From October 6–21, Carrie and I will be traveling with her parents and sister to Italy. We’ll be staying just outside Florence near the village of Montespertoli, tucked into a villa in the countryside.
Our plan? See as much art as possible, of course. Florence alone offers enough to keep any art lover busy for a lifetime—The Uffizi, Accademia (hello, Michelangelo’s David), the Duomo, Santa Croce, and the Bargello. Beyond Florence, we’re hoping to explore hill towns and castles scattered across Tuscany.
I’ve been brushing up on my Italian during my commute. At this point my biggest accomplishment is being able to say, “Non parlo molto bene” almost perfectly. I’m also reading Renaissance Florence by Gene A. Brucker to give myself a little historical grounding before walking the same streets where so much of Western art was born.
I know many of you have spent time in Tuscany. What advice do you have? What sights, experiences, or practical tips should we make sure not to miss? They don’t all have to be art-related—I’m just as eager to hear about the small villages, the food, and those hidden corners you only discover by wandering.
On the blog front, I’ve banked and scheduled posts so the art business content will continue while I’m away. I’ll also try to share some of our travel impressions as we go.
Looking forward to your suggestions—drop your Tuscany wisdom in the comments!
As an art lover, you can’t spend too much time in Florence. Soak up every moment of art. I brushed up on my italian too, and it was completely unnecessary. Almost everyone speaks english.
Don’t forget to stand on a bridge over the Arno and remember what Mark Twain wrote about it. “It would be a very plausible river if they would pump some water into it. They all call it a river, and they honestly think it is a river, do these dark and bloody Florentines. They even help out the delusion by building bridges over it. I do not see why they are too good to wade.”
Have a wonderful time, Jason ! Lots to see, I bet !!
We spent two summers in Italy a number of years ago. I love Italy! My series, Riccardi d’Italia Is based on our trips and what we saw. I would go anywhere and everywhere. Just explore, go to the small towns. There is also great shopping! You should consider getting tickets for museums and the tourist things that you want to go see. We did all the tourist stuff that you mentioned. But our favorite thing to do would just be wandering around going where our feet take us. Tuscany is wonderful and so beautiful this time of year. Should go to a winery in Tuscany. Hopefully you’re going to go to Rome as well and hopefully Venice. The Amalfi coast is gorgeous. I love everything in Italy. You will have a great time!
In Rome, Trattoria 4 Leoni has a pear pasta (invented there) which should not be missed. Their Florentine steak gets great reviews as well. The cafe at the Pitti Palace is a nice place to have an aperitif at the end of the day.
If you make it to Sienna, I had the best meal of my life at La Taverna di San Giuseppe (ribeye with peppercorn sauce). Warm, lively atmosphere, with an inviting stairs down to their cheese cellar.
In Cortona, we stumbled on La Bucaccia – Da Romano, where we had an exceptional lunch. The archeological museum there is interesting.
Prepare to spend a few days in the Uffizi Gallery. Buy your tickets online and avoid the lineup then just show up and go through the side door.
The best advice I can give you is: don’t drive! Public transport is much better. Shanks mare even better. Have fun.
Hey, Jason!
Have an art-filled trip! Chris and I will be in Italy from Oct. 17-28. Land in Milan, head to Venice, take a scenic train day-trip into Switzerland, back to Venice, Florence a couple of days, then Rome. Can’t wait!
When you are in Florewnce, you will know of course all the major tourist attractions, so no need to repeat all of that. But make sure not to skip Piazzale Michelangelo. We did not go there during our first couple visits, because I thought – I have no interest to see just another copy of Michelangelo’s David. But when we finally got there, we discovered that there is this incredible view of the city of Florence. Not to miss for sure!
Thank you for the reference to the book, I will check it out!
That is the infamous postcard view by day and at twilight. Also be sure to see the Ponte Vecchio as the sun rises and sets.
Best restaurants are often the ones where you go down in a basement rather than up for a view. Restaurants close after lunch and reopen for dinner, but there are snack bars for between those meals. Most shops close for lunch and reopen later, and many stay open for the evening passagiata.
There is only one bookseller that sells English language material (I forgot the name). Shop the Mercado Centrale and the leather market for quality shoes, bags and jackets. Enjoy!!
The most interesting and unusual place I went in Florence was Museo della Specola (Natural History Museum) to see the wax anatomical castings.
Location: Via Romana, 17, near the Pitti Palace.
https://www.sma.unifi.it/index.php?module=CMpro&func=viewpage&pageid=387&newlang=eng
Enjoy your trip!
Check out the Rick Steves website. Not only are his guidebooks excellent, but the site has a travel forum where you can see recent posts from travelers. Florence is great. Even the food in touristy spots is great (at least it was when I was there 25 years ago).
St. Miniato al Monte – a monastery on a hill above the Piazzale Michelangelo. Go for evensong in the late afternoon to hear the monks sing. Check out the cemetery behind it.
Fisesole , a hill town outside Florence with Roman ruins. Can be accessed by the city buses. Beautiful.
Lucca, a small town nearby with original Renaissance city wall
Boboli Gardens and Giardino Bardini garden
La Specola Museum – biological collections and quirky and cool
Great place to see a movie – Giunti Odeon Theater
Our tour guide in Florence suggested that we go to Carrara for a marble quarry tour which was where Michelangelo sourced his marble. Unfortunately, we were unable to go but it seemed like it would be an amazing place to visit. The Florentine steaks are picture worthy and delicious. We also had a tour and tasting at a sheep farm in Tuscany where they make Pecorino cheese, Fattoria Pianporcino. It’s not too far from the lovely hilltop town of Pienza. It is special just to bask in the plazas people watching with a beverage in hand. One of my favorite things about Italy – the people. They are friendly and enjoy engaging in conversation. You will have a fabulous time! I look forward to hearing about your adventures.
There is so much to see and do there. Whenever possible get your tickets in advance to save time. You’ve listed sone of the big attractions already. I would add the Duomo museum (near the Duomo) and the Pitti Palace (which looks like a big fortress from the outside but (as with so many places in Italy) contains treasures. Also, the Medeci Chapels (https://en.m.wikipedia.org/wiki/Medici_Chapels). It is not self-indulgent to have gelato every day. Be brave with your Italian – you only learn by making mistakes. Have a wonderful time!
Be sure to visit the town of San Gimignano, as well as the villages in Cinque Terre. They are both a day trip from Florence and totally worth it!
Happy traveling!
Lu
Have a wonderful trip!! I’ve had the good fortune to be in Florence 3 times, but it sounds like you’re hitting the important highlights. Botticelli took my breath away, at the Uffizi seeing it in person was a revelation. Medici Chapel, Pitti Palace if you can fit it in. Just walking the streets and realizing this is living history. A souvenir I bought on our last trip was from a pen shop on Via Cavour 43r Firenze, Casa Della Stilographica.The pen I purchased wasn’t too expensive, but turned to be a Peneider, which has been made in Florence for over 200 years. (Just random chance that I selected it) Just brings back all the great memories. Just an idea… Lucca is a wonderful medieval, walled city if you have the chance to venture around Tuscany.
Have the veal.
We enjoyed visiting these two sites in Modena, as a change of pace from the art museums:
1 – Acetaia Villa San Donnino is a family-run producer of traditional balsamic vinegar. Located in a beautiful Art Nouveau villa built in 1910, designed by Lieutenant Claudio San Donino and adorned with frescoes and decorations by Aroldo Bonzagni, this acetaia offers a truly unique experience. Visitors can enjoy guided tours that include a walkthrough of the production facilities, an introduction to the balsamic vinegar production process, and tastings of various products.
2 – And we loved Casa Museo, Luciano Pavarotti’s home museum in Modena
http://www.casamuseolucianopavarotti.it
Have a fabulous trip!
One of my favorite places! All of Tuscany is beautiful. Spent many weeks in Tuscany and suggest Arezzo, Sienna and Orvieto as some great side trips. Also, the Cinque Terre is just a 2.5 hour easy train ride away and worth every minute. I am actually in Italy (Florence, Vernazza and Piedmont) in October as well! Hope your trip is fabulous. Don’t miss the gelato!
Museo dell’Opificio delle Pietre Dure — small, features inlaid semi-precious
stonework (fabulous)
Museo dell’Opera del Duomo – an engineer’s delight, shows how the cathedral
dome was built
The Duomo itself — by all means, climb to the top!
Il Corridoio Vasariano — not generally open to the public, a “secret” passage that
goes from the Uffizi to the Pitti Palace, above the Ponte Vecchio, lined with
artists’; self-portraits
Bargello — sculpture museum; small, intimate, not massive like the Uffizi
Vivoli gelato — legendary, though there are worthy competitors, including
Badiani
Boboli Gardens — behind the Pitti Palace
Forte di Belvedere — massive stone fort overlooking the city from Oltr’Arno
(other side of the Arno)
San Miniato al Monte — near Forte di B, smaller church, della Robbia ceramics,
lovely
Mercato Centrale — not just the stalls lining the streets, but the interior of the
market building itself, chock-a-block with gory meats, smelly cheeses, and
gorgeous produce (and it’s a lovely metal building)
Accademmia delle Belle Arti — never mind the David, admire the slaves, half-
emerging from their blocks of marble; they show what sculpture is all about!
Fiesole — small town above Florence (opposite San Miniato, etc.); good, humble
restaurant there used to be (many years ago!) Da Il Lordo, right on the main
piazza
Villa Gamberaia — not too far from Fiesole, wonderful gardens
SO MANY GOOD SUGGESTIONS, i CAN’T ADD ANY…EXCEPT, IF IT SUDDENLY RAINS ABOUT 2 PM DON’T BE SURPRISED! It doesn’t last long and all the outside lineups disappear. My party of 3 walked into the Duomo with no wait and pretty well had the place to ourselves while the rain pelted down for about 1/2 hour. I love Florence, such a relief from the madness of Rome. (Which was pretty cool) It rained there about 2pm as well.
When we first visited Florence, many years ago, one of the most memorable occurrences was in the Duomo. If you go around behind the main altar, there is a stairway down to the Medici tombs. In the middle of the landing was a Pieta, by Michelangelo.
Other comments are so true, the people are the nicest in all of Europe.
Another must see is Santa Maria Della Nova, near the train station. The art work in here is incredible.
check out the murano glass blowers studios on the islands outside florence. 13th century to the present. can even try your hand at it. some of the most fantastic creations you can think of made of glass.
So many great suggestions people have made. I will just add one for your wife. Walter Moretti has a small leather shop near theater (I think!) Anyway you can get beautiful handmade leather purses, wallets, and belts for very good prices. And Walter is so charming! A great experience!
That is a fantastic starting point! You’ve captured the historical and literary significance perfectly. To make it more persuasive and appealing to an “art gallery friend,” we should add details about Volterra’s artistic heritage, unique atmosphere, and contemporary art scene (especially the local alabaster craft), connecting it directly to his professional interests.
Here is a persuasive reply, incorporating your start and building on it:
“You will be near a wonderful town called Volterra—you absolutely must go!
It’s famous for its many fine necropolis ruins and the phenomenal Etruscan Museum (Museo Etrusco Guarnacci), which offers an incredible look into one of the most advanced civilizations of the ancient world. You can practically feel the history in the stones.
As an art gallery friend, you’ll particularly appreciate two things:
* The Alabaster Workshops: Volterra is the world capital of alabaster carving. The town is full of small, family-run artisan shops where you can watch sculptors and artists turn this beautiful, translucent stone into contemporary and traditional art objects. It’s a wonderful place to see a living craft tradition.
* The Atmosphere: Unlike tourist-choked Florence, Volterra is a truly authentic Tuscan hill town. Its walled, medieval core is stunning, offering quiet streets, dramatic views, and a sense of timelessness that is truly inspiring.
Plus, literary history adds another layer: D. H. Lawrence wrote Etruscan Places while staying in the area, a beautiful testament to the region’s enduring mystery and appeal.
Make sure you spend at least an afternoon wandering the steep streets and dipping into the artisan studios—it’s a memorable and highly underrated spot.”
With help from Gemini AI!
How wonderful enjoy your trip. Florence was the second stop for me on my honeymoon in 2001. The high point for me was seeing Alessandro Birth of Venus and Prima Vera in the Uffizi. Sipping Limoncello in a cafe with prosciutto. The Palazzo Medici, the Ponte Vecchio…. you can’t go wrong. We also did a day trip to Pisa.
The Museum of Anthropology (Ethnoloy) has a fabulous collection of artifacts the Italians acquired from their travels around the world many many years ago.
I could hardly believe I was nearly the only person in the museum during the many hours I spent there.
Absolutely fantastic!
Grab some great reading for quite times. Laura Morelli is a historical fiction writer who spins wonderful tales about art, love and intrigue as well many factual guides about travels through Italy. Night Portrait was the first of her books I read about Leonardo Da Vinci and also the second world war art thefts. A worthwhile and informative read as well. I have yet to take a journey to Italy but would absolutely check out her guide books.
Wow, great tips!
There’s a good book called The Marriage Portrait, a historical novel set in the Renaissance era & involves the Medicis, art & intrigue.
Generally, pack light & with a little style for Italy.
I like staying a minimum of 2 nights anywhere.
We did a fun cooking class in Tuscany — I can get the name if you want. Driving was challenging & we were late for the class as we got lost even with GPS.
Yes! Learn some Italian! It’s appreciated.
Ciao! KFaub
Try Lamole di Lamole restaurant. The chef is incredible and they will do a tasting and pairing of their foods with their excellent wines.
Casalinga
Have breakfast at Gilli’s!! You’ll love Florence!
Keep your wife off of the Gold Bridge…..
Safe Travels.
I’ve only been to Florence in books and stories from people who have gpne.
You mentioned this was a family trip. And those I have done.
Since you can’t see and do everything, my suggestion is to be mindful of the fact of spending family time. It’s just in a new and wonderful; setting. (no reminders in your case)
Sidewalk cafes, spur of the moment, are always fun as is that off the path place the locals know and covet.
A great dinner in a great space where time stands still and you are perfectly served by astute, proactive, impeccable, and barely visible but attentive servers will be as memorable as any art museum, if my experience in NYC is any measure.
Hi, I live in Rome and love to visit Florence when I can.
It looks like you have the museums covered. Early October is delightful in Italy.
Check out the podcast, Rebuilding the Renaissance by Rocky Roggerio, for compact art history lessons.
There are so many good restaurants and some that cater mostly to tourists. Italian food is highly regional. I avoid places in Florence/Tuscany that serve carbonara, a distinctly Roman dish. Also, don’t be afraid of the wild boar, a specialty of Tuscany and Umbria. Most of all, be Italian enough to take your time and enjoy the experience. I prefer to see less and enjoy it more.
https://www.thelocal.it/20250923/key-dates-the-transport-strikes-to-expect-in-italy-in-october-2025
It looks like you will avoid the transportation strikes that are frequently a problem.
Pack light, then pack lighter. 🙂 Hill towns are hilly which means cobblestone streets and marble stairs.
Good morning, Jason, I’ve been following you for a while, and I’m Italian (sorry for the brutal Google translation). What can I say? Not only is Tuscany worth it, but all of Italy. Even in my little town near Milan, we have a gem, Villa Visconti Borromeo Arese Litta. In Tuscany, the marble quarries in Carrara are also worth a visit!
Once we found it, we visited the Central market in Florence every day, coming away with fresh bread, and enjoying a sandwich. (with or without the tour in this link.)
https://www.airbnb.com/experiences/6094940?c=.pi0.pk21690586450_168862475244&gad_source=1&gad_campaignid=21690586450&gbraid=0AAA
We also found Rick Steve’s audio guide indispensable. We both listened at the same time and shared the experience.
Don’t miss this: https://ilgiardinodeitarocchi.it/en/
Not art related so much, but some of the best olive oil, people, and food are in Montisi and Castelmuzio. I used to teach workshops there (Montisi) every fall for 7 years; miss it. I once visited a design house in Florence with a friend and the owner told us this region (referring to Montisi) was the “True Tuscany.” Might be too far off your route, but I felt the need to mention it. Have a wonderful trip.
do go up to Fiesole and visit the Etruscan Museum there and other such parts. there are some nice restaurants thereabouts. take bus # 7 from town. mid way up there is a nice pizza place at San Domenico. get reservations for museum where ever possible.
Fantastic! Tips? Enjoy, but be prepared to walk your socks off. Wear really comfortable shoes. Also get tickets ahead for all the biggest attractions. Our travel agent got our group, and my personal agent got me Skip the Line entry tickets. Probably cost a little more but well worth it. Otherwise you spend your entire vacation in lines. Some of those mean getting there a little early to the venue. Some small tour groups also saves you steps and from having to rent a car. Most guides are well schooled on lots of history and hidden treasures to see. Check the weather there I was there last of Sept. first of Oct. and it was really hot. Make sure your hotel has air. None of the museums have air or even fans, so expect to sweat.
Even with all that it was a trip of a lifetime for me. Something I will never forget. I stayed over from my group stay and also hit Venice and Rome. So glad I did.
Have a wonderful time!
Susan McKinney
You already have wonderful suggestions. Do not miss the Museo San Marco, which has the largest collection in the world of Ghirlandaio works. It is a lovely place, predictably, on the Piazza San Marco. And a couple of people have suggested the view from the hill at Piazza Michelangeliolo, coupled with the monks chanting in late afternoon. This is truly extraordinary.MG
Jason, you’ll have a ball.Florence won’t be as crowded as it before mid-september. Northern Italian cuisine is amazing — it you didn’t know, the Italians taught the French how to cook. (true)
La Spezia with its harbor is worth a visit, and so is Cararra, where the marble comes from. The Cinque Terrra vilages are worth a day, but are a distance from Florence, though trains are frequent.
Fra Angelico at San Marco.
A short train ride away, to Arezzo for Piero della Francesca’s
“Legend of the True Cross”. a three story fresco.
Hi Jason. I was just in my teens when I visited Italy with my parents, but one thing I do remember about Florence was a Leather Factory we visited. They offered a tour of the facility and explained the entire process of leather production, tanning, and the making of various leather items. (They also offered an English-speaking version of the tour.) I remember being fascinated by the tour. And they also had reasonably-priced leather items in the gift shop. It was a few decades ago, so I don’t remember any additional details. Florence, however, was noted for leather production, so I’m sure there are a number of factories still in existence that offer similar tours. Sorry, I can’t offer more details.
Florence is my most favorite city in the world! It is a lovely mix of old and new worlds and just has a magical feel to it. When were visited we took a cooking class from the Accidental Tourist and learned how to make pasta from scratch and had a private tour in a Tuscany winery. It was a delightful afternoon and evening and we still use the recipes and techniques learned often. Here is a link to their information: https://www.accidentaltourist.com/
They even picked us up and drove us into the Tuscany Hills for the class. Really one of my best days ever! Enjoy your trip and drink some exceptional wine!
In Florence we had gelato at Que Perche. A wonderful treat near the Uffizi, etc. Get up early and get into Florence before everyone is awake. It’s like magic when you do that. We had early tickets for the Uffizi and got into the city well before our admission time. It’s kind of like having the place to yourself for a while. It was breathtaking. Then when we emerged from the Uffizi (we had lunch at their cafe), our breath was taken away again by the crowds where there had been peace a few hours earlier. That’s when we headed for gelato.
We loved Siena. There are three places to get gelato–two are on the “main” street in the old town, but the good one is down and around and out of the way. We learned of them from Rick Steves’ guide book. We loved walking around the town and into the large historic piazza where the red buildings are built with bricks the color of Burnt Siena–imagine that! We visited the Duomo of Siena. Inside and out. It’s marvelous. The historic buildings and the winding streets are delightful to the eyes.
We rented a car for our trip. We stayed in Siena (parked at the train station and walked or took a taxi from the station to our hotel in the old town) and drove to Florence (parked in the big parking lot on the outskirts of Florence and took the tram into the city center and then walked to the magical old part of Florence). Someone tried to scam us on the road. While we drove through a tunnel from Siena to Florence, someone threw something against our car that sounded like a big rock hit the car. We discussed it and saw nothing on the windshield and kept going. Later, a car came by and the driver and passenger pointed at our car as if something was wrong. They pulled off at a pull out. We did, too. The man came to the passenger window and talked about a Boom. He showed us a broken piece on the driver side mirror and wanted thousands of dollars. He showed us stuff on his phone. He was in a hurry because his wife was having a baby, etc. I started asking questions, wanted to see his wife, looked at our passenger side mirror which had a smear of something greasy on it (not paint from his car), and asked more questions. The man ran from us, jumped in his car and drove on. My husband and looked at each other, shrugged, and continued on. A bit later, we saw the “damaged” car in a pullout waving for us to pull over. We kept going. When we got to the parking lot at Florence, we checked the car and found a perfectly round dent on the passenger side, so we’re guessing they threw a ball bearing to hit the car and start their scam. We went on with our day and never saw or heard from them again. Fortunately, nothing worse happened and we have a story to tell. If I had to do it again, I would not have stopped where the other vehicle was, but I might have still stopped where were alone or in a rest area to inspect the car for damage, but that was part of the thieves’ plan. It must work for them because it took quite a bit of planning. So . . . be aware.
Enjoy your trip and I can’t wait to see what you saw.
Lots of good suggestions already, Jason. I would second Siena and San Gimignano. My advice on the Uffizi – it’s so big I find it best to focus in advance on one area of special interest, and maybe do multiple visits. Other you get mental constipation trying to take it all in. The view from the top of the Duomo is also special.
Buongiorno!
Piazzale Michelangelo was one of my favorite places to walk to from town — home to a magnificent bronze replica of Michelangelo’s David. From this iconic terrace, you can enjoy a refreshing drink while gazing over the city’s breathtaking skyline. It’s truly one of the most famous panoramic viewpoints in Florence, Italy 🇮🇹.
Just below the piazzale lies a romantic, picturesque rose garden, complete with a small Japanese Friendship Trail — a peaceful place to wander and discover a unique perspective of the Duomo.
And of course, the Uffizi Gallery is an absolute must-see.
Have a wonderful trip — arrivederci! 🌸
Buon giorno Jason,
If you are still reading these wonderful suggestions, I would like to add another one. In addition to art, food, wine, music, leather, and so much more, it is the people you should try to spend time with.
Take your time and chat with Florentines. They are charming, and will tell you a lot about everything.
To get the most out of your trip, I would focus on Florence and surroundings. No need to go to Rome. The Chianti region is very special.
I have lived two years as an art student in Florence, and returned as a tourist several times.
Buon viaggio !
Wonderful suggestions, everyone — so many fabulous places to see! I’ll also be in Florence, participating as one of the artists at the XV Florence Biennale from October 18–26, 2025. It would be lovely to meet in person if you happen to visit the Biennale during that time.
There’s one little wonder that hasn’t been mentioned yet and is truly worth seeing: Michelangelo’s drawings on the walls of a “vault” beneath the Medici Chapel. It has only recently been opened to the public, with access limited to just four visitors at a time. The entrance is through the New Sacristy — an unforgettable experience for any art lover.
Michelangelo and Leonardo Davincis tombs are in Florence and are right next to each other in a church at a square (sorry cant remember where exactly) it was really interesting to see their final resting places and I had a spiritual experience after visiting their tombs that evening, I swear Michelangelo’s spirit was walking me through Florence showing me his David and other works the rest of the stay there. Also climb the bell tower at the green marble church Florence Cathedral, the view is great! San Gimigano is beautiful and take the funiculari train ride up the hill to the family owned restaurant at the top, OMG the homemade pasta pappardelle with asparagus blue cheese cream sauce, was the best pasta I ever had! Drink the table wine, everywhere, so amazing!
Ooops, the Finiculari is in the town of Montecatini Terme, Italy, about 25 mins away from Florence! Not in San Gimigano, but San Gimigano is a beautiful walking town!