TUSCAN GETAWAY
e quindi uscimmo a riveder le stelle.
pure e disposto a salire alle stelle.
l'amor ch'move il sole e l'altre stelle.
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Dante initially lured me to Florence ten years ago, and for that reason, I have no choice but to begin my Tuscan weekend itinerary with his timeless words. His flare for the dramatic is understandable once you have set foot in Tuscany; every inch of the region drips in art and beauty. As I was jogging along the Arno earlier this evening as the winter sunset begin to turn shades of pink and purple over the Renaissance capital, I couldn't help but to think even the sky always looks like a piece of perfectly planned and executed art. While I credit Florence with being my first true Italian love, this section is going to take a step outside of the bustling and always overcrowded Tuscan capital to shine light on a few of the countryside gems that simply can't be missed (da non perdere) if you're in the area. As always, while the trains are more functional in Tuscany than they are in some of the southern regions, I recommend tackling this itinerary with a car. Many of the smaller villages simply don't have a train station, and you'll be stuck paying a hefty taxi fee to arrive there anyway. Rent the car, the true beauty of each of these itineraries comes in the flexibility and spontaneity of tweaking your plan along the way.
DAY 1: FIRENZE
​By Train: You'll arrive in Santa Maria Novella train station and depending on your luggage count you can either get a taxi there or walk. Busses in Florence do exist, but the process of getting the ticket, validating it, finding the appropriate stop etc is likely not worth the hassle if you're staying in the city center. Florence is a walking city at its core and everything is reachable in <25 min waking time.
By Plane: You'll arrive at Amerigo Vespucci airport and can either take a taxi or the *new* tramvia from the airport to the SMN station
By Car: You're in the driver's seat. Be aware of two things: 1) There are a ton of virtual speed traps around the city center, so pay careful attention to the speed limit and 2) DO NOT enter the ZTL unless your rental car needs to be parked in a garage for return inside the ZTL. IF you are keeping your car for the night and planning to drive to the countryside and are staying in the center, you MUST park outside of the ZTL and walk to your destination. If you're staying at a hotel in the center, call or email ahead to see if they can give you a work around for this. You can find the ZTL boundaries and times here.
In Florence, there are plenty of options to consider for an enjoyable stay. These range from high end to mid-range to a simple AirBnb (though these will be harder to find and more expensive as the Italian government tries to restore balance in housing prices for locals)
Luxe: Four Seasons Hotel Florence, there's no better hotel in the city. Or if you're a Bonvoy enthusiast, St. Regis Firenze.
Mid-Range: Any of the AdAstra properties including SoprArno, Oltrarno Splendid, and the namesake, AdAstra
Budget: Air BNB in Florence is a good option. However, unfortunately even Air BNB prices have soared in recent years with the explosion of tourism. I would recommend looking in San Frediano or Sant'Ambrogio for a more local, and also more budget-friendly, accommodation.
Depending on your arrival time, the day in Florence should be one of relaxation and meandering to take in the sights of this open-air museum. While Florence may be one of my favorite cities, if you have had the "Tuscany conversation" with me before, you've heard me say that all of the things that visitors love about Florence can be found in the small, surrounding towns without the background noise of incoming tour busses and jammed sidewalks. I understand the urge to try to cram in a full Florence trip in this single day, but allow this first day to be a warm-up for the spectacular Tuscan road trip on which you are about to embark. As many of my friends have heard me say, Florence is just the "tip of the iceberg".
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With that, I'll offer you some of my favorite places to visit when I first arrive in Florence. If you're there in time for breakfast, I recommend stopping into La Ménagère, a French-style cafe, bar and concept store that is both delicious and a feast for the eyes. While you're in the area, if you are up for a quick and easy (but high-impact) cultural visit, go across the street to the Cappelle Medicee (The Medici Family private chapel and sepulcher). If you did extra-impressive planning, try to score tickets to Michelangelo's Stanza Segreta (Secret Room) that recently reopened on November 15, located inside the Cappelle Medicee. As an extra piece of advice for luck for snagging one of the covered spots (only 4 people for 15 minutes, 45 minutes of lights out between groups) try calling this number instead of using the website, some spots are available via phone that aren't online. If you are in this area for lunch, I recommend Trattoria Sergio Gozzi with a stop for a glass of wine at Casa Del Vino which seems like a nondescript bar at first glance but offers amongst the largest selections of natural wines in the city.
I love walking through the neighborhood of Santa Croce (always stopping in the church and taking an extra moment in the cloisters just before the exit). Behind Santa Croce is the bohemian, local area of Sant'Ambrogio where you'll find the market that Florentines more commonly frequent than the touristy Mercato Centrale. There are a number of stalls and even actual sit-down restaurants in the market, or if you are looking for something more on the go, try Semel for a panino that is a little on the lighter side and adorned with more exotic fillings than the everyday schiacciata. If you are in that area, another classic Florentine option is Trattoria Cibrèo which offers a more approachable menu than the famed formal ristorante.
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Spend the Afternoon wandering through the Oltrarno, or the south side of the River Arno where you'll find vintage and boutique shops along Borgo San Frediano and Via Serragli. If it is a nice day, consider visiting the Boboli Gardens, and make sure not to miss the Palazzina e Bastione del Cavaliere and the Buontalenti Grotto just before exiting. I would recommend dinner on the south side of the river for a more local experience. Osteria Santo Spirito is a staple in the area, and offers excellent Florentine classics. Despite its fame in recent years, it remains a place for tourists and locals alike. Two other options are Trattoria I Raddi (Via Ardiglione, not the one right on the piazza) for a very local and casual experience. If you're looking for something with more atmosphere, Il Santo Bevitore is one of my favorites, and don't forget to leave time before dinner to stop at Il Santino (the wine bar next door) for an aperitivo.
DAY 2: FIRENZE TO SIENA
If you are renting a car from Florence I would recommend using one of the agencies that rents out of the Interparking Garage Europa Firenze on Borgo Ognissanti. There are a few companies that use this space including Avis, Europecar, Sicily by Car, but overall I find this location most convenient to the city center. There are a few agencies that rent out of the train station (Hertz) and out of the airport, but that is rather inconvenient from the center. If it is after November 15, REMEMBER: ask if there are snow chains in the car (it's a law) and any time of year DO NOT drive in the ZTL.
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The title of this segment is a bit of a misnomer because I wouldn't necessarily recommend staying right in the town of Siena. While it is beautiful to visit, and if you have an entire day you can certainly find enough things to do in the town, there are many beautiful properties in the area. My personal favorite is Hotel COMO Castello Del Nero where you not only have a stunning hotel in a former castle with rustic farmhouse style decor, but also a newly renovated spa that not only provides the option of booking services but also has a steam room and outdoor hot tub. The pool is open late into the winter for the brave, and you can take a walk in through the property vineyards and olive groves before having a leisurely breakfast overlooking the Tuscan countryside. Another highly recommended accommodation in the Siena region is Dievole Wine Resort.
Depending on the time that you leave Florence, the time of year, and your level of jet lag, you may want to book a spa treatment and pass the afternoon leisurely. If you're up for some activity, I would recommend stopping at the hotel and then going for lunch at the modern cantina of Antinori Nel Chianti Classico. The restaurant, Rinuccio 1180, offers refined twists on Tuscan dishes while sitting in the distinct structure that looks more like a piece of modern art than a winery. The restaurant is only 10 minutes driving from COMO Castello Del Nero making it a convenient stop after dropping luggage all the hotel. Nearby towns that are worth an afternoon visit are Castellina in Chianti, Greve in Chianti, or Siena.
For dinner, venture into Siena for an excellent culinary experience at Osteria Le Logge. Ask to see the Etruscan wine cellar if possible that is just down the street and contains library wines from decades past. If you happen to be in Siena on a Sunday and Le Logge isn't an option, Osteria Da Divo offers a unique setting in the lower levels of the restaurant where the Etruscan caves have actually been used for the dining room. The olio nuovo that we recently had here is amongst the best that we found in the days after the Tuscan olive harvest this fall. Other recommendations for dinner include Enoteca I Terzi and La Compagnia dei Vinattieri.
DAY 3: SIENA TO PIENZA
I'm going to pause for a moment to make a bold statement. The drive from Siena to Pienza is truly one of my favorites in the entire world. After numerous times of careening down the hill over the back side of Siena and taking in the scenery as it turns from wooded countryside into goldenrod rolling hills punctuated with the rich green of the Cyprus trees in distinct patterns that make this region of the Val d'Orcia a coveted and well-deserved UNESCO World Heritage site, I can say that it never gets old. As I pass the rather run-down town of Buonconvento and take the turn hugging along the base of the seemingly never-ending Tuscan foothills, my heart often starts beating quickly both out of excitement to be back in one of my favorite places as well as my excitement for my passenger who is usually about to experience this stunning landscape for the first time.
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There are a few options for how to approach this drive and I have done it the various ways so here I will offer two possible solutions depending on whether you are experiencing relative hunger or thirst, because we all know that both are rare when traveling in Italy.
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The first option would be to go back toward Siena and go to Félsina for an outstanding wine tasting in a particular plot of land between the Colli Senesi and Chianti Classico. The wine is not only excellent and one of our family favorites, but the tour is an experience where you ride into the vineyards in style (see below) to see for yourself the beautiful landscape where the magic is made. The tasting room is simple but warm and like my preferred Tuscan wine-tasting experience, not overly formal or fussy.
The second option, I must admit, was a bit of a happy accident during my last trip out into the countryside. Before going, I read several articles including this one from my favorite writers at Italy Segreta that talked about Dario Cecchini, and as a Dante lover I was no doubt entertained, but also frankly confused. The descriptions of the macelleria seemed to suggest it was a store more than a restaurant, so I forged ahead with my plan to continue toward Pienza. It wasn't until I was sipping a glass of the property's own Sangiovese at COMO Castello Del Nero when another guest began talking about traveling from Monaco every few months to visit his favorite restaurant in Tuscany. While there's no doubt you can find excellent food here worthy of bimonthly visits, which one could possibly stand out so considerably that you pass on the opportunity all of the other options in the area? Dario Cecchini, once again. So I threw my plans out the window and hopped in the car the following morning to see what all the fuss was about.
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The fuss, is indeed, due to perhaps the best steak in Tuscany. Strangely enough, Dario's cows are raised in Spain at a family farm that believes in animal dignity and well-being, and with whom he has been working for 35 years. Dario's culinary practice involves using the entirely of the animal in various preparations so as to eliminate any waste. The dining options are as follows: There is a lunch seating for the 4-course steak or vegetarian tasting menu at 1pm, if you come after this your option is to have the "steak of the day" usually accompanied with wine and a contorno for €25 a man. There is another seating for dinner. The preparation of the steak occurs before your eyes, and is truly a culinary experience. In this sleepy town that has really nothing else, there is the best steak in Tuscany with a almost corny but still somehow on the side of literary tastefulness theme of Dante, and if this sounds as weird to you as it did to me, do yourself a favor and make the pitstop.
Depending on whether you opted for the Félsina wine experience or lunch at Dario's, be prepared for a solid 2h drive to Pienza. Though the distance is actually modest, the winding Chianti countryside means that the drive takes longer than you may expect. Allow some time to stop and pull off here or there along the way to take pictures or pop into one of the towns along the Strada di Castelli (Road of Castles) which includes the towns in the aforementioned article like Radda in Chianti, Castellina in Chianti, and Greve.
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Once you arrive in Pienza, check into La Bandita, a uniquely "urban" hotel right in the main medieval center of Pienza founded by a New York based music producer and his wife. Within the walls of this quaint and, from my point of view, perfect Tuscan town, I find the surprisingly design-forward, modern hotel to be a welcome contrast. While there are great restaurants in Pienza including those in the Bandita guide that you will be sent prior to check in, the hotel restaurant is really spectacular and has a year-round heated garden in which to enjoy your meal. The staff are friendly and personable, and for the music buffs out there, after dinner head up to the library bar that features the owner's impressive collection of vinyls and awards collected over the years. Bring the last drops of your bottle of wine for dinner, or dive into the honesty bar that is always stocked with thoughtfully curated local wines.
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If you choose to venture out for dinner, I would like to briefly make a suggestion on top of those that La Bandita has excellently curated for Trattoria Da Fiorella. This restaurant began as a choice on a whim and has provided a living-room-like atmosphere for some of my most memorable meals in my favorite Tuscan town. We typically choose to come here for lunch, but its open for both lunch and dinner year-round, and in addition to the wine selection on the menu, for a small corkage fee you can choose your own wine from one of the shops that stock local, small-production Brunello and Montepulciano to bring along with you.
DAY 4: VAL D'ORCIA
In case you couldn't already tell, I love this valley. It merits taking the time to spend a day or two exploring the region to get a feel for the local life here. Hopefully waking up in Pienza, you will see the gentle fog burning off of the valley with the rays of the sun that make the wheat fields seem to glisten like golden strands of angel hair. You can walk out of la Bandita to the right down to the piazza where you will find the main church as well as the Piccolomini Palace in the square. Order a coffee and a pastry and sit outside in the square taking in the quaintness of the town. Then stop into the church and notice the Piccolomini family crest adorning the stained glass windows that allow the light to stream through and make the otherwise somewhat plain church magically illuminate. You have the option of touring the palace and climbing the clocktower of the town hall as well, but if your time is limited I would prioritize taking in the views as you walk along the Via Santa Caterina. If you have the time, you can take the 20 minute walk down to the site where one of the more famous gladiator movie scenes was shot or visit the church of Santa Caterina which at the moment is under construction, but is worth a visit if accessible. If you prefer to stay in the town for lunch, a fan favorite is Sette di Vino but every time I have visited, they have been closed so I can't provide an honest review. What I can say is that the aforementioned Trattoria da Fiorella (if you opted to dine at La Bandita the night before!) has never disappointed. I went back a few weeks ago and it was just as good as ever.
My advice for the afternoon would be to take some time to explore the surrounding area which may include a trip to the quaint San Quirico d'Orcia or a stop at the Termi di Bagno Vignoni for more R+R (or if you missed it while at Como Castel del Nero). If you are interested in diving into the food culture of the Pienza region, the uncontested champion is the Pecorino di Pienza. Of course, you likely have heard of pecorino before traveling to Pienza, but it's likely that you have in mind Pecorino Romano, a harder, saltier version of the sheep's milk product. Pienza's pecorino is scarcely found in the USA because of food regulations. If you want to learn more about this delicacy of the Val d'Orcia, the best place to go is Podere Il Casale, a working farm, caseificio (cheese factory), and restaurant that not only offers delicious cheese, wine and olive oil with an unbeatable view, but you certainly will leave with new facts about this Tuscan treasure. If you are doing some prep reading before your viaggio, check out this​ NYT article that does a nice overview of the beloved cheese (we will give them a pass for choosing a picture of Montepulciano to be front and center in an article about Pienza...).
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If cheese and sheep don't sound like your cup of tea and you'd rather a glass of wine, Ciacci Piccolomini D'Aragona is the place to go. This vineyard, located just outside of Montalcino in a town technically called Castelnuovo d'Abate is my favorite winery to visit in all of Italy, and I keep coming back. Not only does it have a heartwarming history that involved the original owner leaving the vineyard to one of her hard-working field laborers, but the atmosphere can't be beat and the staff couldn't be more accommodating. Additionally, it remains a family business and the children of the family work at the vineyard in various capacities. While all of these things are details that make the visit to the vineyard particularly special, it would be remiss not to mention the excellent quality of the wine. I believe wholeheartedly that Ciacci Piccolomini produces one of the best Brunello wines in the region, and it is a small area full of stiff competition. Ciacci is always my first choice, but I recently visited Podere Le Ripi and was highly impressed by the experience of the tour and tasting. They have several wines that deviate from the traditional Brunello method but remain high-quality, and the playful names of the wines and the whimsical cartoon depictions of regional animals on the label are an endearing touch. While you may not recognize this small azienda by name, you surely will recognize the owner whose family name may have been printed proudly on your morning cup of coffee: Illy.
Whichever option you choose for your afternoon, find time to stop at the Cappella della Madonna di Vitaleta, just over a 10 minute drive from the historical center of Pienza. You may have seen photos of this secluded church flanked on either side by the iconic cypress trees, but sitting here having an aperitivo at the adjacent bar run by the family that owns the tiny place of worship is a truly special experience. You will see cars parked along the side of the road just after a little wooden sign pointing the way. The only way to reach the chapel from the parking is via a 10 minute walk on a dirt path. Be sure to ask about going inside if the doors are locked, the owners of the bar have the keys and will let you have a peek. Note that the bar closes in the winter from the 1st of November to mid-March, but you can visit the outside of the chapel year-round.
DAY 5: BACK TO FIRENZE
When I first came to Florence to study, I was overwhelmed by the beauty of the city, the art, the history, and the culture that began in this open-air museum. The wealthy Florentines of the Renaissance period had power that cannot be overstated, and their contributions that can be found all over Europe trace back to their Florentine roots. While Florence will always, always be my first love in Italy, traveling through rural Tuscany has made me realize that the richness of this region only grows stronger as you venture out from the capital. Each town has its own distinct story, one that continues to be written each and every day but that maintains the foundation laid by generations past. I never tire of seeing the unprecedented craftsmanship and pride that the residents have in carrying out the traditions of their adopted or given homeland. While it is undeniable that a visit to the Tuscan countryside elicits a sense of nostalgia for the past, I cannot wait to continue to watch the motivated, young Tuscan entrepreneurs (like John Voigtmann of La Bandita or Margherita Batelli of Sartoria Toscana) write the story of rural Tuscany in the years to come.
