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travel blog: san juan (and more), puerto rico


I know every time I post a travel blog I gush about how much I am in love with the place I’ve just visited, but that’s how it should be, right? So I did want to note that there are places I’ve gone that I just didn’t totally dig, so I simply don’t write about those – I truly only share the YAY’s. So in that spirit and classic Annie fashion, get ready for me to go ga-ga over Puerto Rico in this post, because our trip was perfection! <3

The kindest people, the most vibrant culture, the picturesque weather, the scenery, the endless things to do and all of the cute roaming kitty kats made this trip such a memorable one. It's amazing what a little sea-air can do when you've been stuck in the Chicago winter for months – it was a total refresh and reset, exactly what we needed.

But don’t think we sat at the beach for six days! If you’ve followed my other travel blogs, you know we like to go-go-go on vacation and soak up every experience (and calorie) we can. So this trip was no different. I’ve posted below all of our highlights based on where to stay, what to do and where to EAT. I hope you find this helpful if you’re headed to PR, or that you get inspired to go there ASAP! 😀

Let’s go!

Here are some easy jump links in case you want to reference anything quickly:

To Stay

To Do

To Eat

To Stay
Dave and I are pretty active vacationers, so where we stay is honestly an afterthought at times. We just kind of need a place to rest our heads after busy jam-packed days – so when Dave booked The Dreamcatcher I was kind of stoked to be heading someplace that looked like it had a tad of its own magic.

It’s a vegetarian bed and breakfast which I’ll get to later (yes, I’m aware my blog has “meat” in the title). But after checking out the photos of all the quaint and unique rooms, the open spaces, and yes – the menu – I was excited. Walking up to the hotel is like finding a little gem of a peaceful tropical resort in the middle of a residential neighborhood.

We were immediately smitten with all of the outdoor spaces. And more than just being smitten we were INSPIRED. They had incense going outside which was so lovely! I find it overwhelming when inside, but outside it just gives such a subtle nice scent – took me back to the two minutes I thought about being a hippie in high school. There were also water features everywhere so Dave and I immediately made an insane list of additions we want to make to our own backyard oasis this summer. Water feature – check!

Our room was perfectly pink, with a hammock. This is for sure what dreams are made of.

Around every little corner there are little bits (or big ones) of decor that you can just tell the owners put their hearts and personality into.

The owners also bring their doggies around most days, which was lovely for us with three kitties at home we were missing – especially since this little tripod was running around (we missed our tripod Scooter!)

I also have to mention after nights out on the town it was so lovely to come back to this beautiful space and share a bottle of wine in the open area in the middle of the hotel. Nearly every night we ended up here for a night-cap.

Now onto the food! Every morning the chalkboard in the kitchen listed the 5 or so options that you could choose from – the choices were different each morning. Again, all vegetarian and all simply out of this world. From brussel sprout toast to pumpkin puree and chia pudding, everything was super inspiring (and delicious). We ended up attempting a lot of these recipes as soon as we got home (especially putting hummus on toast under an egg – why didn’t we think of that)?! You can check out my copycat chia pudding with papaya here.

I really can’t recommend The Dreamcatcher enough. The space really became a huge part of our vacation as opposed to just somewhere to sleep. We’ll most certainly be back, and if you’re headed there soon I really hope you look into staying here!

To Do:
First things first, you absolutely have to visit El Yunque National Forest. It is a breathtaking place to see in person with the ocean visible on one side and waterfalls and palm trees in the mountains on the other – I’ve never really been anyplace else like it. And you should bring your bathing suit (I wish I would have known!) as people were hopping in the water under the amazing waterfalls.

Next up, and this is an obvious to-do, but visiting Old San Juan was so fab, we kept going back again and again. The beautiful architecture, adorable local shops and stunning waterfront were fun to explore.

When in Old San Juan, you should also visit Parque De Las Palomas – which is a lovely little park filled with pigeons. They land on kids who are feeding them and fly in swarms – I had to duck down behind Dave a few times, but it was pretty cool to see.

From the downtown area of Old San Juan, we walked along the water to Castillo San Cristóbal, which is the largest fort built by the Spanish in the “New World.” Admission is free and the views are amazing. There was even a giant iguana crawling around that scared the shit out of me. But I guess he seemed pretty chill.

Also in Old San Juan we were lucky enough to hit up the San Sebastián Street Festival. It is a five-day event that starts the third Wednesday of January and runs through Sunday. During the day there are local artisans set up selling art, foodie stuff, cigars and more. And at night there’s live music on multiple stages and people having cocktails in the streets. It was pretty epic and certainly worth scheduling your trip for if you want to experience a crazy fun party.

This woman stole the SHOW. Sound up. 😀

On the cocktail front, Dave was determined to try La Gasolina – a drink made of rum, tequila and fruit juice. HELLO.

I obvi had to try it too.

Let’s just say it’s likely best to try it if you’re already a few deep.😂

Back to regular San Juan, another fun way to spend a night during the weekend is at La Placita, which reminds me a lot of Bourbon street in New Orleans. There are open-air bars circling around a little center where everyone dances to live salsa music. The happy vibe in the air is at an 11 here – definitely don’t miss.

Sir Dave even got taught how to salsa by these lovely two gents:

There are also very yummy mojito’s here y’all. 😀

Last, if you happen to be into cigars, I would highly suggest visiting Willy. As with our normal vacationing behavior, we tend to yap to everyone around us and make friends – it’s a good way to get the inside scoop on what to do. A nice guy we were talking to mentioned to Dave that the best cigars come from Willy, and that to get them you just had to give him a call and head over to his place.

We figured, what the heck, let’s go see Willy! We made an appointment and he welcomed us into his home where he makes all of his cigars. He walked us through all the different varieties he makes and showed us the tobacco leaves and rolled some right in front of us. It was such a cool experience. Sir Dave was in his element and as happy as a cigar-smoking clam.

I don’t know a whole hell of a lot about cigars, but Dave liked the ones he purchased so much, he already placed another order from Willy to ship to us in Chicago so definitely worth the visit if this is up your alley.

And one more fun stop for Cigars is Don Rey’s, which is close to La Placita where they have live music playing – like this jazz trio – and you can sit outside and have a cold one. It was perfection.

To Eat:
My favorite part! Let’s talk food. I have to start with what we thought was by far our best meal in Puerto Rico – hitting up the ‘pork highway’ in Guavate for some lechon. It is a beautiful drive from San Juan to Guavate – which is nestled up in the mountains among lush greenery.

The day to go is on Sunday, per our pals at our hotel. There are a variety of places to stop, but we stopped at the first place we saw because we were drooling. There were a variety of little stands and some live music going on as well as the reason we were here – whole pig roasts.

We tried a little bit of everything. We tried the lechon, the ribs, blood sausage (more of a Dave thing), plantains and rice. Everything was fantastic.

This was for sure one of the best ribs I’ve ever eaten.

And the dancing. Don’t even get me started on how wonderful it was that there were people dancing to live music nearly everywhere we went. Loved it.

Another fun foodie road trip is to Piñones which has a sea-side road that hugs the beach and is peppered with little street-food kiosks. We decided to go to Kiosko El Boricua based on the reviews and it did not disappoint.

We tried a pollo pionono, which is stuffed and fried sweet plantains.

The carne pastelillo was my favorite. Simple, but flavorful and what a flaky crust. Yum.

We also had the shrimp alcapurria, which is a type of fritter. Delish.

And just across the street, this was the view from the beach. Looked fake, honestly, so perfect.

In terms of restaurant visits, I think we hit the jackpot. I did some research beforehand and made reservations at a few places – Marmalade being one of them. Marmalade is in Old San Juan and describes its menu as Caribbean and French and has a fantastic tasting menu, which is how we ordered. It’s also a super hip and welcoming space which was a nice way to spend an evening after running around town.

Kicked off the evening with a pineapple mojito.

I ordered the Heirloom Golden Beets which included raw hearts of palm, haas avocado, organic radish carpaccio, goat cheese grapefruit & almond vinaigrette – so lovely and refreshing as a starter.

Dave ordered the Paella which was “sushi esque” bite size pieces of crispy andulusian style paella filled with smoked chicken, peas and peppers flavored with a saffron-garlic espuma & a chorizo-tomato sauce. He said it was one of the best things he ate on the trip.

Next up I had the Jamón Ibérico which had grilled Californian nectarines with homemade lemon mascarpone cheese
resting beneath veils of pata negra ham & a champagne-nectarine vinaigrette.

For Dave’s 2nd course he had the Hudson Valley Duck Cocotte – boneless duck legs layered with baked parsnips, cabbage and nutmeg yams bound with a foie gras gravy. I just heard “mmmmmm’s” from Dave during the time he had this dish in front of him. Silent otherwise. Lol.

For the main, I can absolutely not remember what kind of fish this was (blogger problems) but it was fantastic.

We also had the Niman Ranch Natural Hormone-Free Lamb Tagine, a Moroccan-French style braised lamb with ras el hanout organic chick peas with marcona almond pomegranates & harissa spiced green olives. I mean, gimme.

And, yes – since we did the tasting menu, we had dessert coming too. So full, but totally worth it. I had an 8-layer chocolate situation that I ate every last bite of.

Dave had the bread pudding, which was ridiculously good.

We loved our experience here, and all of the above was $69 per person, which felt like a steal. The owner and chef even came out and chatted with us – all around, fabulous evening. Oh, and added benefit, if you walk around Old San Juan at night you just might find a gaggle of kitties that need snuggles.

The next quasi-fancy dinner out we had was at Santaella which I also think is a must-visit if in Puerto Rico. The atmosphere was cozy and romantic…ooh lala.

It was pretty dark in the restaurant, so not a lot of great foodie shots, but wanted to share our entrees because they were divine.

I had a simple but very flavorful farm-fresh chicken dish with mashed potatoes and asparagus.

Dave ordered the asian skirt steak, which was phenomenal. The steak had really complex flavors that we couldn’t quite put our fingers on – sweet and savory. Loved it. And we ate that entire side of plantain straws.

Really lovely place to have a nice meal, we’d go back again for sure.

The last place I want to share with you is La Coctelera.

It is a great spot within walking distance of the Dreamcatcher and the atmosphere was fun and the bartenders were friendly and very knowledgeable. I could see this place being a hit in Chicago or New York, easily. I had a killer old fashioned and Dave had a really unique whiskey + mezcal drink, which I kept trying to steal sips of. We also had great food here – sliders and flatbread pizza.

Sitting at the bar with that cocktail glow was one of the few times we grabbed pictures of ourselves, so I must present our happy vacation bar selfies.

And with that last photo of our big heads, it’s a wrap!

I really can’t say enough good things about this trip – and one of the reasons it was so good was because we were open to any and all suggestions from everyone we met. Our Uber drivers, the staff at the hotel, folks we met at La Placita or friends we made sitting next to at a bar provided nearly all of the adventures above. So my advice is don’t plan to much, talk to everybody and let the day take you where it may!


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