Beautiful beaches, historic sites, delicious food and a tropical rain forest make Puerto Rico’s capital, San Juan, one of the most enchanting destinations in the Caribbean. And guess what? It is just an half an hour flight from the British Virgin Islands (lucky me) and in the past two years I have found myself visiting this tropical getaway frequently. From exploring the city in a couple of hours while I was in transit to (long) weekend trips to two-week holidays – I’ve done it all and… I thought that I had seen it all.
Well, I was wrong! Last month we went to San Juan for a long weekend and we stayed at our close friends who have been living in the city for several years now. They have showed us all the local hotspots and hidden gems. And today is your lucky day because I am sharing them with you!
San Juan's ultimate (long) weekend itinerary
So if you want to explore San Juan like a true local, this ultimate long weekend itinerary with lots of insider tips is for you!
Friday afternoon – an authentic Caribbean beach experience at Los Pinones
Assuming that your flight is in the morning and you’ll arrive (early) in the afternoon, you will have some time to do some exploring. Drop your luggage at your hotel, put on your swimmers and drive along the two-lane Road 187 to the beachside town of Los Pinones for an authentic Caribbean beach experience.
On your way to Los Pinones you will pass numerous roadside food kiosks selling Puerto Rican treats. Pull off the road to try the alcapurrias (plantain and yuca fritters filled with meat) and bacalaítos (cod fish fritters) on the way! These hearty fritters are Puerto Rico’s most addictive fried snacks sold at every beachside kiosks and roadside stands.
On the other side of the road, you’ll find hidden tracks running through the sand dunes with parking spots carved out overlooking the waves of the many beaches along the route. Grab a cheap beer, pina colada or coconut water, soak in the scenery and relax… You’re in paradise.
Friday night – swanky dinner and cocktails in Condado
Contrast a day of fritters and sand with a swanky dinner in Condado. It’s a well-developed neighborhood with upscale resorts, designer shops, and some of the best restaurants on the island.
Cocina Abierta is a great casual option with one of the coolest decors in Condado. Try the grilled Spanish octopus terrine and the duck confit stuffed mofongo. There is also a great vegetarian selection. If you feel like something fancier (go for it - you’re on vacation!) head to La Perla restaurant at La Concha Hotel. This signature seashell-shaped luxury restaurant serves great seafood. I loved the fennel duster diver scallops with truffle white bean stew and smoked bacon! After dinner, head to nearby Sabrina for a nice vibe and some innovative cocktails.
Saturday morning and afternoon – explore Old San Juan
On Saturday morning, head to Old San Juan and have breakfast at St Germain before you start exploring the beautiful old city. This charming bistro is located in a historic colonial building in the heart of San Juan and serves yummy breakfast sandwiches and croissants. In the afternoon or in the evening (trust me, that breakfast will taste like more!), visit the upstairs cocktail bar the Mezzanine for a truly unique cocktail experience.
When your belly is full, spend the day strolling around historic Old San Juan’s cobblestone streets. Tucked among the peaceful plazas are also plenty of shops, galleries and bars. But do not forget to visit El Morro and Castillo de San Cristobal as nothing captures the history of Puerto Rico more than Old San Juan's massive fortresses.
For some more colorful history, pass by Casa Estrecha. It is the smallest house in Puerto Rico. At 1.5 meter wide throughout, this bright yellow house in Old San Juan is one of the narrowest in the world.
Stroll down Calle de la Luna for more colorful colonial buildings and for another obligatory photo stop, head to la Calle San José to snap a selfie with a giant colonial door bearing an image of the Puerto Rican flag (in black and white), known appropriately as La Puerta de la Bandera.
At the end of the afternoon, take a sunset stroll along Paseo de la Princesa, located just outside the city walls. On weekends, you're likely to find all kinds of stalls lining the road selling crafts and local treats. In the distance, you'll see the beautiful fountain and behind it the calm bay of San Juan.
Saturday night – dine and dance at Santurce
On Saturday night head to Santurce, San Juan’s up and coming neighborhood that attracts a fashionable and arty crowd.
For a contemporary mind-blowing vegan dinner, go to Basico. Although the name might tell you otherwise, the food is everything but basic. Chef Jerome Valencia creates weekly menus showcasing his innovative and (utterly) delicious vegan cuisine. We decided to try the entire menu (don’t judge us) between the four of us and every single dish was just incredible. My favorite main was the sweet plantain and jackfruit cake with seitan and rye, topped with sunflower seed cheddar sauce. Dios mío! It was just too tasty. The quinoa-sage arancini’s with artisian cultured almond ricotta and cilantro-spinach almond pesto as well as the cashew-cheese cheese cake with hibiscus glaze were also to die for! Vegan or not, you’ll be blown away by the food (and the charming chef Jerome)!
If you need more options for dinner, head to the culinary mecca for the hip, the trendy, and the hungry: Lote 23 (also referred to as El Lote). This once-abandoned lot has been transformed into a new hotspot for foodies with a lot of eating to do. It is a gathering of high-end food carts with lots of choices. Too many choices? Let me help you. You can’t go wrong with the yummy gourmet croquettes at Croqueteria or the delicious pulled pork sandwich with spicy mayo (called revolucion es orden) at Pernil es Patria. Looking for something healthier? There is a nice poke bowl stand too. After dinner, chill things down with Señor Paleta’s popsicles. And when things start to get quiet at El Lote, head to La Placita where small bars will be blasting salsa tunes all night long.
Sunday morning – hidden natural playgrounds at El Yunque
On Sunday morning it’s time for a dramatic change of scenery. You’ll be heading to El Yunque National Rainforest. But first, breakfast. On your way to the rain forest stop at Degree 18 for a yummy acai bowl to start the day and then head to the jungle!
El Yunque is a beautiful tropical rain forest about 45 minutes from San Juan. This national reserve is a haven for hikers with a variety of well-known hiking trails to choose from including the Picachos Trail and El Yunque Trail. Most people also visit the observation tower at El Yunque Peak for a breathtaking view of the lush green forest.
But if you want to discover the rain forest’s hidden gem, only known by locals, head to Luquillo. Over many years, the rushing waters of the rain forest have made some natural playgrounds, complete with pools and water slides. There is a place in Luquillo called Las Paylas were the rocks in the waterfall are really smooth and make for some (not well-known but) really fun and adrenaline boosting natural waterslides.
On your way there, you can tell by the area that you are off the beaten track and you’ll likely make a few missed turns before you get here. There are no large signs, or advertisements, but merely a porch of a private property with Las Paylas painted on it. For just a few dollars you can park at the driveway of this house and walk through the owner’s yard down a path to the natural water slides. I know. It’s a bit odd but… it works fine and it’s really worth it! And no, the rocks don’t hurt as you slide down.
Sunday afternoon – lively beachtime at Luquillo Beach
After the rainforest, continue along Route 3, heading east, and look out for signs directing you to Luquillo Beach. This beach is extremely popular among locals for its lively yet relaxed atmosphere, and it will make for a complete change from the rainforest. For a more tranquil experience, just walk around the corner and you’ll find a more serene beach setting excellent for long beach walks.
For dinner, there are the famous kiosks of Luquillo, small shacks and tiny restaurants that serve up a blend of local specialties, oysters, finger foods, greasy snacks, and cheap drinks. It's a complete departure from Friday’s and yesterday's gourmet food.
Sunday evening – bioluminescent kayak tour
If you’re up for a late night out, head to Fajardo’s bioluminescent bay (it's a 20 min drive from Luquillo beach) where you can take a glow-in-the-dark nighttime kayaking tour – note that you’ll need to book this organized tour in advance. After paddling for half an hour, you’ll reach the amazing Laguna Grande of Fajardo. Touch the water with your hand or paddle and millions of microscopic bioluminescent organisms light up like fire flies. It is beautiful, and paddling through the mangroves is fun, especially when there is traffic both ways.
Monday morning/early afternoon – take it easy
It is your last day in Puerto Rico and time to take it easy. The best way to do that is to hit the beach in the morning. You have a few choices on which beach to go to in San Juan. For those staying in the resort strip of Condado or in the Ocean Park neighborhood, the choice is easy, because the beach is at your doorstep. You can't go wrong with either option, but I like Ocean Park Beach for its laid back vibe.
"calories don't count while on vacation"
Since calories don’t count while on vacation, you might as well sneak in a final lunch before you head to the airport. Where to go for soul food? Kasalta is a popular cafeteria style bakery in San Juan’s Ocean Park neighborhood loved by the locals. They have an excellent variety of smoothies, deli sandwiches, soups, cakes and pastries. I tried the sancocho (a local hearty stew – the perfect comfort food) and a mortadella sandwich, both really good! For a lighter lunch head to the close by Berlingeri Cocina Artesanal, a great vegetarian lunch spot. Wash down your lentil soup, stuffed avocado and vegan banana bake with a blueberry smoothie.
How to get here
While some Caribbean islands can be quite remote and a pain to get to, Puerto Rico is a convenient destination with direct flights to San Juan from most major US cities as well as some European capitals. Also, American citizens do not need a passport because it’s a US territory. Making San Juan the perfect place for a weekend getaway!
How to get around
For this itinerary, I have mostly used a scooter and Uber. Although Puerto Ricans are not used to seeing people scootering around, so expect to be stared at¸ I found this the best way to get around especially in Old San Juan and it was lots of fun too! For the rain forest and the bioluminescent tour, you’ll need a car or an Uber. San Juan is the first place in the Caribbean where I got to use Uber and it worked great!
With love from Paradise,