Top 20 Most Beautiful Places to Visit in Tuscany

The romance of Tuscany has kindled many an imagination from writers to painters to philosophers and film crews over the centuries. From all our collective trips to this famously spectacular area here are 20 of the best and most beautiful places to visit in Tuscany, Italy…

1. Elba Island – a laid-back Tuscan island turned trendy under-the-radar destination

The largest Island of the National Park of the Tuscan Archipelago Elba is rich in history dating all the way back to the Ilvati tribe and later The Etruscans, The Romans and in 1814 Napoleon himself was exiled here.

Now it’s an increasingly trendy under-the-radar destination for those in the know and makes a beautiful place to visit in Tuscany.

Visit for the impressive fortresses and Napoleonic residences, the laid-back island atmosphere and to make the most of the beautiful sandy beaches and clear blue sea which could almost rival the Caribbean!

My must-do highlights of Elba Island

• Explore one of the most ancient buildings located on Elba Island, the Fortress of Volterraio, where you can enjoy breathtaking views of the gulf of Portoferraio.
• Experience a sunset boat tour around the island whilst taking in the magnificent scenery and enjoying an aperitif created from local products.
• For those who love an adventure, hike up to the Capanne Mount, the highest peak of the island which is well known for capturing the best panoramic pictures of the island.
• Kayak around the beautiful island and take the chance to swim in their crystal-clear waters.

Our unique villa choice for Elba Island – Agriturismo Galenzana

• To book, check prices or availability for Agriturismo Galenzana

2. Siena – Italy’s loveliest medieval city which is one of the best places to visit in Tuscany

The Ancient city of Siena is easily one of the prettiest places to visit in Tuscany, although be prepared for crowds! It’s full of amazing medieval buildings and the fan-shaped Piazza il Campo, where the world-famous ‘Palio’ horse race is run twice a year.

The square can be seen in all its glory in James Bond ‘Quantum of Solace where it was the location for a spectacular chase scene!

There are a host of grand palaces and municipal buildings around the ‘centro storico’ including Palazzo di Publico at the base of Torre del Mangia which must be climbed for truly breathtaking views of the city below.

My must-do highlights of Siena

• Visit the Siena Cathedral that features an exterior built from white stone and marble, and a spectacular interior design.
• Enjoy an evening of fine dining at Ristorante Tar Tufo whilst overlooking beautiful views of the southern farmland across Siena.
• Experience an array of local delicacies on a wine tasting tour located at an organic wine cellar in Siena’s breathtaking hills.
• Take an E-bike tour to explore the picturesque lands of Siena in a unique way.
   

Our unique villa choice for Siena – The Nest

• To book, check prices or availability for The Nest Siena

3. Lucca – a picturesque city known for its well-preserved Renaissance walls encircling the historic centre

Much quieter than Sienna, Lucca is dominated by its almost completely intact city walls. As the city grew and evolved the walls were maintained and have now become a sort of high park around which you can walk or cycle whilst admiring the beautiful historical city within.

Traces of Lucca’s ancient history are still visible in the shape of its piazza and the archaeological remains beneath some of it’s most prominent churches and the red rooves and white walls of the old residences add to the charm of this compact little city.

My must-do highlights of Lucca

• Take a stroll around the stunning Communal Botanical Gardens which hosts a vibrant selection of trees, plants and flowers.
• Taste a variety of vintage wines in a secret wine cellar hidden under the famous Vinni Liquori Vanni.
• Learn how to cook delicious fresh pasta and tiramisu that you can then enjoy with your friends and family.
• Discover white gold at the Carrara marble quarries that built the Pantheon and Michelangelo’s David.

Our unique accommodation choice for Lucca – Palazzo Rocchi B&B 

4. Florence – the beautiful capital of the Tuscan region and home to Renaissance art and architecture and an iconic cathedral

From Ponte Vecchio to the Uffizi Gallery. Michaelangelo’s David to the greeny grey marble of the Duomo Florence is one of the most iconic cities in the world.

Stroll through its ancient streets and you will feel like you’re part of a painting yourself. It’s a shoppers haven too, with wonderful weekly vintage markets around the Duomo and of course the famous jewellery and leather shops on and around the old bridge.

It is also a vibrant place for a night out with fantastic pubs and wine bars to choose from and restaurants of course! As with all Italian cities, I suggest avoiding eating on the main piazza’s and exploring some of the side roads instead!

Also, if you have a chance take a bus up past the beautiful aristocratic villas of the merchants of old and have a drink in Fiesole whilst enjoying panoramic views of the city stretched out before you!

My must-do highlights of Florence

• Climb 414 steps to the top of Giotto’s Bell Tower and experience the magnificent views overlooking the city.
• Enjoy a day of shopping at San Lorenzo outdoor market where you will find some unique goods and souvenirs.
• Visit one of the most famous art masterpieces in the world, the statue of David created by Michelangelo.
• Finish off a day of exploring by watching the sunset cast a sensational light across the city at Piazzale Michelangelo.

Our unique accommodation choice for Florence – Palazzo Tolomei, Residenza D’Epoca

• To book, check prices or availability for Palazzo Tolomei, Residenza D’Epoca

5. Chianti wine region – one of the most beautiful places to visit in Tuscany known for its gorgeous scenery and world-famous wines 

The Chianti Wine district is everyone’s perfect picture of Tuscany. Red roofed houses clad in bright climbing flowers, quaint streets, gentle emerald green hills covered in vineyards and enough wine tasting establishments to satisfy the most discerning connoisseur!

If you’re a foodie this is also the place for you, with numerous restaurants and agritourism serving up delicious locally sourced traditional dishes such as Spaghetti al Vino RossoRosso, Ragu or the more modest but equally delectable Ribollita.

I recommend hiring a car to get the best of the district as public transport can be very limited.

My must-do highlights of Chianti wine region

• Visit the historic and remarkable Brolio Castle perched on a hilltop overlooking the town.
• Hire a car and take a drive through the breathtaking vineyards and picturesque scenery on offer.
• Indulge in what Chianti is famous for, the delicious olive oil, cheeses and handmade salumi as well as their mouth-watering wines.
• For those who love art, take a trip around the contemporary sculpture parks located across 17 acres of trails.

My cool and unusual hotel pick for the Chianti region – Hotel Villa Casalecchi

• To book, check prices or availability for Hotel Villa Casalecchi

6. Val d’Orcia – a region filled with quintessential Tuscan landscapes and pretty villages

The rich and harmonious landscapes of Val d’Orcia that traverse the River Orcia in southern Tuscany are among the most beautiful in Europe.

Golden fields of wheat and sunflowers, olive groves, and vineyards make up just some of the patchwork of this breathtaking valley.

Named as a UNESCO World Heritage Site in 2004 Val d’ Orcia’s vibrant nature, punctuated by ancient hill towns has been the inspiration for many a Renaissance painting and is an absolute must on any visit to Tuscany!

My must-do highlights of Val d’Orcia

• Visit the fairy tale location of Cappella Madonna di Vitaleta and capture some of the most picturesque shots in Tuscany.
• Enjoy a glass of wine whilst you watch the sun go down over Monticchiello at one of the most beautiful spots, La Guardiola.
• Taste the famous Vino Nobile di Montepulciano in Montepulciano after enjoying a romantic stroll through the charming town.
• Have a unique and unforgettable experience at the magical Bagni San Filippo hot springs.

My cool and unusual hotel pick for the Val d’Orcia region – Hotel Osteria Dell’Orcia

• To book, check prices or availability for Hotel Osteria Dell’Orcia

7. Pisa – an elegant and famous city which is best known for its iconic leaning tower

When you hear the word Pisa, you automatically think of the famed landmark, but Pisa is not merely a leaning tower, but the city surrounding it.

Withing Pisa you will see countless impressive sites including classic Roman and Gothic architecture along with the world-famous Renaissance Piazzas around every corner.

Although you will be awestruck by the spectacular architecture, do not merely choose to visit the largest churches alone. Consider a visit to Santa Maria della Spina. It is smaller than others but truly worth the trip.

My must-do highlights of Pisa

• Visit one of the most Instagrammable landmarks in the world, the Leaning Tower of Pisa.
• Spend an evening partying the night away at the Arno Vivo musical festival hosted along the river.
• Enjoy a relaxing day reading a book or drinking coffee at the famous Giardino Scotto.
• Take a trip to the local produce market in Piazza delle Vettovaglie where you can taste an array of delicious and fresh delicacies.

Our unique accommodation choice for Pisa – La Torre Garbata 

• To book, check prices or availability for La Torre Garbata 

8. Arezzo – a city with museums, monuments, antique churches, shops and restaurants but away from the crowds! 

Arezzo is one of my favourite places in the world let alone Tuscany! This compact and colourful city sits atop one of the many Tuscan hills and showcases some of the best examples of Florentine architecture outside of Florence itself.

The wonderful Piazza Grande with its many coats of arms set into the surrounding walls is a really wonderful place to sit and watch the world go by.

If you climb up to the top of the city you are met with a beautiful vista of rolling Tuscan hills and vineyards. The city is quite alternative and during July becomes alive with music and artisan markets.

Best of all although Italians have cottoned on to the merits of Arezzo the rest of the world tends to skip it, meaning that you don’t have to deal with crowds of tourists and inflated prices, but instead have the space to enjoy a really authentic Tuscan experience.

My must-do highlights of Arezzo

• Find some unique treasures at the piazza Grande market hosted every first Sunday of the month.
• Take a private walking tour to discover the beautiful sites and landmarks of Arezzo.
• Taste your way through Arezzo’s best wines on an E-bike tour whilst enjoying the picturesque scenery and surroundings.

Our unique accommodation choice for Arezzo – Cuprena Farm Stay

• To book, check prices or availability for Cuprena Farm Stay

9. Maremma – a pristine rural landscape set alongside an unspoilt Italian coastline

To get away from the crowds in Pisa and Florence head out to the coastal area of western central Italy, Maremma. Originally marshland, it was drained and then became a wonderful under-the-radar destination in Tuscany.

Here you can expect a wide range of landscapes including vineyards, long blue beaches, black rocks, wooded mineral hills, marshes, interesting archaeological sites, natural reserves, flatlands, and even thermal baths.

There’s also plenty of other attractions in this beautiful Tuscan region including several art cities, natural parks, ancient churches, some great museums, Etruscan sites, and also medieval villages.

If you want to be a bit more active then try windsurfing, kite surfing, biking, and hiking.

My must-do highlights of Maremma

• Visit the famous and extravagant art park, Niki de Saint Phalle’s Tarot Garden, inspired by Gaudì.
• Take a trip to one of the most picturesque and unique towns in Tuscany, Pitigliano, that is built from Tufa stone.
• Make sure to stop for a refreshing aperitivo at one of the cool and hip establishments along the boardwalk.
• For those who love sports, have a go at kite surfing on the Mediterranean sea in Fiumara.

Our unique accommodation choice for Maremma – Podere Maremma Spa & Ristorante

• To book, check prices or availability for Podere Maremma Spa & Ristorante

10. Volterra – a medieval hilltop town which offers stunning Tuscan views

Definitely one of the most beautiful places to visit in Tuscany, 1770 feet above sea level Volterra perches like a Gothic fairytale at the top of a rugged hill, as you wind your way around the hill and enter the town through the intricately sculpted gate in the medieval walls it is very easy to see why Stephanie Meyer chose this as the home of the ‘Volteri’, the oldest and most powerful vampires in the world!

Refreshingly the town hasn’t cashed in on this connection and, whilst you will find the odd Edward keyring or fridge magnet among the other knick-knacks in the souvenir shops they by no means dominate the floor!

The town is a real delight to stroll around with ancient piazzas, and churches and spectacular views of the land around it. Stop for a delicious Calzone on the main street and you won’t be hungry for hours!

My must-do highlights of Volterra

• Hire a tour guide to show you around the treasures that Volterra holds and discover the best spots for an Insta-worthy view.
• Explore the ruins of the ancient Roman Theatre and baths and delve into the history of how life used to be.
• Get to know the well-known Volterra tradition of alabaster at the Ecomuseum and even buy some as a memorable souvenir.
• Admire the medieval architecture with a stroll through the town whilst experiencing the flavors of Middle Ages Street food.

Our unique accommodation choice for Volterra – Agrihotel Il Palagetto

• To book, check prices or availability for Agrihotel Il Palagetto

11. San Gimignano – a pretty UNESCO hill town in Tuscany encircled by 13th-century walls

Since 1990, San Gimignano has been noted as a UNESCO World Heritage Site featuring 13 ancient towers offering a unique skyline within the area.

This ancient village is among Tuscany’s most notable sites and not only will you enjoy strolling the city and taking pictures of these remarkably well-kept buildings, but you will also enjoy an array of white wines harvested from the region.

San Gimignano has a unique place in Tuscany’s history and is actually known as the Manhattan of the Middle Ages. A trip to San Gimignano will bring you back to the heart of Tuscany and allow you to connect with the region’s true roots.

My must-do highlights of San Gimignano

• Adventure to the top of the 13th century skyscraper, Torre Grossa, and enjoy the picturesque views overlooking the beautiful countryside.
• Visit the famous Gelateria di Piazza and taste the most delicious and creative gelato in San Gimignano.
• Hire a vespa for the day to explore the Italian town in a unique and fun way
• Indulge in a romantic dinner at Agriturismo Taverna di Bibbiano accompanied by breathtaking views of San Gimignano.

Our unique accommodation choice for San Gimignano – Rocca degli Olivi 

• To book, check prices or availability for Rocca degli Olivi 

12. Forte dei Marmi – a chic seaside town to explore in Tuscany known for its beaches and upscale boutique stores

Forte del Marmi is not merely a chic, hip town in Tuscany, but one that dates back to the 16th century during the Roman era.

This fortress was responsible for bringing marble to the surrounding areas as the local marble quarry was one of the biggest industries within the city.

World-famous beaches and luxurious accommodations are what is Forte del Marmi is known for among world travelers today. Elegance and picturesque settings make any trip to Forts del Marmi one to remember.

My must-do highlights of Forte dei Marmi

• Visit the vibrant downtown for a shopping trip where you can purchase high-end brands from the luxury boutiques.
• Experience the lively nightlife in Versilia that has been entertaining celebrities since the sixties.
• Enjoy fine dining excellence and exquisite tastes at one of the five Michelin Star restaurants. 
• For a more relaxing pace, take a stroll along the pier where you can take in picturesque views of the Mediterranean Sea.

Our unique accommodation choice for Forte dei Marmi – Resort Miramonti

• To book, check prices or availability for Resort Miramonti

13. Collodi – a pretty medieval village to explore in Tuscany which has connections to the author of Pinocchio

Collodi is among Tuscany’s famous villages. It is another fortified village with a tumultuous past and has been keeping residents safe for centuries. Today. Collodi has long since left its war-ridden past, but residents have worked diligently to ensure the city remains historically preserved.

It’s also famous for having given the author of Pinocchio, Carlo Lorenzini, his pseudonym (originally from Florence he spent part of his childhood there and took its name, signing his works as Carlo Collodi) and they even have a whimsical Pinocchio Park to celebrate the wonderful connection.

Other activities in Collodi include strolling through its Italian-style garden and Villa Garzoni. If you happen to visit during the last week in August, you will encounter the celebration of Saint Bartholemew, among Collodi’s most notable celebrations.

My must-do highlights of Collodi

• Have your picture taken next to the world’s tallest wooden Pinocchio statue that stands at 63 feet hight.
• Visit the interactive, fun Pinocchio Park and check out one of the most popular features, the fountain of the Terrible Dogfish.

14. Castello di Ama – a beautiful vineyard where wine and art meet and a stunning place to explore in Tuscany

Wine is a must in Tuscany and among the top-rated vineyards in the region is Castello di Ama. One visit to this immensely beautiful part of the country will engulf you in Italy’s remarkable wine culture.

One of the most beautiful wineries in Tuscany, Castello di Ama offers multiple wine tastings and tours, but if you want the true experience, consider a stay at their secluded and romantic villa.

Castello di Ama is also home to Il Ristoro, their onsite restaurant in which diners are treated to a dining experience to cherish. Local wines are paired beautifully with local produce to enhance the meal.

15. Pienza – an idyllic Tuscan village that began life as a model Renaissance city

The charming hilltop village of Pienza in the midst of the magnificent Val d’ Orcia is widely considered the ‘Ideal city of the Renaissance.’

The entire place was the brainchild of the great humanist Enea Silvio Piccolomini and architect Bernardo il Rossellino and was meant to exemplify the principles and philosophy of the Italian Renaissance.

Pienza became the solid materialisation of these utopian ideals beginning with the harmonious trio of the cathedral, the papal palace, and the town hall.

My must-do highlights of Pienza

• Experience the cheese and wine tour where you can indulge in the mouth-watering tastes from one of the most charming towns.
• Slow down and take a stroll along the Pienza walls to enjoy the breathtaking views of the countryside.
• Visit the Palazzo Piccolomini, a pioneering piece of architecture featuring a beautiful rooftop garden.
•  Take a trip to Pienza’s Duomo well known as being a crown jewel for one of Pope Pius II’s project.