lot of ways to spend time in San Juan and what I laid out is just a sampling of what the Puerto Rican capital can offer you. It is one of my favorite destinations for a short trip and since it was only four days total, you know I’ll be back for another visit soon! For a short getaway, you can’t go wrong with going to San Juan!

Four Days in São Paulo (A Travel Guide)

“While it may not have the beaches of Rio de Janeiro or the musical and rhythmic vibes of Salvador, Sao Paulo is well worth at least a couple of days of your time when you visit Brazil.”

The largest city in Brazil by population and by size has a tendency to be overlooked by tourists around the world. While it may not have the beaches of Rio de Janeiro or the musical and rhythmic vibes of Salvador, Sao Paulo is well worth at least a couple of days of your time when you visit Brazil. Not only does it have a storied history of immigration from other parts of the world such as Italy and Japan in the 18th and 19th centuries, which does continue to this day, There are also a number of museums and cultural exhibits to check out to learn more about the city’s history and its locals.

However, if you only have four days in Sao Paulo, longer than a layover but shorter than an actual vacation, it is a great place to get away if you want to experience a big and cosmopolitan city on a reasonable budget. It is easy to get around the metropolis due to its affordable metro system ($1) or its bus system, which covers every major neighborhood. As I mentioned, Sao Paulo is probably the most diverse food city in Brazil with cuisines from all over the world being represented. While I am originally from New York, I would rank the Pizza in Sao Paulo up there with my home state and even up there with the pizza I had in Italy. If you have a long weekend, Sao Paulo is the place to go for both cuisine and culture.

Day #1

If you’re flying there from North or Central America to Sao Paulo / Guarulhos International Airport, you’ll likely have the whole morning and afternoon to head to your hotel in the city, drop your bags off, and check-in to your room if possible. You’ll likely be quite hungry but not so jetlagged that you can’t enjoy your first day in Sao Paulo. For a good bite to eat and to check out some of the exotic fruit offerings that Brazil has to offer, let’s start by checking out the Municipal Market (Mercado Municipal) in the center of the city.

The Mercado Municipal is particularly known for its huge mortadella and cheese sandwiches, which can be as big as someone’s face. Along with the ‘bolinho de bacalhau’ (salt cod croquettes), you’ll be in heaven after the long flight. Wash it all down with a nice cold beer in a small glass (chopp) or a nice freshly made juice and you will be feeling ready to go for the rest of your first day. Personally, I recommend going to the Bar do Mane, which is on the bottom floor of the huge market. It might take you some time to find it, but it has the best sandwiches, according to the local gossip and the service was quite quick.

Depending on where you’re staying, it shouldn’t be too long of an Uber or taxi ride over to the famous Museum of Football (Museo do Futebol), open from Tuesdays to Sundays with visiting hours open until 6 PM each day. Tickets are about $4 USD and it is perhaps the coolest museum in the city. Located in the upscale Pacaembu neighborhood inside of the Estadio Municipal Paulo Machado de Carvalho, this unique museum will tell you all you need to know about the history of the beautiful game in Brazil. From the origins of football in Brazil to historical spotlights on Brazilian legends like Pele and Ronaldinho to displaying signed jerseys of Marta, Brazil’s best female football player, the museum is a wealth of football knowledge and information. You will also learn some Portuguese sayings for football rules and regulations as if that wasn’t enough.

The museum is easy to walk through and you only need about two to three hours there to cap off a great afternoon. Most of the museum exhibit is in English, but you may need to rely on your audio guide to hear in English or another language to describe what you are seeing. Capping off a great tour is being able to check out the views from the stands of the actual football stadium that the museum is based in. On a clear day, you can see some of the Sao Paulo skyline and also see some preparations being made if there is a match going on later that night since the stadium is still being used for club-level games now and then.

Now, your mouth may have been watering from my writing about the Pizza in Sao Paulo, so I am going to give you some good advice on where to go for some of the best pizza in the city. It’s not too far away from the football museum so you can head straight there or maybe relax in your hotel in Pinheiros, Jardins, or Villa Olimpia for an hour or so to take a nap, shower, and get ready for the evening.

Now, there are a number of different locations, but Braz Pizzaria is not a typical chain at all. I recommend the location in Higienopolis since it is within walking distance from Pacaembu where the museum is or close to the metro if you don’t need to go back to your hotel first. With a nice ambience, friendly service, and the feeling that you only get when you’re in legitimate pizza joint, Braz is a great place for good portions and delicious pizza.

Beyond just Pizza, I recommend the pepperoni bread to start off with, a bottle of wine (even if you’re dining alone), and the Caprese pizza is a good choice for the main dish. The pizzas are served in a small or large size and if you’re used to eating with your hands in your country, in Brazil, that’s rather a bit of a taboo! Pizza slices are served to the customer by the server and you are encouraged politely to use a fork and a knife to cut and eat the pizza. As a New Yorker who takes pride in my folding and hand-using skills for pizza slices, this was a bit of a shock but as they say ad-libbing, “When in Sao Paulo, do as the Paulistanos do!”

Your 1st day in Sao Paulo was a massive success and maybe you want to head out for the night. I would recommend saving up your energy for tomorrow instead. Pay your pizza bill, head back to the hotel, and rest up. Your next few days will be both busy yet enjoyable and don’t worry, you will have a caipirinha soon, I promise you.

Day #2

You wake up after resting well and having had a full night’s sleep. You’re ready to enjoy your 2nd day in Sao Paulo. Let’s get a good breakfast first at my favorite bakery in Sao Paulo: The Padaria Boulevard (Bakery Boulevard), which is close to the Higienopolis metro station and has a great selection of cakes, pastries, eggs, sausage as well as a great assortment of juices to choose from including acai, my personal favorite of them all. I highly recommend getting a nice sandwich or a hamburger too if it’s later on in the morning or early afternoon.

If you want to instead stay close to Avenida Paulista (Paulista Avenue), which is closer to downtown, a great backup choice for breakfast is the Padaria Bella Paulista, which is a lot bigger place, has a huge selection, and has an unlimited breakfast / brunch option for about 45-50 Brazilian Reais. Also, it’s close to the metro and is great if you have a big group of friends or family with you on your trip. If you’re traveling solo, I think Padaria Boulevard is a good option to choose instead.

Now that you have a full belly, walk it off by going onto the famous Avenida Paulista to walk off some of those calories. This famous avenue is known around the world and is the financial center of Brazil. Most comparable to Times Square in New York City or Istikal Caddesi in Istanbul, Avenida Paulista has numerous shops, restaurants, and museums to tide you over for a few hours. I recommend stopping by a juice bar if you get thirsty, but the 2.5 kilometer walk from end to end is a great way to get accustomed to the hustle and bustle of the Paulista capital.

Some of the best views of Sao Paulo are from the Mirante (Lookout point) at the top of the SESC Paulista building not too far from the Brigadeiro metro station. Going earlier in the afternoon means it’s going to be less crowded at the lookout point but the view of the entire megalopolis at sunset is breathtaking and well worth a try. If you can swing it, you can also have a coffee and a snack there after you’re done taking pictures and checking out the amazing view.

Continuing on with this day’s theme of Paulistano must-sees, there are some great museums on the avenue such as Japan House:A cool cultural center with different exhibits on Japanese architecture, culture, and history; this attraction is a great way to spend some time. You can also browse the bookstore with books on Japanese cooking and culture. I would not forget to drink some Matcha tea at the café and have some Matcha cake too which is delicious. Just a few blocks down the avenue is the Sao Paulo Museum of Art or MASP, which has a renowned collection of portraits, paintings, and impressionist art from around the world.

While this museum is not in the same league as the French Louvre or the British Museum, the collection is formidable, the ambience is quite nice, and you can definitely spend at least two hours here enjoying the art. Another hidden gem of a museum which you can substitute for MASP is the Pinacoteca museum, very close to the heart of the city, and near to Luz metro station. If you are looking to learn more about Brazilian art and culture, the Pinacoteca has the best collection for it in the whole city. You can also spend a few hours there without any issue.

With the sun starting to go down, it’s time to unwind a bit while still enjoying the early evening. It’s time for you, dear traveler, to have a nice caipirinha and enjoy some of Sao Paulo’s famous street murals. The Beco do Batman (Batman’s Alley) is a really cool area in the neighborhood of Vila Madalena where local street artists create amazing building-sized urban art murals reflecting on current events, politics, sports and even comic books. Strolling down these streets with a caipirinha in hand or even at an outdoors bar with deck chairs is a nice way to wind down your day after a lot of sightseeing.

Before you head back to your accommodation, it’s dinner time. Let’s keep it light after a big breakfast but I am going to suggest the Z Delicatessen just a few blocks away from the street murals. Owing its existence to both eclectic hipster tastes in Jewish food and the city’s immigration history with the Jewish community in Sao Paulo being among the largest in all of Brazil and South America, this deli’s pastrami fries are exquisite, and the deli sandwiches are well worth the menu price. I would recommend taking an Uber or a taxi back to end the night because you’ve earned after walking a number of kilometers throughout your 2nd day.

Day #3

Hopefully, you were able to get a good night’s rest after a long Day 2 in Sampa. I am going to take it easy on you in Day 3 and you’re also going to eat well. Let’s start the day off by heading to the Japanese district of Liberdade, my favorite neighborhood in all of Sao Paulo. There is an excellent outdoor food market as well as crafts fair going on each Saturday so if you can make it here on Day 3 and it’s a Saturday, please go to Liberdade. You can enjoy different foods like Yakisoba (stir fry noodles), Nikuman (steamed pork buns), or some fried pastels from one of the many food stands.

This neighborhood buzzes on the weekend and it’s a lot of fun to walk around, perhaps buy a souvenir, or even snap a few photos. The vendors are friendly and not too pushy. You’ll enjoy going to some of the Japanese or Asian grocery stores as well to check out some of the imported products and food stuffs for sale. Liberdade has its own metro stop on the blue line and is not too far from the center of the city.

Having gotten your breakfast on the go and maybe having bought a gift for your loved one, it’s time to spend a few hours at the biggest park in Sao Paulo: Parque Ibirapuera. With stunning sightlines, nice picnic areas, and quite a few museums, Ibirapuera is an oasis of calm in a hectic city. While not very accessible by metro, a quick uber or taxi ride from Liberdade makes it a pretty reasonable trip pricewise.

I would walk around, snap some photos, maybe check out the Museum Afro Brazil or the Planetario do Ibirapuera. You can’t go wrong with buying a coconut water from a nice vendor and getting some exercise in by walking through the huge park. If you have a soccer ball with you, kick it around. I also recommend bringing a towel or a blanket if you have one and catching some sun as well while you think about your next stop. Personally, I like to go at an easy pace when I travel for four days so it’s good to have a day in the park where you’re not rushing around. A park is also a great place to maybe meet some locals, join a soccer game, or even do some reading.

Now, you’ve definitely worked up an appetite for dinner and it’s Saturday night, do you know how lucky you are? I hope you are ready because it’s time for Feijoada. The Brazilian national food dish is mouth-watering, scrumptious, and so delightful. I miss it a lot now that I am away from Brazil. It is prepared around the Portuguese-speaking world, but the Brazilians go all out in preparing it. Primarily, it is a stew of black beans with beef and pork, but you are also adding rice, fried kale (couve), along with some sweet plantains (bananas).

To cleanse your palate, the restaurant will also offer you some orange slices to help with the digestion. It is an amazing dish and I personally like the Star City Restaurant in Santa Cecilia, which has been serving feijoada and other dishes from the region of Minas Gerais since 1953. There are dozens of options to choose from for having Feijoada on a weekend in Sao Paulo, so it depends on how far or close you want to go. I do recommend having it before you leave Sao Paulo or even Brazil in general. I can definitely say you have not experienced Brazil until you have eaten feijoada once or even twice if you’re a big eater like I am.

Before we close out Day 3, I want to mention a wild card option before you head back to the hotel. If you’re visiting in-season, please do consider checking out a Brazilian football match as Sao Paulo is host to three teams competing in the national league. Whether it is Corinthians, Sao Paulo FC, or Palmeiras, you cannot go wrong with buying a ticket for yourself to check out an amazing atmosphere and seeing some amazing football players show off their skills. If you have had too much Feijoada though, it may be best to watch a game that night at a local bar where you can have another caipirinha or a cold bottle of beer. Saude! (Cheers!)

Day 4

Your trip to Sao Paulo is coming to an end today but you can still make the most of your 12 hours in the city before your flight leaves in the mid-afternoon or in the evening. I highly recommend checking out one of the best coffee shops in the city: Coffee Lab, which sources its coffee from all over Brazil and whose pastries and desserts are also phenomenal. Whether you are a fan of drip coffee or of a nice cold Frappuccino, Coffee Lab has some of the best coffee and you can even take some home with you as they do sell their coffee beans in bags where you can see both the highlighted aroma of the coffee itself, and where in Brazil the coffee beans came from.

If you are still craving a last-minute museum, I would recommend the Museum of Japanese Immigration, which is also in Liberdade and only takes about two hours to get through and is highly educational. Continuing with museum options about immigration, though I never made it there, I have heard good things about the Museum of Immigration of the State of Sao Paulo to get a full overview of the history of immigration in the city and the state. Millions of immigrants have made Sao Paulo their home and the museum does a good job of highlighting all of the different groups who came over and for what reasons.

Now, before you head off to Guarulhos, if you’re still hungry and prefer a full meal than the airport food court or the airplane food later on, I seriously recommend taking a taxi for a late afternoon visit to the churrascaria. Unlimited meats, an open salad and pasta bar, and dessert offerings, what’s there not to like? Similar to feijoada places in Brazil, churrascarias can be found all over Sao Paulo but I am definitely going to recommend Angelica Grill in Higienopolis, which is open not just at night but in afternoon too, which is perfect before you head on your flight. Don’t be afraid of the chicken hearts, go for the picanha piece of beef, and remember to not overdo it at the salad bar and it will be a great send off for an amazing four days in Sao Paulo!

Remember to follow these recommendations as you see fit but a lot of these places are ones that I grew fond of during my time in Sao Paulo. I hope that your visit brings you much enjoyment and joy as a tourist and a traveler. Boa sorte! (Good luck!) and Aproveite! (Enjoy!)