Skip to main content
Travel InspirationItalyTravel Tales

Tuscany Tour Diary – Tuscany Staycation

We are incredibly grateful for our talented, frequent tour guest Khajha Rogers to give us permission to use her photos and perspective on our Tuscany Staycation in this Tuscany tour diary. Make sure you don’t miss reading all her captions! Hopefully you will enjoy the experience of the tour through her eyes as much as we have!

October 8th

Day 1 of our tour, the Adventures with Sarah Tuscany Staycation, was trains and automobiles and food and views!

Lunch and architecture in Monticchiello:

I love traveling by rail and there’s just something about a small platform
And in black and white, they are even better
tuscany tour diary - tuscany staycation 2023
The antipasti at lunch was so fresh and so wonderful.
Spin around, point and shoot, and get the most picturesque shots in any direction at all.
Red door, red salvia plant.
Another red-doored home in Monticchiello.
Enormous white cat, asleep in the shade near the cistern.
You know it’s charming because of the cute bicycle along the stone wall.
This is the city gate at Monticchiello, dripping in caper plants.
One of our first stops was Monticchiello for lunch and this view!
The peak of the former volcano, Monte Amiata, peeking out to the right.

Next stop, the Etruscan museum in Chianciano. Roberto, our guide/host, brings so much to this stop. Never, ever underestimate having a guide during key points in your travels. A passionate guide will bring so much to your experience as you watch the subject matter spring to life which is especially helpful when talking about something like the Etruscans, who most of us never studied in school.

This small poster depicts what Diana looked like on her chariot, reins in hand.
We didn’t discuss these particular artifacts, on display to the left of Thesan, but I assume by the way they’re displayed that they are related.
Thesan, the goddess of the dawn.
“Etruscan Museum of Chianciano Terme, in Tuscany. It had been found in 1986 by young people from the local archaeological association.”
Sarcophagus and other burial items. The reflection at the top of the photo is from another sarcophagus just across the way that seems to float nicely above the scene.
Cinerary Urn Statue of a mother and child. Chianciano, 5th century BCE
Not much bronze statuary remains from this period, as the bronze was melted down later for weapons and so on. But this arm of Diana, still holding the chariot reins, is really something. This artisan clearly understood the musculature involved in that grip.

My friends, we arrived at Roberto and Patti’s home/B&B outside of Asciano as the sun was setting and the view has absolutely blown my head off of my shoulders.

Podere Casalciccia is a joy and a delight at all hours of the day but this shot of the Milky Way last night was a showstopper!
Dinner was in the sweet small town of Asciano. I could tell you about the pasta with kale/sausage or the roasted chicken but I actually want to chat about the antipasto. It was a toasted piece of bread with cheese melted over it and so many slices of what was, for all intents and purposes, very thinly sliced bacon.
tuscany tour diary - tuscany staycation 2023
So, anyhow this is my view for a few days, the clay hills of Tuscany.

October 9th

Day 2 of our Adventures with Sarah Tuscany Staycation was SO GOOD.

Sunrise photos, a visit to Monte Oliveto Abbey, a short stop. In the incredibly cute village of Lucignano D’Asso, lunch in Chiusure, afternoon free, cooking dinner with a neighbor & our hosts’ son.

Someone has shed their exoskeleton.
Sunrise from the house, outside the kitchen.
Sunrise from Podere Casalciccia, just a few steps outside our bedroom door.
Monte Oliveto Abbey. Benedictine monks live here
The whole room is wonderfully decorated but I especially love the cat on the wooden piece in the center. Roberto mentioned that they had to move it to this room that you can’t go into because people were touching the cat to feel the muscles that the artist created by using different thicknesses of wood.
I really love the sort of black and white looking frescoes.
That’s the Colosseum in Rome in wood. And to the right, the tambourine gets darker where it’s tucked further into the cabinet.
The pictures along the choir boxes are all in wood. Truly amazing work. The lighting was not great but these shots give you an idea.
Only wood!!
Allegedly, there’s a lesson here about lust and carnal pleasures and getting struck down for desiring the flesh. I just think her wings are gorgeous!
This is a self portrait of Sodoma, complete with badgers on leashes.
The artist, Sodoma, included Castel Sant’Angelo and the Tiber river into this panel.
This is an unfinished fresco, more or less the sketch layer that goes on first to inform the artist throughout the rest of the process.
Oh, cats and dogs
One of the interior courtyards.
Contrast of sky and terra cotta.
So many gorgeous lines.
I do love a long, arched corridor.
Lucignano D’Asso, the land that time forgot. Although I didn’t snag a picture of it, there are still the remains of some of the fascist activity in the area and the town was basically abandoned by the 50s. (I didn’t make great notes this day so I might have some details fuzzy.)
Crazy cat lady, doing as she does in Italy.
The market was closed but this would’ve been a great lunch spot.
Doors. Ceilings. Cats. Goats. Italy is full of my favorite subjects.
The most picturesque little hill town.
Dopolavoro (literally after work).
This is the spot you go at the end of the day to gather and the sign is still there.
I’m running out of captions for all of these doors and windows.
Around every corner, another scene worth capturing.
Our lunch was in Chiusure and the approach was quite uphill but the views made it seem easier. The building peeking out of the trees was a small castle and is now a retirement home.
A variety of old bottles of Chianti. And a sign that I should translate.
Our restaurant was full of trinkets and whatnot and I loved these 2 shelves.
Chiusure is known for artichokes, they have a festival each year. Most of the buildings have artichoke-shaped planters outside.
Clay hills in the background, smiles up front.
Not kidding, pals, the house at the end of the road is where we are staying. 
The band is back together and to celebrate, we’re enjoying the bottle of rosato that we bought at Villa Calcinaia.
This kitty is Clyde. He can’t be let inside or else he poops in the house plants.

October 10th

On day 3 of our Adventures with Sarah Tuscany Staycation, we visited Siena and Madonna Bella winery, had a great walk and a lively dinner. Each day is better than the one before.

Siena was more gorgeous than I recalled!
On the way to the cathedral, we detoured to the entry to the road that goes under the oldest hospital in Europe (from around 1090). This road used to be to bring in supplies and whatnot
The whole gang with our Sienese guide, heading up-up-uphill to visit the cathedral.
The contrada that won the Palio in August was the goose (Italian = oca), so their flags (red, white and green with a goose) were displayed afterwards, staying up through the big celebration which was just this month.
The gothic arches on the outside of the Fontebranda. There are actually 3, one in front of each pool (one for drinking, one for animals to drink and the last was run off from the middle one that the tanners and dyers and millers used.)
Siena has no river so from the 13th century, it collected rain water to use for drinking and milling and everything else. This one is the oldest and called Fontebranda.
Siena’s cathedral is a real treat. Outside is dripping in gold and arches and statues.
Inside is a total mindboggle.
That dome is no joke!
The floors are often covered with protective panels but we’re fortunate to be here at this time, when they are uncovered. The wild thing is, although it’s a church, it’s not all religious subject matter. Rather, there are philosophers and statements about fortune and so on.
The statue of the Three Graces (Zeus’ daughters) in the middle of the room was placed there in the 15th century at the request of the Pope, to the protests of some who didn’t think it appropriate to put nudes in the church.
In addition to the frescoes inside the Piccolomini Library, there are gorgeously illuminated choir books that are a bit ignored while most tourists are looking up!
These dogs are lapping up spilled blood.
Nicola Pisano’s carved stone pulpit.
This smaller side dome has the sweetest circle of cherubs in the top. They look so playful
Somehow, I only got one shot of the Campo and it’s not even a great one. It gives no perspective at all about the unusual shape of the space but I didn’t find a better angle on our brief visit.
This was the family home of the founder of the Mount Oliveto abbey, he renounced his family’s wealth to follow his spiritual path
Coins and other metal trinkets found on the winery property.
Pottery found as Roberto and his brother were working the land of their winery Madonnabella Siena.
The view from our table at Madonna Bella winery. While other guests tasted wine and ate their lunch on their own, we had Roberto at the head of our table, explaining each wine and chatting with us about the food pairings.
Siena, seen through the branches of an olive tree. Harvest is in another week or so, pressing is immediate and 6 bottles will be shipped to us November 1!
Patti (Roberto’s wife) and the 2 dogs met us for a long walk in the late day. These fields are usually wheat or rapeseed or sunflowers but they are gone for the year and there’s been no rain for 45 or so days.
This area was a sea back in, you know, olden days. Patti says you can find shells and things in these features. They are called biancane.
We walked to the Site Transitoire, created in 1993 by a French artist.
“On the day of the solstice, the sun sets in the opening of the great stone window, creating a truly magical spectacle. The work is located in a quiet area, where art and nature meet, producing an incredible view across the crete senesi.”
This farmhouse seen from the Site Transitoire was another great view.
It was a great walk. So great.
The shadows are getting long.
Late edition to the album so it’s out of order chronologically. This is our intrepid group about 2/3 of the way around our desert loop. Not pictured are the 2 dogs that accompanied us on the journey, who are sleeping in the shade behind the sculpture.
The sun was setting toward the end of our walk.

October 11th

Day 4, Adventures with Sarah Tuscany Staycation and I’ve been on vacation long enough at this point that figuring out the day of the week is tough. ????????‍♀️

Today, we ventured into Florence (a return engagement for mom and I). So glad we did because, while the rest of the group wanted 2 hours to shop in the a.m., we wanted time to visit the Bargello Museum which we didn’t find time for last week on the other staycation.

More street art! There’s some good ones in Florence!
Another Clet Abraham. Appropriate that this guitar wielding one is in front of Hard Rock Cafe.
Roberto took us inside Casa dei Tessuti, which has been in business since 1929.
Casa dei Tessuti, walls and walls of fabric.
These are Versace fabrics

As usual, lunch was a treat but not photographed. Roberto took us to a spot the locals go to where we ate outside, along the Arno river.

It’s in the church called San Salvatore in Ognissanti in Florence.
Just a spot that caught my eye while we were killing time.
One of the old city gates. We entered our lunch spot just underneath the red and white sign in the lower left.
Ciao again Florence!
I asked if we would by chance be going to Piazzale Michelangelo to check out the view and Roberto said no. On the way to lunch, he let me know that he pivoted a little so that he could make it happen! He’s the bees knees!

We had plenty of time to rest at the farmhouse in the late afternoon and I even got to do some laundry in an actual washing machine!

Dinner was amazing with the highlight for me being spinach ravioli in a butter sage sauce, made from scratch by Michele, Patti and Roberto’s son.

Sure, another sunset photo at Podere Casalciccia, perché no?

October 12th

Day 5 of this Adventures with Sarah Tuscany Staycation had some of the best moments so far!

We visited Villa Geggiano. It’s been in the Bandinelli family since the 1500s and we toured the home and garden with Andrea Alessandro Boscu Bianchi Bandinelli, who is quite charming – and very down to earth, for a Count.

Villa Geggiano
Roberto and I, reflected in this aged mirror.
The paper on this book cover is magnificent and so well preserved.
School books in the blue room, full of the most divine calligraphy.
The dining table was a pool table at one point. The pockets were filled in, as you can see.
A small blue velvet diary on the most gorgeous desk.
This is a hot chocolate pot in the ladies sitting room.
This is the kitchen, complete with one of the greatest fireplaces, large enough to sit in
The ballroom.
There was a Pope in Andrea’s family and the plaque above the bed signifies that he slept here.
The wine cellar, seen from the bedroom window.
Andrea, pointing out the humorous subject matter in the vignettes in the ceiling. The walls in this room are painted fabric.
The “fish” the women are fishing for are men. The men are shooting gold coins at the women, who look like hares, to get them.
Oh my gracious, I simply cannot.
Again with the cats and dogs scuffle.
The entryway is entirely painted in outdoor scenes. The child’s toy horse at the end of the hall was given to the family by Ferdinand, the Archduke of Tuscany and was last ridden by Andrea when he was a boy. He accidentally broke off the left ear and no child was allowed to ride it again.
These cabinets look like they were painted yesterday, the colors are so vibrant.

Next up, a lunch stop in San Donato in Poggio at La Toppa. A lovely spread provided by the owner of the restaurant, which has been operating for 50 years this year.

San Donato in Poggio, lovely medieval Hill town. We are between the 2 gates at this entry point. And the arched window to the right is the home of a lovely couple who Roberto knows and they spontaneously invited us inside.
This color!
Someone has a great spot from which to watch the world, small as it is here.
Terra cotta jack-o’-lantern.
The purple glass hanging on this arbor above the street is giving me ideas.
Decoration inside La Toppa, where we had lunch.

Quick stop in Castellina in Chianti to check out some of the town’s fortifications and a lovely drive back home to rest a bit before dinner.

This is Castellina in Chianti and we are just inside the medieval wall here.
This town was bombed in WWII and a portion of this church had to be rebuilt from new stones.

Bonus night sky photos before bed time.

A church in Asciano, where we’ve enjoyed a couple of group dinners.
Top: no filter
Bottom: a little pop
Sunsetting on our farmhouse.

October 13th

Day 6, our last full day of this most wonderful Adventures with Sarah Tuscany Staycation is in the books.

Toadflax, aka wild snapdragon.
I called shotgun in the van today and was thrilled to snag a through-the-windshield shot of the sun through the fog.
More fog, more dewy webs.

Up and out for a drive to Montepulciano with a short orientation walk and then a couple of free hours to explore.

The main square of Montepulciano. The red bricks in a herringbone pattern were outstanding!
Everywhere you look, it’s another gorgeous postcard!
The church is San Biagio, nestled below Montepulciano.
The courtyard of a b&b, owned by a friend of Roberto’s. It’s wild to me that a person can own something like this
2nd best espresso of the whole 2023 trip!! No lie. (Best was at Madonna Bella winery.)
There was a public WC near this church. Literally all I know about it
This crew is a whole lot of fun! I’m going to start a petition to get the Bernicks on one of our tours next year!!
A WATER BOTTLE FILLING STATION WITH FIZZY WATER!!! As I said, Montepulciano was rad.

In case you should run across this machine, there’s a wee button next to where it says frizzante that both starts AND STOPS the flow.
A couple of city gates in our rearview mirror.
I really loved Montepulciano.
The whole lower part of this building was covered in these plaques. I should totally look into whatever that’s about.

Next stop, the most delicious lunch. Then, we had a stroll around Pienza. After a couple of hours to rest at the farmhouse, we had amazing pizza and beers with Roberto and Patti and I think it was one of my favorite dinners!

Playing around with filters again. I’m endlessly amazed at how much data is in the picture even if it looks too dark to get much out of.
High, painted arches make me so happy.
Just inside a city gate at Pienza and above us, a pomegranate tree is absolutely doing its thing.
Inside, the cathedral was so pretty. A mix of gothic and renaissance.
Pienza’s cathedral. Because it was built on clay instead of sandstone, the back half of this church is a meter lower than the rest of the building. The downhill slope was very dramatic.
Castelluccio di Pienza, a fortified castle on the hill above Dopolavoro La Foce, our lunch spot.
Our sweet farmhouse stay is almost over. I love Rome, our final stop this journey, but it sure will be hard to leave this quiet space.

October 14th

Our last wake up at the farm included a sunny morning (day 1 was like this as well but the rest of the days it was socked in with the loveliest fog on the fields.)
The view from the dining room with hot, handmade pastries each a.m., couldn’t be beat.
I’d never seen this painting and we saw the original in the Uffizi and then it ends up above my bed at the farm!
Truly cannot get enough.
Could probably never get enough of these clay hills and the way the shapes change as the sun arcs over.
Such a good view, I couldn’t pick which pic I liked better.

Final day of the Tuscany Staycation. We drove to the Tuscan coast (it has a coast?!) and visited the town of Talamone. Followed by lunch at a campground restaurant (you had to see it; it is beyond description) for the greatest seafood lunch.

So many shades of gorgeous sea water. And in the way distance you can see the island the Costa Concordia ran aground near.
Roberto coaxed us to the bottom of a staircase that ended on the water.
tuscany tour diary - tuscany staycation 2023
This tunnel was awfully long.
Talamone has stunning coastal vistas.
Like I said, the wind was strong. There was a competition for parasurfers (??)
tuscany tour diary - tuscany staycation 2023
Roberto wanted selfies with us and what Roberto wants, he gets!!
Looking back toward the lighthouse. You can see from the flag that the wind was strong.
Thanks, seabird, you improved this shot tenfold!
tuscany tour diary - tuscany staycation 2023

Roberto delivered us to the door of our hotel late in the afternoon. The 4 of us (we’re still with our pals) reconvened for aperitivi. Afterwords, we took a night walk to the big sites and wrapped it all up with our favorite gelato.

(NOTE: this is not part of the Tuscany tour, but Roberto will drop you off in Rome, so you can choose to complete your trip with a tour of the monuments!)

Swoon. This building. I tell ya, it makes my heart race.

It was hard to say goodbye to our hosts, but Rome is such a happy place for me that I can’t be too sad in this moment.

Took A and J to San Francesco church to see the Bernini. Paid 1€ to illuminate it.
The light went out just as I snapped this one. Kind of cool, actually.
Colloseum
Aperitivi at Cambio!
Heading up to the Campidoglio, looking over the forum.
Trevi Fountain
Rome at night is one of my favorite things.
Looking back up the Capitoline Hill.

Tags:

AWS Staff

AWS Staff

This post was published by the Adventures with Sarah team. Click here to find out more about the people that make everything at AWS happen.

Next Post

Recommended For You

packing for sicily agrigento temple ruins ItalySicilyPackingDestinations The Essential Guide to Packing for Sicily Italy

The Essential Guide to Packing for Sicily Italy

AWS Staff
AWS StaffApril 23, 2025
travel to morocco desert camel ride shadows MoroccoTravelTravel InspirationDestinations Morocco 101: Our Essential Tips for Travel to Morocco

Morocco 101: Our Essential Tips for Travel to Morocco

AWS Staff
AWS StaffMarch 12, 2025
packing for sardinia italy rocky beach DestinationsItalySardiniaPacking Our Guide to Packing for Sardinia, Italy

Our Guide to Packing for Sardinia, Italy

AWS Staff
AWS StaffFebruary 25, 2025

Leave a Reply

THE ADVENTURE STARTS NOW.

THE ADVENTURE STARTS NOW.

THE ADVENTURE STARTS NOW.

THE ADVENTURE STARTS NOW.

THE ADVENTURE STARTS NOW.

Amazon
Store

VISIT NOW

Favorite
Travel Bag

VIEW HERE

Partners &
Collaborations

LEARN MORE
HAVE A QUESTION?

We're here to help

CONTACT
Founder and Executive Director

Subscribe to our newsletter for exclusive travel tips, insights, tours promotions and more!

© Adventures with Sarah • Website by WPG

Terms & Conditions

Disclosure