19 Years, 4 Days, One Incredible City: Florence with Brant
I turned 45 this week. Brant and I celebrated our 19th wedding anniversary. And instead of a big party or a quiet dinner at home, we decided to do something we’ve never done before: fly across the world to Florence, Italy, for four days of pasta, wine, ancient art, Aperol spritzes, and just us. No kids. No jobs. Just us.
I asked on Instagram if y’all wanted a recap of everything we did, saw, ate, and wore—and I was hit with so many DMs and poll votes saying YES. So here it is. Every detail. The meals that ruined me. The rooftop views. The wine windows. And how we somehow crammed a lifetime of connection into four days of jet lag and laughter. I’m including outfit picks, favorite spots, links to our tours, and a few regrets to help you plan your own trip.
Travel Days
We left Anchorage and had a five-hour layover at JFK. We used that time to rent a room at the TWA Hotel—a total vibe if you've never been—and it made the overnight flight to Florence slightly more bearable.
Once we arrived in Florence on Friday morning, we checked into our hotel: a DoubleTree located on the Oltrarno side of the river. It looked completely different from the older, historic hotels on the other side of town. This one was modern, clean, and quiet, with a working elevator and air conditioning—two things I knew I needed in the middle of an Italian summer. The continental breakfast was included with our stay, and it was so good. I only made it down one morning before a tour, but I still wish I would've gotten up for it on the other days.
Friday: A Cab Ride I Won't Forget + A Meal That Ruined Me
That first night, we took a cab to Osteria Caffe Italiano. And when I say the cab ride was an experience—I mean it. Brant has traveled all over the world, and even he said it was one of the craziest car rides of his life. Tiny alleyway streets, shared with bikes, Vespas, and pedestrians, and yet somehow our driver zoomed through like it was nothing.
I had read about the pizza place attached to Caffe Italiano, and I went there with that in mind. But once we arrived, I asked Brant if he wanted pizza or pasta, and he said pasta—so we ended up dining at the Osteria instead.
An Aperol Spritz that gave me life.
That meal ruined me. It was the best food we had the entire trip. No reservations, no wait, just a few open tables and some of the best service and food I’ve ever had. Anthony Bourdain once said: go where the people go. If there’s a line, it’s worth it. If it’s empty, maybe skip it. This place wasn’t packed, but it was right. And the steak we shared there was better than the one I’d eat at Za Za later in the week.
This truffle carbonara? It wrecked every pasta dish that came after. No notes.
Friday night’s bistecca fiorentina. Rare, rustic, and ridiculously good. The potatoes deserved their own standing ovation.
After dinner, we walked around the corner to an Irish pub. They had karaoke going, and even though we were jet-lagged and way past our normal bedtime, we stayed out, ordered drinks, and ended the night in a haze of laughter and off-key singing.
Closed the night out with ‘Shoop’ at an Irish pub down the street. Jet lag? Never heard of her.
Saturday: Rooftops, Wine Windows, and a Steak That Didn't Live Up
We set an alarm Saturday morning because we didn’t want to sleep the whole day away. We were definitely moving at a glacial pace after too many Aperol spritzes the night before, but we eventually rallied and made our way into the heart of Florence.
We grabbed sandwiches from two iconic spots: Pino’s and All’Antico Vinaio. At Pino’s, we sat inside, which was exactly what we needed — it was warm outside, and the indoor tables gave us a much-needed break from the heat. From there, we wandered through the streets and stopped at Vivoli, where I ordered a chocolate affogato made with chocolate gelato, a shot of espresso, and rum. Brant got the traditional version with vanilla gelato and no alcohol. We compared the two, and mine was absolutely the winner.
We said yes to both sandwich spots—because when in Florence, you don’t pick favorites, you eat your way through them.
Because espresso and gelato weren’t enough—we had to pour rum on it. No regrets.
Sometime after that, we stumbled across one of Florence’s famous wine windows and of course had to try it. Then, later in the day, we circled back and each shared a sandwich at All’Antico Vinaio. It wasn’t back-to-back — we spaced it out and made the most of every bite. The timing worked out perfectly. There were no lines when we arrived at either spot, but after we left, both had lines stretching down the block. The good news is they moved quickly. Brant preferred All’Antico, but I was team Pino’s all the way.
Discovered a literal wine window built into a centuries-old wall. Florence said “romance,” and we said “cheers.”
Later that evening, we stopped by View on Art, a rooftop bar located on the rooftop of Hotel Midici and included a postcard view of the city. No reservation, no line — just a couple of cocktails and a perfect golden hour. After that, we headed to our 10:00 p.m. dinner reservation at Za Za. I was excited because of all the hype, and while the ambiance, decor, service, and wine were great, I have to be honest — the food didn’t compare to our dinner the night before. Even the steak I had at Osteria Caffè Italiano was better than the one at Zaza. I liked it, but I didn’t love it.
View on Art delivered: good drinks, golden light, and a husband who still makes me laugh after 19 years. Magic hour, for real.
Sunday: Bikes, David, and a Rooftop Romance
We started the day wanting to have breakfast at Rooster Cafe, but the bus timing kept getting delayed. So instead, we decided to rent bikes. And let me tell you, it was almost the site of my first European panic attack. We were riding alongside traffic, other cyclists, tour buses, and pedestrians, and it was a lot. I did it because Brant wanted to do it, and looking back, I’m glad we did it—but it was intense.
Biking Florence: cute in theory, chaos in reality.
Rooster Café, you understood the assignment.
After the bikes, we went to our tour of the Accademia Gallery to see Michelangelo’s David. We booked through Viator: "Skip the Line: David Guided Experience," which cost $29.09 per person (not including museum admission, which was about 40 euros total for both of us). The tour was in English, about an hour long, and totally worth it.
Seeing David in person? Unreal. Pictures don’t do him justice—he’s larger than life and carved with so much detail it gave me chills.
After the museum, we stopped at Don Nino on Duomo Square and had a cannoli—half hazelnut, half pistachio—and it was everything I needed.
The kind of tableside service I could get used to.
We grabbed a cab home (public transit was delayed again), and then napped and got cleaned up. That evening, we stayed on the Oltrarno side and walked through an outdoor art and vintage market before eating dinner at Gusta Osteria. I had originally wanted to try Gusta Panino, but we got mixed up and ended up at Osteria instead. Food was fine, the setting was cute, and we ate outside overlooking Piazza Santo Spirito.
After dinner, we found a rooftop bar, Loggia Roof Bar, the popular spot of Hotel Palazzo Guadagni. We didn’t have a reservation, but they sat us inside near open windows, and eventually moved us outside once a table opened. We stayed for hours, drinking wine, talking, and soaking in our last full night in Florence.
Wrapped up our night with this view and a glass of white wine. It honestly felt like a scene out of a movie. Florence, you have my whole heart.
Monday: Tuscany Day Trip
We booked our full-day Tuscany tour through Viator for $402.92 total for both of us. That included stops in Siena, San Gimignano, and Pisa. The tour was guided, and we met at 8:00 AM on the other side of the river.
Our first stop was Siena. We visited a stunning Gothic cathedral and had time to wander the town on our own. From there, we drove to Fattoria Poggio Alloro, an organic family-run wine estate for lunch. That lunch included multiple courses and a wine pairing—plus as much wine as you wanted to drink. The setting was unreal. Olive trees lined the path to the tasting room, and it felt like something out of a movie.
Living my best vineyard life and pretending I know anything about tannins.
By the time we got to San Gimignano, we were all a little tipsy and fully bonded with our fellow bus travelers. San Gimignano is home to the world’s best gelato (which we tried), and I picked up a cute little leather tote.
When the gelato is literally award-winning, you eat it before it melts… and then consider a second.
From there, we headed to Pisa. Our tour included entry to the Leaning Tower, and yes, we climbed all 250+ stairs to the top. Right outside the gates? A McDonald’s. And yes, I went in to use the bathroom, but you had to show a receipt, so I tried the spicy nuggets, fries, and these bacon cheese balls. And yes, they were good.
We got back to the hotel around 9:30 PM. Brant had picked up a bottle of wine from the winery, so we opened it, packed, and tried to rest before our early morning flight.
Final Thoughts
Siena’s version of a coffee shop corner table. Not mad about it.
There are definitely a few things I’d do differently next time. First of all, I should’ve packed a pair of tennis shoes. I went full fashion blogger mode and left all my practical footwear at home, and I’ve been paying for it ever since. My feet and calves are still sore, days after getting home. I also wish we’d had more time. I would’ve loved to explore more museums, do more people-watching, and take my time window shopping — not just for content or souvenirs, but for the joy of wandering with no schedule.
And here’s a pro tip I wish I’d remembered: always carry your passport with you when you’re out shopping abroad. I missed out on saving money using VAT forms because I didn’t have mine with me when I bought two (yes, two) Longchamp mini bags that I absolutely “needed.” Lesson learned — if you’re traveling internationally and think there’s even a chance you’ll make a purchase worth bringing home, bring your passport with you just in case.
But more than anything, this trip reminded me how much I love being with Brant. After a year of quick hellos and short visits in between his work travel, having four uninterrupted days together was a gift. It gave us space to reconnect, to laugh, to talk without the background noise of kids or schedules or grocery lists. I’ve never stopped loving him, but I fell in love with him all over again on this trip.
Nineteen years in, and I can say with full honesty that I love him more today than I did when we said “I do.” Florence gave us more than good pasta and wine windows — it gave us time. And that was the most beautiful part of all.
Lesli
P.S. Wondering what I packed and wore throughout Italy? I put all the outfits (and links!) in one place for you here: What I Wore in Italy →
19 years in and still crushing it—this time with a Chianti backdrop.