Are you wondering where to stay in Tuscany? Whether you’re coming for a weekend or embarking on the Tuscan vacation of a lifetime, keep reading to discover the top 15 places to stay in Tuscany.
One-of-a-kind, picturesque and rich in history, Tuscany is widely considered to be one of the most beautiful places on Earth.
A true treasure trove of historic sites, Tuscany has Renaissance art, quaint villages with medieval heritage and a truly incredible landscape with a distinct pastoral atmosphere encompassing its rolling hills.
Tuscan cuisine is known far and wide, but the region truly shines in its mastery of wine production.
Where to stay in Tuscany: Best areas
1. Florence, the most popular place to stay in Tuscany
There may be no other city with the beauty, cultural significance and romance of Florencia, Tuscany’s capital city and main tourist hotspot.
With a history spanning over 3,000 years, Florence is perfect for exploring centuries-old art and architecture thriving amongst modern adventure and nightlife.
Once a political pawn battled over centuries of Italian rule, Florence grew to become a leading city in cultural expression and innovation, led by visionaries Michelangelo, Leonardo da Vinci and Galileo.
Today, the history of Florence is told through world-class monuments, churches and museums, enchanting visitors every day. As there is so much to see and do in Florence here, as well as great options for accomodation for every budget, this city is a great place to stay in Tuscany.
Rent out a bike or set out on foot to see the mighty Arno River running through Florence. Stretching over the water is the Ponte Vecchio, a medieval stone arch bridge and photographic fixture of Florence, where you’ll also find vendors selling jewelry and souvenirs.
Neighboring the Ponte Vecchio are the Ponte Santa Trinita and Ponte alle Grazie bridges, which provide a picture-perfect landscape at sunset.
Next hit the Duomo di Firenze, Florence’s main architectural centerpiece, with its famous brick-red capped dome. Climb the 463 steps to get up to the lantern at the very top, Florence’s highest point.
The Cathedral, located within the Piazza del Duomo, is one of the most visited places in the world.
Though often crowded with visitors and vendors, the Piazza boasts several feats of amazing architecture. Giotto’s Bell Tower, the Baptistery of St. John and the Museo dell’Opera del Duomo are all located here.
Art lovers will be blown away by all the Renaissance masterworks that Florence has to offer, housed in several amazing museums around the city. The famous Uffizi Gallery includes one of Botticelli’s finest pieces, The Birth of Venus, alongside other religious works.
Head to the Galleria dell’Accademia to see Michelangelo’s famous statue of David, carved from a block of marble into an exquisite, life-like sculpture of the biblical hero, as well as other works collected by the powerful Medici family.
The Da Vinci Museum is also well-worth checking out, with immersive exhibits displaying Da Vinci’s early forays into gravity, design and mechanics.
Don´t miss a visit to the Palazzo Vecchio, and the beautiful Boboli Gardens, connected to the Palazzo Pitti, are spread across 45,000 square meters and were also established by the Medici family.
They provide a welcome sanctuary from the city center and include several sculptures, expertly-trimmed gardens and grottos, including Giambologna’s Bathing Venus.
When you get hungry, grab a classic Italian gelato or stop by the Mercato Centrale, a food market located within a 17th-century building offering fresh produce, artisan snacks and great wine.
Florence has by far the best nightlife in Tuscany and Italians do late-night partying well. Whether you’re looking for a relaxing wine night at one of the city’s many cocktail bars or electric disco at a nightclub, Florence has it all.
In terms of accomodation, Florence also has the largest network of hotels, including five-star luxury hotels concentrated within the main district, and cheaper hotels and hostels outside the city center.
If you want to see Italy’s most famous art and many of its historical sites, Florence is a great place to stay in Tuscany. But if you’re looking for a quieter pace of life in the Tuscan countryside, keep reading!
BEST PLACES TO STAY IN FLORENCE
- ($$$) Hotel Bernini Palace
- ($$) Palazzo Castri 1874
- ($) Hotel Alba Palace
2. Siena, where to stay in Tuscany in a beautiful medieval town
Known for it’s world-famous wine, romantic atmosphere and slower pace of life, Siena is like time-traveling to medieval Italy.
With a history that dates back to the Etruscan age and beyond, Siena has a distinct collection of churches, museums and other archaeological sites full of hidden treasures.
Take some time to stroll Siena’s cobblestone streets, picking up local treats along the way, and discover how Siena blends past and present into a modern city.
Siena is primarily known for its gorgeous, well-preserved central piazza, Il Campo. Regarded as one of the greatest medieval squares in Europe, Il Campo is formed in a tilted shell-shaped “square” of red brick, built on the intersection of three main roads.
The piazza itself is divided into 9 sections, each resembling a fold in the Virgin Mary’s cloak, the patron saint of Siena. You can always catch tourists hanging out in the square, sitting under Siena’s towering city hall, Palazzo Pubblico, in the warm weather.
Adjoining Palazzo Pubblico is the 87m high Torre del Mangia, once of the tallest secular towers in medieval Italy. Today, you can climb the 400+ stairs to experience panoramic views of Siena from the bell tower.
Every year, Il Campo is the site of the Palio, a biannual horse race and the most important event in Siena. Riders representing 17 “contrade,” or city wards, race in circles around the piazza in honor of Madonna of Provenzano.
The event draws in thousands of spectators every year and is a true festival celebrating medieval times.
Siena is also well-known for its spectacular church Duomo di Siena, a beautiful Gothic cathedral. Inside are priceless masterworks of art by Donatello, Berini and even a young Michelangelo, as well as an ornate marble floor and exquisite frescoes of divine biblical events.
Siena is famous for its unique Sienese food and wine. “Pici” is a classic spaghetti-like dish served in most restaurants, while “ricciarelli,” is a must-try Sienese biscuit served for dessert.
Siena’s place in the Chianti region means there’s a diverse selection of wine found at most local bars and restaurants, making it the perfect place to stay in Tuscany for wine aficionados.
Siena also has some great hostels for backpackers, as well as several AirBnB’s and hotels within the main city center.
BEST PLACES TO STAY IN SIENA
- ($$$) Grand Hotel Continental Siena – Starhotels Collezione
- ($$) Palazzo Ravizza
- ($) Albergo Chiusarelli
3. Chianti, best area to stay in Tuscany for wine and vineyards
Located within the center of Tuscany, Chianti isn’t just a beautiful region of Italy. Chianti wine, made by special grapes grown only in this region, is served in traditional Italian restaurants all over the world and is often considered the “Bordeaux of Italy.”
Beyond its wine-making prowess, Chianti offers several incredible sites and activities, as well as secret treasures hidden within its small medieval villages.
If you’re looking to take a winery or vineyard tour, Chianti is the perfect place to stay in Tuscany.
Greve is a small village located in the center of Chianti Classico, known for its beautiful town square, complete with surrounding loggia and a statue of explorer Giovanni da Verrazzano, Greve’s most famous son.
The square hosts an antique market every Easter Monday and a farmer’s market every Saturday. The popular Museo del Vino, a museum dedicated to showcasing the production and impact of all things wine, is also located here.
Be sure to stop by the medieval hilltop town of Radda, complete with picturesque views over the surrounding vineyards. Radda is the certified home of Chianti Classico wine, so much so that the Radda nel Bicchiere wine festival takes place here every year.
While there are hundreds of vineyards within this region, the largest one in the Chianti area is the Barone Ricasoli, a castle with gardens and a museum that offers daily wine tastings.
Chianti Classico, the “oldest zone of origin” in Chianti, has the greatest options for accommodation.
Several of the smaller towns have hotels, while old Tuscan villas located on vineyards and olive groves regularly rent out rooms throughout the year.
BEST PLACES TO STAY IN TUSCANY IN CHIANTI
- ($$$) Villa Le Calvane
- ($$) Borgo San Luigi
- ($) Casalta Boutique Hotel
4. Val d’Orcia, a scenic valley that has inspired thousands of Italian postcards
Rich in green and golden landscapes stretching for miles, incredible vineyards, quaint farmhouses and a distinct medieval history, Valle d’Orcia is a lush green valley encompassing the Orcia river.
Located in southern Tuscany, this area is a UNESCO World Heritage site recognized for its cultural and historical significance.
Small, picturesque villages and farms dot the area’s undulating hills and the landscape’s beauty and pastoral atmosphere have inspired artists and photographers for centuries.
Agriculture is the main source of livelihood here, with growers producing grain, olives and livestock at peak times during the season.
A beautiful photo spot in Valle d’Orcia is the Cappella Madonna di Vitaleta, a small chapel built in the 12th century with a stunning surrounding scenery.
Be sure to check out the Romanesque Abbey of Sant’Antimo, a working abbey built in the 12th century surrounded by miles of vineyards and olive groves.
While Val d’Orcia doesn’t have as much in the way of historical sites, the region is famous for its high quality food items.
While Tuscany is known for its wine in general, Val d’Orcia has a distinctive “wine road,” with vineyards stretching between Montalcino and Montepulciano.
Wines here are produced to a very high Denominazione di origine controllata (DOC) standard, meaning red and white wines must be composed of a certain percentage of local Tuscan grapes.
This dedicated attention to detail and quality makes wines hailing from this region world-class.
Most of the hotels here are classic Tuscan villas, with many including pools and vineyards of their own. Prices can get quite high for this style of accomodation, but are perfect for a luxurious stay away from the crowds.
BEST PLACES TO STAY IN VAL D´ORCIA
Read also: Best places to stay in Florence, best places to stay in Rome, best places to stay in Cinque Terre, best places to stay in Venice, best places to stay in Verona
5. Lucca, a well-maintained, pedestrian-friendly city with churches and greenery
Commonly referred to as the city of 100 churches, Lucca is a charming town and a beloved Tuscan city.
Located on the Serchio River, Lucca has broad Renaissance walls encircling the city center, ornate churches and rustic cobblestone streets.
Unlike some other towns on this list, Lucca is not a hilltop village, giving your climbing legs a well-deserved break.
Lucca is preserved and independent, with extensive archaeological remains and various towers and villas ranging back to the 12th century. Lucca is also great for recreation, as a large park surrounds the city.
The large ring of walls surrounding Lucca are the dominating feature of this town. Once serving as military fortifications, the walls now protect Lucca’s historical city center and ancient secrets, keeping the modern world at bay.
Extensive greenery now covers the walls and locals and tourists alike can bike, walk with a gelato or simply rest beneath the shady trees and look out at the 14th century towers rising above the city.
Take a stroll through the old town, where you’ll see Lucca’s best-preserved sites, including a Roman amphitheater, traditional piazzas and churches.
The amphitheater is located in the Piazza dell’ Anfieatro and was once the site of gladiator shows and games during the first century. Nearby is Via Fillungo, a bustling shopping street with upscale boutiques and craft stores.
Many come to Lucca to see its elegant churches, filled to the brim with Renaissance art. The San Martino Cathedral is also extremely popular, housing the famous Volton Santo wood carving depicting Jesus Christ, which has drawn in believers and art-lovers for centuries.
Lucca has incredible restaurants, cafes and smaller gelato shops perfect for a hot Italian day, often featuring classic Italian musical performances.
Lucca is a great place for accomodation and a perfect base stop for many areas in Tuscany, with Pisa, Florence and Siena all fairly easy to get to by car.
There are many Renaissance-style apartments for rent and boutique hotels directly within Lucca’s city center, but also great villas available in the surrounding countryside.
BEST PLACES TO STAY IN TUSCANY IN LUCCA
6. Arezzo, where to stay in Tuscany for artists, shoppers and dreamers
You may recognize Arezzo’s beautiful medieval town square featured in the Oscar winning film, “Life is Beautiful,” chosen for its cultural magic and Etruscan history.
Slightly beaten off the tourist path, Arezzo is a hidden gem in Tuscany’s crown. Art-lovers will enjoy impressive masterpieces spread throughout the city and those in need of retail therapy will love the shopping options.
The Church of San Francesco, Arezzo’s main medieval church, homes the Legends of the True Cross frescco, considered to be one of painter Piero della Francesca’s master works.
Nearby is the Piazza Grande, Arezzo’s main city square. Buildings surrounding the square were built in different periods of history, giving this Piazza a unique architectural look.
The stunning Palazzo delle Logge is here, designed by painter Giorgio Vasari. Artisan workshops once thrived under the portico and have now been converted to small cafes and trattorias.
You’ll also find the beautiful Church of Santa Maria della Pieve, towering into the sky with different shaped exterior holes. Inside is a crypt and an elaborate gold and silver bust of San Donato, Arezzo’s patron saint.
On the first weekend of the month, the Piazza hosts a large Antiques Fair, one of the most popular in Tuscany. Beyond the square, you can walk towards Il Prato, a shady green spot perfect for relaxing under the pines.
Arezzo also has great shopping and market stalls in its narrow streets, where you can pick up souvenirs, textiles, and aromatic spices.
The Archeological Museum Mecenato also houses many prehistorical and Etruscan artifacts and is worth a stop. Arezzo doesn’t have a ton of major sights or activities, so you can definitely see the city all in one day.
But, if you’re looking for a relaxing Tuscan vacation that has all the shopping, dining and quiet you need, Arezzo is your prime destination.
BEST PLACES TO STAY IN AREZZO
- ($$) Etrusco Arezzo Hotel; Sure Hotel Collection by Best Western
- ($$) iConic Resort & Grand Spa
- ($) Hotel Arezzo Sport College
7. Pitigliano, a steep hilltop town with a strong Jewish history
Affectionately known by its nickname, “Little Jerusalem,” Pitiglano is a secret medieval gem. This town’s multicultural history and charm are certainly worth exploring and make for a great place to stay in Tuscany.
Dramatically placed atop a tufa ridge, Pitigliano was once a haven for Jews escaping the rough ghettos of major Tuscan cities in the 16th century.
Before that, archaeological evidence suggests a distinct Etruscan community, with several Etruscan tombs spread throughout the valley.
While you can see most of the town’s sites within a day, there are several small hotels and rental homes within the city’s center if you fall in love with Pitigliano’s charm, as many have for centuries.
The Jewish Quarter of Pitigliano is located within the city center and has several sites open to visitors. There is a small museum, a restored synagogue and a Kosher butcher area.
Be sure to check out the Palazzo Orsini, a 14th century fortress-turned-museum housing Etruscan artifacts and Renaissance artwork.
Pitigliano is perhaps best known for its network of underground tunnels and caves beneath the city, dug through the tufa rock. These sacred pathways, called Vie Cave, are open for public exploration.
Be sure to check out The Cathedral of Saints Peter and Paul, a beautiful church built during the Middle Ages housing several masterpieces of artwork, 18th century frescoes and a Carrara marble bas-relief of Maria Assunta with Saints Rocco and Francis.
Walking along Pitiglano’s walls will give you insight into its Etruscan history, once providing protection against invaders. A 16th century aqueduct also runs along the side of Pitigliano and across Via Cavour.
Pitiglano’s restaurants feature traditional Tuscan home-cooking and prime Maremma valley wine, including the region’s white wine staple, Bianco di Pitigliano.
After dinner, explore Pitigliano’s “vicolo,” or small alleyways connecting its larger streets. The beautiful cobblestone and aging buildings make for a great picture under the sunset.
In terms of accomodation, Pitigliano has several small, cozy three-star hotels with modest rooms and smaller apartments in the main old town.
BEST PLACES TO STAY IN TUSCANY IN PITIGLIANO
8. Pienza, an “ideal city” with spiritually-influenced architecture
Pienza is a small hilltop village within Valle d’Orcia known for its stunning piazza, churches and traditional pecorino cheese, considered the best in Tuscany.
The road to Pienza features winding roads, golden fields of vineyards, olive groves and Italian cypress trees, giving this landscape a magical glow.
Once known as Corsignano, the town was revitalized by legendary humanist Enea Silvio Piccolomini, who would later become Pope Pius II, into an “ideal city” with distinct Renaissance features.
The Piazza Pio II is the village’s central square, designed in a trapezoidal shape by architect Bernado Rossellini with several formidable buildings.
The Cathedral of Santa Maria Assunta, built in 1459, is a magnificent religious monument with three interior naves and beautiful altarpiece paintings.
Next to the cathedral is the Palazzo Vescovile, or Bishop’s palace. Once the home of Pope Alexander VI, the building now contains the Diocesan Museum. Here you’ll find religious manuscripts, Renaissance artworks and ancient tapestries.
Walk along the Corso Rossellino to one of Pienza’s artisan cheese shops selling the world-famous pecorino cheese, made from local sheep’s milk.
While you can hit all of Pienza’s main sights within a day, many stay for the utter romance and magic of Pienza, captured in aptly named streets like Via del Bacio, or “Street of the Kiss,” and Via dell’Amore, or the “Street of Love.”
Although Pienza is small, it surprisingly offers several options for accommodation, including quaint B&Bs, charming hotels and villas dotting the countryside.
BEST PLACES TO STAY IN PIENZA
9. Montepulciano, a medieval town known for its production of wine and speciality food
Perched stately atop a hill, the charming medieval town of Montepulciano is a city of elegance, Renaissance architecture and some of Tuscany’s best red wines.
Start a day here at the Piazza Grande, Montepulciano’s main city square, located at the highest point in Montepulciano. The 14th century town hall, Palazzo Comunale is located here and offers panoramic views of the city and surrounding countryside.
The Montepulciano Cathedral is located within the Palazzo and houses several works of art, including Taddeo di Bartolo’s Assumption of the Virgin.
Montepulciano’s oldest church, the Church of the Madonna di San Biagio, is widely recognized by its large exterior dome and beautiful Renaissance stylings.
Wine lovers are sure to enjoy Montepulciano, famous for its red vintage Vino Nobile. You can enjoy tastings of this wine in several cellars beneath the city or in the famous, 1,000-year-old Contucci Winery.
Montepulciano is famous for its food specialties served in world-class restaurants and cafes along Il Corso, a charming thoroughfare lined with beautiful Renaissance buildings.
Arista, or pork with rosemary, fennel and sage is a local delicacy, often paired with regionally-produced olive oil and honey.
The town also offers great shopping, with leather goods and hand-made crafts produced from local olive wood.
Hotels in Montepulciano are spread out throughout the countryside and offer luxury accommodation amongst the olive groves and shady Tuscan trees.
BEST PLACES TO STAY IN TUSCANY IN MONTEPULCIANO
10. Pisa, the home of the famous Leaning Tower
A city of Italian legend, Pisa is a fantastic and historically-dynamic city located on the western coast of Italy.
From its involvement in various battles of the Middle Ages to its rise as a major maritime republic, Pisa has seen a boom in population in the past decade and major architectural revitalization.
Featuring world-class museums, stunning churches and picturesque scenery along the Arno River, this city is the perfect jumping off point for discovering all of Tuscany and a great place to stay for an extended visit.
To start, head to the internationally-famous Leaning Tower of Pisa in the Piazza dei Miracoli, an important center of medieval art considered sacred by the Catholic Church.
An architectural wonder, the Leaning Tower was constructed in the 12th century on a somewhat shaky foundation, giving it the famous tilt it’s known for today.
While it’s said the tower will still lean for another 200 years, careful preservation by the city has gone into preventing a total collapse. Visitors can climb to the top of the tower and experience panoramic (if tilted) views of the entire city.
The beautiful Cathedral of Santa Maria Assunta is also located here, with ornate exterior stylings of stone and marble and frescos within the interior dome of the basilica.
Located next to the Leaning Tower is the Pisa Baptistery, standing at 54m high with exquisite orange tiles on the dome and arches.Next, stroll along the Arno river to see five bridges arching over the water, as well as classic Renaissance homes and buildings.
The National Museum of Pisa is also located here, featuring several notable artefacts, manuscripts and paintings dating back to the 12th century.
Opposite the museum is the Church of Santa Maria della Spina, a small but dynamic 13th century church with adorned white and green striped stone walls and various sculptures.
Unlike many areas on this list, Pisa does have some good nightlife in the form of nightclubs, pubs and wine bars frequented by students and tourists.
Because of its popularity, Pisa has a lot of hotels and hostels ranging in budget and offerings. Although you can hit most of Pisa in a weekend, this city is great for exploring and is worth a stop on any Tuscan itinerary.
BEST PLACES TO STAY IN PISA
- ($$$) Pisa Tower Plaza
- ($$) Grand Hotel Duomo
- ($) Hotel Pisa Tower
11. Livorno, where to stay in Tuscany in a beautiful and modern seaside town
A small city situated on the Ligurian Sea, Livorno isn’t as well-known as some of its sister cities. But, this beautiful seaside town has a dynamic history and lots to explore, from its preserved archaeological remains to its international atmosphere.
Livorno is a modern city and you won’t find as many medieval-age fixtures here. But, due to the importance of Livorno’s port to historical Tuscan trade, you will find a melting pot of culture and multiethnic influences.
Towards the end of the 16th century, Livorno saw the rise of a large Jewish community of traders, so much so that there is now a major Synagogue in the city.
Beyond its culture, Livorno is a great place to stay in Tuscany if you’re looking to get away from the crowd and experience inexpensive luxury.
Start a day here by checking out the Fortezza Nuova, a late 16th century fort. Originally constructed to protect Livorno’s port, the fort now towers over Livorno’s canals with preserved ancient walls.
Travelers can walk through the beautiful gardens and grounds hidden within the fort, as well as explore some of its secret passageways.
Beyond the fort, check out Livorno’s port, which still functions as an important trade and travel destination. You’ll see classic Italian seaboats bobbing in the wind, as well as larger cruise ships offloading excited tourists every day.
Surrounding Fortezza Nuova is Nuova Venezia, an enchanting quarter designed with Venezia-style finishings. The quarter has ancient canals crossing the district, complete with bridges and boats reminiscent of Venice itself.
If you’re visiting Livorno with kids, the Livorno Aquarium is a top spot, complete with colorful fish, and sea life.
The beautiful Chiesa di Santa Caterina is located in the nearby Via della Venezia and features a central basilica with stunning artwork and a patterned marble floor.
Livorno is famous for having some of the best seafood on the Tyrrhenian coast.
Head to the Mercato Centrale for some great food, served by over 200 different stalls with fresh produce, meats and cheeses and premium local wine. Outside, you can shop for clothing, accessories and souvenirs from pop-up vendors.
Livorno is accessible by train if you’re coming from Florence or Pisa and though the town is fairly small, there are many great hotels looking out on the water. There are also great villas in the surrounding countryside, making this walkable and dynamic city a great place to stay in Tuscany.
BEST PLACES TO STAY IN LIVORNO
- ($$$) Grand Hotel Palazzo Livorno MGallery
- ($$) Max Hotel Livorno
- ($) B&B Ricci
12. Viareggio, where to stay in Tuscany for great beach vacation
Fondly called the “Pearl of the Tyrrhenian Sea,” Viareggio is a small, sandy town with prime access to the sea. Experiencing considerable growth in the past decades, Viareggio explodes in color and energy when the season of Carnival hits.
There are over 10km of beaches running along the La Passeggiata, a boardwalk dotted with cafes, restaurants and gelato shops.
Viareggio is now a seaside resort destination, but still very active in the fishing and shipbuilding industries, fundamental to the city’s booming economy.
If you’re looking for lively nightlife, great shopping and fun in the sand and surf, Viareggio is a great place to stay in Tuscany.
The Carnival of Viareggio is one of the most popular carnivals in all of Europe. Thousands of visitors dressed in costume come to Viareggio to watch the elaborate papier-mâché floats and parades, many of which depict current cultural and political events.
Taking place between the end of January and beginning of March each year, the Carnival always features a float of Burlamacco, the official mascot of the Carnival, and an Ondina float, honoring Viareggio’s historical ties to the sea.
If you’re coming to Viareggio just for Carnival, be sure to book accomodation in advance to get the best availability.
Be sure to also check out the Viareggio Carnival Citadel, a large network of warehouses where you can see float artists create in action.
Head out early to grab a spot at one of Viareggio’s white-sand beaches, where you’ll be treated to a spectacular day under the Tuscan sun full of wind-surfing, swimming and paddle boarding.
The Plage Maurizio and Bagno Irene are large, designated sunbathing areas where you can rent a sunbed for the day.
Be sure to check out Viareggio’s historical bathing establishments, including the famous Bagno Balena, modernized to include showers, pools and restaurants.
Experience Viareggio’s unique cultural atmosphere by grabbing an afternoon cocktail at Gran Caffe Margherita, a Viareggio historical institution where leading “who’s-who’s” of Italian history once dined.
Viareggio has some great seaside hotels, as well as AirBnB-style rentals scattered throughout the city.
Clubs, restaurants and bars are also ocean-facing and can get wild as the night goes on, but if you’re looking to dance in a beautiful Tuscan city and catch some golden rays at the beach, Viareggio is your place.
BEST PLACES TO STAY IN VIAREGGIO
- ($$$) Grand Hotel Principe Di Piemonte
- ($$) Palace Hotel
- ($) Hotel I 4 Assi
13. San Gimignano, where to stay in Tuscany in a town filled with medieval towers and noble history
Sitting stately on a hilltop, San Gimignano is a small, walled medieval town located within Siena. Known for its careful preservation of historical sites and increased tourist popularity, San Gimignano still retains its charming Italian village feel.
This area is famous for its skyline of medieval towers that once provided protection (and flair) for feuding noble families of the Middle Ages, with only 14 of 72 total towers still standing today.
Due to its important history, especially as a resting point for pilgrims travelling to or from Rome, the town is now designated as a UNESCO World Heritage Site. If you enjoy discovering medieval history and architecture, San Gimignano is certainly worth a visit.
Start in the triangular Piazza della Cisterna, aptly named for the cistern served by the well in the square’s center. Paved with brick and surrounded by medieval towers, the Piazza was once a bustling marketplace and site of public performances.
The Palazzo Razzi is a particularly stunning building near the well with two elegant windows. Continue under the Arco deo Becci, one of the gates in the surrounding medieval wall, to the Piazza del Duomo.
Once the center of political and religious life in the Middle Ages, this paved brick city center has three formidable buildings, including the 12th century Church of Collegiata with its stunning interior frescoes depicting biblical stories from both the Old and New Testaments.
Also in this Piazza are the twin towers “Torri Gemelle.” Once belonging to the wealthy Salvucci family, the towers were a show of ultimate supremacy, now having stood for over 700 years.
San Gimignano has some incredible restaurants with traditional Tuscan cooking. One of Italy’s best wines, the Vernaccia di San Gimignano, hails from this region.
At night, when the tourist crowd dies down, the streets of San Gimignano become especially magical and romantic. There’s several options for accommodation within San Gimignano, but also more rustic bed and breakfasts in the surrounding countryside.
BEST PLACES TO STAY IN TUSCANY IN SAN GIMIGNANO
- ($$) Relais Cappuccina
- ($$) Hotel Bel Soggiorno
- ($) Leon Bianco
14. Crete Senesi, a lunar-like landscape with medieval fortifications
Located directly to the southeast of Siena, the unique area of Crete Senesi is unlike any place in Tuscany.
The terrain is made up of rich clay called mattaione, spread across woods and hillocks resembling white dunes that create an other-worldly presence switching in color at different times of the day and year.
While Crete Senesi doesn’t have as much in the way of activities or historical sites, its solitary oaks, cypresses and small farms spread across gently sloping hills make for a picture-perfect place to stay in Tuscany if you’re looking to get out of the city.
Start a day here in the small village of Aciano, known for its medieval architecture and 12th century Roman-style Church of Saint Agatha, which includes an old bell tower and two stunning masterpiece frescoes inside.
The nearby Cassioli Museum contains paintings by local Sienese artists and the Corboli Museum displays artefacts recovered from local Etruscan tombs.
Be sure to also visit Buonconvento, often called one of the most beautiful villages in Italy. Visitors will love this town’s authentic medieval quarter, with traditional red brick buildings and cobbled streets.
The heart of Buonconvento is the Via Soccini, where you’ll find the bulk of the town’s restaurants, cafes, the Religious Art Museum and the Chiesa dei Santi Pietro and Paolo, the town’s 11th century church.
Another site in Crete Senesi is the Abbey of Monte Oliveto Maggiore, a large, 14th century Benedictince monastery displaying many Renaissance works of art.
If you’re looking for big sky vistas and beautiful landscapes, a drive through the area of Crete Senesi is well worth it. In addition, this area is known for its white truffle production, so be sure to grab a dish at any of the great restaurants in this area.
Because of its spectacular atmosphere, Crete Senesi has many hotels scattered throughout the small villages, offering great views and relaxing gardens.
There’s also many holiday homes available for rent that are perfect for a quiet and relaxing Tuscan vacation.
BEST PLACES TO STAY IN TUSCANY IN CRETE SENESI
15. Cortona, a charming hilltop town with a Medieval history
Widely known as the gorgeous setting for the movie, “Under the Tuscan Sun,” delightful Cortona is a town in southern Tuscany. Once a center of Etruscan history, Cortona sits on a hill enclosed by ancient stone walls.
Its placement offers panoramic views of the surrounding valley and distant Lake Trasimeno. While this village is small, it’s inviting and rich with history, held in its museums, fortresses and archaeological sites.
You’ll love the wide selection of wine and complementary cuisine served here.
While Cortona’s streets are steep and narrow, the views and destinations are well worth the exercise. Start a day here in the Piazza della Repubblica, Cortona’s main city square and a historical landmark. Back in Roman times, the city forum was held here.
At the center is the Palazzo del Capitano. Cortona’s town hall and bell tower that once served as the cardinal’s residence. Nowadays, you can sit at an outdoor cafe in the Palazzo and people watch over a glass of wine.
The Molesini Wine Shop, a staple of the square since 1937, is great for sampling local wines and food products.
Be sure to visit the Piazza Signorelli, Cortona’s second bustling town square.
Named after Luca Signorelli, a leading artist of the Italian Renaissance, Piazza Signorelli hosts a flea market every Sunday, where you can find fresh produce from local farmers, quality Italian baked goods and cured meats and cheeses.
On the fourth Sunday of each month, Cortona hosts an antique market where you’ll find ancient collectibles and other hidden treasures spread amongst 50 exhibitors.
Cortona is home to several museums and beautiful Italian churches. Tour the Etruscan Academy Museum, home to hundreds of amazing artifacts and finds from the Etruscan tombs of Camucia and Sodo.
Surrounding Cortona itself are hundreds of Etruscan tombs and a large network of old Roman roads. Meloni and Tanella are two large burial sites that are both still being unearthed.
Cortona is the perfect place to stay in Tuscany if you’re looking for that quaint Italian village feel. Small shops, wine bars and restaurants are scattered throughout the main streets, with many serving Chianina cattle meat, a Validichiana speciality.
Cortona gets especially packed in the summer months, especially as tourists come for the Tuscan Sun Festival, so be sure to book early.
The main options for hotels and smaller B&Bs are located within the main piazzas. There are also several amazing villas and boutique hotels dotted around the countryside that can be rented out for the week.
BEST PLACES TO STAY IN CORTONA
- ($$$) Relais La Corte dei Papi
- ($$$) Relais & Châteaux Il Falconiere
- ($$) Cortona Resort & Spa – Villa Aurea