The sunny Italian region of Tuscany provides infinite allure for travelers. Artists, winemakers, monks and merchants make their home in the rustic medieval hilltop hamlets, rolling hills of olives and wine, bucolic farmlands strewn with poppies and sunflowers, and marvelous cities sush as Florence. Read on to discover our favorite Tuscan treasures.
Florence – The Streets Less Traveled
The large crowds that visit Florence in the summer can make it feel a bit like Disneyland. To find real Florentine flavor and space to breathe, cross one of the three bridges over the Arno River to the district. Less crowded than the other side, its medieval backstreets are a labyrinth of picturesque lanes, alleyways, nooks and crannies. While you should definitely try to see attractions like Pitti Palace, the lovely Boboli Garden and the lesser-known Bardini Gardens beyond it, when you get to Oltrarno, leave the map behind and just wander. Let yourself be surprised by narrow lanes that open onto a piazza, antique shops and artisan studios where contemporary craftsmen continue Florentine traditions such as sculpture, leathercraft, metalwork, woodwork, goldsmithing and bookbinding. Superb family-style trattorias feature fresh and simple ingredients—and are mostly undiscovered by tourists. Practice your Italian in small markets, cafés and gelaterias as you sample local specialties and explore piazzas like Santo Spirito and Piazza Pitti.
Florence – Medieval Church with a Breathtaking View
Signs lead the way to a medieval hilltop church beyond Oltrarno and the old city walls of Florence. The story of San Miniato al Monte goes back to 250 A.D., when St. Minias—an Armenian prince turned Christian hermit—was beheaded for his faith. Legend has it that St. Minias carried his own head over the Arno River and made his way up the hillside that overlooks Florence, where he laid himself to rest. The church was built in his honor in 1013, with an adjoining monastery erected around it. Michelangelo looked after the church during the Siege of Florence (1530), devising a plan of defense that included placing two cannons on top of the bell tower and hanging monks’ mattresses from its walls to absorb the impact from incoming cannonballs.
Meticulously planned, the church is filled with fascinating symbolism, geometry and zodiacs (its façade resembles an owl). Impressive frescoes can be found inside and out. The adjoining gift shop sells honey, soap and liqueurs made by the monks. On summer weekdays, the monks accompany mass with Gregorian chants in the crypt at 5:30 p.m. Day or night, regardless of the season, the view is outstanding.
Arezzo – A Medieval Pot of Gold
Southeast of Florence, Arezzo presides on a hill overlooking four valleys. A haven of goldsmiths and jewelers, it’s also home to boutique shops and beautiful Renaissance and Romanesque architecture of red brick, stucco and stone. Monuments, churches and museums like the Casa di Giorgio Vasari provide historical and artistic interest, while small alleyways, piazzas, quiet streets and the Corso Italia—a pedestrian-only avenue to the old city center—make it a great, uncrowded place to explore on foot.
The steeply graded Piazza Grande in the old town marks the center of this ancient commune and features a town hall that dates back to the 6th century. Take a seat at one of the surrounding cafés for a cool drink, gelato or panini. Pop into the town’s tavernas and trattorias to sample local specialties like acquacotta (peasant bread soup made with porcini mushrooms), ribollita (a bean and vegetable soup) and the famous Chianina steak (aka Bistecca Fiorentina), paired with one of the area’s fantastic wines.
Summer events in Arezzo provide great souvenir shopping and entertainment. On the first Sunday of the first full weekend of each month, an antique fair is staged on the Piazza Grande. Spilling over to adjacent streets, hundreds of stalls offer everything from wrought-iron implements, cooking utensils and furniture to art prints, paintings, books and handblown glass. In June (on the third Sunday) and September (on the first Sunday), the piazza transforms into a medieval square that hosts the annual Joust of the Saracens, a knights’ tournament held here since the Middle Ages.
Vinci – Home of the Master
Find all things da Vinci in this little town. In addition to the Leonardiano Museum (filled with the legend’s models and plans), you can visit La Casa Natale di Leonardo, the olive farm where Italy’s most celebrated Renaissance man was born. Artists still thrive in this area, including the brothers of Fratelli Taccini, who have a studio just south of Vinci. The three siblings—Alessandro, Fulvio and Vittorio—carry on the legacy of their father. Blending traditional, modern, Tuscan and Italian sensibilities in their incredible ceramics and artwork, they have been honored with exhibits at the Vatican and around the globe.
Take a tour of the studio or sign up for a class at the Fratelli Taccini pottery school. Taking place in the brothers’ bottega (workshop), the training includes everything you need to know to create paintings, ceramics and sculpture, such as using a potter’s wheel and working with modeling clay. Choose a partial-day class or dive in with a weekend course.
Sinalunga – The Hill Town Less Traveled
Just 30 minutes from Siena on the border of Umbria, Sinalunga is perched atop a hill like many Tuscan towns, but has a working-class appearance that makes many pass it by. As a result, it’s still quite charming. Piazza Garibaldi hosts a weekly Tuesday market and is home to a stuccoed church and Bar L’angolo, where men congregate to play cards, sip espresso and enjoy outstanding gelato. Just south of town, Locanda dell’Amorosa is a Tuscan fairytale with its long, cypress-lined driveway leading up to a 14th-century hamlet that’s now a luxury hotel. It makes a great base for exploring Tuscany, but you may not want to leave the pebbled courtyard and stunning surroundings, which are populated by grapevines and olive trees. When you get tired, take a nap in the manor house among its period artworks and antiques. Finish the day with a garden-grown supper on the covered terrace.
Catellina in Chianti – Tuscan Castle
Castello La Leccia was already in existence in 1077 when 16 owners claimed rights to this hilltop paradise. Bombed during World War II, the castle’s medieval tower was partially destroyed, along with an 18th-century wing of the villa. Since then, the great-grandchildren of owner Giuliano Daddi have infused new life into this incredible piece of Tuscan history through meticulous reconstruction.
A tree-lined driveway sets the stage and delivers guests to the castle’s perch, which enjoys a stunning 360° view of the Tuscan valley. It’s hard to resist sitting on the pebbled terrace surrounded by roses, looking over olive groves and vineyards or strolling through the manicured garden, taking in the sweet smell of jasmine. You can also lounge by the pool with a book from the castle shelves, and tour the estate’s winery in the afternoon for a fascinating history and a sample of the farm’s bounty. At the table, wine and olive oil that are sustainably grown and harvested onsite are served with traditional Tuscan cuisine. Twelve elegant, spotless rooms feature wooden floors and beamed ceilings—but it’s the outstanding views and warm hospitality that elevate Castello La Leccia to Tuscan perfection. Photo courtesy of Castello La Leccia.
Monteriggioni – Isolated Mountain Fortress
Along the backroads of Tuscany between Florence and Rome, you’ll find olive orchards, wild poppies and the walled village of Monteriggioni. Built in the 13th century by the Siennese as a military outpost along the Florentine border, Monteriggioni’s massive walls and 14 towers still stand. Walk through narrow, winding alleys past rustic houses and the public gardens that were once the primary food source of the inhabitants of the town, and imagine what life was like for the soldiers, farmers and artisans who once lived here.
Monteriggioni’s heritage is placed on display during the annual Medieval Festival in mid to late July. With amazing period costumes, performers, music, demonstrations and food, the festival fills the town’s piazza. Photo courtesy of Relais La Costa.
Carrara – The Italian Marble Mecca
North of Pisa in the shadow of the Apuan Alps, Carrara is renowned for its white marble. Home to marble mines for over 2,000 years, it is here that Michelangelo spent years of his life personally quarrying stone for his sculptures, including David and the Pietà in Florence. Emperor Augustus even refashioned Rome from brick to marble, using the finely grained, hard stone that could withstand weather and discoloring.
In front of the home where Michelangelo lived in Carrara, the Cathedral of St. Andrew is made entirely of this exquisite white marble. Sculpture studios and sculpture schools dot the town. To discover the genesis of all this grandeur, take a 4×4 jeep tour to see the fantastic Fantiscritti Mines. It’s not far from town, but you’ll need to navigate hairpin turns to get there. In addition to exploring the small, outdoor museum with its marble-working tools, you can tour the huge mine chambers that are the size of cathedrals. Within the soaring walls of the quarry, you’ll learn how the cutting and pulling of marble blocks has turned into an art form. The setting is so visually compelling, it has served as the backdrop for fashion shows as well as Lamborghini and Maserati ads.
Travel Tips: Tuscany
Since Tuscany is such a popular destination, a mind-boggling amount of information exists for visitors. We’ve narrowed it down to eight great tips that get you on the right track. Read on for pointers on how to dress, where to eat, what to say and where to stay on a summer journey to Tuscany.
Late is Great
Although its neighbor, Switzerland, shines in punctuality, Italy is the relaxed, carefree opposite. Do not expect timely trains or buses, and leave yourself extra time when you take public transportation to special events and appointments. During the summer, Italians tend to dine later—lunch around 1:00 p.m. and dinner after 8:00 p.m. Restaurants are often closed between meal services, unless they’re located in a popular tourist area. Italians generally enjoy leisurely dining. Waiters typically won’t interrupt you with a bill, so you’ll need to request one. In the hot summer months, Italian piazzas come to life late in the evening when locals enjoy the social scene.
Take the Wheel
To get to Tuscany’s small towns, driving is the only way to go—unless you’re planning a hiking or biking tour. You’ll need a good map or GPS; review road rules and signs before taking the wheel. The modern toll highways, called Autostradas (A), are the fastest way to get between major cities, while Provincial (SP), regional (SR) and state highways (SS) are often more scenic. The winding Via Cassia (SR2) and Via Chiantigiana  (SR222) in Chianti are great examples.
Driving and parking in cities like Florence, Siena and even ancient medieval towns can pose a challenge due to pedestrian-only zones, narrow passageways, one-way streets and limited traffic zones (ZTL) that require special permits. To get around this, use a car park outside of town (see parking maps for Florence and Siena) and walk in, or drive to a rail station and take the train or a cab into town.
Speak the Language
Outside of large cities (and even in some parts of them), Italians may give you a blank stare if you speak English. If you speak a little Italian—even using a few key phrases with hand gestures—you may get a more welcome reception from locals. Take a phrase book or download a translation app for your smartphone, and you can generally make your way around most places and have a unique cultural-immersion experience, to boot.
If you want to download an app, try the SayHi Universal Voice Translator, which translates whatever you speak into your iPhone®, iPod touch® or iPad® so that someone else can hear it.
Rent A Villa or Farmhouse
Many travelers dream of spending time in the Tuscan campagna (countryside). A great way to do this is by renting a private residence. An agriturismo is a working vineyard or farm, where owners live onsite and rent out rooms or apartments. Many offer all meals or some meals (full board or half board). Tastings and tours of the farm may also be included. If you prefer your own plot of land to share with family and friends, book a private villa. [http://www.homebaseabroad.com/test-properties/properties.php?region=Tuscany&sort=Name&start=0] Owners of villas rent out suites or the entire villa to one party, normally for weeklong periods. Villas typically consist of a kitchen, living room, bedrooms, bathrooms and outdoor areas; owners usually do not live onsite. You can choose a villa located on a vineyard, one with a pool, or one with special services like wine tasting, private excursions, concerts, cooking classes or a private chef.
With an abundance of fabulous regional dining at your fingertips, you’ll want to get a taste of the real Italy at the right places. The Guida alle Osterie d’Itali lists simple, honest Italian trattorias and osterias known for regional cuisine with warm, casual ambience. Now in its 17th edition, this guide focuses on locales that best portray local flavor and character, with an emphasis on quality, value and artisanal tradition. Formerly available only in Italian, the new edition, Osterie & Locande d’Italia, comes in English and includes accommodation listings that reflect Italy’s old-fashioned hospitality. It’s a great resource when you’re on the road.
If you’re looking for an unusual overnight, try an Italian monastery. These historic centers often offer inexpensive accommodation to both pilgrims and secular travelers. Rather than luxury, monasteries offer spiritual simplicity as practiced by the monks, often within superb scenery and spectacular ancient buildings. Options include:
- Foresteria del Monastero di Camaldoli: Located east of Florence; 11th-century Benedictine monastery; borders a national park
- Foresteria del Santuario della Verna: Located east of Florence; built in the 13th-century; run by Franciscan friars
If you want to visit a monastery, but don’t want to stay overnight, try these:
- Monte Oliveto Maggiore: Located south of Sienna; be sure to catch the Gregorian chants
- Sant’Antimo: Located south of Montalcino; two-bell tower
What to Wear
Italians are notoriously fashionable and tend to dress more formally than Americans—especially in the city. In the heat of the Tuscan summer, women should leave the jeans at home and stick with lightweight, light-colored capris, casual dresses, skirts, shorts, cotton blouses and nice tees. It’s a good idea to bring a cardigan for cool nights and overzealous air-conditioners. Men should pack lightweight pants and long shorts in breathable fabrics, along with short-sleeved collared shirts. As always, good walking shoes will make your trip much more enjoyable.
Respect the Culture
When visiting Italy’s religious attractions, visitors should be respectful, dress modestly and cover up. Even if guards aren’t present to enforce the rules, parishioners at some churches may find it offensive if you wear shorts, tank tops and sleeveless clothing. “Church appropriate” means shoulders, thighs, midriffs and cleavage should be covered. Hemlines should fall to the knees or lower. If you want to wear a sleeveless dress or top, pack a lightweight shawl or cardigan (in a tote) to put on. Pack lightweight capris or a knee-length skirt if you plan to visit a church.