Everything I Wore on My Florida Vacation ☀️🌴
Plus, here's a look at everything we ate, drank, and did.
I love a vacation outfit moment. Primarily because it’s the culmination of weeks (or let’s be honest, months) of planning in my head.
The closet gymnastics and thrift hunts in preparation remind me of how my mom always says:
“Half the fun of a trip is the anticipation leading up to it.”
I must say, I’m fully in her camp.
Outfit planning is one of the few ways you can connect with the excitement of your trip before you’re even there. And once you are, it gives you the confidence to dress for the moment and the intentionality to make your days and nights extra special.
This time around, I was planning for a Florida getaway with my boyfriend to celebrate our May birthdays that are exactly one week apart to the day.
Now, that we’re back from our trip, here’s a look at everything I wore and everything we did:
☀️🌴 Thursday
Sarasota Day Trip
After flying into Tampa Wednesday night, we kickstarted our trip Thursday morning with a lovely breakfast with my boyfriend’s mom. We ate at my allergy-friendly go-to spot, Another Broken Egg Cafe, where I ordered the gluten free lemon blueberry goat cheese pancakes.
Then, we were off to pick up our rental car and head an hour south to Sarasota.
It was my first time visiting the city, but I had the best tour guide. We strolled through St. Armands Circle, perusing shops and stopping for hydration at the Daiquiri Deck and lunch at Columbia Restaurant, the oldest Spanish restaurant in the U.S. and Florida’s oldest continually operated restaurant.
We both had the Spanish bean soup (garbanzo beans, ham, chorizo, and potatoes in a chicken and ham broth) that transported me back to my host mom’s lentil and chorizo soup in Salamanca, Spain.
Oh, and I sipped on a delicious red wine sangria … that I spilled on my white dress …
Speaking of my white dress, here’s what I wore:
After a long walk on the beach and a drive through the suburbs, we headed to Naples, where we holed up for the rest of our trip. And this time, I was the tour guide.
☀️🌴 Friday
Beach, Pool, and Tennis
Since we made the executive decision to spend our first evening sipping margaritas before heading to The Pub for fish and chips and wings, our Friday morning was spent grocery shopping.
After that, we hit the beach for an hour before black clouds drove us back to the complex’s pool. The storm never came, so after drying off, we hit the tennis courts for a late afternoon session.
Here’s what I wore:
Charcuterie
By the time we were done playing and showered, I made the call to postpone our evening out in favor of slowing down and relaxing with candles, cosmos, and charcuterie on the lanai. The boardgames were laid out, but in typical “us” fashion, we spent hours chatting instead.
☀️🌴 Saturday
Birthday Bungalow Welcome
Saturday was my boyfriend’s actual birthday, so I wanted to make the day extra special. Every year, I plan a themed birthday for my sisters, so my boyfriend needed the full themed treatment.
Traveling was not about to hinder my plans, so instead, I used our location as part of the decor and went with “Birthday Bungalow.”
My favorite touch was the laminated welcome note and itinerary:
Welcome Birthday Brunch and Tennis Hour
The birthday boy’s choice of sips and nibbles, per the itinerary, was breakfast out, so we ate at Epiphany Gluten Free Bakery. We split a coffee, and he had a breakfast sandwich while I had coffee cakes.
Next, it was tennis hour.
Here’s what I wore this time around:
Beachside Relaxation and Tiki Bar Cabana Service
We called it quits with tennis once we could no longer ignore the dark clouds and wind. We headed back to the condo and cooled down on the lanai with lunch — a “Pub Sub” (Publix Deli Buffalo Chicken Tender Sub) for the birthday boy.
Then, it was time for beachside relaxation. After an hour or so, the return of the dark clouds meant it was time to walk down the beach with our chairs to the Ritz Carlton’s Gumbo Limbo for Piña Coladas and storm watching.
Steakhouse Dinner Reservation
The itinerary’s rooftop sunset cocktails did not happen because — you guessed it — the dark clouds were back, and it was a full Florida monsoon. Instead, I moved up our reservation and we headed straight to Cooper’s Hawk.
We shared a bottle of the CHMX red, from Baja, Mexico. To eat, he had the trio of medallions (Horseradish, Bleu Cheese, and Parmesan-Crusted Filet Medallions) with Mary’s Potatoes and asparagus, while I had the filet mignon with Mary’s Potatoes and broccolini. Plus, the birthday boy got a rich chocolate cake.
In the end, the torrential downpour was perfectly timed because we soaked up the evening until they were closing down for the night.
Here’s what we wore for the perfect date night:
☀️🌴 Sunday
Beach Day
Sunday was a break from the courts thanks to tennis elbow that left a knot the size of a golf ball in my forearm. Instead, we had a slow morning before heading to the beach.
Here’s what I wore:
Rooftop Sunset Drinks and Dinner
By the time my skin had enough sun, it was time to get ready for the evening. We combined the missed rooftop sunset drinks with Friday’s postponed dinner plans.
Cocktails were at Tigress Restaurant and Rooftop Bar at the Perry Hotel. I had the Li Chi Sour (mizu lemongrass shochu, chrysanthemum, lychee, lemon) and he had the Ideal of Harmony (vodka, coconut green tea, banana, sparkling lime & yuzu).
Dinner was at Bar Tulia, where you must sit at the bar and order a cocktail seasonally created by the bartenders. I had the Rosemary Riviera (gardener gin, strega, honey, rosemary) and my boyfriend had a bartender creation.
For food, we split the grilled Atlantic swordfish with umbrian lentils, honeycrisp apple, and smoked pancetta.
Here’s what we wore:
☀️🌴 Monday
Our last non-working day
For Memorial Day we went to the Delnor-Wiggins Pass State Park beach where we spent the day shelling (I found six sand dollars) and swimming.
The afternoon called for a pool cool down and a last tennis match. But my favorite part of the day was how we ended it: wine and charcuterie on the beach during sunset while recapping our getaway and chatting about our future together.
Here’s what I wore: Wet hair, my sun hat, and a dress from middle school that lives in my Naples closet.
What can I say? On the last day, I didn’t want to waste any moments of our final evening in paradise.
This article contains affiliate links, which means I may earn a small commission if you make a purchase through them — at no extra cost to you — to help support The Handwritten Edit. All links have been carefully curated, so I hope you enjoy!
Explore my full ShopMy page, or use my link to start shopping or start creating.
Omg when I tell you I SPRINTED to the comments to say... that's right by my hometown!! Sarasota is so fabulous, and the 1905 salad at the Columbia Restaurant is my absolute fave. Next time you visit, gotta check out O'Leary's Tiki Bar. The Birthday Bungalow looked 10/10 perfect place to relax!