View of Florence from the Piazza Michelangelo
Greetings fellow wine travelers!
The following travel article is quite long, and is most suited for those with an interest in traveling to Italy, with an emphasis on Tuscany. If you don’t want to read the entire article, just skip to the town that you have interest in. If not familiar with the area, it will give you some decent insight. And if you have traveled to Italy previously, you may come across some new information on the towns covered below. The towns covered below include, in this order: Florence, Volterra, San Gimignano, Bolgheri, Castiglione della Pescaia, Montalcino, Montepulciano, and Siena.
In this edition I’m going to share some of my adventures on a recent solo excursion I was fortunate enough to experience in September and October 2023. Part of the trip involved renting a vehicle for 13 days and driving first from the Renaissance jewel of Florence, to the hilltop town of Volterra, then on to the wine Mecca of Super Tuscan wines, the tiny village of Bolgheri, and after that to the seaside town of Castiglione della Pescaia. From there I drove to the wine village of Montalcino, the region where all Brunello wines come from, and then to another iconic town of the Renaissance, Siena, before returning the car to Florence and heading to Rome by train.
One of the primary purposes of the trip was to explore the traditional foods and wines of the region. Enjoying the sights and history of these intriguing places provided an additional incentive for the adventure. Each venue has its own rich history and classical treasures which would demand more than just a few days to thoroughly appreciate.
View of Cathedral of Florence (Duomo) from Giotto’s tower
Let’s begin with Florence, the largest city in Tuscany, and a town possessing surreal beauty and a wealth of history. Most people consider Florence the crown jewel of Tuscany, and for good reason. I arrived there via a two hour train ride from Milan. One of the finest ways to get an overview of this place is from the Piazza Michelangelo, a large square that lies in the rolling hills above the city, just across the Arno River. From the foothills overlooking Florence, it provides an incomparable, panoramic view of this lovely city. I took bus 12 from a stop near the main train station, and after enjoying the incomparable view, walked downhill from the piazza, across the nearest bridge, and back into the city. It’s an easy and lovely walk and takes only about 15 minutes. The bus ride from the station to the piazza takes more than 30 minutes, as it winds often with lots of stops and peekaboo views of the town.
Once across the river you will find yourself very near a local landmark; the Basilica of Santa Croce. It’s a great place to visit if you appreciate history, for it contains the tombs of some very famous Italians, including the classic artist Michelangelo and famed astronomer and inventor, Galileo, to name just two. The tombs themselves are lavish works of art. No reservations are required to enter the Basilica and on the day of my visit the line was quite short. The visit requires a modest entry fee.
Florence is the city that became the center of the great re-awakening of Western thinking, known as the Renaissance, where Medieval thinking gradually gave way to transformative modern thought, literature, science and art. The city abounds in tourist sites, especially if you have any interest in Renaissance art or history of western culture. The highlights of these attractions include the Uffizi Gallery (with one of the finest collections of Renaissance art in the world), the Accademia Gallery (more art and sculpture including the original statue of David carved by Michelangelo), the Duomo (the Cathedral of Florence), Giotto’s Bell Tower next to the Duomo, the Baptistery of Saint John in front of the Duomo, with its iconic bronze doors, the Palazzo Vecchio (old palace) located in the Piazza della Signoria, and the aforementioned Basilica of Santa Croce. You might also want to take in the Pitti Palace with its expansive Boboli gardens just across the river, that offer another splendid view of the city, and the famed Ponte Vecchio, the last remaining covered bridge in Florence. Hitler demolished the others in a attempt to slow down advancing allied forces near the end of World War II.
Obviously, Florence has a long and storied history. The Baptistery of St John represents the oldest of the aforementioned sites; it was providing religious services beginning in about 1128. Located right in front of the facade of the Cathedral (the Duomo), its interior remains marvelous even by today’s standards. Although it’s currently undergoing renovation, it remains open to the public for a small entrance fee. On the day I visited, there was about a five minute line to gain entrance. The place is quite surreal, especially when one considers that its construction began in about the year 1059.
Giotto's Tower and the long line to enter Duomo
While all these sites offer great opportunities for learning and taking photos, they can be time consuming and somewhat expensive. Many require reservations to avoid long lines. This is especially true of the Uffizi Gallery. Unless you’re a student of that period, the museum requires a professional guide to be fully appreciated. It also requires at least several hours of time. While entry into the massive Duomo is free, there is often a lengthy line that requires a minimum of 45 minutes of waiting to gain entrance. The wait time for the Accademia Gallery has similar issues, although usually not as lengthy.
As an alternative, many of the best sights remain readily available. Walk down the famed shopping street Via del Calzaiuoli street (also known as the Caz) from the Duomo to the Piazza della Signoria, and while there take in a walking tour of the Palazzo Vecchio (the Old Palace). The Palazzo’s grand entry hall is quite impressive, and has provided an ominous ambience for several movies, including Inferno starring Tom Hanks, partially filmed here in 2016, and Hannibal starring Anthony Hopkins, filmed in 2001. It’s reasonably priced and comes with a professional guide, and the wait times are usually very reasonable (I made an appointment to come back at a certain time that proved very accurate for the start of the one hour tour). Usually the climb up Giotto’s Bell Tower is not that crowded, costs about 10 euros, and affords spectacular views of the town and of the Duomo. It does require hiking up about 300 narrow medieval steps to reach the top, but it’s worth it. There’s a great outdoor market about a block off the Caz that features Italian leather goods that’s quite popular. You can even rub the nose of the bronze boar at the entrance to the market for good luck. Even veteran shoppers here indulge in this grand tradition.
More “freebies” include the aforementioned Piazza Michelangelo and the Piazza Signoria; an impressive square surrounded by a myriad of restaurants and historical statues. One of the statues, standing directly in front of the Palazzo Vecchio, is an excellent replica of Michelangelo’s David. It involves an interesting story. Although everyone knew that David was a masterpiece when Michelangelo finished the sculpture in about 1504, no one thought it might need protection from the elements. So originally it stood where the replica stands today; in front of the old palace. And there it remained for some 370 years, until some bright souls noticed that it had begun to suffer severe damage from the prolonged exposure to the burning sun and torrential rains of Tuscany. The masterpiece required significant restoration and was wisely relocated to the Accademia Gallery in the late 19th Century, where it remains today, resting safely indoors upon an impressive pedestal, illuminated by a lovely domed skylight.
Newlyweds leaving the Piazza Signoria in Florence
Florence is located in the Chianti Classico wine region of Tuscany, so its enjoyment represents an integral part of the city’s life. Numerous wine bars, known as enotecas, abound. Most restaurants offer an extended assortment of reasonably priced wines. Most Italians do not want to spend an exorbitant amount on their vino to enjoy with their everyday meals.
One amazing establishment where wine really takes the spotlight is the Cantina Antinori. The Antinori name represents one of the largest wine producers in Italy, turning out wines ranging from the basic to the sublime. The Cantina Antinori features some of the best wines from the Antinori empire, as well as an extensive menu of Italian appetizers, pasta dishes and meat dishes. It’s housed in a beautiful Renaissance style mansion located in the Piazza degli Antinori, about halfway between the main train station and the Duomo. That’s about a 10 minute walk from each.
I arrived in the early evening without reservations, and while the hostess informed me that the main dining room was booked for the evening, she did have open spaces in the adjacent bar area. It turned out I was the only one sitting there for most of the evening and it provided a lavish and peaceful spot to enjoy dinner and wine. My servers turned out to be an engaged couple that were both knowledgeable about wine and very fun to hang with during dinner. The Cantina served excellent Antinori wines by the glass, and I indulged in a Brunello and a high end Chianti Classico while enjoying an excellent tomato bread soup followed up with an entree of Tuscan steak tagliaota, prepared medium rare. Afterwards, I had a house made tiramisu with a glass of white dessert wine. All in all, it made for a very memorable dining experience. Prices were moderate considering the quality and beautiful ambience of the establishment. My dinner cost around 120 euros before tipping.
Panoramic view from the rooftop bar of the Caffe La Terrazza
After three nights in Florence, I took off in a rental car and made the nearly two hour drive to the hill top town of Volterra. This is a historic town perched atop a steep hill that has panoramic views that on a clear day stretch all the way to the distant island of Corsica. Only residents and commercial vehicles are allowed to drive within Volterra’s ancient walls. Visiting Volterra is like stepping into a time machine that takes you back about 500 plus years. Needless to say, it has tons of history, evidenced in part by one the gates leading through its storied walls that date back to about 200 BC. Volterra was first settled by the Etruscans, and later conquered by the Romans. The narrow, twisting streets simultaneously conjure up thoughts of mystery, romance and windows into the distant past. There’s a plethora of great little restaurants, museums, art galleries and wine tasting bars to keep one busy. Try checking out the small square, Piazetta dei Fornelli, just before sunset for a cocktail at the only bar on the square, and panoramic sunset views stretching all the way to the sea.
One wine bar that I highly recommend is Scali, located right across from the small but distinctive St. Michael’s Church. The friendly and knowledgable proprietor, Massimo, can enthusiastically set you up with numerous variations of Italian wines, plus food plates from his fridge that will complement the wines. He especially has expertise in locally produced Tuscan wines. He set me up with a tasting of four different wines for 20 Euros. He’s also extremely courteous. When I left the tasting, I inadvertently left my glasses behind. Shortly later, he came running down the street to return them to me. I found that friendliness quite common with the Italian people in general.
Volterra makes a great base for exploring the nearby towns and pastoral rolling hills of this part of Tuscany. I made an easy day trip to the more famous nearby town of San Gimignano with its magnificent ancient towers and many pedestrian-only walking streets that cater to throngs of tourists daily. It’s a fun visit although parking can prove challenging. This visit will require plenty of walking. Although both towns offer great sightseeing and plenty of opportunities for dining and buying local products, I slightly prefer the less touristy and road less traveled town of Volterra.
View of San Gimignano from its highest tower
A word of caution about Volterra; don’t plan on parking next to your hotel. If you stay inside the walls of the hillside town (and they surround virtually the entire town), you will probably have to park your car in the public parking area at the bottom of the hill. Parking is free, but it’s quite a steep walk into the town itself; lots of steps. There are several temporary spots (usually for 30 minutes) where you can park near one of the gates through the ancient walls to unload your luggage. Finding your hotel once inside the walls can also prove a challenge. My car’s navigation system did not work inside the walls, nor did Google Maps. Your best bet is probably the friendly tourist information office located in the middle of the main square, the Piazza dei Priori. The town is quite small, so locals can direct you to the tourist office. The tourist office will provide you with a very useful map of the town, and guidance to your shelter.
A scenic hour-and-a-half drive from Volterra, the Bolgheri area of Tuscany became the next stop along the journey. Bolgheri represents the village that provides the centerpiece of the Super Tuscan region of Italy. Super Tuscan is a term used more by international wine critics than Italians. About 30-plus years ago, innovative Italian winemakers decided they’d had enough of the restrictive rules required to make the officially recognized status of DOCG and DOC rated wines (previously considered the highest quality Italian wines). These bold vintners decided that instead of complying with a detailed set of rules to get the “higher” standards of the Italian government, that they would create their own blends from whatever grapes they thought would make superlative wines. Hence, these wines come only with the IGT rating, meaning that the grapes used in the wines come from a particular geographical area.
These winemakers introduced several grapes to the wine making process that had rarely (ever?) been used previously in Italy. Most notably several famous French grapes were utilized; Cabernet Sauvignon, Merlot, Cabernet Franc and Syrah. After years of growing and blending, the results proved stunning. Thus we have some of the most famous names in Italian, and even worldwide, winemaking. Ornellia, Macchiole, Sassicaia, Solia, Guardo al Taso and Tignanello, represent some of the most famous of these wines. And the wineries producing these gems are essentially all located less than 8 miles from the scenic, but tiny village of Bolgheri.
The village of Bolgheri lies at the end of a beautiful, rural road encased by towering Italian Cypress trees. It is indeed tiny, and may be fully explored in less than two hours. Restaurants, wine shops, bars, and tourist shops provide the attraction for visitors. None of the actual wineries are located in the village, but are mostly found along a “highway” just outside the town; the Strada Provincinciale Bolgherese. This route can best be described as a lovely 6 mile rural road that passes vineyards, woodlands, a few restaurants, and numerous Super Tuscan wineries, as it winds it’s way to the Bolgheri village. Most of these wineries allow tours and tastings, but only with a reservation. I tasted at both Macchiole and Guardo al Taso. Both tours were excellent, and cost between 60-100 Euros.
I did have a great experience purchasing some wines at one of the many wine shops, known as Enotecas in Italy. I purchased a half case of six different Super Tuscan wines from the Enoteca Tognoni, a small but lovely establishment near the towering entry gate to the village. They were mostly lessor known local wines and not particularly expensive. The six bottles cost me 242 euros, and another 70 euros for shipping. The amazing thing was that the half-case arrived at my home within only 8 days, in perfect condition. That was some 5 days before I arrived home from Italy! I’ve purchased many shipments of wine from Europe, and the usual time for shipping is between 20-40 days.
There are some less famous wineries where you can taste without a reservation. One such place is Tenuta Di Vaira. Its location right on the main highway, and its distinctive and ultra modern rust colored building makes it easy to spot. No reservations are required for entry, although they have a nominal charge for wine tasting by the glass or certain pairings. A friendly and knowledgable staff provides assistance. I want to give special props to Anja in that regard!
The picturesque road to Bolgheri
During my three days in the area, I fortunately found an amazing place to stay, the Podere Vignanova. This place represents one of the best values in lodging I have experienced in my more than twenty European trips. It’s actually an “Agriturismo”, which in Italy means that the property produces an agricultural product from nature, grown upon the estate. In this case, they make fantastic olive oils. Rooms here consist of 16 large-sized suites. Each suite has its own covered private parking stall, and mine had a huge private outdoor patio that overlooked the vineyard and olive grove. I did not have an upgraded room, so I believe that most of the rooms have such a patio. They also feature an indoor swimming pool and spa facilities. This area lies very close to the Tuscan coast, and the Podere even has a private parking lot for beachgoers, and a restricted beach area for guests, so as to not have to compete with the heavy summer tourist crowd. They pretty much think of everything to ensure the enjoyment of the guests. This place only opened in 2019, and I don’t know if it’s officially received a star rating yet, but I would give it 5 stars plus.
Although they have no restaurants per say, they do have a lovely indoor/outdoor dining area where an optional breakfast is served each morning. It includes an expansive buffet, plus custom orders from their chef (such as omelettes) if the guest prefers. The breakfast costs, including special orders from the onsite chef, 10 euros! The outdoor patio sits among the vineyards that surround the property, and provides a halcyon respite to enjoy the breakfast feast. They also have a lovely manager, Erica, who proved most helpful in providing information about nearby sights, wineries, local restaurants and making reservations for dinners and wine tastings. She even came out to rescue me when my navigation system failed to find the place. I cannot say enough about her cheerful and helpful attitude. It boasts a convenient location too, being only about a mile from the aforementioned road to Bolgheri. It’s only about a 15 minute drive to the town of Bolgheri, and about a 10 minute drive to the beach.
"Main Street" & the tiny palace in the village of Montalcino
The village of Montalcino is a real treat. A large and ancient fortress located just on the edge of town has a small but excellent entoteca that provides a multitude of tasting options at various price ranges. I opted for three different wines in tasting portions for 25 euros. If you have the inspiration, one can scale the fortress walls and get an amazing view of the Tuscan plains stretching endlessly far below.
From the fortress it’s an easy walk into the village, which essentially has one main walking street where almost all the commercial establishments, including restaurants and enotecas, are located. Some of the restaurants feature sidewalk cafes, and some have panoramic views of the rolling Tuscan countryside. In the very center of the village you will find the Palazzo dei Priori, a tiny palace indeed, with a bell tower that soars above the narrow main street. Venturing away from the main street will often require hiking up the very steep side streets. The main street provides a fun night for strolling along while sampling various Brunello wines and then settling down for a freshly cooked dinner of local delicacies. Although almost all Italians dine later than Americans, aside from the restaurants and a few bars, Montalcino rolls up the sidewalks early, so don’t plan on any late night clubs or parties, unless you make you your own.
Tuscan Sunrise from my room in Montalcino
Sunset view of Siena
Like its longtime rival Florence, Siena lies within the Chianti Classico region of Tuscany, and so Chianti proves as one of the favored wines here. While not really a wine town like Montalcino or Bolgheri, locals love their wines and it’s always easy to find an enoteca offering a nice array of Tuscan wines. Siena has a plethora of dining options. The non-meat panini sandwich became a lunch staple here. It’s so simple yet so delicious; a fresh roll laced with olive oil, then freshly cut tomatoes, mozzarella cheese, and some greens (lettuce, arugula or basil) and a dash of salt and pepper. Very basic and very amazing!
Fabulous Feast at at the Osteria Sotto le Fonti in Siena
For dinner one night I enjoyed a great steak alla Fiorentina with a fresh tomato salad and broiled potatoes at the Osteria Sotto le Fonti, which provides an informal rustic ambience with great food at relatively reasonable prices. This Osteria is located just outside of Siena’s venerable walls.
Siena has the reputation as the birthplace of the unique pici pasta. It consists of hand rolled pasta strands made without eggs. The resulting noodles resemble spaghetti, except thicker. The increased thickness and roughness of the hand rolling gives the pasta the ability to better hold sauces. I tried several plates of this during the trip, and found it very tasty. It’s very rarely seen here in the States.