puerto rico, winter ’19 | the full rundown.

I was in the middle of the busiest month of my 2018 wedding season when Michael asked me if I wanted to take a trip together during my eventual off season that would follow. Michael and I are *slightly long distance (it’s roughly a 2.5 hour drive between my place in Chicago and his in Bloomington, IL), so when my busy season picks up and I’m often on the road for weddings, we see a bit less of each other due to our busy schedules. So I jumped at the opportunity to plan something fun in the midst of all this, and the two of us started brainstorming on possible destinations. We both found ourselves coming back to Puerto Rico as a top contender, and after looking up flights and AirBNBs and talking the potential game plan, we had a winner.

I had never gone on a trip with just myself and a boyfriend before, so I had NO idea how this whole thing was going to turn out – with four different bnbs, and a ferry station with limited and vague online info, and planning when and where to grab a rental car, there were a lot of variables that could “go wrong”, so I think it’s fair to say we were both a little justifiably nervous to see how this whole thing would play out for us. We definitely hit a few bumps throughout our trip (as one does), but there’s something satisfying about working your way through a new area – about getting it right and getting it wrong, and remembering that it’s ok to screw up and to figure out where you’ll go from there together, and something about that makes you appreciate the sights and the smells and the sounds that much more. As much as there were a few moments when Michael and I were freaking tired and probably secretly thinking “shit, all inclusive would have been so much easier”, there were even more moments when we were laughing and exploring and a bit in awe of everything we were experiencing. A handful of people reached out to me after I posted some photos from this trip asking for recommendations about some of our favorite parts, so I decided to put together a little post with a breakdown of our time in PR, complete with links and additional tidbits that might help someone else craft a route of their own while visiting. There’s a few photos too, but not nearly as many as I’d normally take on my “good camera” — to be honest, I shot mostly video on this trip, because sometimes a girl needs to take a breather. Michael may have actually done a bit more photo taking than me this time around, so you’ll see more of my face within this post than usual.

So, here it is! The full breakdown of our time in Puerto Rico.

San Juan | Day 1-3

We flew into San Juan in the afternoon, and we took a cab from the airport to our first AirBNB in the Parque/Ocean Park area of the city. We initially wanted to book a room at The Dreamcatcher based on a recommendation from a friend, but the rooms were a bit more expensive than we were looking for considering the length of our trip + overall amount of overnight stays we had ahead of us, so we instead found an AirBNB property with The Dreamcatcher’s owner, Sylvia, and it’d be hard to overstate how much we loved this spot. We stayed in The Treehouse, which was a unit upstairs overlooking the outdoor space, complete with an outdoor shower. The home also had a communal garden/patio space full of plants (!) with an outdoor kitchen area, and we drank coffee + tea out there throughout our stay. It was pretty wonderful.

Day one fave spot: Tresbe | This open air restaurant was just down the street from our AirBNB, and was so dang good that we ate there three times throughout our trip (not exaggerating). The sushiritto there was possibly one of my favorite things I’ve ever eaten, and I’ll be dreaming about their fish tacos for a looooong time. It’s too bad that I don’t have any photos of said food outside of iPhone shots, but I have plenty of video clips, which are better for salivating over dream meals anyway.

Honorable Mention: We also went to a spot called Panuchos for margaritas and Mexican food later that night, which was delish.

On day two, we slept in and then went for a run + ate breakfast at our bnb, then spent most of our afternoon at the beach, which was only a few blocks from our place. That night we walked to a spot in the Santurce neighborhood, Lote 23 (fave spot on day two!), which is an outdoor space full of food trucks. We filled up on a bunch of great food + cocktails (fave drink there: gentlemen’s buck), then picked up some booze and made drinks at our bnb that night while making a plan of attack for the following day’s rainforest trip.

Day Three: We did a lot on this day, so I’ll bullet point up below.

– Breakfast at Pinky’s: Diner-esque breakfast spot near our bnb. So good.

– Picked up our rental car: We did an Avis rental car out of San Juan, and made our way toward the rainforest. [Sidenote: we went back and forth a bit at first on whether or not we should rent a car vs. ubering/taking local public trans for this portion of the trip — we were both super happy with the car rental, and I totally recommend it if you plan to venture outside of San Juan/OSJ during your time in PR.]

– Pit stop at Degree 18 Juice Bar along the way: this place was recommended to Michael from a friend, and it was the COOLEST. Their smoothies were so good, there was a beautiful patio + hammock space for hanging, and we also roamed around the garden space out back.

El Yunque National Rainforest: We spent the afternoon in El Yunque, and based our route within on some other rainforest tour routes we’d seen when looking things up online. We checked out La Coca Waterfall, Yokahu Observation Tower, and did some hiking at Juan Diego Falls.

We decided to end our last hike of the day by taking a dip in the waterfall at Juan Diego (worth it), and then made our way out and back to the car. We had taken our sweet time changing out of our wet clothes and into dry ones when we realized we only had a few minutes to spare until 6 pm when they closed the gate, and when we arrived at the gate at 6:03 pm, we realized we’d made our first big mistake of the trip and had been officially locked in. (LOL) We found a spot within where we had service to do some googling to see if there was a solution (I literally googled “what to do if you get locked in el yunque national forest”, to no avail) contacted our new AirBNB host to let her know we wouldn’t be making it that night, and planned to ration our two granola bars and sleep in the car that night. In the meantime our AirBNB host took it upon herself to call emergency services in the area, and within a few hours, two uniformed men showed up to take down our information and unlock the gate for us (some kids had told us earlier in the evening that you get fined if they have to come unlock the gate for you — based on our limited Spanish and their limited English, we are still *pretty certain there was no fine involved — I’ll let you know if I end up getting a bill down the road :) ). We grabbed some late dinner at a Puerto Rican spot along our route to Ceiba, where we stayed for the night in order to catch the ferry to Culebra the next morning. Our Ceiba AirBNB could be best described as economical (fine print: cheap, but it had a bed and we weren’t stuck sleeping in a rental car, so it certainly felt like a win), and we posted up while watching The Office and scrounging up quarters to quietly do some late night laundry without waking the neighbors. Traveling ain’t always glamorous, you feel me?

Day 4-7: Culebra

The ferry terminal to travel to Culebra had recently changed from Fajardo to Ceiba (which we found out the night before leaving on our trip), so we cancelled our previously booked AirBNB in Fajardo upon learning this and found the overnight spot in Ceiba instead. Here’s the updated ferry schedule/details we used, and the ferry process was pretty straightforward once we got there. We bought round trip tickets and took a *very rocky ferry ride to the island (a whoooole lotta people were getting sick on this ride, but luckily neither of us needed the puke bags they were passing out); the ride back wasn’t bad at all, so we may have just happened upon some rough waters that day.

Most people get around Culebra by Jeep or golf cart, so we rented a cart upon arrival. We were staying at a (really great) airbnb that had a kitchen, so we picked up groceries and planned to cook a lot of our meals during our time on the island. We spent the rest of the afternoon hanging by the pool on our property, made some stuffed peppers for dinner (complete with warm gin drinks because we forgot to buy ice), and had a chill night in.

We spent a good chunk of our time in Culebra reading and getting sun (and getting tipsy) on Flamenco Beach, making breakfast at our place, hitting up a few of the spots in town (Dinghy Dock for seafood, a pizza place I can’t recall the name of, a tiki bar I went to barefoot after someone snagged my flip flops while we were out for a walk on the beach that day). We left the windows open at the bnb and let the breeze roll through throughout our stay, and our whole time there was laid back and pretty freaking perfect.

I’m not sure why I’m being v awkward in this pic, but it’s the only one we snapped that gives a good glimpse of Flamenco Beach, soooo we’ll just go with it and pretend I’m not making a face that looks like I’m confused and/or pooping.

The view of the “town” portion of Culebra from our AirBNB, which was at the top of a hill in a more rural part of the island.

Day 7-10 | Old San Juan 

Day 7 was mostly a travel day — we took the ferry back, hopped in our rental car at the terminal, and made our way back to San Juan. We stayed in an AirBNB in the heart of Old San Juan for the last leg of our trip, so we pit-stopped at two of our favorite spots from the first leg (Tresbe and Lote 23) while waiting for our check in time to roll around. It was the last day of Hamilton’s Puerto Rico show (which took place just down the street from Lote 23), and I fangirled real hard when a camera crew rolled in with a man we eventually found out was Lin-Manuel’s dad. (!!) After checking into our AirBNB and dropping off our rental car, we went out for beertails and sliders at La Taberna Lupulo. There were a ton of bars on this street (which was walking distance from our place), so given more time there, I’m sure you could find a bunch of great spots. We were thinking about doing a sunset cruise during our time in OSJ, but both felt ended up feelin’ like going into full chill mode with some beach posting up + finishing our books instead, so we opted for that.

We went to a couple of other great spots in OSJ (had a real great lavender mule at La Factoria, tried our first mallorcas at La Bombonera, ate some amazing seafood at a place down the street from us that I can’t recall the name of, and had SUCH a good brunch at Abracadabra in Santurce before grabbing our flight back on the coldest day of the Polar Vortex). Both of our vehicles started despite sitting on the streets of Chicago for over a week during the coldest weather all winter, and we shoveled them out with our sunburns providing warmth (jk, we were freezing and I was slightly concerned about getting frostbite). To sit here and tie up our trip with a pretty little closing-sentence bow feels a bit trite at the moment, so I’ll just leave it at the fact that this was a REAL good one. Get yo’self to Puerto Rico as soon as possible and I promise you won’t regret it.


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