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Authentic Italy – Top 10 Things To Do in Tuscany

April 2, 2020

Exploring the Tuscany countryside is a top things to do in Tuscany

Fancy a trip to Italy (even if only online)? Riley Contributor Mary Noe shares her list of the top 10 things to do in Tuscany


Ah, Tuscany. World-renowned for its exceptional wine, stunning landscapes, and vibrant cuisine, Toscano is also home to priceless artwork, authentic medieval traditions, and exuberant personalities. Just the name of this fabled region conjures daydreams of relaxed lunches on a sun-soaked patio under the shade of a geranium-rimmed pergola.

Tuscany was named after the Etruscans, the first major pre-Roman civilization to inhabit the area. Located in central Italy, Tuscany is easily accessible by flights directly to Florence and to nearby Rome and Pisa. With a western coastline on the Ligurian and Tyrrhenian Seas, Tuscany boasts mountain ranges, fertile plains, and miles of lovely rolling hills, and has long been one of the top places to visit in Italy.

The iconic Tuscan landscape – golden fields lined with narrow Italian cypress, hillsides studded with olive trees and acres of lush grapevines and giant sunflowers – enchants its visitors, as do the medieval towns, cobbled streets, gnarled vines, historic wineries, and endearing people. 

The birthplace of Michelangelo and the Italian Renaissance has much to offer the discerning visitor interested in exploring both the well known and the hidden treasures of Tuscany.

Here are a few of my favorite things to do in Tuscany.

1. Visit the Tuscan World Heritage Sites

Exploring the backstreets and the rooftops of Florence is one of the best things to do in Tuscany
Exploring the historic center of Florence is a must-do when in Tuscany (Photo: Jonathan Korner; Main Feature Image above, Luca Micheli)


Tuscany is home to seven World Heritage Sites, designated by UNESCO (United Nations Educational, Scientific and Cultural Organization) as ‘of special cultural or physical significance’. Some are quite well known, for good reason. These include:

  • The Historic Centre of Florence, a living tribute to the glorious artwork created during the Italian Renaissance
  • The Historic Centre of Siena – this medieval city south of Florence was once its cultural, political, and artistic rival
  • Pisa’s Piazza del Duomo, which features four monuments including the famous ‘Leaning Tower’ of Pisa
  • The Historic Centre of San Gimignano, the stunning hill town known for its impressive towers

Less well known, the Val d’Orcia region, with its flat chalk plains out of which rise almost conical hills with fortified settlements on top, is what many envision when they picture Tuscany. The Historic Centre of the City of Pienza (with the beautiful Piazza Pio II and surrounding buildings) is recognized as an early example of Renaissance town-planning concepts.

The Medici Villas and Gardens in Tuscany – 12 villas and two gardens spread across Tuscany that influenced palaces across Europe with their focus on architecture, gardens, and the environment – round out this concentration of World Heritage Sites.

Learn more about Italy’s many important UNESCO, visit


2. Rent a Villa in Tuscany

Why not consider a luxury villa, such as this example from leading rental company Tuscany Now More
Why not consider a luxury villa, such as this example from leading rental company Tuscany Now More?


For a truly immersive experience, one of the top things to do in Tuscany is to rent a villa and live like a local! Whether you’d like to holiday in a quiet Tuscan farmhouse, a historic hilltop village apartment, or in the bustling center of a larger city, villa rental can be ideal for a family or group. 

Villa rental specialists at Tuscany Now & More can help you choose the perfect location for your stay. Their portfolio includes more than 140 handpicked, exclusive properties in Tuscany and scattered about Italy, including villas in Chianti, Cortona, Florence, Montepulciano, Pisa, Lucca, San Gimignano, Siena, and the Tuscan coast.

Client Susan Balla says, “I’d always had the desire to rent a villa in Italy to have a beyond-memorable experience with my closest family and friends,” and was referred to Tuscany Now & More by a business associate. “My fiancé and I were looking for an ideal location to have a traditional Catholic wedding, whilst being able to house and entertain 20+ of our closest family and friends.”

“The particular location we chose in Greve in Chianti included a spacious 10-room villa with a gourmet kitchen, as well as a perfectly preserved chapel on property where we could be married. The big bonus was the amazing grounds surrounding the villa and an infinity pool for outdoor entertaining. We also rented a second, smaller villa nearby through Tuscany Now that accommodated more family and friends.”

Tuscany Now delivered a “decadent experience,” she says, “with breathtaking surroundings, spacious accommodations, and the opportunity to have amazing food, wine and cultural experiences.”

Learn more about these great villa rentals in Italy at


 3. Sip the Fine Wines of Siena’s Enoteca Italiana

Top things to do in Tuscany include visiting Enoteca Italiana to sample their wines in these cellars
Enoteca Italiana in Siena offers a vast variety of Italian wines to sample (and purchase)


Tuscan winemakers produce such world-class vintages as Brunello di Montalcino, Vino Nobile di Montepulciano, Chianti, and Vernaccia di San Gimignano. Wondering how to choose your favorite vintage, or perhaps which winery to visit?

Although it seems impossible to taste or visit them all, make the Enoteca Italiana in Siena the first stop on your tasting journey. An enoteca is a local Italian wine shop, and the Enoteca Italiana – one of the top attractions in Tuscany – merges wine museum and tasting room in this state-run collection of thousands of bottles representing Italy’s finest wines.

The Enoteca, located in a stunning 16th century Medici fortress in the center of Siena, offers samples of the widest variety of Italian wines offered anywhere in Italy. One of the most enjoyable experiences is to relax and sip a velvety Chianti Classico inside the medieval enoteca or outside on the lovely terraces. Wine can be bought or ordered for delivery in Italy and internationally. 

Visit the Enoteca Italiana website at


4. Picnic in Siena’s Piazza del Campo

Pull up a chair and enjoy people watching at Siena’s Piazza del Campo shown here in summer
Siena’s Piazza del Campo is the perfect place to enjoy some al fresco food… and some people watching (Photo: Mateus Campos Felipe)


The city of Siena was designed around this shell-shaped piazza, one of Italy’s most beautiful plazas – and the perfect spot to relax and enjoy the bustle of Sienese life. Open one of the bottles of wine you chose from the Enoteca Italiana, and purchase local culinary specialties at Antica Pizzicheria de Miccoli.

Located just off the piazza on Via di Città, the shop beckons with a stuffed boar’s head perched above the entrance. Purchase panini to go, or customize your own feast with local olives, pecorino cheese, pancetta, boar sausages, crusty bread, and panforte (a traditional Sienese fruit and nut cake) – all delivered with gusto and flair.


5. Savor Local Specialties at Antica Macelleria Falorni

Steak tartare from Antica Macelleria Falorni
Just one of the wonderful meat dishes available from Antica Macelleria Falorni


If your taste of local delicacies leaves you hungry for more, take the lovely Via Chiantigiana road between Florence and Siena to the idyllic Tuscan enclave of Greve in Chianti. There you will find Antica Macelleria Falorni, one of Italy’s oldest and most renowned butcher shops.

For nine generations, the Falorni family has provided premium local meats, including the famed Cinta Senese (black Sienese pig), wild boar, and Chianina (Italian beef used for the famous bistecca alla fiorentina, or Florentine-style steak). Their traditional shop is located on the Piazza Matteotti, Greve’s main square, and also offers a variety of salami, prosciutti crudi, pancetta, coppa, capocollo, and bresaola, as well as local cheeses.

The extensive menu includes meat and cheese boards, soups, salads, lasagna, beef tartar, sandwiches, Grandma Beppa’s recipes (including wild boar and roasted pork specialties), desserts, and a selection of excellent local wines served by the glass or bottle. Their motto is “mangia meno, mangia meglio” or “eat less, eat better” – although this may prove difficult to follow when faced with their array of mouth-watering specialties.

Learn more at


6. Visit the Abbey of Monte Oliveto Maggiore

Visiting the Monte Oliveto Maggiore abbey during a service or choir rehearsal
A visit to the abbey at Monte Oliveto Maggiore is an unforgettable experience


Another of the top fun things to do in Tuscany is to take a step back in time to the age of the Gregorian chant, which is still sung by the Benedictine monks who reside at this red-bricked abbey. A medieval palace, complete with drawbridge and massive tower, the Abbey of Monte Oliveto Maggiore was built in 1320 and is located in the Crete Senesi (or ‘Senese clays’) area south of Siena.

Revel in solitude while strolling through the Cloisters, which are adorned with priceless frescoes dating from the late 1400s. Visit the Monumental Library, home to thousands of ancient tomes, and the Abbey Museum, which displays valuable paintings and ancient woodwork. The Refectory, where the monks take their meals, is one of the largest spaces in the abbey and is elaborately decorated with huge frescoes.

The Church, with its famous wooden inlaid Choir, was built between 1400 and 1417. Visitors are invited to attend services and participate in Mass. See the website for schedules and, if possible, time your visit to hear the monks sing the Gregorian chant – a “song that vibrates the inexpressible, the nostalgia of God and the values of the spirit, pacifies and tones the mind and heart.”

Visit the small abbey shop, where the monks sell their own La Flora di Monteoliveto (a herbal liqueur produced following an ancient recipe), along with herbal teas and other botanicals from the abbey gardens. While on property, you can also tour the historic abbey winery and taste (and purchase) the monks’ fine wine and olive oil.

Here’s the abbey’s website:


7. Play Golf

Golf Club of Uccolino greens in summer
Playing a round at the Golf Club of Uccolino is one of the top things to do in Tuscany


Golf may not come to mind as a typical Tuscan pastime, but Italy offers lovely and challenging courses, with several of the best in Tuscany. One of the most beautiful is the Golf Club of Uccolino, located in the verdant hills of the Chianti region south of Florence. Uccolino offers an impressive course lined with cypress and pine trees, and has hosted numerous international events, including the 40th Italian Open in 1983.

Bernhard Langer, Severiano Ballesteros, and Greg Norman are among the many champions who have played here and, in 2009, the club was awarded the Gold Medal for sporting achievement by the Italian Olympic Committee.

Learn more at


8. Tour The Poggio Amorelli Estate

A visit to Poggio Amorelli Estate is one of the best things to do in Tuscany
The Poggio Amorelli Estate offers an intimate tour experience of one of the country’s top family-run wineries

For a lovely afternoon, join the Mazzarrini family at their Poggio Amorelli estate in the heart of the Chianti region. The estate is the perfect spot to take a guided tour of the vineyards, winery, and cellar of one of Tuscany’s exceptional wineries. Follow your tour with a tasting of the estate’s excellent wines and Vin Santo del Chianti (an Italian dessert wine).

If possible, arrange in advance to extend your visit after the tour and treat yourself to a lunch featuring the estate’s own homemade pasta, olive oil, and selections of Poggio Amorelli’s special vintages. Your meal may feature parppardelle pasta with rich wild boar sauce, freshly harvested truffles, luscious pecorino cheese with local honey, and bruschetta toasted over an open fire. Famiglia Mazzarrini produces six types of wine, Vin Santo, grappa, and olive oil, and all can be shipped internationally.

Visit their informative website for news of their tours and other fun things to do in Tuscany at


9. Experience The Paliodi Siena

Palio di Siena horse race photogalluzzi
The Palio di Siena is all heart-stopping horse racing action (Photo: photogalluzzi)


Perhaps the most famous annual event in Tuscany is the Palio horse race. Held in the Piazza del CampoSiena’s main square – the historic race is run twice each year, on July 2nd and August 16th.

A medieval tradition dating from the 1400s, Il Palio pits horses and riders from 10 of Siena’s 17 districts, or contradas, in a harrowing and sometimes dangerous race around the dirt-covered plaza. Bareback jockeys wearing the brightly colored costumes of their contrada circle the horses three times around the piazza in a dizzying, furious rush to victory.

Equally alluring are the celebrations held by each contrada in the days leading up to and following the race, including dinners, parades, and the blessing of horse and jockey. Contrada members in ceremonial dress sing while parading through the streets, accompanied by flag bearers and drummers.

Loyalty to one’s contrada is fierce, competition between neighborhoods is strong, and the pageantry is unequalled. Once you have experienced the camaraderie and majesty of Il Palio, you may wish to join a contrada yourself!

Learn more about this fascinating race at


10. Hire a Private Guide

Exploring Tuscany with a private guide will expose you to off-the-beaten-path treasures (Photo: Simon Rae)
Exploring Tuscany with a private guide will expose you to off-the-beaten-path treasures (Photo: Simon Rae)


Exploring Etruscan tombs, touring medieval towns, taking a cooking class, biking, hiking, wine-tasting – it’s difficult to choose which Tuscan excursions to try! Consider hiring a private guide, who can work with you to customize your adventures and coordinate all the details.

Tomas Pedani of We Drive You Tuscany expertly combines his extensive knowledge of wine, local food, and his love of the area to help plan and deliver your perfect Tuscan adventure.

“From the famous wineries of Chianti, Montalcino and Montepulciano, the enchanting hill towns of San Gimignano and Volterra, the cheese center of Pienza, and, of course, the cultural treasures of Florence, Siena, Pienza and Lucca,” Tomas’s team is “dedicated to the proposition that your time in Italy is precious, and it is their mission to maximize your enjoyment of every moment.”

Whether you wish to tour a working pottery studio, visit the goats and taste freshly made cheese at a creamery, lunch at a historic winery, or simply arrange for car service, Tomas can assist with planning your trip. Personable and magnanimous, Tomas loves his homeland and will be delighted to share it with you.

To learn more about these enjoyable things to do in Tuscany with a private guide, visit




Contributor Mary Noe is a freelance writer who offers a fresh approach on local happenings, keeping readers current on travel, community, and lifestyle trends.


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