Well, I did it again… I way overpacked for Puerto Rico. Last year, I planned lots of super cute tropical outfits and only ended up photographing two. This year, I told myself I couldn’t repeat my overpacking mistakes… And even though I frantically took out a bunch of stuff last minute before leaving for the airport, I’ve still only worn four of the 10 outfits I packed! I just rarely take tropical vacations, so when I do, I end up packing every bright and colorful tropical item I own—even though what ends of happening is I wear a swimsuit most of the time and then just throw on something simple for dinner because I’m tired and sunburnt. Sheesh, when will I learn??
Monday, February 12
I slept horribly last night, but thankfully I was still able to pull through and be productive (it was looking dicey there for a minute—coffee does nothing for me but a few power naps got me through). I would never wear this skirt into the office, obviously, but it’s one of my favorites, even though I haven’t worn it in forever. All my jeans were dirty and I didn’t want to wear anything I might pack for my trip, hence a sweater and corduroy skirt.
Sweater: Gap, $30 ($0.77 per wear), last worn here | Black Skirt: Francesca’s, $35 ($0.88 per wear), last worn here | Black Booties: Vivaia, gifted for collaboration, $140 ($2.64 per wear), last worn here | Striped Socks: DSW, $10 ($2.50 per wear), last worn here
Tuesday, February 13
Today was so hectic as I tried to finish up several work and personal tasks before my vacation. I’ve worn this outfit before, aside from the cute charm necklace from Brighton. My mom got me a charm bracelet for Christmas with charms from the four new states we visited together last October (Pennsylvania, Delaware, Maryland, and New Jersey). I haven’t been wearing it as a bracelet yet because of the cold weather and long sleeves, so I got the idea to transfer the charms to a chain instead for the time being. I’ve loved wearing it as a necklace!
Sweater: Sundance Outlet, $45 ($3.00 per wear), last worn here | Cropped Flared Jeans: Express, $25 ($0.60 per wear), last worn here | Velvet Flats: Sundance Outlet, $60 ($4.62 per wear), last worn here
Wednesday, February 14
My aunt, cousin, and I carpooled to the airport today to start our vacation! We met my dad after security, who had flown from Boise earlier that morning. I didn’t wear anything particularly cute (especially the running shoes—purely to save space in my suitcase) but I did realize after the fact that my Philadelphia Love t-shirt was a fun piece for Valentine’s Day.
We flew Southwest through Orlando to San Juan. Little did we know that Valentine’s Day is one of the best days to travel! We got free drinks on both of our flights (they also offer that on St. Patrick’s Day, Halloween, and Southwest’s birthday), and we stumbled across a super random karaoke station in the Orlando airport right before our second flight. I knew I had to get up there—I sang “Living La Vida Loca” to get into the Puerto Rican spirit—and then the Southwest lady surprised each singer with a $100 travel voucher. I couldn’t believe it, but it was such a memorable way to start our trip!
The flights were easy but we didn’t make it to San Juan until midnight. Thankfully my other aunt who lives on the island picked us up and took us to her house on the east coast for the week!
Love Tee: Philadelphia airport, $25 ($12.50 per wear), buy exact here | Cropped Flared Jeans: Express, $40 ($0.62 per wear), last worn here January 2023 | Running Shoes: REI
Thursday, February 15
We had a lazy morning catching up outside in the 70 degree weather under the palm trees, treating ourselves to quesitos from a nearby bakery (rolls of puff pastry with cream cheese in the middle). We all piled into the golf cart, a new addition since we were here last year, and motored over to the beach, where we spent much of the afternoon. There was hardly anyone there and it was SO relaxing to float in the water and sip on Medallas (basically Puerto Rican Coors Light).
We all got dinner at one of my aunt’s favorite restaurants in Fajardo and enjoyed their delicious mofongo, which is a Puerto Rican dish comprised of mashed up plantains, chicharrón (fried pork skins), garlic, and a protein and sauce of your choice—I got the shrimp in garlic sauce. After beaching much of the day, I just threw on this thrifted gingham maxi dress for something quick and simple!
Gingham Dress: Thrifted, $20 ($1.54 per wear), last worn here | White Sandals: DSW, $45 ($0.49 per wear), last worn here
Friday, February 16
My dad and I spent the morning relaxing on the beach again before we all drove to San Juan to meet up at my grandpa’s house. We got dinner in Old San Juan at our favorite stuffed avocado shop and then tried a nearby gelato place that is all the rage with the locals (the line was long but it was very yummy!). Afterwards, we stumbled upon some dancing in the square and decided to join in for a while—salsa, merengue, and even a sort of line dance that I wasn’t familiar with.
On our trip last year, I was very disappointed by the lack of nightlife in Old San Juan, but my aunt said a lot of things still hadn’t gone back to normal due to a combination of Covid and the hurricane. I know cruises have also really negatively affected the area, as lots of places close at 8 pm just to cater to those groups. But this time around, it felt very different—lots of restaurants and shops were still open after dinner and there were tons of people milling about. It’s hard to say if things have already improved that much from last year to this year, or if it’s because we just weren’t there on a Friday last year. Either way, I’m just glad we stumbled across some life this time around—it felt abandoned during our last visit!
White Top: Hand-me-down, last worn here | Denim Shorts: Target, $18 ($0.62 per wear), last worn here | White Sandals: DSW, $45 ($0.48 per wear), last worn here
Friday, February 16, Cont.
After enjoying the impromptu dancing in the square for a bit, we drove over to the Old San Juan Hotel (now called the Fairmont El San Juan Hotel), which is where my great aunts and uncles used to go dancing all the time and would even take my dad dancing when he visited as a kid. The hotel is beautiful and very glamorous, with mahogany everywhere and huge chandeliers. It looks like something out of a Bond film. I changed into this thrifted geometric dress (although I ultimately wore my nude heels instead of these orange wedges) for something a little more dressed up.
While there was some dancing at the Old San Juan, my aunts said they’ve renovated the place post-hurricane so there was less room to dance, and those who were on the dancefloor were really good. We decided just to sit, drink, people watch, and enjoy the incredible old-school band.
Geometric Dress: Thrifted, $9 ($1.80 per wear), last worn here | Nude Heels: Amazon, $46 ($3.83 per wear), last worn here
Saturday, February 17
We had a slower morning and then drove about an hour to Santa Isabel, where my great aunt’s 100th birthday party was being hosted (the whole point of the trip!). I’ll share more about it in a later blog post but it was such a special experience; I’m so grateful I was able to make it to the event. I wore this floral maxi dress that I got for my Las Vegas trip last September and got so many compliments!
After the party, which ended around 8 pm, we drove over an hour further to Cabo Rojo on the west coast of the island and stayed in an AirBnB. I saw so many new parts of the island on this trip, which was really exciting! I learned that it’s actually much dryer in the south of the island and they even have fires sometimes, which came as a shock to me—the parts of PR I have been to have always been so humid and lush.
Floral Maxi Dress: TJ Maxx, $20 ($10 per wear), last worn here | Nude Heels: Amazon, $46 ($3.54 per wear), last worn here
Sunday, February 18
We spent nearly the entire day at Buyé Beach, which is known to be one of Puerto Rico’s best beaches. Unlike the beach near my aunt’s house, which is on the Atlantic Ocean, this beach touches the Caribbean, so it has those beautiful turquoise waters and white sand. The only downside is that it was absolutely packed—hundreds of people, with the associated annoying smells and sounds. My aunt was saying that the beaches generally aren’t that busy this time, but I think because this was a holiday weekend, it was much more crowded than usual.
I still enjoyed the beautiful water a lot, and we made our way to dinner after a long beach day. I bought this orange maxi dress at Marshall’s on a whim yesterday during a pitstop. I didn’t try it on in the store (which I never do, but we were in a rush) and was so pleasantly surprised when it fit perfectly! I absolutely love the bright orange.
After dinner, we walked around Boquerón for a bit, which is kind of the “it” spot for nightlife. There are tons of bars along the water, live music, karaoke, dancing, and vendors, like a Saturday market. We had wanted to eat dinner there to enjoy the sunset but it was just too packed! I’m glad we were able to see it at all.
Orange Maxi Dress: Marshall’s, $20 ($20 per wear) | White Sandals: DSW, $45 ($0.48 per wear), last worn here | Sunglasses: Loft, $20 ($0.71 per wear), last worn here | Purse: Shop LC, gifted by brand, $24 ($2.00 per wear), last worn here
. . . . .
Which of this week’s fun tropical outfits is your favorite? I still miss the days I had a spring break in school, so it’s extra exciting to go on vacation around that time of year and pretend like I won’t have a pile of work to catch up on when I get back, ha. I know I mentioned lots of Puerto Rican spots and foods in this blog post, but I plan to share a more comprehensive travel guide in the coming weeks! Stay tuned.
Miles of smiles,
Grace