A Whirlwind Girls’ Trip To San Juan, Puerto Rico: How to Plan The Best Itinerary

July 7, 2024
things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

Destination Guide: Best Things to Do in San Juan, Puerto Rico | San Juan is a perfect weekend destination, a gorgeous city you can explore in just a day or two...here are some of the best things to do in San Juan, itinerary ideas, Puerto Rico trip ideas, what to do in San Juan, where to stay, where to eat & drink, & more! It's a perfect girls' trip, romantic getaway, easy weekend trip.

With sparkling turquoise water, historic Spanish forts, hundreds of brightly-colored buildings, and a vibrant local culture, San Juan transports you to another world…despite the fact that you’re *technically* still in the U.S. (from a travel/passport standpoint).

Though it’s super easy to visit for Americans, Puerto Rico often gets overlooked in favor of other Caribbean islands like the Bahamas or Jamiaca.  And while it doesn’t offer the swanky all-inclusive resorts that other islands have, it instead tempts visitors with more of a DIY option for history, architecture, culture, food, beaches, and even rainforest.

Destination Guide: Best Things to Do in San Juan, Puerto Rico | San Juan is a perfect weekend destination, a gorgeous city you can explore in just a day or two

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San Juan is the capital of the island of Puerto Rico, affectionately known by locals as La Isla Del Encanto (the Island of Enchantment) or Borinquén (the native indigenous name).  The island has been a U.S. territory since 1898 (though politically it sits in murky waters since it’s never become a state…that’s for a different post), so U.S. citizens can visit without a passport.

It’s just like flying anywhere in the U.S.—no customs, you can use U.S. dollars, and you’ll find English spoken widely (though Spanish is the first official language).  But you can experience an entirely different (and extremely warm, welcoming) culture, geography, history, and cuisine.

I’d visited San Juan a couple times before (once for a focused trip, and once where I spent most of my time in Rincon with a quick-hit in San Juan), but it had been MANY years.  I was dying to get back, as the island had definitely gotten under my skin.

While San Juan is amazing and worth a few days of your time, I also strongly advocate for renting a car and spending time in other parts of the island…the chill beaches of Rincon, the islands of Culebra and Vieques, doing a coastal roadtrip in less-populated areas.

Destination Guide: Best Things to Do in San Juan, Puerto Rico

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Where to stay in San Juan

I’ve written a deeper post on this, so recommend checking it out.  There, I talk about how I struggled with finding a hotel in San Juan that ticked my main boxes AND got good reviews (especially around service, value, and the overall experience).  This seems to be a broader Puerto Rico issue at the moment.

So for that reason my feelings on Condado Ocean Club are a bit mixed (mostly relative to cost), but I did still overall love it and it was a stand-out option in San Juan.  It offers both a pool AND easy beach access, which is a rarity in San Juan.  It’s adults-only, our ocean view room was absolutely lovely, and the location is great.

Note, if you’re looking for a proper lazy beach vacation at all-inclusive resorts, San Juan may not be the best destination for you…there are other Caribbean options that play in that space more.

For other beach-and-pool options, check out the Condado Vanderbilt Hotel next door (luxury, more resort-like) or La Concha Renaissance.  Or if you’re looking for the more historic Old Town vibe, look into Decanter Hotel (rooftop bar!) or Hotel El Convento (boutique hotel housed in a former convent).

Read my detailed review on Condado Ocean Club here!

Sunrise on the beach - best things to do in San Juan, Puerto Rico

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beach in Condado, San Juan, Puerto Rico

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What to pack

I live in sundresses…a lot of mine (like the blue polka dot dress below) are from StitchFix.  Amazon is also where I get a lot of my dresses these days.  Some good styles would be a t-shirt dress, a tank dress, or something flowy with fluttery cap sleeves (I brought the latter).  I am also in love with my black built-in bra dress from SOMA, which you can see in some pics.

Underneath them I wore my new obsession for warm weather trips, these super thin anti-chafe, cooling shorts, or bring THIGH GLIDE.

I also brought one pair of lightweight, breathable stretchy travel pants (Athleta and these Eddie Bauer ones are my faves) to pair with a lightweight sleeveless or short-sleeve top.

While I brought my cute white sneakers, I ended up living in my beloved cute/comfy walking sandals (and had my favorite Naturalizers wedges for dinners/evenings).

Don’t forget a swimsuit (this one is my new fave!) and you definitely need sunscreen…here are my favorite body sunscreens for travel and my fave face sunscreens.  I also relied on my my go-to natural non-toxic makeup (which does great in sweaty weather!), polarized sunglasses, and a headband (for keeping my hair out of my eyes in the wind).

If you’re going full beach and pool vacation (vs. lots of exploration), I have a detailed packing list for that type of trip as well!

girl walking polka dot dress Plaza de Armas San Juan

girl in blue polka dot dress walking in colored buildings of Old San Juan

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How to get around & other tips

Getting around San Juan is fairly easy, as the main tourist areas are very walkable.  You can also grab an Uber easily, though traffic can be quite bad (make sure you leave extra time to get to the airport, especially during rush hours).

I do NOT recommend renting a car to get around San Juan itself…you need special permits to drive and park in Old San Juan and the traffic is bad.  It’s just a hassle.  However, if time allows I would definitely recommend renting a car (even just for a day) and exploring other parts of the island.  Car rental and driving is super easy here, I always check both DiscoverCars and RentalCars.com to find the best deals, but Discover is usually the winner.

One annoying thing that I found around San Juan in general was that a 4:00pm check-in time was the norm—I mean, what the heck?!  This goes back to what I was saying above about just a lackluster hospitality industry in general (I don’t know if this is more of a post-hurricane recovery thing or something else).

What’s the best time to San Juan?  Usually December to March is the peak season as they’re the “dry” winter months and you have gorgeous hot weather while the U.S. is freezing.  Expect higher costs and more crowds.  April through June is a great time to visit, while the weather’s still good but a little less crowded.

June through August is a crapshoot, with more heat and rainy season, and possible hurricanes, and then September through November is peak hurricane season and planning a trip here is pretty ballsy (still rainy season, but probably good deals to be had if you book last-second and know there aren’t hurricanes in the area).

view flying into San Juan Puerto Rico

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Things to do in San Juan: a whirlwind itinerary

Okay, let’s talk about all the amazing activities in San Juan and the surrounding area.  I had planned for four days in the area, including maybe a day trip.  Unfortunately, due to diabetic cat shenanigans back home, I had to cut my trip short and so had right around 48 hours in San Juan.  I still made the most of it, however!

A lot of what you’ll see below is just DIY exploration…wandering the beautiful old streets and marveling at the colorful buildings, visiting some of the historical sites, eating and drinking everything in sight.  You don’t need fancy tours to explore San Juan well.

But if you have the time and inclination, there are some great options.  First, let’s talk food and drinks…I would have LOVED to have enough time for a walking food tour, or a craft cocktail walking tour/bar crawl.  Having to depart early made that not possible, but I strongly recommend trying one.

The other thing I was heartbroken to miss was a chance to get out on the water.  Y’all know I love me a boat.  If you’re looking for that—AND YOU SHOULD—this day sail looks amazing, as does this sunset sail (there are even better options if you have a way to get to Fajardo).

Castillo San Felipe del Morro in San Juan

Then there are further afield options…over a decade ago my bestie and I did a full-day tour that included El Yunque Rainforest, Luquillo Beach, and the bioluminescent bay kayaking that was a great all-in-one option (this tour gets great reviews and is similar, maybe minus the beach).  This bio bay tour from San Juan looks good, though the best way to see the bio bay is unquestionably from Vieques.

But if you’re only staying San Juan, this may be the way to go.  (If the bio bay isn’t in the cards for you, this nighttime kayak tour in Condado lagoon with LED lights looks…fascinating.)  A lot of the best tours require you to get out to Fajardo for pickup, which would be very expensive by Uber or taxi but if you have time and rent a car, it’s totally doable (but I haven’t included them here since that’s more of a barrier).

I often feel like the El Yunque tours are too big and touristy (this small group option is an exception), so a more off-the-beaten-path option would be this unique northern coast tour, which looks amazing.

activities in San Juan, Puerto Rico - visit the Bacardi Factory for a tour or mixology class

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Fall in love with the colored buildings of Old San Juan

So, diving into my favorite things to do in San Juan…and I could not in all honesty start anywhere else.  The history and colorful buildings of Old San Juan are magical!  This part of the city is a UNESCO World Heritage Site, and worth spending plenty of time just wandering around.

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

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The sheer diversity of styles and colors is amazing…I also love how many have tiny architectural details and decorations.

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

things to do in San Juan - a perfect weekend destination - walk the colorful streets of Old San Juan

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Make a quick stop by Plaza de Armas

While you’re meandering up and down the cobblestone streets of Old San Juan, make sure your path takes you through Plaza de Armas.  It’s one of the city’s main squares, and boasts a couple beautiful fountains and the town hall.

things to do in San Juan, Puerto Rico - Plaza de Armas in Old San Juan

things to do in San Juan, Puerto Rico - Plaza de Armas in Old San Juan

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Climb around the Castillo San Felipe del Morro

Better known as El Morro, this “fortalezza” (fort/fortress) has become a visual icon of Puerto Rico, almost synonymous with San Juan.  Castillo San Felipe del Morro is the main part of Old San Juan that’s a UNESCO World Heritage Site, as well as being part of our National Park System.  It’s been an important military outpost for almost 500 years, first for the Spanish and then for the United States.

Everyone will agree that this is a must-do activity in San Juan.  As you approach the fort, which kind of anchors the end of Old San Juan, you’re first greeted with a massive green lawn that surrounds it.  This is a popular place for people to hang out, picnic, and fly kites (it is WINDY).

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort

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Unfortunately we did it dirty on this visit, as we came twice but only got to spend like…15 minutes inside!  On the first night we came to see the sunset (which was a bit muted, but still offered a cool vibe).  Be aware that the fort closes for entry at 5:00pm (check times and ticket prices here), but you can still walk around the outside grounds.

The second day, we had to leave by a certain time to get to our Bacardi distillery tour, so we ended up racing in and out.  We snapped a couple pics of the gorgeous ocean views, then sadly had to grab our Uber.

Don’t be us…spend at least 30-45 minutes here exploring the fort.  You could consider a guided tour of the fort and Old San Juan, or can use this Spotify playlist to give yourself a DIY guided tour of the fort (as well as San Cristobal).

PRO TIP:  Your entry fee gets you into both San Felipe del Morro AND San Cristobal within 24 hours (including split over two days), so plan your itinerary accordingly to avoid double paying.  First thing in the morning or late in the afternoon are the best times to visit both forts, to avoid cruise ship crowds.

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort at sunset

girl smiling polka dot dress San Juan

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort at sunset

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You can’t miss Santa María Magdalena de Pazzis cemetery, which hugs the coast next to the fortress, but *technically* outside the city walls.  The location was both because the Spaniards had a strong fear of the afterlife, but also because of a belief that being close to the sea aided in their journey to “the great beyond”.

historic cemetary near Castillo San Felipe del Morro fort

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El Morro is one of the best sunset spots in San Juan as well.  Sadly the actual sunset was a bit meh, but the dramatic stone fortress against the setting sun is not to be missed!

One thing to shout-out…we were super short on time both times we came to the fortress, and completely missed the Paseo de Princessa.  Don’t make the same mistake!  It starts from El Morro and the original city gate, then gives a scenic walk including a large fountain and promenade, the cathedral, some great murals, and lots of shopping.  I’m honestly so bummed we missed it.

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort at sunset

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort at sunset

best things to do in San Juan, Puerto Rico - visit the historic Castillo San Felipe del Morro fort at sunset

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Don’t miss Castillo San Cristóbal!

So, I realized that in my memories I’d combined El Morro and San Cristóbal together.  While El Morro gets more of the hype, San Cristobal is almost as cool, and is a can’t-miss activity on your San Juan itinerary.  It might secretly even be a little bit better??

San Cristobal anchors the other end of Old San Juan, an easy 10-15 minute walk from El Morro.  We actually came here first and purchased our tickets here, and then used them the next morning (within 24 hours) to get into the other fort.

This fort also closes at 5:00pm so we were racing the clock by getting there at like 4:30pm.  It was a cursory exploration at best, but still very much worth it.

San Cristóbal is the largest and best preserved Spanish military fortification in the Americas…which is really saying something with San Felipe del Morro just a 10-minute walk away!  Its primary purpose was protection from land attacks (vs. sea).  It somehow flies more under the radar, with fewer crowds than El Morro.

Construction began in the 1600s, and the fort was actievly used all the way through World War II, when the sentry boxes were used by US troops to scan the waters for German U-boats.

what to do in San Juan, Puerto Rico - visit the historic Castillo San Cristobal

what to do in San Juan, Puerto Rico - visit the historic Castillo San Cristobal

what to do in San Juan, Puerto Rico - visit the historic Castillo San Cristobal

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I feel like there’s maybe a bit more to do here vs. the other fort.  It has several levels, including the beautiful sentry boxes (those little domed lookouts), a stunning panoramic view on the third floor, dungeons, stacks of cannon balls and little signs telling of the history of various rooms, and long underground tunnels.

best activities in San Juan, Puerto Rico - visit the historic Castillo San Cristobal

best activities in San Juan, Puerto Rico - visit the historic Castillo San Cristobal

best activities in San Juan, Puerto Rico - visit the historic Castillo San Cristobal

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Snap a quick pic of Capilla del Cristo

Exploring all of Old San Juan is easy from either fort, so just start at one end and work your way along.  But make sure to stop by the beautiful little Capilla del Cristo, a small sanctuary built on the city walls.

If you’re dying for a photo without people around, try first thing in the morning (though lighting may be tricky).

things to do in San Juan, Puerto Rico - walk Old San Juan's streets & see Capilla del Cristo

things to do in San Juan, Puerto Rico - walk Old San Juan's streets & see Capilla del Cristo

things to do in San Juan, Puerto Rico - walk Old San Juan's streets & see Capilla del Cristo

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Sip on a pina colada from the source…maybe??

There are actually competing claims to where the pina colada originated.  Barrachina says they were the first, but so does the Caribe Hilton.  I planned to try both, but only had time to stop in at Barrachina.  They have a nice little courtyard and a proper bar as well, but a separate lin if you’re just wanting a “to go” pina colada.

And it was…okay.  It tasted slightly of bleach or highly treated water, I’m guessing from the ice, which made it a harsher flavor.  Definitely not the decadent creamy and tart flavor I’m used to in a pina colada.  If you’re pressed for time, this is skippable.

things to do in San Juan, Puerto Rico - try a pina colada at Barranchina

things to do in San Juan, Puerto Rico - try a pina colada at Barranchina

things to do in San Juan, Puerto Rico - try a pina colada at Barranchina

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Visit Casa BACARDÍ

So maybe forget that (possibly pretend) historical cocktail opportunity and go get yourself an *actually* good cocktail…you know I can’t resist a winery or distillery experience so on our last afternoon we decided to head across the bay in San Juan to Cataño, to check out the famous Bacardi factory for ourselves.

Bacardi is the world’s largest rum distillery/factory, and I wish we’d had more time to spend and just chill, because they’ve done a great job making it the type of place where you want to just pull up a chair and have a drink.

We chose to do the mixology class, versus the other regular tour-and-tasting options.  I made the booking that morning and there was still some availability, but I’d definitely recommend booking a bit ahead if there’s a particular day and time you want (you can book directly on their website as well).

After our welcome drink we got a perfunctory trolley tour and then lined up in a classroom to make two different cocktails.  It was quite the rowdy crowd and a big-ish class, but my cousin and I had a blast together—this is definitely one of the most fun things to do in San Juan if you have the time!

Read more about our Bacardi rum distillery tour here!

activities in San Juan, Puerto Rico - visit the Bacardi Factory for a tour or mixology class

activities in San Juan, Puerto Rico - visit the Bacardi Factory for a tour or mixology class

activities in San Juan, Puerto Rico - visit the Bacardi Factory for a tour or mixology class

activities in San Juan, Puerto Rico - visit the Bacardi Factory for a tour or mixology class

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Spend some time on the beach

Puerto Rico has some beautiful beaches, and even though the best ones are in other parts of the island, San Juan still offers some good choices.  Our hotel in Condado had a beach and so that was the easy option, but I can vouch that the Isla Verde part of Carolina (to the east of Condado, near the airport) has much better beaches.

On my very first visit to the city (over a decade ago), we stayed in a cute little rental in this area, and so walked to the beach each day.  But you can also easily Uber over here, it’s like 10 minutes (you’ll just need your own beach gear).  There are a number of beaches to choose from, but Alambique might have the prettiest turquoise waters.

things to do in San Juan, Puerto Rico - spend the day on a beach

things to do in San Juan, Puerto Rico - spend the day on a beaches of Carolina

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Spend some pool time

I can’t believe it’s taken this long to get here!  But while I love LOOKING at the beach, I want to BE by a pool.  I don’t need sand getting all up in my biz.  That’s why having access to a pool at my hotel was such a focus for me (since this was intended to be a combo “trip/vacation”…a.k.a. some exploration and some lazing in the sun.

But finding a good pool option that’s also in a great location is harder than it sounds in San Juan.  So make your choices as you see fit, but for me, I wanted to get some February sun and sip a rum cocktail while lounging by a pool with my Kindle…devouring “A Court of Thorns and Roses” because my cousin made me (and then sent me memes based on the chapter I was on, LOL).

pina colada and ocean in San Juan

Condado Ocean Club in San Juan

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Enjoy San Juan’s nightlife

I’m notoriously bad at this, mostly because I’m a deep introvert and also lazy.  What tends to call my name is cocktail + Kindle + jammies.  And, like…get off my lawn.  But this trip was also weirder because of the aforementioned diabetic cat shenanigans, so I ended up spending my first evening on the phone with the vet, and our second night we were kind of tired and decided that Kindle was the answer.

But my research suggested that La Placita de Santurce is a great place to find live music, bars, and great foodie spots at night, including live salsa dancing in the square.  Do be careful at night, as not all parts of Santurce are safe (so taking an Uber to La Placita and back is advised).

The neighborhood is also recommended during the day, as it’s a bit quieter but has great restaurants, cafes, and amazing street art.

nighttime building in San Juan

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Where to eat & drink in San Juan

I had a loooooong list of places I wanted to try in San Juan, and barely scratched the surface due to cutting my visit short.  But I did find some major gems in just a day or two in the city.

Let’s start with coffee and breakfast…Atabey was just a few steps from our hotel so I grabbed coffee here a couple times (and they had a pretty good-looking food menu).

I also discovered a true hidden gem also right across from the hotel.  ReVital Coffee is basically impossible to see.  They have a very interesting, extensive menu.  I got their GOAT latte (goat milk and rosemary…interesting but a bit goat-y) and an iced espresso tonic.  There was so much to choose from that I was a bit overwhelmed.

After I left, my cousin found 787 Coffee, an adorable shop with a couple locations around the city.  They give you iced coffee pouches that are super cute.

On our last morning we took an Uber over to Dos Cafes in the Santurces neighborhood.  This place is SO cute and chill.  I got a couple delicious cortados (ha, I got dos cafes), a yummy cheese pastry, and pretty decent chicken & waffles.  I wish we could have explored the Santurces neighborhood more but it was raining.

what to do in San Juan, Puerto Rico - sip cortados, eat traditional mofongo, & more

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

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We also stopped in Old San Juna at Cafe Cuatro Sombras, a pretty coffee shop and coffee roasters, with food options as well.  The coffee I had (both cortado and iced) was really good, and I also sampled their avocado toast with smoked salmon, a guava pastry and a pastry with beef and plantains.

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

what to do in San Juan, Puerto Rico - sip cortados, eat traditional mofongo, & more

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I wanted to do a LOT more cocktail bar exploration, but at least got to stop at La Factoria.  It’s a multi-layered (or multi-roomed?) speakeasy-esque bar and club that’s pretty famous—including for its drinks.

We went mid-afternoon and the first room was super busy but the second inside bar was chill so we bellied up to the bar.  I got the San Juan Grog cocktail, which was super good.

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

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For dinners, I’ll start with the best.  We dined at Cafe el Punto, a traditional Puerto Rican restaurant in Old San Juan.  We hadn’t made a reservation so there was a bit of a wait, but not too bad.  I definitely recommend getting reservations for dinner in the city!

Our fried cheese bites appetizer and fried plantains with guacamole were both delicious.  Then I’d ordered the mofongo with skirt steak and it was AMAZING.  Seriously, this place is awesome!  Their cocktails were good too.  Then, though we were stuffed, we shared the cheese flan and passionfruit mousse, and both were awesome.  This gets my vote for where to eat in San Juan, if you’re looking for traditional cuisine.

what to do in San Juan, Puerto Rico - sip cortados, eat traditional mofongo, & more

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

On our first night we went to Semilla Kitchen.  It was walkable from our hotel and my cousin was starving, having just arrived.  We got there at 7:30 and it was still quiet, but was hoppin’ shortly thereafter.

Our tuna tartare tostones app was pretty good, as well as the cod (it was thinner than I’d imagined).  The salmon main was okay but I had to step outside for a vet call and it got cold (which is not the restaurant’s fault), and I wasn’t in love with the pumpkin ravioli.  My sangria was delish.

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

things to do in san juan,what to do in san juan,san juan puerto rico,things to do in old san juan,activities in san juan

So even though I’d planned on four days to truly immerse myself in San Juan, you can see that I was able to see and do so much in less than 48 hours!

Other whirlwind city explorations you’ll love:

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Destination Guide: Best Things to Do in San Juan, Puerto Rico | San Juan is a perfect weekend destination, a gorgeous city you can explore in just a day or two...here are some of the best things to do in San Juan, itinerary ideas, Puerto Rico trip ideas, what to do in San Juan, where to stay, where to eat & drink, & more! It's a perfect girls' trip, romantic getaway, easy weekend trip. #sanjuan #puertorico #girlstrip

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