Ultimate Travel Guide To Tuscany Italy’s Most Enchanting Towns

Tuscany Italy Travel Guide

Table of Contents

Tuscany Italy is a land of sprawling vineyards, skinny cypress trees, silvery clusters of olive groves, a sun-tinged villa dotted here and there amidst cascading green hills that fade to purple in the twilight hours. The valleys are vivid with shifting hues of green and yellow, red flowers bloom everywhere, and the distant mountains fade to dusky purple in the evenings. 

Originally home to the mysterious Etruscans, the landscape is steeped in history, and hints of its ancient past remain in the ruins scattered about the region. Medieval walled villages perch atop many of the hills, while Florence remains its pulsing heart, brimming with art and culture (and busloads of tourists).

Pool Castello Banfi Il Borgo Tuscany italy

I don’t believe there’s a “right” or “wrong” way to visit Tuscany Italy; it just depends on your personality. 

Love museums and cathedrals and shopping and don’t mind large crowds? Stay in Florence or just outside of the city. Want to relax and unwind in a quiet valley near vineyards? Opt for a room or villa in Montalcino, particularly the Val d’Orcia region.

Once you’ve settled on a base, exploring the surrounding cities like Siena, Pienza, and Montepulciano is easy since they are all within relatively close driving distance of each other. 


Castello Banfi Il Borgo Tuscany Italy

Suite Castello Banfi il Borgo Tuscany Italy
Doorway to the Suite Poggio all’Oro

Originally built in the 1700s, the Castello Banfi – Il Borgo is now a luxury boutique hotel with 14 rooms, each one carefully renovated and unique. The hotel, restaurants, and winery continue to win awards and accolades, and Wine Enthusiast named it one of the “Top 10 Wine Getaways of 2018.” 

If it’s available, reserve the Castello’s most luxurious room: Suite Poggio all’Oro. It’s a large suite located directly across from the check-in area. Decorated in traditional Tuscan style, the suite offers a king-size bed, two separate sitting areas, two large bathrooms, each containing walk-in rainfall showers, and one a massive soaker tub that you can practically swim in.  

Castello Banfi Il Borgo Tuscany Italy
Castello Banfi Il Borgo Tuscany Italy
Castello Banfi Il Borgo Tuscany Italy
Castello Banfi Il Borgo Tuscany Italy

The room is also a “wine suite,” meaning there is an additional cooler containing rare vintages from Banfi’s Poggio all’Oro Riserva collection. Of course, you have to pay separately for those selections, but you’re given multiple complimentary bottles of wine by simply being guests in the suite.

A free continental breakfast is offered every morning on the terrace adjacent to the heated pool; however, if you’re like me and want to just have a coffee in the room, there is a Nespresso machine as well as hot tea selections.

Castello Banfi Il Borgo Tuscany italy
Castello Banfi Il Borgo Tuscany Italy

The surrounding grounds and vineyards are inviting, and the hotel staff is happy to organize hiking or biking tours, in addition to horseback riding and even hot air ballooning. 

After a long day of touring wineries or nearby villages, unwind in the outdoor heated pool overlooking the vineyard valley.  

Pool Castello Banfi Il Borgo Tuscany italy


Aperitivo Reading Room Castello Banfi Il Borgo Tuscany Italy

Every evening, in the relaxed atmosphere of The Reading Room, complimentary selections of wine and light, savory bites are offered to whet the appetite before dinner. 

Browse various books and old-world maps while you savor a Banfi Brut Prosecco or a glass of rich, earthy Brunello wine made from 100% Sangiovese grapes.  

Reading Room Castello Banfi Il Borgo Tuscany italy
The Reading Room
Maps Reading Room Castello Banfi Il Borgo Tuscany Italy


Dining Castello Banfi Il Borgo Tuscany Italy

The Castello Banfi – Il Borgo offers two on-site restaurants: La Taverna (open only for lunch) and La Sala dei Grappoli (dinner service only).  

La Taverna is casual yet refined. The menu is filled with traditional Tuscan dishes like Ribollita, a hearty soup with naturally leavened Monte Amiata bread, and Banfi extra virgin olive oil. Another traditional dish to try is the Pinci Pasta with Wild Boar Ragout. For information on the menu, click here. 

Dessert La Sala dei Grappoli Tuscany Italy Castello Banfi
Dark Chocolate Dome with Rum and Hazelnuts
Dessert Wine La Sala dei Grappoli TheRoadTaken2
Sample Menu (Subject to Seasonal Changes)

For dinner, there is the exquisite La Sala dei Grappoli, where the chef creates flavor combinations that remind you why cooking is an art. Because we had booked our stay through their website and were staying in the Poggio all’Oro Suite, we were treated to the Chef’s Table Experience, which includes a 5-course dinner paired with Banfi wines. 

In reality, it seemed like there were about 10 courses due to the variety of palate-cleansing bites served in between the courses. Truly impeccable. There were so many creations that I would never have ordered, and yet having tasted them loved them

An eye-opening (taste-opening?) experience. The wine pairings were the perfect complement to every bite, and I can’t remember when I had a more memorable meal. 


Castello Banfi Wine Tuscany Italy Travel
“If the vineyards are the soul of Castello Banfi, the winery is its very heart” | CastelloBanfiIlBorgo.com
Winery Castello Banfi Italy Tuscany

The winery tour begins at the Castello Banfi – Il Borgo parking lot, where you meet your fellow wine tour guests and guide then caravan to the wine-making facility, which is about 3 miles from the Castello. 

The facility is vast. In its early stages, the wine is contained and monitored in massive steel cylinders. The guide takes you along a catwalk surrounding the cylinders and then down into and through the processing area. 

Wine Barrels Castello Banfi Italy Tuscany

The entire facility is well-maintained but can be noisy and industrial in places. But, there are also areas of true beauty, particularly in the aging rooms, where the wine-stained barrels are stacked to the ceilings, and the smell of oak and aging grapes engulf your senses. 

So much care is taken here. While we didn’t learn much more than we already knew about the Brunello wines of Tuscany and the actual process of winemaking (having been on other tours),  it was still gratifying and definitely worth the visit. 

For more information on visiting the winery and reservations, click here. 


“The building lies below the castle itself, once serving as a wine cellar of sorts in medieval times and being built up over the ensuing centuries. Inside, you can find the entire range of Castello Banfi wines, from San Angelo Pinot Grigio to big wines like our Brunello di Montalcino, BelnerO, SummuS ed ExcelsuS, which can be purchased by the bottle, case or in various gift packs.” | CastelloBanfiIlBorgo.com 

Even if you don’t go on the full tour, stopping at L’Enoteca for a tasting is a treat. For one thing, it’s beautiful. 

A long, spacious, rustic room with a curved tasting bar located at the end where we were lucky enough to meet Pam Mariani, the mother of the current proprietor, Cristina Mariani-May. Such a friendly lady with helpful recommendations for nearby restaurants in Sant’Angelo in Colle as well as insisting that we close out our tasting with a sample of the aged Banfi Grappa which is one of her personal favorites. 

After tasting it, I loved it so much I bought a bottle. I intend to treat it like an hourglass. When it’s gone, I’m booking a flight back to Italy. 

*Note: L’Enoteca is also able to ship wine directly to a wide variety of locations. 

For more information on wine tasting at L’Enoteca, click here. 


santangelo in colle tuscany italy theroadtaken2

Welcome to the tiny village on a hill overlooking the wine valleys of Montalcino in the heart of Tuscany Italy.

In the evenings, the hilltop hamlet offers a quiet place to watch the sunset, with the only sounds being either the tolling of the bell or the tinkling sound of china and silverware spilling over from its two restaurants. 

Yes, there are only two restaurants, and they are both worth a visit. 

Sunset SantAngelo In Colle Tuscany Italy
Sunset View from Sant’Angelo in Colle


Il Leccio is housed in a cozy, rock and timber building with a wine cellar that extends deep below the main floor. 

The food is straight-from-the-garden fresh, as in, the chef literally walks outside to a garden and collects items to prepare the next ordered dish. 

Everything we ordered here, from the eggplant parmigiana tartlet with fresh ricotta to the handmade ravioli drizzled in a sage and butter sauce, was so savory. 

Il Leccio Tuscany Italy

Wanting to linger, we ordered the dessert of the day. The couple seated next to us loved the desserts so much, we watched as they ordered four (two of them being the Pear cooked in Moscadello with a side of Pistachio Gelato). 

I don’t know if I’ve ever seen two people order four desserts, but they have my respect. Even the waitress was slightly stunned. She asked them, “E vero?” Is it true?” 

But it was, and Il Leccio made two people very happy that night in Italy. And I was reminded never to be afraid to order exactly what you want, especially when you’re on vacation. 


Trattoria Il Pozzo Montalcino Tuscany Italy

Trattoria Il Pozzo is the larger of the two restaurants in Sant’Angelo in Colle, and it also offers a menu loaded with authentic Tuscan cuisine and friendly attentive service. 

All dishes are made from scratch, including the pasta, of course, and I particularly enjoyed their take on the country Tuscan soup, Ribollita. Click here for the recipe…

I could have made that my meal, actually, but the rest of the menu looked so good I couldn’t resist trying their pinci pasta, a type of pasta local to the Tuscany area that is made by hand-rolling the pasta into long, tiny tubes. 

If one restaurant is closed, don’t worry; the other will be open, but locals (and tourists like me) enjoy eating at both of these establishments, so be sure to call ahead and make a reservation, just in case. 


Florence Italy Tuscany Travel
View of Florence from the Piazzale di Michelangelo

Florence is a city filled with many of the things that make life beautiful: stunning architecture, classic art, delicious restaurants, and not to mention the fact that it’s steeped in history, particularly in regards to the Renaissance. 

Think of the now-iconic people who called Florence home: da Vinci, the Medici family, Michelangelo, Galileo, Dante, Machiavelli, Vespucci…individuals whose contributions still influence the modern-day world. 

Not to mention that Florence is a magnificent city.  I know many people who even say it’s their favorite city in all of Tuscany or even all of Italy. But, in my experience, it’s just too overrun with humanity. At least in May, I found that to be the case, especially as you draw closer to the city center. 

Cathedral Santa Maria della Fiore Florence Italy
Florence Italy Tuscany Travel

Regardless of the crowds, Florence is (and I’m sure will continue to be) a highly sought-after destination city, so to avoid added stress caused by waiting in long lines, book its sites ahead whenever you can and go early. 

Then, once you’ve toured those “must-see” museums, churches, and towers, let yourself get lost in its maze of narrow streets filled with fine leather goods or cool down and rest your (most likely) weary feet in a tucked away trattoria or the quiet gardens overlooking the city. 


The Galleria dell’ Accademie is filled with art, predominantly sculptures, although there are paintings as well. But, the main reason everyone visits is because of Michelangelo’s David (pictured below). The statue is synonymous with the city itself. 

“The work was assigned to Michelangelo by the workers of the Florence cathedral on 16 August 1501…. On 8 September 1504, the statue was unveiled to the city, to the admiration of all people… The sculpture, with its carved base, is 517 cm [just over 16 feet] high and weighs 5560 kilos [12,257 pounds].”


Michelangelos David Galleria Accademie Florence TheRoadTaken2
Michelangelo’s David

It wasn’t until 1873 that the decision was made to move Michelangelo’s David from its original location in the Piazza della Signoria to the Galleria. 

It took 9 years for architect Emilio De Fabris to finish the “Tribune” where David is displayed today, and during those 9 years, the massive statue stood in a protective wooden box. 

If you plan to visit, reserve your tickets ahead of time by clicking here. 

*Note: The museum is closed on Mondays. 

You can purchase a combined pass to view the mass of artwork, sculpture, drawings, architecture, fashion, and gardens housed in these three locations. 

Some highlights include Botticelli’s Birth of Venus and Allori’s Judith with the Head of Holofernes.  Additionally, by buying the ticket online, you get to take the fast-track lane upon arrival, saving your feet for what counts instead of shifting back and forth while waiting in a long line.

To reserve your tickets ahead of time, click here. 

cathedral santa maria del fiore florence italy


Welcome to the third-largest church in the world. When the cathedral was completed in the 15th century, it was the largest in the world until the completion of St Peter’s Basilica in Rome and St Paul’s Cathedral in London surpassed it. 

Dedicated to the Virgin of the Flower in 1412 (hence its name), the cathedral stands as a reference to the city itself, whose symbol is the lily. Originally designed by Arnolfo di Cambio, he began work on the new cathedral in 1296.  

Facts aside, the cathedral and its massive dome designed by Filippo Brunelleschi are stunning. So massive. And, its exterior of alternating colors of pink and green against the white creates an intricate and colorful facade that seems unusually fun, bright, and practically cake-like for a cathedral.

Exterior Florence Cathedral Italy Florence
Gelato Florence italy

The colors are even reflected in the gelato flavors displayed in heaping dollops in the shops near the cathedral. 

The entrance is free to visit the cathedral, although the museum is closed on the first Tuesday of every month. Also, remember to dress appropriately. To quote their website:  “It is forbidden to enter with bare shoulders and legs, sandals, hats and sunglasses.”

If you want to tour the museum, you can pre-purchase your tickets. If you’re interested in climbing the 463 steps to the top of the dome (no elevators), you can do so for free; however, a reservation is required to better regulate the number of people going up and down at one time. 

For ticket and reservation information, click here. 

Florence Cathedral Italy Travel
Florence Cathedral Italy Travel


Ponte Vecchio Florence Italy
Florence Italy Arno River Travel

At one time, Ponte Vecchio (the oldest bridge in Florence) was the only available crossing over the Arno River until 1218.  And based on the number of people crossing back and forth on it at any given time, you would think it’s still the only way to cross the river. 

Though the bridge was originally built as a means of defense, it has housed merchants since the 13th century. The first merchants were fishmongers and tanners and butchers, but due to the stench created in those lines of work, in 1593, Ferdinand I decided that only goldsmiths and jewelers be allowed to occupy the bridge. 

Far less stinky work. And gold and jewelry are what you’ll see being sold today, although the quality, I think, is not quite what it once was. Still, it’s a lovely piece of Florence’s history. 


Villa Olmi Firenze Florence Italy
The individual suite where we stayed at the Villa Olmi Firenze

Located 2.5 miles from the Florence city center, the Villa Olmi Firenze is an oasis originally built in the 18th century. Their website claims that they offer: “The intimacy of a home. The services of a luxury hotel.” A claim which I found to be accurate. 

Gardens surround the villa, the heated pool is large and refreshing after long days of sightseeing, and there is also an outdoor covered terrace for dining.

The garden terrace room is fairly large with an ornate bed and a wood beam and tile ceiling with a soft gold sofa and a kitchenette off to the side. The French doors open out to your own private garden, where there are lounge chairs and a covered swing.

If you stay here, or even if you don’t actually, don’t miss out on a dinner at Osteria Brucia Tegami, a short walk from the Villa. 

The Osteria offers a selection of fantastic local wine, and everything on the menu is pure perfection.  Although they offer classic “Italian” desserts like Tiramisu, skip it if they have Apple Pie on the menu. Proof that all that matters is simple, quality ingredients. 


Piazza del Campo Siena Italy
Piazza del Campo

There are moments in Siena that, for a second, make you feel as if you’ve time-traveled to some Medieval era. 

Thankfully, not the era when the Black Death was sweeping its deadly scythe across the region, but a more placid time when its now-famous medieval monuments were in place, and the people went about their usual business of eating, drinking, going to school, and pretty much just enjoying life as the Italians do.  

Siena Italy Market

Since, through some miracle, the city escaped damage during World War II, Siena is remarkably intact, which is why it received its status in 1994 as a UNESCO World Heritage Site. 

Located about 30 miles away from Florence, it’s actually a pleasant drive through the countryside. However,  parking in Siena can be tricky because you’ll want to avoid the ZTL fines (limited traffic zones) for driving within the city limits. 

Only authorized vehicles are allowed to limit traffic congestion and wear and tear on the historic roads, so choose one of the parking decks at the base of the city walls and walk (ride the escalators) to the hilltop city. In our case, we parked in the “Santa Caterina” deck on the west side of the city and took the many escalators upwards and onwards until we had officially reached the city limits. 



This cathedral conjures up words like “glorious,” “impressive,” “magnificent,” and it’s one of the many structures in the world that makes you want to try and find an unobscured, unpeopled spot and rake your eyes over every colorfully etched detail. 

There will most likely be a line to enter, but don’t mistakenly hop in it because you’ll need to purchase a ticket in the corner building across from the cathedral where the gift shop is also located. 

For more information on reserving tickets and specialty tours, click here. 

*Note: Be sure to wear appropriate clothes. If you happen to be wearing a bare-shouldered outfit, gauze capes are provided. Men are required to remove hats as well. 

Once you enter, it takes a moment for your eyes to adjust to the dim, dark gold light. The space is both a place of worship and reflection: tradition and history built upon more ancient history—a weirdly wonderful hybrid of sanctuary, library, and historical artifact. 

I found it mostly quiet inside except when a procession of drummers, waving green and red flags solemnly proceeded into the cathedral, dressed in the traditional garb of colorful tights and plush, plumed hats. 

Everyone grew quiet as they marched into a small, ornate chapel where there was quite a bit of chanting and then a turn, and the procession retraced its steps the way they came. 


Looking at the alternating black and ivory striped columns, I couldn’t help but feel like I had stepped into what must be the oldest and most glamorous Sephora in the world. 

Once your eyes take in the massive columns, your gaze rises to the soaring ceiling with its blue and gold dome hinting at a night sky, even though it was blazingly bright outside. 


And then there is the floor. The artwork under your feet is as integral and fascinating as the paintings and sculptures. Some historians even consider the floor one of the cathedral’s most prized possessions. 

Although it was begun in the 14th century, like so many items of great worth, it took a long time to complete. 

In this case, the 19th century. “The technique used to transpose the various artists’ ideas onto the floor is known as graffito and mosaic marble inlay.” | OperaDuomo.Siena

Floor Graffito Siena cathedral Italy TheRoadTaken2

While it’s hard to choose a favorite aspect of this cathedral, I felt particularly moved by the Piccolomini Library. 

The vaulted ceiling is intricately painted with frescoes, but the real showstoppers are the massive illuminated manuscripts from the 15th century that line the walls. 

Fresco Ceiling Siena Cathedral TheRoadTaken2
Illuminated Manuscript Siena Cathedral TheRoadTaken2

You would think there wouldn’t be anything else to do or see at a Cathedral, but there is SO much more here. 

For example, the “Gate of Heaven,” “The Crypt,” “The Baptistry,” “Beneath the Cathedral,” and of course, the Museum Gift Shop. If I had to choose one additional add-on, my suggestion would be the “Gate of Heaven.” 

At the top of the cathedral are a series of rooms where you can walk above the vaulted ceiling and look down into the cathedral below, as well as have access to panoramic views of the city outside. 

The name “Gate of Heaven” is derived from the Biblical story of Jacob’s dream, where he was climbing the ladder to Heaven and saw angels ascending and descending. 

When he awoke, he exclaimed: “This is none other but the house of God, and this is the gate of heaven.” 

Image courtesy of operaduomo.siena.it



The Piazza Del Campo is the nucleus of Siena, built on the exact intersection of the three main hills that make up the city. Its first documented mention was in 1167, and it is still home to one of Siena’s most celebrated events: the Palio. 

Occurring annually on July 2 and August 16, 10 out of the 17 “Contrade” (representing each city division) racehorses around the Campo. It’s an event that spans several days combined with a lot of pageantry and, of course, a lot of crowds. So, if you plan to attend, reserve early. 

While there are several large restaurants and cafes spanning the rim of the Piazza, many of them catering to tourists with big, bold pictures of food on the menu, there is at least one small gem offering authentic Tuscany Italy dishes in a smaller, rustic atmosphere: Osteria La Mossa.

Osteria La Mossa Siena Italy
Osteria La Mossa | Piazza del Campo



After some delicious samplings of candies, cookies, and truffle oil at Nino & Friends, we were walking back to the car when we literally stumbled upon Il Battistero Siena — Fine Wines Shop:  my favorite #hiddengem in Siena. Thanks so much to Rita (our host and sommelier) for making the tasting both memorable and highly informative.

Before I even touch on the wine tasting, a note must be made about the atmosphere. The tasting takes place in an ancient subterranean chamber with only a few rough-hewn tables cozily set amidst the brick and stone. 

The air is chilly, but the lighting is soft and warm. The samples of the wine are served alongside wedges of aged Pecorino cheese accompanied by fresh, sliced bread heavily drizzled with locally sourced olive oil. 


Admittedly, I’ve always been more of a Brunello fan, but the 2015 Chianti Classico from Castello dei Rampolla is now a new favorite.  We also tasted the Fuligni Ginestreto 2016 Rosso di Montalcino, and it was also quite nice. 

As you learn more about the wine and the process, you additionally get to learn more about the history of the building. 

Rita even showed us the trapdoor entry to the 15 miles of secret passageways dating back to the Etruscans and was used in the Middle Ages as a secret exit for the reigning Pope. 


The wine tasting usually takes around an hour, but you could easily spend more time here sipping wine and steeping yourself in the history of Siena and its many secrets. 

Il Battistero is also a highly rated B&B if you’re looking for a friendly and centrally located place to stay in Siena with beautiful rooms and suites. 


Even if you’re not into touring massive cathedrals or art galleries or any of the other “tourist” sites, Siena is just a beautiful place to walk around.  

Browse the leather and pottery shops, get lost in an antiquarian bookshop, and let luck and wonder lead the way. 


Piazza di Spagna Pienza Italy TheRoadTaken2

Driving through the Val d’Orcia region of Tuscany Italy to get to Pienza was when I actually had the realization that the legendary beauty of Tuscany was not just hype. 

There is so much for the eyes to take in that you glide along in silence. Maybe an exclamation here or there, or a comment like, “I wonder how much they’re asking for that villa…?” 

But, back to Pienza.

It’s classified as a UNESCO World Heritage Site because it is where Renaissance “town-planning concepts” were actually first used. It was meant to be an “ideal city,” meaning that its buildings and main square would correspond to perfect proportions. 

Using the characteristics and alignment with nature and the stars, the city’s design was meant to inspire “men’s hearts with serenity and peace” with the goal being to “improve the moral, spiritual, and judicial qualities of citizenship.” 

It took only 3 years to achieve, from 1459-1462, and it is the only city of its kind. 

Pienza Cathedral Italy TheRoadTaken2
Historic City Center of Pienza
Flower Seller Pienza Italy TheRoadTaken2

While I don’t feel like the city inspired quite all of those qualities in me, I was, after all, only there a short time. 

*Note: Unless you live there or have a special driving permit, don’t forget to park just outside the city, where there are several designated parking areas. The ZTL fines are real, and they will get you.  

While many of Tuscany’s hilltop towns and areas are so beautiful to see and experience, Pienza is uniquely memorable. 

For one, it’s not typically overwhelmed with tourists. The village is small and easily walkable, and every enchanting street will tug you towards it, luring you with blooming fragrances, the sharp scent of pecorino from a tiny cheese shop, or some vine-covered ristorante or osteria beckoning you to come and try. 

Entrance to Pienza Italy TheRoadTaken2


Like so many buildings in Italy, this particular church was built over the ruins of an older church, with the new version being constructed in 1459. 

The travertine exterior glows white, but once you step inside, you might think you’ve just been transported to a church in Germany. 

Central Cathedral Pienza Italy TheRoadTaken2
Cathedral Columns Pienza Italy TheRoadTaken2

The interior clearly suggests some German Gothic vibes, but that was also by the design of Pope Pius II, who was born in Pienza as Enea Silvio Piccolomini. 

If you want to read more about the design of the city and this Cathedral’s unique architecture, click this link to take you to the UNESCO site. 

The church is free to enter, but some of its real treasures lie beneath it in the ominously named “Crypt.” 

The entrance to the museum and crypt is located outside and to the left of the cathedral. The entry price is only a few euros per person, and it’s definitely worth a peek inside. 

The museum consists of only 1 large room and contains a wall with some of the original carvings from the first church. In addition, some stone etchings depict Daniel in the Lion’s Den. There are also Flemish Tapestries on display and a few other items of note. 

The stairs to the crypt are located in the far corner of the museum. Though much of it is locked or closed off, the crypt is deep and dark below, with narrow passages winding off that circle back around in a maze-like fashion. 

While no one was ever supposedly buried there, it’s still not a place where I would want to be in the dead of night.

The Crypt Pienza Cathedral Italy TheRoadTaken2
Crypt Passageway Pienza Italy TheRoadTaken2


Once you’ve had enough of crypts and cathedrals, take to the cobblestone streets and do a little shopping. If you love cheese like I do, then Pienza is the big cheese wheel of fortune. 

Known for their own unique style of Pecorino, the cheese is made from sheep’s milk and is usually aged 5-18 months. 

If you want to purchase some or stop in to gaze at the colorful wheels and breathe it in, I recommend Marusco e Maria or La Bottega Del Naturista. Both are located near each other on the Corso il Rossellino (the main street through town). 

If you’re looking for something non-perishable that also won’t cause a customs nightmare, then check out a true one-of-a-kind boutique (also on the Corso il Rossellino near the cathedral): Filiz Ozturk Fashion.

Filiz Ozturk Fashion Pienza

“The boutique of precious dreams. The choice of the best materials coming directly from Turkey used to make handcrafted jewels and unique accessories. A wonderful trip, bridging Italy and Turkey, fashion and design through the universal language of handcraft, taste and creativity.” 


I couldn’t resist. This silky blue wrap was like wearing a watercolor painting. 

Susan Cook Filiz Ozturk Pienza Italy TheRoadTakenTo
Wearing a one-of-a-kind Filiz Ozturk Silk/Wool Wrap

If fashion, jewelry, and accessories aren’t on your agenda, then there are also quite a few hand-painted pottery shops, with my favorite being the one just across the street from the main square. 

As far as I could tell, it didn’t even have a name, but the pottery in the window was classic Tuscan. 

Pienza Shop Italy TheRoadTaken2
Pottery Store Pienza Italy TheRoadTaken2


I wish I could tell you that I personally tried every ristorante and osteria in Pienza, but, sadly, I can only officially report on two establishments. However, I can also report that given a chance, I would jump at the opportunity to go back to both. 

First up: La Buca di Enea

Choosing this “stuzzicheria” was easy; it started to rain, and there it was. 

Buca di Eneo Pienza Italy TheRoadTaken2

We had no idea what the name meant, but it was warm, inviting, and the menu had several selections that we wanted to try.  The barley and mushroom soup is incredibly savory plus hearty, and the Bruschetta with Pecorino is a perfect way to start.

Mushroom Pasta La Buca di Enea Pienza Italy TheRoadTaken2
Bolognese La Buca di Enea Pienza italy TheRoadTaken2

Curious, we asked the chef what the restaurant’s name meant since Google Translate was clearly not figuring it out. It was supposed to be the “Cave of the Pope” (Eneo being his given name). 

But, the translation usually turned into “The Pope’s Hole,” which was definitely more unfortunate. But, good for a laugh. 



Down a hill and around behind the church where the views of the valley stretch for miles is Idyllium—its doorway encased in flowering vines with creamy white umbrellas set out front. 

Bledy, the bartender, is amiable, and the bar is comfortable with soft leather couches. 

The interior is decorated in a Bohemian, eclectic style with furniture from different eras placed at a comfortable distance about the ancient stone and brick room that was once part of the old church.

If you’re not sure what to order, go for the Papale Papale made with London Dry Gin, Shrub di Lamponi, and Limone Fresco, served cold without ice in what looks like a grail cup. 

Culture Tip: In Italy, you never drink alcohol without having some sort of food to go with it. At Idyllium, they bring you a small bowl of salty baked corn chips and sliced bread with fresh prosciutto, thinly sliced and layered on top to nibble on while you enjoy your cocktail. 



Montepulciano Italy TheRoadTaken2

Welcome to another beautiful medieval Tuscan town on a hill! You would think after having visited one (or two), you might have your fill, but each one has its own distinct personality. 

And some, like Montepulciano, are known for its distinctive wine: Vino Nobile.

*Here’s your friendly ZTL reminder. Park outside of town.

While Siena accommodates the less-than-athletic with escalators to whisk you up the hills to the city, Montepulciano makes you work for it.  

On the trek up the hill, don’t miss the huge metal horse statue in the park to your left. and then passed through the arch into the city itself. The city is a treasure trove filled with cheese, wine, and salami.

Salumeria Montepulciano Italy TheRoadTaken2
Enoteca Montepulciano Italy TheRoadTaken2

But to reach the main piazza, the climb must continue. A cute little tram will shuttle you to the top, although I still recommend walking, so you don’t miss anything like a quick tour of the beautiful Chiesa di Sant’Agostino, a perfect place to pause and catch your breath.

Montepulciano Cathedral Italy TheRoadTaken2
Interior Montepulciano Cathedral Italy TheRoadTaken2

Continuing the climb, you will pass several enotecas, luxe leather goods shops, and art galleries. When you finally reach the main square, the Piazza Grande, you are literally on top of the town. 

Main Square Piazza Montepulciano Italy TheRoadTaken2
Bell Tower Montepulciano Italy TheRoadTaken2
Cobblestone Main Piazza Montepulciano TheRoadTaken2

Even though the square is architecturally stunning, expansive, and breezy, the best views are behind the square overlooking the valley. From that vantage point, you feel like you can see forever. 

Valley of Montepulciano Italy TheRoadTaken2
La Bottega del Nobile Montepulciano Italy TheRoadTaken2

Fun Fact: Montepulciano is home to the “Bravio delle Botti,” otherwise known as a wine barrel rolling contest that takes place every year on the last Sunday in August. 

There’s quite a lot of fanfare–flag-throwing, traditional medieval dress, trumpet-blowing–and then, the barrel rolling, uphill. Whichever team can roll their 187-pound barrel up the curving streets to the Duomo at the top is the winner. 

In all honesty, I had trouble just propelling myself to the top. The thought of rolling a massive barrel to the top of the city quickly turns into a scenario where I’m running down the hill with the barrel chasing me like the big boulder in the first Indiana Jones movie. What a way to go.

But, the barrel rollers start their training early. You might even see them honing their skills on the main roads as you drive through the Tuscany countryside. 

Montepulciano Barrel Rolling TheRoadTaken2

While the Val D’Orcia covers quite a large region of Tuscany Italy, there is a specific road I recommend driving: the SP88. This map shows you how to get to it from Montepulciano, but it’s easy to access regardless of which direction you are coming. 

This stretch of road…

We weren’t prepared for it. We thought we had seen all the beauty that Tuscany Italy had to offer, but in this case, we obviously had not. I was snapping pictures with my iPhone out the car’s window (definitely looking like a crazy tourist and not caring). 

I was torn between trying to capture it or just take it in and enjoy the moment. It was like rolling through a sea of green. Almost overwhelming to try and take it all in. 

But, I’ll be quiet now and give you a glimpse of what I’m trying (and probably failing) to describe.

Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2
Val D'Orcia Tuscany Italy TheRoadTaken2

There’s a reason why people worldwide continue to seek out Tuscany, Italy. Its wines, the food, the history, and just its sheer natural agrarian beauty. 

But I find myself wanting to go back because of how it makes me feel while I’m there.  

Tuscany Italy has some intrinsic quality, still removed from modern stresses.  You can fill each day with sightseeing and wine tours, or you can sit and spend an afternoon reading under an umbrella. 

I spent one entire day in Tuscany with a horrible sinus infection, and I didn’t do a single thing except make myself copious amounts of green tea, wrap myself in a robe, and halfway read a book while staring out the window towards green fields of vineyards. 

I was sneezing my face off, and it was one of the most relaxing days of the whole trip. 

So, no matter what you do in Tuscany Italy, you’re not missing out. It’s a lovely place with friendly people. So, let yourself relax, do what makes you happy, order four desserts even, and enjoy the fact that you’re there

Susan Cook TheRoadTakenTo Castello Banfi Il Borgo

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