Tuscany is one of Italy’s most gorgeous and most visited regions. Known for its rolling hills, covered in grape vines, dotted with vineyards and intermingled with rustic, medieval cities, the amount of charm is nearly overwhelming. As you travel through the countryside watching stunning Italian couples glide past on Vespas, hair blowing in the wind, sun setting behind the most fantastic scenery imaginable it’s hard not to feel like you’ve accidentally wondered on to the set of a movie. It just doesn’t seem real. You can’t believe that this has been going on somewhere in the world and you haven’t found out about it until now.
“The Tuscan countryside whizzed by in a kaleidoscopic whirl of shapes and colors. Green grass and trees melded with blue sky, purple and yellow wildflowers, peachy-orange villas, brown-and-gray farmhouses, and the occasional red-and-white Autogrill, Italy’s (delicious) answer to fast food.”
– Jenny Nelson
Since Tuscany is a massive region filled with dozens of cities, both large and small, separated by fairly decent distances, this post will be slightly different than most. First, I will outline the major cities in the region (Florence, Pisa, Siena, Sam Gimignano), outlining what to do in each. Then I will outline itineraries to and from these cities that you can follow if you have more time to explore outside of the main hubs. I will outline these itineraries in such a way that it will be easy to combine 2 of them, if you have even more time, or to simply daisy-chain them all together for one spectacular trip. Make sure to pull up a map while planning your trip so you can see how it all fits together.
Florence
Florence is the magical capital city of Tuscany. It is both different than any of the other stops in this area as well as different from pretty much any other city in the world.
As Mark Twain once put it, “This is the fairest picture on our planet, the most enchanting to look upon, the most satisfying to the eye and the spirit. To see the sun sink down, drowned on his pink and purple and golden floods, and overwhelm Florence with tides of color that make all the sharp lines dim and faint and turn the solid city to a city of dreams, is a sight to stir the coldest nature, and make a sympathetic one drunk with ecstasy.”
Florence received its own write up on this blog and the best way for you to read up on what to do, where to go and where to stay and eat, is to simply click on the photo above which will take you to that write-up.
Wine Tastings around and closer to Florence
If you’re in Florence, you’ll find you don’t need to go far for wine tastings! In the surrounding areas, we recommend the following wineries (these are still best reached with your own means of transport, as public transportation is very limited or not available).
TORRE A CONA (Rignano sull’Arno)
Torre a Cona is a beautiful wine resort in Rignano sull’Arno. It offers tastings of wine and their Tuscan products in the old barn on the farm, which today houses the wine shop. The tastings and tours of the farm (the cellars and gardens of the Villa) are done by appointment. Find all contact info on the official website.
Set on the hills of Vinci, known as the city of Leonardo, Fattoria Dianella has over 25 hectares of vineyards. Here, Francesco and Veronica Passerin d’Entrèves follow the entire wine-making process, from growing and harvesting their vineyards to the vinification process in the winery and aging in the cellars below the Medici-era villa. In the cellars, they have created a small museum dedicated to showcasing all steps of wine production.
Visiting Fattoria Dianella is a breeze as they are always open to visitors. They will welcome you into their cellar where you will be able to explore the winery until you get to the wine shop for a tasting. On request, it is also possible to visit the vineyards. Just call ahead to book a time. Tastings of two wines is 12EUR; if you add local cheeses, salami and bruschetta then it is 18EUR.
Located in Mugello, about 30 miles north of Florence, Fattoria il Lago organizes guided tours to their winery and tasting of their wines, including their Chianti Rufina DOCG wine and extra virgin olive oil.
Built by the infamous Florentine family de ‘Pazzi, Trebbio Castle is located on the hills of Florence just outside the town of Santa Brigida. They offer organized tours of the cellars, wine tastings and a light lunch for both individuals and groups. Visit the official website for more details.
Things to Do in Tuscany Day Trips from Florence
Taste Truffles in San Miniato
Day trip from Florence or Pisa (in between the two)
Truffle Hunting
“Tuscany’s culinary experiences are endless, but hunting for truffles is definitely the ultimate Tuscan adventure. The most exquisite of all is tartufo bianco pregiato (the prized white truffle), found between September and December in San Miniato, halfway between Florence and Pisa, but different varieties of this precious Italian delicacy grow year-round in the Tuscan woods.
Searching the countryside for this rare and exciting product is a wonderful, unique activity, and there are lots of opportunities to enjoy it. Giulio Benuzzi (aka Giulio the Truffle Hunter) is one of the best expert truffle hunters around and offers everything from guided walking tours through a Florentine forest with his trained dog Eda to workshops, cooking classes, and gourmet truffle tastings.” – Giulio The Truffle Hunter
Bistecca alla Fiorentina at Del Fagioli
Few dishes are more quintessentially Tuscan than bistecca alla Fiorentina, the thick, perfectly grilled T-bone cut from the region’s highly prized Chianina cattle breed. If it’s melt-in-your-mouth steak you’re after when in Florence, Del Fagioli is one of the best places in town to get it.
Established in 1966, this family-run trattoria in Santa Croce specializes in authentic home-style Florentine classics. The dining area is a quintessentially Florentine as the steaks they serve and the house Chianti that you wash it down with.
Besides the bistecca alla Fiorentina, which they are world-renowned for, make sure to try the other items on their menu like ribollita (traditional bread soup), penne strascicate (scrambled pasta), bollito misto (mixed boiled meats), and their signature fagioli all’olio (white beans drizzled with olive oil).
Farm-to-Table Eating at Il Canto Del Maggio
Of all the authentic dining experiences one can have in Tuscany, nothing really compares to the “zero kilometer” agriturismo experience for which the region is particularly known. By zero kilometer they mean that all the ingredients to the food you eat will be from the immediate area. This is the epitome of farm-to-table eating and an experience you should seek out will visiting Tuscany.
One of the best places for such an experience is a place called Il Canto Del Maggio. Nestled in the Valdarno countryside, around 40 minutes from Florence, Il Canto Del Maggio specialize in serving freshly prepared, seasonal foods, in a traditional setting straight from their bountiful organic garden. Meals can be enjoyed either in the traditional dining room or outside on the gorgeous terrace and are accompanied by delicious local wines.
Pisa
Pisa is a must stop for a day simply to see the leaning tower, if you’ve never seen it before (if you have, you can skip Pisa entirely). Pisa, like Florence above has had its own write up on this blog and the best way to explore that city is to read that post by simply clicking on the photo above.
Siena
Piazza del Campo
Piazza del Campo is the main public space of the historic center of Siena. It has been called one of Europe’s greatest medieval squares. Make sure to climb Siena’s famous bell tower, the Torre del Mangia, and if you’re lucky enough to be in town at the right time of year, you can see the twice-a-year horse race, the Palio di Siena, which is held around the edges of the piazza.
Sword in the Stone
One of the top things to see in Siena is their famous Sword in the Stone. As legend as it, Saint Galgano (1148 – 3 December 1181), a Catholic saint from Tuscany born in Chiusdino, in the modern province of Siena, Italy, led a rather ruthless life before suddenly abandoning his evil ways in favor of pious hermitage in a place now known as Rotonda di Mentesiepi. Galgano is said to have had two visions that spurred on this drastic change. First the Archangel Michael came to him in a dream and told him that he would be protected by the Archangel himself. In the second version, Galgano’s horse is said to have suddenly stopped obeying his commands and instead led him to the top of Montesiepe. Atop this hill the Archangel Micheal supposedly appeared to Galgano along with the 12 Apostles and the creator himself. After the vision, Galgano wanted to mark the spot with a cross, but not having any wood to build a cross he decided to use his sword. The legend states that Galgano drove his sword into the hard rock like a hot knife cutting through butter and that sword immediately became fused with the rock so that nobody could remove it.
Today a chapel that contains his robe as well as his tomb is built near this supposed sword in the stone. At the Rotonda at Montesiepi, near the ruins of the Abbey of San Galgano, you can see the hilt of a sword protruding from granite stone. An analysis of the metal conducted in 2001 confirmed that the “composition of the metal and the style are compatible with the era of the legend.” The analysis also confirmed that the upper piece that protrudes from the stone is connected to a continuous, invisible, lower piece and that they belong to the same authentic artifact.
Medieval Sweets in Siena
No visit to Siena is complete without tasting its traditional dolci. Among the most famous are Cavallucci (anise-flavored biscuits with candied orange peels), ricciarelli (soft almond cookies), and the famous panforte (spicy cake with dried fruits). All of these delightful treats can be found in the dozens of sweet-smelling pasticerrie lining the city’s picturesque cobblestoned streets.
You’ll find the best pastries in Siena at Nannini, the oldest pastry shop in town and one of the most renowned in all of Italy. Established in 1944, Pasticceria Bini is another Sienese pastry institution famous for its crispy, almond-studded cantuccini. If you’re looking for an incredible panforte margherita make sure to stop at Pasticceria Sinatti. Also, a local favorite is La Nuova Pasticceria where they have been making excellent freshly-baked ricciarelli (sugar-dusted almond biscuits) since 1961.
Siena’s Palio
Twice a year (July 2nd and August 16th) Siena plays host to one of Europes most fascinating medieval traditions. Dating back to the 14th-century games that used to be played in the square and particularly the horse racing that started in 1590, this anything goes, bareback, horse race around the dirt-packed Il Campo has been one of the coolest events to see in Italy for hundreds of years. Garish, colorful costumes and competition between rival contrade (traditional neighborhood wards) usually makes for a festive and ruckus crowd. Massive feasts are set up along outdoor tables that stretch for blocks on the medieval side streets as a festival atmosphere takes over the entire town.
Val d’Orcia
Just few minutes from Siena, Val d’Orcia pops out of the idealized landscape of vineyards and cypress trees that you thought only existed in your mind when you imagined Tuscany. Val d’Orcia is hands down one of the most romantic areas of Tuscany. Dotted with cypress trees, tiny vineyards and medieval castles, the natural beauty of this area cannot be overstated. As if that weren’t enough Val d’Orcia is known for its abundance of natural hot springs (particularly the towns of ¸Bagno Vignoni, Bagni San Filippo and Vivo d’Orcia), making it a great place to spend a relaxing day.
This whole area, a designated UNESCO World Heritage Site, extending from the hills south of Siena to Monte Amiata, boasts very famous towns such as Pienza, Montepulciano, Montalcino, Monticchiello, Bagno Vignoni, and San Quirico d’Orcia. Jump in the rental car and spend a day exploring the countryside and you won’t be disappointed.
San Gimignano
San Gimignano is a medieval, walled town that is known as the New York City of the medieval world due to its skyline filled with many towers. San Gimignano has plenty of historic plazas, filled with a maze of cobblestoned streets, offering enough nooks and crannies to spend an entire day exploring. This is one of the best preserved medieval towns in all of Italy.
One of the most wonderful experiences in San Gimignano is accompanying an expert and his dogs on a truffle hunt. Learn how to recognise and search for truffles in a stunning private oak forest, before enjoying an authentic Tuscan lunch.
World’s Best Gelato in San Gimignano
Be sure not to miss San Gimignano’s world championship winning gelato shop, Gelateria Dondolini. The gelateria, which has been featured on TV shows with the likes of Gordon Ramsey as well as in multiple movies, has its own herd of cows which produce the organic milk that they use to create their award winning gelato which they mix expertly with the freshest local ingredients, fruits from local farms, Sicilian pistachios, and San Gimignano DOP saffron..
This small hidden gem, tucked away in the along the quaint medieval main square of San Gimignano, is worth the trip alone. Run by former gelato world champion Sergio Dondoli, this is arguably the best place in the world to indulge in homemade Italian ice-cream.They specialize in an eclectic array of flavors including some truly unique styles like white wine and pink grapefruit with sparkling wine, which actually has a bit of fizzy sensation added to the gelato.
Some of the most beloved specialties include Rosemary Baby (with raspberries and rosemary), Crema di Santa Fina (orange cream with Bourbon vanilla from Madagascar, San Gimignano saffron, and pine nuts from Pisa), and Vernaccia Sorbet made with the best vintage Vernaccia wines of the area.
Chianti Wine Region
Chianti Classico spreads from Florence to Siena and includes the municipalities of Greve, Panzano, Radda, Gaiole, Castellina and Castelnuovo Berardenga.
While in Chianti you will undoubtedly hear the legend of the black rooster – the logo and trademark of the premium wine from the region, Chianti Classico. It dates back to the 13th century when it was drawn on the banners of the Chianti League, the military and administrative institution. But it is also linked to the ancient conflict between the republics of Florence and Siena. Tired of constant battles to define territories in Chianti, they agreed to settle the dispute with a contest, where a knight would leave each city in the morning at the crowing of a cock. The Florentine knight would head towards Siena, and Sienese’s towards Florence, and where the two met, they would seal the border. The Florentines entrusted their wake up call to a black rooster, which they’d kept hungry the night before. The Sienese chose a white rooster, which they gave a hearty evening meal. The hungry Florentine rooster woke his knight earlier and he was able to annex a larger portion of Chianti for Florence.
The Chianti region is known the world over for its vintage wines, but less so its vintage cars. But this shouldn’t stop you from taking the most entertaining wine tour in Tuscany through the Chianti hills. Here you can tour the region in a vintage Fiat 500 spending the day whizzing around the Chianti countryside.
Self Guided Tours of the Region
There are many different itineraries to choose from. Please click on the link above to find some recommendations from Tuscany’s official tour website. You’ll find self guided tours for the Chianti Classico route, which has stops in the towns of Greve, Gaiole and Castellina. Another itinerary focuses on the Pesa Valley, including Tavarnelle Val di Pesa, San Casciano Val di Pesa, San Donato in Poggio, Badia a Passignano and other hidden gems in this insanely beautiful area.
Itineraries
Florence to Siena
1 day Chianti driving itinerary
This trip can be completed in one single day so long as you get an early start. You’ll simply head south from Florence heading towards Greve, in the Chianti region, where your trip will start. Greve is often referred to as the ‘doorway to Chianti.’ This lively town is famous for its particularly shaped piazza or square which has served as a marketplace for the castles and walled villages in the surroundings since the Middle Ages. The square has a triangular shape and large porticos along all three sides that protect visitors from sun and rain while shopping.
In the center of the square, the bronze statue of Giovanni da Verrazzano dominates; he was an explorer that discovered the Bay of New York. At the top of the square stands the Church of S. Croce, originally a medieval church and long since remodeled according to the Renaissance Revival architectural style. Inside the church, you will find a few works of sacred art including the triptych depicting Madonna and Saints by Bicci di Lorenzo.
Greve features many different enotecas and vineyards where you can taste Chianti wine and enjoy local food. The surrounding shops that line the piazza are filled with workshops, wine bars, and restaurants where you could spend an entire day hopping from shop to shop. One particular shop that comes highly recommended is Antica Macelleria Falorni, a historical butcher shop that sells only typical products produced in Chianti.
VITICCIO (Greve in Chianti)
Just north of Greve, a short 5 min drive up the road is Viticcio Winery Estate, you can do wine tastings every day of the week, these are set up by appointment. Just call and you’ll be able to arrange a visit at the time that best meets your schedule.
This is a family-run winery, so most likely you’ll find a family member guiding you on the journey into the world of wine, starting from their vineyards to the winery before moving on to the tasting of their wines, which you can choose to buy afterward as well. Read more details about their wine tastings and tours on their official website.
Ristorante Villa Bordoni
For the ultimate foodie getaway head to Villa Bordoni, a gorgeous countryside villa in the hills outside Greve. Their restaurant is one of the best in the area. They have a tremendous wine cellar featuring more than 200 different bottles from some of Italy’s best vineyards.
If you want a little more of a hands on experience they also host the Chianti Cooking School on their grounds. You do not need to be a guest at their on-site hotel to learn the art of Tuscan cooking. It is open to anyone who wishes to make a reservation.
Here a professional chef will teach you the secrets of rustic Tuscan cuisine in the hotel’s open kitchen. Classes involve the preparation and, of course, eating of a complete four-course meal complete with wine to pair it with.
Villa Bordoni also owns Enoteca Il Cardo, a stunning wine bar in the hilltop wine village of Panzano, where cooking lessons can be accompanied by wine, olive oil, and balsamic vinegar tastings. Click on the link above to learn more.
Panzano
Panzano is the most populous town in Chianti and sits just a few kilometers south of Greve.
There are several wine bars and restaurants in Panzano that offer wine tastings. A popular place to visit is the Antica Macelleria Cecchini, a butcher shop famous for its Florentine steak and where the owner is known to recite passages from Dante’s Divine Comedy while serving customers.
Not far from the historic center stands the Pieve di San Leolino, an ancient rural church dating back to the year 982.
Castellina
Moving towards Siena you’ll reach Castellina in Chianti which dates back to the Etruscans.
The town features a massive castle and the impressive Via delle Volte, an underground series of roads that run around the city, offering breathtaking panoramic views.
The Church of S. Salvatore merits a visit; rebuilt after the Second World War, the church displays a beautiful late 14th-century fresco by a Tuscan master.
Radda
Leaving the Chiantigiana road and taking the SR429 you will come across the town of Radda in Chianti, which, to this very day preserves its original medieval look. The ancient walls still defend the center of the town and its maze of cobblestoned streets.
Spend some time getting lost wondering this maze of streets and indulging on local wine. There’s a number of enotecas where you can sit outside sipping on Chianti while enjoying spectacular panoramas of the rolling hills covered in vineyards that surround the town.
Near Radda stands the Castle of Volpaia, an ancient walled town which we recommend visiting. The castle in sandstone has a distinctive dark color that makes it different from other castles in Chianti. In spite of the marks of the numerous wars between Florence and Siena, the main structure can easily be recognized in the massive tower and one of the minor towers. We suggest a stop at the Commenda of S. Eufrosino, a 14th-century church transformed into a wine bar. Today the Castle of Volpaia is a small tourist town where you can experience the ancient culture of wine.
THE CASA DEL CHIANTI CLASSICO (Radda in Chianti)
Opened in June 2014 within the former Convent of Santa Maria al Prato in Radda in Chianti, the “Casa del Chianti Classico” is the first “house of wine” for the Chianti Classico Wine Consortium. The “Casa Chianti Classico” offers the chance to taste and buy from the largest collection in the world of Chianti Classico labels, and offers a terrace with a view to enjoy a lunch or dinner and many events, courses and exhibitions dedicated to wine. Most of these are concentrated in the summer months, but the wine shop and terrace is open year round. For more information, visit the official website linked above.
Gaiole
Not far from the Radda and the Castle of Volpaia stands Gaiole in Chianti, another town dating back to the Middle Ages. Gaiole was historically an important marketplace for the castles in the surrounding area because of its position between Chianti and the Valdarno (Valley of the Arno river). It was also one of the three original strongholds of the League of Chianti in the 1300’s. Gaiole is still an important point of interest in this area with wine and art festivals routinely held in the main square.
There are several castles and fortified towns around Gaiole that deserve a visit. For example, the Castle of Vertine, the Castle of Meleto, Pieve of Spaltenna and Castello di Brolio can be visited, look into a special wine tasting and winery tour.
CASTELLO DI BROLIO (Gaiole in Chianti)
The Enoteca del Barone Ricasoli is open for tastings, both for individuals or for groups, both upon booking. Here, in addition to being able to taste and purchase the Ricasoli wines, you can also buy quality products from local producers, such as honey and olive oil.
Castelnuovo
Castelnuovo Berardenga, founded in 1366, was located on the border between Florence and Siena. Built by Siena, it remained under their control until 1555, when they were defeated by the Medici Family.
Just outside of the town borders you will find the enchanting town of San Gusme, and some lovely photo opportunities of a little town which seems to have been lost in time. The Certosa of Pontignano merits a visit, not only because it is a stunning monastery structure for events, but also for its more recent historical significance, as it served as a safe haven for Jewish and political dissidents during WWII. If you enjoy ancient history, make sure to stop at Pieve a Pacina, less than 3 km from the town center, one of the oldest churches in the area being built as early as 714.
Castelnuovo Berardenga
In the southern area of Chianti, Castelnuovo Berardenga dates back to the 1360s and developed as Siena’s stronghold due to its strategic position on the border of the Sienese region.
Siena
Wine and Food Tour:
Try this 9-hour wine and food tour from Siena combines sightseeing with delicious food & incredible wine tasting in some of the area’s most beautiful destinations.
In addition to exploring the enchanting hilltop towns of Montalcino and Montepulciano, partakers have the opportunity to visit a couple of wineries, sample delicious local wines (including Nobile di Montepulciano) and food, and learn the art of making pecorino cheese in the pretty UNESCO-listed Renaissance town of Pienza, where it originates.
Places to Stay near Siena
Siena to Viareggio
Monteriggioni
In the countryside of Siena there is another Tuscan hill town that definitely deserves a reference in this article: Monteriggioni.
Mentioned in Dante’s Inferno, this stunning settlement features perfectly preserved ten-meter-high fortified walls, along with fourteen towers that can be seen for miles. Monteriggioni is known for its medieval festival, celebrated every year in July. This small walled town can be completed in about an hour.
San Gimignano
See Above
Volterra
Volterra is one of the most beautiful hill towns in Tuscany. It’s a walled town thats remarkably a well-preserved, as evidenced by its medieval and Renaissance buildings, its Roman theatre and its Etruscan sites.
Must-see attractions include the Piazza dei Priori, home to the magnificent Palazzo dei Priori, the Palazzo Pretorio with its Tower of the Little Pig, the Romanesque Cathedral and its Baptistery, the Roman Amphitheatre and much more.
Certaldo
Certaldo is a beautiful little town perfectly located between Siena and Florence. Dating back to the Etruscans and the Romans, it is a great place to enjoy Tuscan food especially during the Boccaccesca Festival held between September and October.
Do Volterra and Certaldo on the way to Viareggio
Viareggio: Beach
Eat at L’Oca: They have an amazing Burrata Ravioli
Wine Tasting in Chianti Classico.
Take your time navigating the roads between one town and the next and stop at any of those intriguing signs that say “vendita diretta” which means they sell directly to the public.
A Private Tour that you can check out HERE is very highly recommended.
Siena to Arezzo
This itinerary can be done as a string of continuous visits if you want to go from one town to the next or you can simply take day trips from wherever you are staying near Siena to one or two towns at a time, and simply let the day come to you.
Pienza
Small, but one of the best towns in Tuscany, Pienza is famous for two reasons – firstly for being the capital of pecorino cheese and next for being a UNESCO World Heritage Site.
Val d’Orcia
See Above
Montepulciano
Nestled between the Val D’Orcia and Val di Chiana, Montepulciano is a quintessential Tuscan medieval village, famed for its light red wine. Surrounded by a landscape of rolling hills, it has castle walls and ramparts, plus thermal springs.
Cortona
Perfectly placed from its hillside perch to reach both Siena and Arezzo, Cortona is the epitome of those Under the Tuscan Sun dreams and one of the most popular places to see in Tuscany. While the town has crumbling piazzas and beautiful baroque church of San Filippo Neri to explore, you’ll also enjoy the panoramic views from its walls of olive groves and miles of the archetypical Tuscany countryside dotted with cypress trees.
Cortona’s steep streets provide an unforgettable view over Lago Trasimeno and the Valdichiana. Made famous by the film Under the Tuscan Sun, Cortona was briefly the second most popular Italian destination for US tourists after Venice, and while not as well known these days it can still be filled with the occasional tour bus. That being said, its quaint medieval streets that climb the towns steep hills have yet to lose an ounce of their charm
Anghiari
Looking to escape the crowds? Anghiari is one of the best towns in Tuscany for an escape. It is set in the wonderful landscape of Valtiberina, an area which sees few tourists compared to other parts of Tuscany.
Tastings in Chianti near Arezzo
The Days of Wine in the province of Arezzo: Every Wednesday and every Sunday from April to October wine producers in the province of Arezzo organize an event dedicated to their local Chianti wines, open to all, which include tastings of wine and local specialties.
For more than 8 years, local wine producers in this area have been making it very easy to visit their “cantinas” (wine cellars) and do some wine tasting by organizing a calendar highlighting a different vineyard every Wednesday and Sunday in the months from April/May through October. They have fixed prices & no reservation is necessary, each vineyard has its own day making it easier to decide where to go, set dates from May through October.
Livorno, Lucca and the Area around Pisa
Lucca is a city right outside Pisa, to the East, between Pisa and Florence. Around Pisa there exists a smattering of towns and cities that are well worth a trip if you have time. You can either start this itinerary in Florence by heading west to Pistoia, then to Lucca, Ponte della Maddelena, Barga, Isola Santa, Forte Dei Marmi, Pisa and then on to Livorno. Or, you can do it in reverse. If you are starting off in Pisa, you can easily skip Livorno, if you don’t want to drive in the opposite direction before starting the trip to Florence.
Pistoia
Pistoia, a city just 30 minutes from Florence, was actually nominated as the Italian capital of culture for 2017. It’s not well known outside of Italy and thus is one of the few places in Italy relatively untouched by tourism. You should consider visiting Pistoia before everyone else finds out how gorgeous it is.
Lucca
One of the most authentic towns you will find in the region. Known, for its medieval walls. Make sure to take the time to walk the walls and enjoy their gorgeous views of the city.
Olive Oil Tasting in Lucca
Tuscany may be synonymous with wine tours, but sampling the area’s famous olive oil is an equally rewarding foodie experience. Nestled in the fertile hills of Lucca, Fattoria Di Fubbiano is known for producing some of the world’s finest extra-virgin olive oils, plus some award-winning Colline Lucchesi DOC wines.
Centered around a 17th-century villa, the farm resembles an ancient Tuscan hamlet and offers guided tours of the winery, as well as wine and olive oil tastings on request. To sample a slice of the farm life and learn about the oil and wine making process, visitors can also spend their vacation in one of the traditional apartments on the estate.
Ponte della Maddalena (Just a Quick Stop)
If you’re travelling between Lucca and Abetone, be sure to plan a stop at the Ponte della Maddalena, also called the Devil’s Bridge. It is one of the most photogenic spots in the whole region, so be sure to have your camera at the ready.
Barga (Just a Quick Stop)
Hidden away high in the Appenine hills, Barga is a must-see. Another medieval town, it is dominated by views of the Pania della Croce mountain in the Apuan Alps.
Isola Santa, Apuan Alps (Just a Quick Stop)
Situated in the heart of the Apuane Alps a short trip from Florence, is this quiet, beautiful village. Built in the middle ages Isola Santa, served as a resting point for pilgrims traveling through. In the 1950s, the inhabitants left after the construction of a hydroelectric dam. However, in subsequent years, it has been restored and is now a charming oasis of lush greenery, centuries-old buildings, and a teal-blue lake. Take your cameras because this place is very, very photogenic.
Forte dei Marmi (Just a Quick Stop)
A chic location mostly frequented by the rich and famous is Forte dei Marmi. This coastal town is one of the most charming locations in Tuscany and is much more pleasant to visit during the colder months, as it is often crowded and expensive during the summer.
Livorno
Tuscany’s best seafood can be found in Livorno. Fresh fish and seafood reign supreme in Livorno, a vibrant multiethnic port town on the Etruscan Coast. Known especially for its cacciucco (fish stew) and torta di ceci (chickpea pie), the city is a veritable foodie’s dream, with one of the biggest covered markets in Europe and buzzing, reasonably priced restaurants galore. The local cuisine is honest, simple, and influenced by the various cultures that have passed through and settled here throughout history, most notably the Jews.
For a true flavor of Livorno, head to Cantina Senese, a charmingly unpretentious eatery in the historic center, where harbor workers and neighborhood families crowd in to feast on divine mussel soup, fried cod and anchovies, and the ubiquitous cacciucco a Livorno.
Other tasty options include Trattoria Antico Moro and Osteria del Mare, both specializing in fresh, authentic home-style seafood dishes.
Tuscany’s Chocolate Valley
Stretching from Pisa all the way to Prato, the Chocolate Valley is where you’ll find some of Italy’s leading artisan chocolatiers, along with their small factories and gourmet boutiques.
A pioneer in the production of chocolate in Tuscany is Roberto Catinari, who opened his legendary chocolate shop in Agliana over 30 years ago after studying with Swiss chocolatiers for two decades. His rich, velvety pralines, which come in more than 100 varieties, are still regarded as some of the nation’s finest.
The area also includes the spa resort of Monsummano Terme, where Andrea Slitti, the first non-Frenchman to win the prestigious Grand Prix de la Chocolaterie de Paris, serves up decadent treats in a charming café; as well as the village of Pontedera, where widely-famous Amedei, run by the Tessieri family, produces what is arguably the best chocolate bar in the world.
Another must stop on your Chocolate Valley tour is Casa De Bondt in Pisa, whose Dutch-born confectioner has been chosen among the 15 best chocolate manufacturers in the world. His award-winning creations are flavored with Sicilian lemon, toasted coffee, or bergamot, and visitors can also participate in courses and tastings.
Grosseto/Elba (Itinerary from Siena to The Isle of Elba)
Dinner at a Wine Estate
You can’t leave Italy’s premier wine-producing region without visiting some of the area’s fantastic wineries. And if you only have time for one, let it be the famous Castello Banfi – a family-owned estate/hilltop castle hotel with a storybook setting in Montalcino. Featuring 7,000 acres of vineyards, it produces some of Italy’s finest red wines, including award-winning Brunellos, which can be tasted at their delightful Enoteca Alle Mura, along with grappa, Salsa Etrusca, and a selection of Tuscan sheep cheeses and cured meats.
Try to plan your visit around lunch or dinner, as the two Tuscan restaurants on the premises (La Taverna and La Sala dei Grappoli) serve splendid regional food with a haute twist in glorious surroundings.
Pitigliano (day trip)
Carved from volcanic stone, Pitigliano is one of the most charming towns in southern Tuscany. Here you can find Bronze Age, Copper Age and Neolithic remains. It also has a Medici aqueduct in the centre of town and a lovely Jewish neighbourhood.
Saturnia (just a quick stop)
If you want to escape from the world for a while and drift away into the bliss of a spa treatment, head for the natural hot springs of Saturnia. These are the best known Tuscan springs, perfect for rejuvenating your body and mind.
Michelin Dining in Maremma
Tuscany is currently home to 35 Michelin-starred restaurants, but a time-warp stone hamlet in the Maremma region is perhaps the last place you would expect to stumble upon one. And yet, there it is – tucked into a stone house amidst the quiet cobbled streets of Montemerano.
Run by much-admired chef Valeria Piccini and her husband Maurizio, Da Caino serves memorable two-star Michelin meals in an elegantly inviting 9-table dining room. The cuisine, although deeply rooted in the regional identity, is experimental and refined, with dishes like wild boar with fennel or fresh Argentario anchovies with tomato sorbet.
Meal with a View at Il Pellicano
Set into a small bay along the breathtaking Argentario coast, Il Pellicano feels straight out of The Talented Mr. Ripley. This is one of Italy’s most enchanting and storied addresses, where beautiful, carefree socialites have been coming to live out their dolce vita fantasies ever since the ‘60s – whether lounging by the glistening pool, soaking up the sun on the fashionable rocky beach, or lingering over luscious alfresco lunches overlooking the sweeping Tyrrhenian Sea.
This legendary hotel near the pretty seaside town of Porto Ercole is a destination in and of itself, one that captures nearly everyone’s vision of a perfect Italian summer. And this being a country of sensory pleasures, food is very much at the center of the experience.
You don’t need to be a guest to savor a marvelous candlelit dinner at the Michelin-starred Pellicano Restaurant or to feast on the day’s catch at Pelligrill’s open-air terrace perched above the Med. Depending on your mood, you can sip on superbly mixed cocktails with a view at Bar All’Aperto or treat yourself with a spectacular Super Tuscan from the remarkable La Cantina cellar. Wine tastings, mixology courses, and cooking masterclasses with Michelin-starred chef Michelino Gioia are also available.
Giglio
Another small island located in the Tuscan archipelago, Giglio is frequented only by those in the know. It’s not touristy at all, and absolutely stuffed with romantic spots, hidden beaches and pristine clear waters. What more could you want on a trip to Tuscany?
Massa Marittima (can be skipped if you don’t have enough time)
Head south in the region and you’ll find Massa Marittima just north of Grosseto, in southern Tuscany. With medieval buildings topped with red roofs, it has a lot in common with the small towns of northern Tuscany making it a unique place to see in Tuscany’s Maremma area.
Elba
Just two hours by ferry from the city of Livorno and you can easily be in Elba, the third largest island in Italy, known for its beautiful beaches, with plenty of things to see and do.
Places to Stay Near Siena
Castel Monastero
But the hotel really comes into its own outside the rooms – Castel Monastero’s buildings, oozing character and history from its wishing well to its bell tower. Located on a vineyard, alongside views of the vines, Castel Monastero produces its own wine including a Chianti Classico. There is also a spa with a steam room, sauna and various whirlpools, a saltwater therapy pool in which you can float away your cares in mineral-rich water, plus it has wellness programmes with a focus on weight-loss, detoxing and rejuvenation.
Another stand out feature is its food. It has a Gordon Ramsey restaurant, Contrada, serving his take on gourmet Tuscan and Italian cuisine. Dining there is pretty special. I had a tasting platter of starters, lobster with tomato gazpacho, pecorino cheese ravioli, catch of the day brined in salt and rosemary, and Neapolitan baba with rum, lime cream, black cherry and Strega liqueur ice-cream.
But where Contrada served up a modern take on Tuscan food, the hotel has another restaurant La Cantina, serving more traditional dishes, in a vaulted 13th-century cellar.
There, executive chef, Nello Cassese gives cooking demonstrations. He whipped us up a pappa pomodoro made with different varieties of tomatoes and bread, plus perhaps the most famous of Italian desserts – tiramisu.
Festivals in Tuscany
As one of the world’s culinary meccas, it’s no surprise even the tiniest, most remote village in Tuscany celebrates its local specialty with a sagra (local food festival). The region is overflowing with fairs honoring everything from fresh wine and olive oil to truffles, chestnuts, and wild boar. Most of these take place during fall and are an excellent way to delve into the culture and discover the area’s most esteemed products.
One of the most famous is Boccaccesca, an annual food and wine extravaganza taking place on the narrow medieval streets of Certaldo Alto. Traditional Tuscan dishes like porchetta and ribollita soup are available to sample during the event, and so are local cheeses, cured meats, and revered wines like Chianti Classico or Brunello of Montalcino.
Other notable gastronomic festivals include the White Truffle Fair in San Giovanni d’Asso, Sagra del Cinghiale di Chianni (the Wild Boar Festival of Chianni), Il Desco in Lucca, and Cookstock in the historic center of Pontassieve.
Places to Stay
Castel Alfi(Near Volterra)
Relais Villa Palagio (outside Florence)
Agriturismo
– Agrotourismo
– Castello di Cabbiano (Near Greve)
– Castelfalfi (Near Volterra)
