ITALY2026

August 31—September 5

Florence

Wine windows, Tuscan hills, museums in smaller doses, and a pizza that could not support its own toppings.

Start with the food tour ↓
Shiloh and Jordyn overlooking Florence from Piazzale Michelangelo
Florence from Piazzale Michelangelo.

Day 6

Monday, August 31

Arriving in Florence

We took the train from Rome to Florence, then walked from the station to B&B Firenze Cittadella 8. At check-in, the owner spent a few minutes mapping out the city for us.

The food tour that evening included meats and cheeses, pasta, wine through a wine window, and Florentine steak. The steak was good, but I’ve had better. I enjoyed the tour as a whole, although it was slightly below the Rome one.

The facade of the Florence Duomo
First look at the Duomo
A traditional wine window in Florence
The wine window
Shiloh holding a glass of rosé from a wine window
Wine from the wine window

The group was good too. During our time in Florence, we kept running into a couple from the food tour, as well as a group from the Rome food tour.

Shiloh and Jordyn beside the Arno River at night
Walking across the Arno at night

Day 7

Tuesday, September 1

Tuscany tour

The Tuscany tour ended up ranking above Pompeii for me. I loved the drive between the cities almost as much as some of the stops. There was a lot of beautiful countryside to look at along the way.

The winery was before Siena. It was decent overall, and most of the wine was good. One was the weakest wine of the trip; not bad, it just needed food to help carry the flavor. We bought gold-aged balsamic vinegar there. Truthfully, I did not really know whether I liked balsamic before this trip, but after trying it again at home, I can confirm that this one is divine.

Shiloh and Jordyn on the Tuscany tour bus
Some of the beautiful Tuscan countryside we saw
Tuscan countryside viewed through trees at the winery
The view from a hike Jordyn found in Siena 

Siena was our favorite stop. We skipped the cathedral and had about three hours to explore, which was enough time to actually enjoy the city. Jordyn found a path that overlooked one of the gates and the Tuscan countryside. A fair bit of the joy came from wandering and finding that view.

San Gimignano was good too, although the hills made it more tiring. Monteriggioni was the weak point. We were given forty minutes there and had seen basically everything after twenty.

Shiloh beneath the towers of San Gimignano
San Gimignano and its hill tax
Shiloh and Jordyn on a narrow street in Siena
Wandering Siena
Shiloh and Jordyn overlooking Siena and the surrounding countrysideMonteriggioni

Day 8

Wednesday, September 2

A slower day in Florence

This was mostly an exploration day. We wandered for a while, then went back to the hotel during the hottest part of the day, which became fairly common during the trip.

Later, we went to Piazzale Michelangelo. It was awesome, but crowded. Several proposals and a couple wedding ceremonies seemed to occur on the steps that we started our excursion on, but later moved from to get a closer view of the city.

Shiloh and Jordyn outside the Fortezza da Basso
Exploring Florence
Small piece of street art in Florence
Something found will wandering
Shiloh and Jordyn among the crowd at Piazzale Michelangelo
The view at Piazzale Michelangelo

We spent about half an hour watching a pigeon search for food while collaboratively narrating its thoughts. Not particularly important, but it is one of those random things I will remember.

Day 9

Thursday, September 3

Accademia, Bargello, and shopping

By Florence, the museums were starting to run together. Jordyn described the problem well: objects can lose the purpose they originally served when they are put behind glass, like displaying ordinary dishes. After the Vatican’s visual overload, we pared Florence down to the Accademia, Uffizi, and a short Bargello visit.

David was my favorite part of the Accademia. We also went through the musical-instrument gallery, where Jordyn liked the hurdy-gurdy. We skipped most of the rest.

Michelangelo's David beneath the Accademia dome
The clear Accademia favorite
Historic musical instruments displayed at the Accademia
The museum also showcased some art students' final work

I liked the statues at the Bargello, but by then we were saturated with museums. A short visit was enough.

After learning that the leather market was now saturated with low-quality products, we went to Benheart instead. I found a wallet, and Jordyn bought a jacket after some convincing.

The exterior of Santa Croce in Florence
Santa Croce from outside
Shiloh and Jordyn at dinner in FlorenceDate night and attempt number 2 for Florentine steak

Day 10

Friday, September 4

Uffizi and pizza class

The Uffizi was good, but overwhelming. No artist besides Caravaggio left a distinct impression. His Medusa caused a visceral reaction, which was probably the point of the piece.

Jordyn and I narrated and laughed at some of the other paintings, which made the museum more enjoyable. We also picked up cat versions of Michelangelo and Leonardo da Vinci as magnets for my sisters-in-law.

Paintings displayed in the Uffizi Gallery
Inside the Uffizi
Caravaggio's Medusa at the Uffizi GalleryThe Caravaggio that got an immediate reaction
Shiloh and Jordyn by a fountain in Florence
Back outside afterward

The Tuscan-farm cooking class that evening was much more hands-on. “Spank the baby” is a phrase we learned during the process because the instructors called the little dough balls babies. We named ours Dylan and Luna.

I volunteered to help make the sauce. My basil was uniformly shredded, but it took longer than everyone else’s, which made Jordyn laugh.

Pizza dough takes two days to make, so they had pieces prepared at different stages to show us the whole process. We chose our own toppings and tried things I would not normally put on pizza, including zucchini. All of the toppings worked. The pizza’s structural integrity did not.

We made the gelato there too.

Bottle of wine during the Tuscan cooking class
Class started off strong with a welcome drink and pizza slice
Shiloh working with pizza dough during the class
Precision shredding the basil
Shiloh and Jordyn preparing pizzas
Stretching the dough babies

Day 11

Saturday, September 5

On to Venice

B&B Firenze Cittadella 8 had a comfortable king bed, a tiny elevator, a tiny bathroom with a pocket door, and air conditioning that worked almost too well. The location, near the train station, was helpful for all the excursions we did in Tuscany.

Next stopVenice →