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Tuscany Sightseeing


Tuscany is a popular Italy vacation destination because of its natural beauty and rich cultural traditions. There are several reasons to vacation in Tuscany. The most popular Tuscany vacations focus on providing stress-relief and relaxation. Tuscany sightseeing includes hill top towns surrounded by the quintessential rolling hills with olive groves.

Tuscany is where 2500 years ago the Etruscan civilization flourished. Today Tuscany is the destination for food and wine lovers. Of course, art lovers will find plenty to see in Tuscany. Above all Florence is the most famous Italy vacation destination in the region of Tuscany.

This Tuscany travel guide provides information about Tuscany’s towns and places to visit. And be sure to check out our curated selection of guided Italy tours that include Tuscany.

Tuscany Location

Tuscany is located in central Italy. It stretches from the center of the country to Italy’s west coast.

To Tuscany’s northwest is Liguria. There you’ll find the Italian Riviera and Cinque Terre.

Directly north of Tuscany is the Emilia Romagna region. Like Tuscany, it is renown for its culinary tradition.

Southeast of Tuscany is Umbria, which medieval hill towns are like Tuscany.

South of Tuscany from the Mediterranean coast east is Lazio, the region where Rome is located.

Tuscany Travel Guide Video

For more about planning a trip to Tuscany watch the Tuscany travel guide video below.

Tuscany Travel Guide Map

Tuscany Sightseeing Highlights

Tuscany has all the elements that make it a great Italy vacation destination. In Tuscany there are thermal Spas, fine food, and authentic quality Made in Italy products.

Tuscany is home to the famous world renown wine vineyards that produce its local wines.

There are also beaches in Tuscany. Viareggio and Forte di Marmi are popular summer Italy vacation destinations.

For families planning a trip to Italy, Tuscany offers plenty for kids. The region offers myriad possibilities for out door activities. Lucca is a fun town to bike around its walls.  Kids love climbing the towers in San Gimignano. Tuscany’s lovely countryside is fabulous for running free as the wind.

See below for more information about Tuscany’s hill towns and the top destinations in Tuscany.


Cortona is a beautiful hilltop town known for its stunning views, historical charm, and cultural heritage.

The area was founded by the Etruscans. Apart from being one of the oldest hill-towns in Tuscany, it is also one of the most scenic. While motoring around Tuscany in a rental car add Cortona to your Tuscany sightseeing itinerary.

The following are some of the top sightseeing highlights in Cortona:

  • Piazza della Repubblica: Start your visit in the heart of Cortona at this picturesque square. It’s lined with cafes and restaurants, making it a perfect spot for people-watching and enjoying Italian coffee.
  • Cortona Cathedral (Duomo): Located on Piazza della Repubblica, the Cathedral of Santa Maria Assunta is a beautiful church with an impressive façade and stunning interior frescoes.
  • MAEC – Museo dell’Accademia Etrusca e della Città di Cortona: This museum houses a significant collection of Etruscan and Roman artifacts, as well as Renaissance art. It’s a must-visit for history and art enthusiasts.
  • Etruscan City Walls: Cortona’s ancient Etruscan walls offer a unique opportunity to explore the town’s ancient history. You can walk along parts of the well-preserved walls and enjoy scenic views.
  • Santa Margherita Sanctuary: Take a short walk outside of Cortona to this serene sanctuary. It’s known for its panoramic views of Cortona and the surrounding countryside.
  • Girifalco Fortress: Perched on a hill above Cortona, this medieval fortress provides stunning vistas of the town and the Val di Chiana valley. It’s a great place for panoramic photos.
  • Santa Maria delle Grazie al Calcinaio: This Renaissance church, designed by Francesco di Giorgio Martini, is a beautiful example of Tuscan architecture. It’s located a bit outside Cortona but worth the visit for its elegance.
  • Piazza Signorelli: Another charming square in Cortona, Piazza Signorelli is home to the Palazzo Comunale and offers a relaxing place to enjoy the ambiance of the town.
  • Shopping: Cortona is known for its artisanal shops, where you can find locally crafted goods such as ceramics, textiles, and traditional Tuscan products. Explore the winding streets for unique finds.
  • Local Cuisine: Enjoy Tuscan cuisine at one of Cortona’s many restaurants. Try classic dishes like pappa al pomodoro, ribollita, pici pasta, and indulge in local wines.
  • Wine Tasting: Tuscany is renowned for its wines, and Cortona is no exception. Consider visiting a local winery or enoteca (wine shop) to sample regional wines, including Cortona’s own DOC wines.
  • Art Galleries: Cortona has been a source of inspiration for artists throughout history. Explore local art galleries to discover works influenced by the town’s charm and natural beauty.

These highlights provide a well-rounded experience of Cortona’s history, culture, and scenic beauty. Depending on your interests, you can customize your visit to focus on specific aspects of this captivating Tuscan town.

Forte dei Marmi

Forte dei Marmi (Marble Fort) is an upscale beach resort town on the northern Tuscan coast. Behind the town up in the mountains the Carrara marble quarries are visible.

The town takes its name from Il Fortino, the fort built by Grand Duke Pietro Leopoldo I of Habsburg-Lorraine to protect the village.

Today beside its beach resort Forte dei Marmi is famous for its festivals that honor Saint Hermes and Saint Francis. It is also famous for its antiques market and the markets in Piazza Marconi and Vittoria Apuana.


Lucca’a regular grid of streets still follows the pattern of the former Roman colony founded in 180 BC. Giant, solid ramparts, built in the 16th to 17th centuries, help to shut out traffic, making the city a pleasant place to explore on foot.

Lucca’s peaceful narrow lanes wind among the medieval buildings, opening suddenly to reveal churches, tiny piazzas, and many other reminders of the city’s long history, including a Roman amphitheater.

The walls surrounding Lucca are a popular destination to bike and walk around the town.


Livorno is an Italian port city on the west coast of Tuscany. It’s known for its seafood, Renaissance-era fortifications and modern harbor with a cruise ship port.

Its central Terrazza Mascagni, a waterside promenade with checkerboard paving, is the city’s main gathering place. Livorno’s “Venezia Nuovo” quarter is aptly named for its canals that run through the city like Venice.

The beaches around the city are known for rocky coast, which extend under the water, making the coast perfect for diving.

Massa Marittima

Set in the Colline Metallifere (metal-bearing hills) where lead, copper, and silver ores were mined as early as Etruscan times, Massa Marittima is far from being a grimy industrial town. Excellent examples of Romanesque architecture survive from the period when the town became an independent republic (1225 to 1235).


Hilltop Montalcino sits at the hearth of vineyards that produce Brunello, one of Italy’s finest red wines. This is a popular destination along the Tuscany wine tour route. It is internationally known. The area where the village is located has been inhabited since Etruscan times.


The village of Montefioralle is one of the oldest in the Chianti area. Its original wall still encloses the village today.


This is one of Tuscany’s highest hill towns, its walls and fortifications offering broad views over Umbria and Southern Tuscany. Its vineyards make the famous Vino Nobile wine. The town was built around the 14th century inside medieval walls.


Monteriggioni is a gem of a medieval hilltop town. Built by the Sienese in 1203, 10 years later it became a garrison town. It is completely encircled by high walls with 14 heavily fortified towers built to guard the northern borders of Siena’s territory against invasion by the Florentine army.

Today visitors can climb its walls. Also walk its ancient walkways.


Pienza is a tiny village located in the famous Val d’Orcia area of southern Tuscany. Due to it being home of Pope Pius II much money was spent making its historic center beautiful. Today its historic center is a UNESCO World Heritage site.

The central Piazza Pio II is framed by 15th-century buildings like the Pienza Cathedral and Piccolomini Palace. The latter was Pope Pius II’s summer residence and features a roof garden with valley views. Flemish tapestries and the pope’s embroidered cape are on display at the Diocesan Museum. West is the Pieve di Corsignano, a Romanesque church with a circular bell tower.

Pienza is known for its pecorino cheese, which comes from the sheep pastures in the valley.


Pietrasanta is located along the Tuscan coast. Its location at the foot of Carrara, where the famous white marble comes, makes this town a favorite among artists and art collectors.  It is also located within a stone’s throw of Forte di Marmi, the popular Tuscan beach resort, and south of the Cinque Terre.



Pisa is often included as a Tuscany sightseeing excursion on the escorted Italy tours that include Florence.

For much of the middle ages, Pisa’s powerful navy ensured its dominance of the western Mediterranean. Trading links with Spain and north Africa in the 12th century brought vast mercantile wealth and formed the basis of a scientific and cultural revolution that is still reflected in Pisa’s spending buildings, especially the Duomo, Baptistry, and Campanile (Leaning Tower). 


Pitigliano is spectacularly situated high above the cave-riddled cliffs of the Lente Valley. Its maze of tiny medieval streets includes a small Jewish ghetto, formed in the 17th century by Jews fleeing from Catholic persecution. Today it is fascinating historic village.

San Gimignano

San Gimignano is located on a hill overlooking Tuscany’s Val d’Elsa. Its historic center is a UNESCO World Heritage site.

During the medieval era it boasted 72 towers that dominated San Gimignano’s majestic skyline. The towers were built by noble families in the 12th and 13th centuries. The tallest, however, was built by the government of course. Today 14 towers remain in San Gimignano.

The town’s geographical position (on the main pilgrim route from northern Europe to Rome) brought it prosperity.

The plague of 1348, and the diversion of the pilgrims route, led to the area’s decline as well as its current preservation.

Today, although only one of the towers, the Torre Grossa, is open to the public, San Gimignano remains rich in works of art, good shops, and restaurants. For families traveling with children climbing the tower provides a good activity. There is also a fantastic gelataria in the town’s piazza.

Outside of San Gimignano a nice agriturismo to visit is Fattoria Poggio Alloro for a nice organic lunch with local seasonal Tuscan food.


Siena has the unique Tuscan quality of being a walled city. Upon entering inside the town the stone roads and tiny streets transport you to a place hundreds of years before.

Siena’s charm is untouched by the corporate hustle and bustle of a large city. The eye catching shops and meandering streets give you a surprise around every corner.

These streets funnel you into the spectacular Piazza del Campo, one of Europe’s greatest medieval squares, where the amazing facade of the Duomo and the Torre del Mangia soar into the heavens. The view from this tower is nothing short of earth shattering. The viewers eye become engulfed in the maze of streets, buildings, and rolling landscape of Tuscany.

Once a capital to rival Florence, Siena is considered one of Italy’s prettiest medieval town. It is still endowed with the grandeur of the age in which it was at its peak (1260 to 1348).

The experience of Siena is truly a travel back in time. Today it is one of Tuscany’s most popular destinations.


Located in the Val di Cornia, it is a medieval treasure within it walls find charming streets and evocative churches. Outside are forests of chestnut trees.


Viareggio is a seaside city in Tuscany. It is known for its beach. Also famous for its annual Carnival (Carnevale), celebrated before the start of Lent.

La Cittadella is a complex that houses the Carnival Museum. The museum features small reproductions of the city’s allegorical floats.

The Villa Paolina Civic Museums include a museum of musical instruments and an archaeological museum. To the southeast, in the town of Torre del Lago, is Villa Puccini, a museum about the composer in his former lakeside residence.


The birthplace of Leonardo Da Vinci is located about 17 miles outside Florence. The history of Tuscany, the Renaissance, and the world is indelibly intertwined with Leonardo’s curiosity and imagination. A visit to Vinci is a pilgrimage to the birthplace of the man who changed the course of history and our world.



Volterra dates back to the ancient Etruscans and early civilization on the Italic peninsula. There are architectural remnants around the town that date to 2500 years ago when Volterra was a key Etruscan city.

Its buildings and walls standing today were built primarily during the Medieval and Renaissance periods.

Today Volterra is a charming Tuscan town popular with tourists. It is known for its alabaster extraction and processing into artistic creations. With less tourists than Tuscan villages such as Lucca, San Gimignano and Siena gives it a more authentic feel.

Guarnacci Etruscan Museum

Tuscany Food and Wine

In a region known for its food, Tuscany’s food heritage is rooted in its rural farming traditions.

A popular traditional dish is “naked” ravioli with ricotta and spinach. Gnudi are “ravioli” deprived of the sheet of pasta that normally encloses them, leaving only the filling. To prepare the dish, the farmer needs only ricotta (sheep’s milk cheese), flour, egg and spinach, plus a simple dressing of olive oil, sage and pecorino cheese.

Tours of Italy that include Tuscany Sightseeing

The following guided tours of Italy include Tuscany destinations along the itinerary. Below scroll down the vacation packages list. The right column lists the places in Tuscany visited. Tour overnights in Tuscany are in bold with number of nights. For more information about the trip click the link.

Italy Tours that include TuscanyTuscany Destinations
8-Day Rome, Florence, Venice Tour with Pisa & VeronaFlorence (2), Pisa
8-Day Tuscany & Italian RivieraArtimino (3), Florence, Lucca, Pisa, Siena
8-Day Venice, Florence, RomeFlorence (2), Pisa
8-Day Rome, Venice, Verona, Florence TourFlorence, Pisa
9-Day Venice, Florence, Rome with Assisi & PisaFlorence, Pisa
9-Day Rome, Venice, Florence Tour with Assisi, Pisa, SienaFlorence, Pisa, Siena
9-Day Tuscany and Amalfi CoastFlorence, Montecatini, Pisa, Siena
9-Day Rome and Tuscany TourChianti, Florence, Lucca, Pisa, San Gimignano, Siena
9-Day Classic Tuscany TourChianti, Florence, Greve, Lucca, Pisa, San Gimignano, Siena
9-Day Tuscany Highlights TourBorgo a Mozzano, Florence, Lucca, Montecatini, Pisa, San Gimignano, Siena
9-Day Tuscany and UmbriaCivita de Bagnoregio, Nettuno, Ostia, Perugia, Siena, Spoleto, Viterbo, Volterra
10-Day Rome, Tuscany, VeniceFlorence, Greve, Montecatini (2), Pisa, San Gimignano, Siena (1)
10-Day Rome and TuscanyFlorence, Montecatini (6), Pisa, San Gimignano, Siena, Vinci
10-Day Venice, Florence, Siena, Rome, Sorrento Tour with Modena, Pompeii, Capri
10-Day Venice, Florence, Umbria, Rome with Pisa, Siena, Assisi, Pompeii
10-Day Lake Como, Venice, Tuscany
10-Day Northern Italy with Italian Lakes, Cinque Terre, Parma, Milan
11-Day Venice, Tuscany, Amalfi Coast Italy Tour
11-Day Tuscany and Umbria tour
11-Day Northern Italy, Cinque Terre, Tuscany Tour
12-Day Venice, Tuscany, Florence, Umbria, Rome
12-Day Northern Italy Tour Italian Riviera, Tuscany, VeniceCarrara, Florence, San Gimignano, Siena, Tuscan Hills (4)
12-Day Rome, Florence, Venice, Milan with Siena, San Gimignano, Verona, Pisa
12-Day Rome, Tuscany, Venice, Assisi with Cinque Terre and Bologna
12-Day Rome, Florence, Venice, Milan with Siena, San Gimignano, Verona, Pisa
12-Day Tuscany, Amalfi Coast, Rome
13-Day Italian Lakes, Venice, Tuscany, and Amalfi Coast Italy Tour
14-Day Best of Italy
14-Day Italian Lakes, Venice, Florence, Rome, Amalfi Coast
14-Day Venice, Tuscany, Amalfi Coast, Rome
14-Day Rome, Florence, Italian Lakes, Venice, Amalfi Coast, Capri Comprehensive Italy Tour
14-Day Amalfi Coast, Rome, Umbria, Tuscany, Florence, Venice
15-Day Sicily, Venice, Florence, Rome Italy Tour
16-Day Italian Lakes, Venice, Tuscany, Amalfi Coast, Rome
17-Day Rome, Sorrento, Orvieto, Perugia, Chianti, Lucca, Parma, Venice
18-Day Sicily and Italy Tour

For more information about Tuscany vacations, tours, and sightseeing click the following links.

For more information about touring Italy click the Italy travel guide.