Your Guide to Exploring Tuscany Off the Beaten Path

Your Guide to Exploring Tuscany Off the Beaten Path

TuscanyAdmin Tuscany vacation

We truly believe that everyone should visit Tuscany at least once in their lives. This iconic province of Italy has so much to offer visitors, from stunning views to breath-taking architecture and, of course, world-renowned food and wine. 

The problem is, most tourists only scrape the surface when they visit Tuscany by sticking to the well-known tourist attractions. 

But there are countless villages and towns with so much to offer that you’ve probably never even heard of. 

If you love the idea of exploring Tuscany off the beaten path, this guide will let you in on Tuscany’s best-kept secrets. 

Why visit Tuscany?

“You may have the universe, if I may have Italy,” – Giuseppe Verdi (Italian Opera composer)

If you’ve never visited Tuscany before, be prepared to fall in love. From the northern border of Cinque Terre, across the peaks of Alpi Apuane to the beautiful towns of Florence, Siena and Montepulciano all the way down to Etruscan in the south, there is so much to explore.

Rich history

You’ve probably heard of the iconic leaning tower of Pisa and the world-class architecture of Florence, but there are also dozens of historic towns and villages dotted throughout Tuscany that are a must-visit. 

From interesting museums to incredibly well-preserved castles and monasteries, the site-seeing in Tuscany is second to none. 

Unbeatable food

Anyone who has been to Tuscany will rave about the food. The countless restaurants and family-run cafes serve up fresh, home-grown food that you’ll crave once you’re home. Whether it’s freshly baked pizza served on a roof terrace or the juiciest sirloin steak seasoned with black truffles, you’ll fall in love with the food. 


Tuscany is proud of its heritage and the festivals and events throughout the year celebrate it with vibrancy. If you’re visiting at the right time of year, these are a must-see:

  • The Palio horse race in Sienna’s Piazza del Campo takes place every July and August. 
  • The Viareggio Carnevale is in February and March, with massive paper-maché floats.
  • The Volterra Medieval Festival is when the medieval streets of Volterra come alive with music, theatre, and juggling.
  • The Bravio delle Botti is a fun barrel-rolling event in Montepulciano in August.

The Practical Stuff

Getting to Tuscany

Before we get to the little known gems of Tuscany, there are a couple of practical points you’ll need to know to plan your trip. 

How to get to Tuscany

There are two international airports in Tuscany:

  • Galileo Galilei International Airport in Pisa
  • Amerigo Vespucci Airport (or Peretola) in Florence

Both have regular flights to and from all major European cities.  

From either airport, we recommend hiring a car to explore Tuscany. Although there is a regular train service to Florence, it’s hard to reach the smaller villages by train or bus.

The best time to visit Tuscany

The major tourist spots in Tuscany are hectic throughout the summer months when the weather is warmest. 

We recommend visiting between mid-September and October, or between April and May. The weather will still be lovely and you’ll be able to avoid large crowds. 

How to get around

There are so many easy ways to get around Tuscany, depending on what your plans are:

  • Train: If you’re visiting large cities, the train is the quickest and easiest way to get around. The lines run between Rome and Bologna in the north, continuing onto Milan and Venice. You can also get regional trains to Pisa, Siena, Lucca, and some other popular cities. 
  • Rental car: For adventures off the usual tourist track, a car gives you much more freedom to explore. They’re affordable to rent and parking is easy even in most small villages. 
  • Guided tour: If you’d like to see some of Tuscany’s hidden gems and learn the history, guided tours are your best bet. You’ll get taken around by local guides and visit all those beautiful spots most tourists never see. 

Hidden Gems to Visit in Tuscany

From unbelievable views and breath-taking architecture to delicious food and welcoming locals, here are Tuscany’s lesser-known gems that we can show you on our guided tours:

Anghiari (Arezzo)

Nestled on a hillside with beautiful views, Anghiari is steeped in history. With stepped alleyways, rustic buildings, and a calm atmosphere, it’s a beautiful place to explore. 

Known for the famous Battle of Anghiari in 1440, the Florentines beat the Milanese army in this town. The battle became the subject of a lost masterpiece of Leonardo da Vinci. The Renaissance fresco is now hidden in Palazzo Vecchio in Florence, behind the fresco by Giorgio Vasari. 

Where to stay

  • B&B Vigna del Poggio: The friendly staff will treat you to fresh figs and olives grown in their own gardens, while you enjoy modern apartments and a peaceful outdoor space. 
  • Anghiari Hotel: This hotel offers a great central location for exploring Angihari and has a popular pizza restaurant which is great after long days of sightseeing. 
  • B&B Maestà di Cudino: With a small pool to cool off in, this rustic B&B has friendly hosts that will gladly share their local knowledge. 

What to do and see

  • Lago di Montedoglio: This is a manmade lake that has some of the best views in Arezzo. Perfect for strolls in the sun or picnics next to the water. 
  • Michelangiolesco Museum: As the birthplace of Michelangelo, this Anghiari museum will teach you about his works and the works of some of his fellow artists of the time.
  • Castello Bufalini: Just outside the town of San Giustino, this castle has truly incredible architecture, a beautiful garden, and wonderfully rich interiors to explore. 

Where to eat

  • Ristorante Nena: with hundreds of great reviews, this is an Anghiari favorite with a range of traditional Tuscan dishes.
  • Cantina Del Granduca: This traditional, small restaurant offers fresh pasta and sirloin steak that melts in the mouth. 
  • Osteria Pizzeria Al Cantuccio: For authentic, stone-baked pizza, this no better place in Anghiari. 

Monticchiello (Val d’Orcia) 

Monticchiello is set behind an old medieval gate that gives you an idea of the rich history held behind the walls. Between the 11th and 16th centuries, this town saw an ongoing struggle between Siena and Florence until finally, in 1559, it was granted to the Medicis of Florence. 

After that, the town lost its strategic advantage and was abandoned by the opposing sides. The town has altered little since the 16th century, retaining its historic charm. 

Where to stay

  • B&B La Casa Di Adelina: Each room in this polished B&B is individually styled and comfy, with a cozy dining room offering a delicious breakfast. 
  • B&B Daria Monticchiello: A modern yet traditional hotel with a beautiful covered patio.
  • Il Mastio di Spedaletto Relais: This luxury hotel is housed in a castle with unbelievable views and exquisite Tuscan food. 

What to do and see

  • City walls: The walls and fortresses of this town are an attraction of their own. 
  • Pieve dei Santi Leonardo e Cristoforo: Translated to the Parish Church of the Saints Leonardo and Cristoforo, this is a Gothic church built in the second half of the thirteenth century.
  • The Teatro Povero: This “poor theatre” was founded in the 1960s as a form of protest to the economic crisis. But it still puts on local shows that are great to watch. 

Where to eat

  • Osteria La Porta: Make sure to grab a seat on the outdoor terrace to take in the stunning views while you try the traditional food with a fun modern twist. 
  • La Guardiola Wine & Food: This is another restaurant with great terrace views, not to mention fresh food and a great wine selection. 
  • Ristorante Terrazza Val d’Orcia: If you want pizza in Monticchiello, this is the place. Don’t forget to try the popular chocolate cake to end your day. 

Castelnuovo Berardenga (Siena)

Found in the south area of Chianti Classico, Castelnuovo Berardenga is just outside Siena. The city got its name from Count Berardo, a Frank who lived in the town during the 10th century. 

If you’re looking for a relaxed, peaceful town with authentic Tuscan living, this is the place to visit. The town is designated a Citta del Vino (City of Wine) because of its preservation of traditional wine production. 

Where to stay

  • Casa Cernano Bed & Breakfast: This is a great spot for families. With a hearty breakfast, playroom and friendly community area for having a drink and listening to music. 
  • Borgo Casato: This is a converted farmhouse with very friendly hosts who will be happy to help you plan your trips.
  • Agriturismo Podere Casato: As well as being a lovely hotel, you can buy the produce grown and made on the property – the perfect authentic gifts to take home. 

What to do and see

  • Church of San Giusto and Clemente: This 19th-century church has a Madonna and Child on display created by a Sienese Renaissance artist.
  • Church of the Madonna del Patrocinio: Another church with a 14th century venerated Madonna that was found in local castle ruins. 
  • Villa Chigi Saracini: Beautiful Renaissance gardens and a landscaped park that is perfect for a peaceful stroll. 
  • Landscape Museum: Learn about the Sienese landscape and history from a well-preserved collection of documents.

Where to eat

  • Bengodi Enoteca Ristorante: The perfect spot to stop for lunch, you can have fresh risotto served from a Parmigiano Reggiano wheel.
  • AnoniMa X: Homemade, authentic Tuscan dishes and a friendly owner who is happy to talk you through the menu.
  • La Taverna della Berardenga: A great traditional menu and extensive local wine list to match. 


This medieval village has records dating back to the 12th century. However, it’s most known for its links with Carlo Lorenzini, the author of the Adventures of Pinocchio. Born in Florence, Carlo spent parts of his childhood in Collodi and ended up taking its name, signing his work Carlo Collodi. 

Where to stay

  • B&B San Gennaro Castello: This boutique farmhouse conversion offers modern rooms and delicious food as well as a family-friendly atmosphere.
  • Agriturismo Villa Colle Olivi: The large antique rooms remind you of the historic town you’re staying in, while the beautiful gardens are tranquil with great views.
  • Fattoria di Petrognano: This large villa complex has a swimming pool and basketball field, perfect for kids. 

What to do and see

  • Pinocchio Park: You can’t visit Collodi without visiting this popular park. With rides for kids, a puppet theatre, and more, it’s easy to spend a day here.
  • Storico Giardino Garzoni: This is a beautiful garden with a butterfly conservatory, labyrinth, and bamboo forest to explore. 
  • Oak of the witches: This 600-year-old tree is impressive to say the least, and is rumored to be Carlo’s inspiration for the story of Pinocchio.

Where to eat

  • Ristorante pizzeria La Cantina di Pinocchio: A quaint, friendly spot for authentic pizza.
  • Ristorante Villa Garzoni: This large restaurant is actually a wedding venue, but also offers a delicious menu for other guests.
  • Ristorante la Filanda-Collodi: Housed in an old, converted Arcangeli spinning mill, this restaurant lets you feel immersed in the history of Collodi. 


Castelmuzio is a medieval town that started back in the 9th century. Although it was known as Casale Mustia then. There are also records of this well-preserved Etruscan-Roman town being called Castel Mozzo in the 13th century, but it’s not clear when it became Castelmuzio.

Where to stay

  • Agriturismo Cerreto: With a nice pool and pretty garden, this is a lovely hotel in Castelmuzio. Not to mention you can buy wine and virgin olive oil made on the property. 
  • Locanda Vesuna Countryhouse: A romantic spot for couples with gorgeous views of the sunset and a pool for warm days.
  • Casa Castelmuzio: The highlight of this hotel is the extravagant living room where guests can enjoy a peaceful getaway. 

What to do and see

  • Monastery of S. Anna in Camprena Farm: This Monastery welcomes visitors to learn about the history and religion of Castelmuzio, as well as spend the day picking fruit on the farm. 
  • Corsignano: This beautiful old church was where Popes were baptized. 

Where to eat

  • Locanda di Casalmustia: This place is as authentic as it gets. It’s cozy and offers tasty, traditional food as well as a small coffee bar downstairs. 
  • La Moscadella: Sit outside and enjoy the wonderful garden full of lavender, rosemary, verbena, cypress trees, and olive groves set on the hillside


This ancient town dates back to the Middle Ages and sits on the site of an Etruscan necropolis. Back in 1291, the Lord of Montisi Simon Cacciaconti degli Scialenga captured the village and destroyed most of the homes and farms. 

When he died in 1295, the town passed to the Spedale di Santa Maria della Scala, who built a grange. It wasn’t until the end of the 14th century that Montisi became an independent commune and remained that way until 1777.

Where to stay

  • “La Grancia” Country Resort: Although now modernized with a pool and restaurant, this is actually a fortified structure from the 14th century, letting you stay in a piece of history. 
  • La Romita: This hotel is known for its gourmet, homemade dishes and small, intimate setting. 
  • Locanda di Casalmustia: Right in the heart of town, this hotel is the perfect base for exploring Montisi.

What to do and see

    • Grancia di Montisi: If you’re not staying at La Grancia, you can still visit to take advantage of the pool, amenities, and stunning hillside views. 
  • Parco Il Tondo: A peaceful park seemingly in the middle of nowhere that’s great for a stroll shaded from the sun. You’ll find picnic benches dotted around, but no playground for kids. 

Where to eat

  • Trattoria della Filiera: This modern complex overlooks Montisi and the rolling countryside, offering a range of local wines and dishes.
  • Trattoria L’Ombelico del Mondo “Il Barrino” di Montisi: For a traditional dinner and a show, this is a great choice.
  • da Roberto, Taverna in Montisi: Great for lunch with a wall full of empty wine bottles acting as the wine list!


The name of this quaint town comes from the major Roman city of Luni which was first established in 177 BC. It was once a powerful town, but a combination of felling trees to make arable land, earthquakes, pirate raids, and malaria caused a quick decline after the 7th century. Eventually leaving the sleepy town of Lunigiana that is now a real gem of Tuscany.

Where to stay

  • Luna & Stelle: Sat in the center of the beautiful village of Filetto, this modern hotel has luxurious rooms and great outdoor space for sunny days.
  • Baglio della Luna Resort: Surrounded by greenery, the location is perfect for weddings. There’s a pool as well as delicious food and friendly staff. 
  • B&b Il Casale al Lavaggio: This converted farmhouse has a swimming pool, greenery, and games – perfect for families with kids. 

What to do and see

  • Magra: This is the peaceful river running through Lunigiana and is a beautiful spot to wander through the mountainous forest.
  • Val di Magra: Translated to the “Magra Valley”, this takes its name from the river and has some brilliant hiking trails and unbeatable views. 
  • Museo Etnografico della Lunigiana: This is a fascinating ethnographic Museum, which is located in an old mill that hugs the city wall – the perfect place to learn the history of Lunigiana. 

Where to eat

    • Convivium venti venti: For refined yet traditional dishes and a great view of the medieval village, this is a great spot. 
    • Locanda all’Antico Mulino: This restaurant is famous for its freshly made pasta and family-friendly atmosphere. 
  • Pizzeria Tipico: In Lunigiana, you won’t find better homemade pizza dishes.


Pistoia was originally an Etruscan settlement before becoming a Roman colony in the 6th century. In 1177, it declared itself a free commune and went on to become an important political center. The residence erected walls and several public and religious buildings which are still well-preserved today.

Where to stay

    • B&B Pistoia Inn: Located near the old town, this is a modern B&B that’s comfortable with a large breakfast to get your day of sightseeing started right. 
    • Casa Rowe B&B: With luxurious modern rooms and delicious fresh food, this hotel stands out in the sleepy town of Pistoia. 
  • Puccini luxury suite: If you’d prefer a self-contained apartment within walking distance to the center of town, this luxury suite is for you. 

What to do and see

  • Zoo of Pistoia: The zoo is a must-visit. Built in 1970, it covers 75,000 square meters and has a range of animals to visit as well as a restaurant and bar to grab a drink. 
  • Cathedral of San Zeno: This is the main religious building of Pistoia and has an unusually decorated ceiling and joists to go see. 
  • Tenuta di Capezzana: Spend a day at this winery doing wine tastings in the sunshine. 

Where to eat

  • Locanda del Capitano del Popolo Pistoia: With homemade pasta, tiramisu, soup, and more alongside unique wines, this is a popular little spot in town.
  • La BotteGaia: Gourmet meals, a wide selection of excellent wines, and a beautiful location with a special view of the town’s main square. 
  • Ristorante Cozzeria Pluma Pistoia: A lovely place if you’re in the mood for delicious fresh seafood.

Plan your dream trip in Tuscany today

With so many incredible towns and villages to explore in Tuscany, it can feel a little overwhelming knowing where you should visit. That’s where we come in. 

If you’re ready to discover Tuscany’s hidden gems off the beaten path and want some expert help making the most of your trip, contact us here, and let’s plan your trip together.