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, 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 stop.
Shiloh holding a glass of rosé from a wine window
Rosé from the wine window.

The group was good too. We kept running into Tom and Carrie during the rest of our time in Florence. We also saw a couple from the Rome food tour twice, which was unexpected.

Shiloh and Jordyn beside the Arno River at night
Our first Florence 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. 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
Out of Florence for the day.
Tuscan countryside viewed through trees at the winery
The view from the winery.

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 countryside
The view Jordyn found.

Day 8

Wednesday, September 2

A slower day in Florence

This was mostly an exploration day. We skipped the Medici Chapels and did not go inside either church. 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. A large tree partially blocked the view from where we were sitting, although it did not really detract from it.

Shiloh and Jordyn outside the Fortezza da Basso
Exploring Florence.
Small piece of street art in Florence
Something found while wandering.
Shiloh and Jordyn among the crowd at Piazzale Michelangelo
The crowd 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 winner.
Historic musical instruments displayed at the Accademia
The musical-instrument gallery.

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 Florence
Dinner after a museum-heavy day.

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 Gallery
The 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
Wine with the class.
Shiloh working with pizza dough during the class
Working with one of the dough babies.
Shiloh and Jordyn preparing pizzas
Making the pizzas.

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 walls were very thin and the “quiet hours” covered about half the day, so we did a lot of whispering. The owner was friendly and helpful, but also a little stingy. The guest kitchen had coffee options but no spoons.

The location was reasonable, but I am not sure I would stay there again. We packed up and took the train to Venice.

Next stopVenice →