Tuscany, located in the heart of Italy, is a true jewel with a rich history. I personally consider it one of the most enchanting places to stay in Tuscany and explore. This region, which in ancient times was known as Tuscia or Etruria, is crowned by its capital, Florence—a city that simply takes your breath away with its Renaissance art, medieval villages, and historical sites, creating an atmosphere that you won’t find anywhere else. If you’re wondering where to stay in Tuscany, this region offers countless options for an unforgettable experience, from luxury places to stay in Tuscany to quaint countryside retreats. ✨
Tuscany is also famous for its wine-growing and delicious cuisine. A stay in a vineyard in Tuscany offers the perfect opportunity to enjoy these culinary delights. It is a paradise for foodies and wine lovers alike! If you are planning a vacation in Tuscany’s wine country, I highly recommend that you research the best places to stay in Tuscany Italy, including vacation homes, castles, or wineries with pools, before booking. Believe me, you’ll want to experience the best this picturesque region has to offer—whether you choose to stay in Tuscany countryside by the sea 🌊 or in the rolling hills 🌄. A farm stay in Tuscany or a castle stay in Tuscany can add a unique touch to your trip.
1. Florence: Best area for a Stay in Tuscany
Florence, the heart of Tuscany, is a city where culture and romance abound in its cobbled streets. With over 3,000 years of history, it is a treasure trove of art and architecture just waiting to be explored, making it one of the best places to stay in Tuscany Italy. ✨
In Florence, you will find world-class monuments, churches, and museums that attract thousands of visitors every day. The Florence Cathedral in Piazza del Duomo is a must-see. This iconic cathedral, along with Giotto’s bell tower, the Baptistery of St. John, and the Museo dell’ Opera del Duomo, offers breathtaking views and unparalleled artistry. Exploring these landmarks will give you a deep appreciation of why Florence is among the best cities to stay in Tuscany.
And let’s not forget Michelangelo’s famous statue of David in the Galleria dell’Accademia, a true masterpiece. The Leonardo da Vinci Museum, the imposing Palazzo Vecchio, and the enchanting Boboli Gardens are also worth visiting during your stay in Tuscany. 🌟
In addition to the sights, Florence offers the liveliest nightlife in Tuscany. Whether you fancy a relaxed evening with wine 🍷 or cocktails 🍸 or want to dance the night away in a disco, Florence has it all, making it one of the coolest places to stay in Tuscany. 🕺
Florence has the largest hotel network in Tuscany, ranging from luxury places to stay in Tuscany to budget hostels. Whether you’re interested in a castle stay in Tuscany, a farm stay in Tuscany Italy, or simply exploring places to stay in Tuscany countryside, Florence is the ideal base. It’s also a prime arrival point, with many flights landing here, making it convenient for travelers planning where to fly into for Tuscany. 🛬
Whether you’re exploring vineyards 🍇 or the scenic hills 🌄, Florence offers a wealth of experiences and sights. It’s a city that perfectly combines culture, history, and charm. For a memorable Tuscany vacation, take your time to discover the best places to stay in Tuscany region, starting with Florence.
Things to Do in Florence 🗺️:
- Climb Giotto’s Bell Tower for panoramic views of Florence. 🌇
- Visit the Uffizi Gallery to marvel at Renaissance masterpieces. 🎨
- Stroll along the Arno River and cross the historic Ponte Vecchio. 🚶♂️
- Enjoy wine tastings 🍷 and traditional Tuscan meals 🍝 in the city’s vibrant eateries.
- Explore the Boboli Gardens and discover hidden sculptures and fountains. 🌳
- Shop for handmade leather goods and souvenirs in Florence’s markets. 🛍️
Is Florence Neighborhood Safe? 🛎️
In my experience, Florence is a very safe city. The bustling areas around the Piazza del Duomo, Uffizi Gallery, and the Ponte Vecchio are lively and welcoming. Like any tourist destination, pickpocketing can occur in crowded spots, so staying aware is always wise. However, Florence’s neighborhoods exude warmth and hospitality, making it a great base for exploring the best places to stay in Tuscany Italy. Whether you’re walking back to your hotel late at night or enjoying the city’s vibrant nightlife, you’ll feel secure in Florence. 🌟
Where to stay in Florence?
- (€€€) Hotel Bernini Palace
- (€€) Palazzo Castri 1874
- (€) Hotel Nella
See also: Where to stay in Florence – The best areas
2. Siena: Best place to stay in Siena Tuscany
Siena, a charming medieval town, is known for its delicious wines, romantic atmosphere, and leisurely pace of life. Staying here feels like immersing yourself in a world where time slows down, allowing you to savor every moment. The unique collection of churches, museums, and archaeological sites makes the city one of the most romantic places to stay in Tuscany. 🌟
The central square, Il Campo, is one of the largest medieval squares in Europe, intriguingly divided into nine sections, symbolizing the folds in the cloak of the Virgin Mary, Siena’s patron saint. If you’re deciding where to stay in Tuscany, this town’s charm and history make it a top choice. My personal favorites in Siena include:
- The Palazzo Pubblico: A breathtaking example of medieval architecture that transports you back in time. 🏛️
- The Torre del Mangia: This 87-meter-high tower offers panoramic views over the city and surrounding countryside. 🌄
- The Palio racecourse: Famous for its historic horse races that showcase the spirit and tradition of Siena. 🏇
- The Gothic-style Duomo di Siena: A stunning cathedral and a treasure trove of art by masters like Donatello, Bernini, and Michelangelo. ✨
A Tuscany vacation in Siena also offers the perfect opportunity to dive into the local culinary scene. From delectable wines 🍷 to traditional Tuscan dishes 🍝, the region is a haven for gourmets and wine lovers. A stay in a vineyard in Tuscany or an agritourism vacation in Tuscany allows you to pair the region’s culinary delights with picturesque settings. Whether it’s a winery stay in Tuscany with a pool or a charming farm stay in Tuscany, the experiences here are unparalleled.
Siena stands out as one of the best places to stay in Tuscany for a memorable and immersive vacation. Whether you’re drawn to its historical sites, culinary treasures, or scenic vineyards, this town promises an unforgettable stay.
Things to Do in Siena 🗺️:
- Climb the Torre del Mangia for breathtaking views of Siena’s rolling hills. 🌄
- Explore the Gothic Duomo di Siena, filled with stunning artworks and intricate details. ✍️
- Stroll through the medieval streets and soak in the romantic ambiance. 🚶♂️
- Taste world-class wines 🍷 and traditional Tuscan delicacies at local restaurants. 🍴
- Visit Il Campo and imagine the excitement of the Palio horse race. 🏇
- Discover hidden gems in Siena’s museums and historical buildings. 🖼️
Is Siena Neighborhood Safe? 🛎️
From my perspective, Siena feels very safe and welcoming. The town’s small size and friendly locals make it easy to navigate and enjoy. Whether you’re wandering its charming streets at night or exploring its historical landmarks during the day, Siena exudes a sense of security. For those staying in the surrounding countryside or vineyards, the peaceful atmosphere only adds to the sense of relaxation. Whether you choose a farm stay in Tuscany Italy or a cozy hotel in the city center, Siena is a secure and delightful destination to explore. 🌟
Where to stay in Siena?
- (€€€) Grand Hotel Continental Siena – Starhotels Collezione
- (€€) Palazzo Ravizza
- (€) Albergo Chiusarelli
3. Chianti: Best area for a stay in Tuscany with vineyards
The Chianti region in the heart of Italy is the cradle of the world-famous Chianti wine, made exclusively from grapes grown in this picturesque area. A vacation in Tuscany would be incomplete without a visit to a winery and vineyard, where the magic of winemaking truly comes to life. 🍷
In the heart of Chianti Classico lies Greve, a charming village known for its delightful square and the Museo del Vino. This museum is a paradise for wine lovers, showcasing the rich history, production techniques, and influence of wine in the region. If you’re wondering where to stay in Tuscany wine country, Greve stands out as one of the best places to stay in Tuscany for an immersive wine experience. 🛍️
Don’t miss the medieval town of Radda, perched on a hill with sweeping views of the surrounding vineyards. Radda is not only a certified wine center but also hosts the delightful Radda nel Bicchiere wine festival, an enchanting event that’s a must for any wine enthusiast. ✨
For accommodation, the Chianti region offers diverse options, from boutique hotels in small towns to luxury villas nestled in vineyards. A stay in a vineyard in Tuscany, such as a villa or winery, offers a unique and memorable experience. If you’re seeking a winery stay in Tuscany with a pool, Chianti is ideal for a Tuscan vacation filled with serenity, wine tastings, and breathtaking views of the rolling hills. 🌄 I highly recommend exploring luxury places to stay in Tuscany or even farm stays in Tuscany Italy, which blend rustic charm with modern comforts.
Things to Do in Chianti 🗺️:
- Visit the Museo del Vino in Greve to learn about the history of wine production. 🍷
- Explore the charming streets of Radda and enjoy its wine festivals. 🛍️
- Take a guided wine-tasting tour through the best vineyards in Tuscany. ✨
- Savor authentic Tuscan cuisine at local farmhouses and restaurants. 🍴
- Relax at a winery with a pool while soaking in views of the Tuscan countryside. 🏞️
- Discover hidden gems in small Chianti villages, rich in history and culture. 🚶♂️
Is Chianti Neighborhood Safe? 🛎️
From my perspective, Chianti is exceptionally safe and welcoming. The area’s tranquil villages, scenic vineyards, and close-knit community create an atmosphere of peace and security. Whether you’re staying in a boutique hotel in Greve or a luxurious farm stay in Tuscany countryside, you’ll feel at ease exploring the region. Chianti’s neighborhoods are ideal for families, couples, or solo travelers seeking a relaxing and secure getaway. 🌟
Where to stay in Chianti?
- (€€€) Villa Le Calvane
- (€€) Borgo San Luigi
- (€) Casalta Boutique Hotel
4. Val d’Orcia: A picturesque place in Tuscany
The Val d’Orcia, a UNESCO World Heritage Site, is a breathtaking valley that stretches along the River Orcia, showcasing lush green and golden landscapes. This idyllic destination, dotted with incredible vineyards, charming farmhouses, and a rich medieval history, is undoubtedly one of the best places to stay in Tuscany countryside. 🌄
The small, picturesque villages in Val d’Orcia are deeply connected to their agricultural roots, producing high-quality cereals, olives, and livestock. A highlight of the area is the Cappella Madonna di Vitaleta, a stunning 12th-century chapel nestled amidst rolling hills—a true photographer’s dream and a symbol of the serene beauty of this region. 📸
For wine lovers, the famous wine route between Montalcino and Montepulciano is an unmissable experience. This route features some of the best vineyards in Tuscany, producing exceptional wines like Brunello di Montalcino and Vino Nobile di Montepulciano. If you’re planning a vacation at a winery in Tuscany, Val d’Orcia offers an authentic journey into Tuscany’s renowned wine culture. 🍇 Pair this with an agritourism vacation in Tuscany, and you can experience the agricultural traditions of the region up close.
For accommodations, Val d’Orcia is known for its elegant villas with pools nestled amidst vineyards. While these can be a bit pricier, they provide a luxurious escape perfect for a peaceful and rejuvenating getaway. Whether you’re considering a vacation home in Tuscany with a pool or a stay in a vineyard in Tuscany, this region promises an unmatched blend of comfort and authenticity. 🌟
Things to Do in Val d’Orcia 🗺️:
- Visit the Cappella Madonna di Vitaleta for its iconic beauty and stunning views. 🌄
- Explore the medieval streets of Montalcino and taste world-class Brunello wines. 🍷
- Discover Montepulciano, famed for its wine and Renaissance architecture. ✍️
- Embark on a wine-tasting tour along the Montalcino-Montepulciano route. 🧭
- Relax at a villa with a pool overlooking the rolling Tuscan hills. 🏞️
- Stroll through the charming villages of Pienza and San Quirico d’Orcia, known for their unique cheeses and historic charm. 🚶♂️
Is Val d’Orcia Neighborhood Safe? 🛎️
From my experience, Val d’Orcia is an exceptionally safe and tranquil destination. Its remote location and close-knit rural communities foster a welcoming atmosphere, perfect for solo travelers, couples, or families. The peaceful countryside, coupled with high-quality accommodations like farm stays in Tuscany Italy and luxurious villas, ensures a secure and serene vacation experience. Whether you’re exploring vineyards, historical landmarks, or the picturesque villages, Val d’Orcia offers a safe and inviting environment for all. 🌟
Where to stay in Val d’Orcia?
5. Lucca: A small town in Tuscany
Lucca, often called the city of a hundred churches, is a graceful and enchanting destination located on the Serchio River. This charming city, surrounded by broad Renaissance walls, offers a blend of history and serenity that makes it one of the best places to stay in Tuscany. 🌟
The city’s cobblestone streets and winding lanes are a delight to explore, and its well-preserved architecture is a testament to its storied past. Known for its archaeological sites, towers, and elegant villas dating back to the 12th century, Lucca is a haven for history enthusiasts. A unique feature of the city is its large ring of walls, which are perfect for cycling vacations in Tuscany or leisurely walks while taking in the stunning views of the surrounding countryside. 🚶♂️
Key landmarks in Lucca include:
- The Roman amphitheater in Piazza dell’Anfiteatro: A historic site now transformed into a lively square with shops and restaurants. 🏛️
- The bustling Via Fillungo: The city’s main shopping street, lined with boutiques and cafés. 🛍️
- The Cathedral of San Martino: Home to the revered Volto Santo, a wooden depiction of Christ that attracts visitors from all over. ✨
Lucca’s rich cultural ambiance, coupled with its elegant churches, makes it one of the best places to stay in Tuscany Italy for a vacation filled with history and charm. Its central location also offers convenient access to nearby cities like Pisa, Florence, and Siena.
Accommodations in Lucca range from stylish apartments in Tuscany to modern hotels and countryside villas, catering to a wide variety of travelers. For those seeking a family-friendly retreat or a serene getaway, Lucca provides the perfect balance of culture and relaxation. A Tuscany vacation here promises an unforgettable blend of history, culinary delights, and scenic beauty.
Things to Do in Lucca 🗺️:
- Cycle or stroll along the city’s Renaissance walls for panoramic views. 🚴♂️
- Explore the Piazza dell’Anfiteatro, a historic Roman amphitheater turned bustling square. 🌄
- Visit the Cathedral of San Martino and marvel at its iconic Volto Santo. ✍️
- Wander through Via Fillungo for shopping and local delicacies. 🍴
- Climb the Torre Guinigi, a medieval tower adorned with ancient trees on top. 🌳
- Enjoy a meal at one of Lucca’s many traditional Tuscan restaurants. 🍷
Is Lucca Neighborhood Safe? 🛎️
From my experience, Lucca feels incredibly safe and welcoming. Its small-town charm, combined with its friendly locals, creates a secure environment for visitors. Whether you’re exploring its cobblestone streets at night or cycling along its walls during the day, Lucca exudes a sense of peace and comfort. Accommodations, ranging from luxurious villas in Tuscany countryside to cozy city apartments, offer secure and tranquil stays. With its relaxed pace of life and rich culture, Lucca is an ideal destination for a worry-free Tuscany vacation. 🌟
Where to stay in Lucca?
6. Arezzo: Best area in Tuscany for markets and art lovers
Arezzo, a hidden gem in Tuscany, may already be familiar to movie enthusiasts as the backdrop for the heartwarming film Life is Beautiful. This enchanting medieval city is the perfect destination for those seeking a vacation in Tuscany off the beaten path. With its artistic heritage, rich history, and tranquil atmosphere, Arezzo offers an authentic and peaceful Tuscan escape. 🌟
Here are some must-see attractions in Arezzo:
- Church of San Francesco: Famous for its fresco cycle, the “Legends of the True Cross,” a masterpiece by Piero della Francesca. ✍️
- Piazza Grande: The lively main square, surrounded by historical buildings and bustling with activity. 🏞️
- Palazzo delle Logge: Designed by Giorgio Vasari, a stunning piece of Renaissance architecture. 🏛️
- Church of Santa Maria della Pieve: A Romanesque architectural marvel with an intricately detailed façade. 🌟
- Mecenato Archaeological Museum: A treasure trove of prehistoric and Etruscan artifacts, perfect for history enthusiasts. 📚
Arezzo is also a haven for shoppers. The city’s charming markets and stalls offer a variety of unique finds, including souvenirs, textiles, and locally sourced spices. Whether you’re strolling through the streets or browsing for treasures, the city has a relaxed and welcoming vibe.
For accommodations, Arezzo offers options ranging from luxury villas in Tuscany countryside to cozy boutique hotels. It’s an ideal choice for a cultural Tuscany vacation, blending art, history, and a touch of serene Tuscan charm.
Things to Do in Arezzo 🗺️:
- Admire the famous frescoes in the Church of San Francesco. ✨
- Stroll through Piazza Grande, especially during the Antiques Fair held on the first Sunday of every month. 🛍️
- Visit the Palazzo delle Logge for a taste of Renaissance beauty. 🖼️
- Explore the Mecenato Archaeological Museum to dive into Etruscan history. 🎒
- Discover the local markets for unique handicrafts, spices, and textiles. 🍴
- Take a day trip to nearby Tuscan countryside for a scenic escape. 🌄
Is Arezzo Neighborhood Safe? 🛎️
Absolutely! From my experience, Arezzo exudes a sense of safety and warmth, characteristic of Tuscany’s smaller cities. Its quiet streets and friendly locals make it ideal for families, couples, or solo travelers. Whether you’re staying in Arezzo’s charming city center or venturing to its surrounding countryside, you’ll find a peaceful and secure environment. The town’s tranquil ambiance, paired with its rich cultural offerings, ensures a worry-free and deeply enriching Tuscany vacation. 🌍
Where to stay in Arezzo?
- (€€) Etrusco Arezzo Hotel – Sure Hotel Collection by Best Western
- (€€) iConic Resort & Grand Spa
- (€) Hotel Arezzo ASC
7. Pitigliano: One of the most beautiful villages in Italy
Pitigliano, with its rich multicultural history, has served as a refuge for Jews since the 16th century and offers a captivating blend of history and culture that enchants every visitor. Long before that, the area was shaped by the Etruscans, as shown by the numerous tombs scattered throughout the valley. A visit to Pitigliano is a true highlight for those seeking where to stay in Tuscany to immerse themselves in history and culture.
The Jewish quarter in the heart of the city is open to the public, offering insight into its remarkable past. Equally impressive is the 14th-century Palazzo Orsini, which houses a fortress with Etruscan artifacts, and the medieval Cathedral of Saints Peter and Paul, completing the historical experience in this unique place to stay in Tuscany.
A special feature of Pitigliano is its extensive network of underground tunnels and caves, as well as the mystical sacred paths, the Vie Cave, open for exploration. These distinctive sites transport visitors to an ancient and mystical past, making Pitigliano one of the best places to stay in Tuscany for those exploring Tuscany’s hidden gems 🌍. Whether you’re staying in a farm stay in Tuscany, a luxury place to stay in Tuscany, or a great place to stay in Tuscany, you will find that Pitigliano is an enchanting destination 🌟.
In addition to its impressive history, Pitigliano is renowned for its exquisite cuisine 🍝 and delightful wines 🍷—a true paradise for gourmets. Those planning a relaxing vacation in Tuscany will find numerous cozy places to stay in Tuscany Italy and charming vacation apartments here 🏙️. Whether you’re drawn to culture, history, or culinary delights, Pitigliano provides an ideal setting for an unforgettable Tuscan vacation ✨.
Things to do in Pitigliano:
- Explore the underground tunnels and Vie Cave for a glimpse into Tuscany’s ancient past 🗺️.
- Visit the Jewish Quarter and the Palazzo Orsini for a rich cultural experience 📚.
- Enjoy delicious Tuscan cuisine and local wines at one of the many cozy restaurants 🍷.
- Discover the best places to stay in Tuscany with a visit to Pitigliano’s luxury places to stay in Tuscany and farm stays 🌴.
- Take a scenic walk around the medieval Cathedral of Saints Peter and Paul 🏞️.
Is Pitigliano Neighborhood Safe?
In my experience, Pitigliano is a very safe place to stay in Tuscany. Its small-town charm and the friendly locals make it an inviting destination for tourists. Whether you’re visiting places to stay in Tuscany countryside or the more luxury places to stay in Tuscany, you can expect a peaceful atmosphere. The town’s historical sites and winding streets offer a welcoming environment, and it’s easy to explore on foot, even if you’re unfamiliar with the area. Pitigliano remains one of those nice places to stay in Tuscany, offering a serene and secure retreat for travelers.
Where to stay in Pitigliano?
8. Pienza: A small town with beautiful architecture
Pienza, idyllically situated on a hill in the Val d’Orcia, is a picturesque village celebrated for its enchanting atmosphere and the world-famous pecorino cheese—a must-try on any vacation in Tuscany. For food enthusiasts, Pienza stands out as a highlight that perfectly reflects Tuscany’s rich culinary tradition, making it one of the best places to stay in Tuscany.
The main square, Piazza Pio II, designed by Bernardo Rossellino, is surrounded by magnificent buildings that add to Pienza’s charm. A particular eye-catcher is the Cathedral of Santa Maria Assunta, built in 1459, an impressive monument that emphasizes the village’s historical significance. Right next to it, the Palazzo Vescovile now houses a museum, offering a deeper look into the history of the region and adding to Pienza’s appeal as one of the best places to stay in Tuscany for culture and history lovers.
For cheese aficionados, Pienza’s Pecorino cheese is a must. A walk down Corso Rossellino, lined with artisan cheese shops, lets you discover various delicious versions of this Tuscan specialty. Strolling along this charming street, accompanied by the enticing aroma of pecorino, makes a stay in Pienza particularly delightful. If you’re considering a more indulgent retreat, luxury places to stay in Tuscany offer an elevated experience to complement the charming village.
Although small, the village provides a range of accommodation options—from cozy hotels in Tuscany to charming villas in Tuscany Italy—for a comfortable and authentic Tuscany vacation. Whether you’re interested in history, culinary delights, or simply the beauty of the Val d’Orcia countryside, Pienza is an ideal choice for your where to stay in Tuscany.
Things to do in Pienza:
- Visit the Cathedral of Santa Maria Assunta and explore the historical significance of Pienza 🏛️.
- Stroll down Corso Rossellino, sampling delicious Pecorino cheese from artisan shops 🧀.
- Discover the village’s best places to stay in Tuscany in the heart of Val d’Orcia 🌄.
- Explore the Palazzo Vescovile and its museum for an enriching cultural experience ✍️.
- Enjoy breathtaking views of the Tuscan countryside, perfect for photo opportunities 📸.
Is Pienza Neighborhood Safe?
In my experience, Pienza is a very safe and welcoming village. The tranquil atmosphere, along with the town’s small size and close-knit community, ensures a relaxing and secure environment. Whether staying in a luxury place to stay in Tuscany or a more quaint farm stay in Tuscany, Pienza remains peaceful and inviting. It’s a wonderful spot for a romantic getawa or a family vacation, offering a secure place for exploring Tuscany’s most romantic places to stay in Tuscany.
Where to stay in Pienza?
9. Montepulciano: A medieval town known for its wine
Montepulciano, a town that seamlessly blends medieval and Renaissance eras, sits majestically on a hill and is celebrated for some of the best red wines in Tuscany—especially the renowned Vino Nobile di Montepulciano. For wine enthusiasts, a visit to Montepulciano is a must, allowing for a fully immersive Tuscany vacation centered around local wines. This makes Montepulciano one of the best places to stay in Tuscany for wine tasting 🍇.
One of Montepulciano’s highlights is Piazza Grande, the highest and most central square in the town. This historic square, surrounded by iconic landmarks such as the 14th-century Palazzo Comunale and the majestic cathedral, embodies the town’s historical splendor. Just outside the city, the Church of Madonna di San Biagio stands as a must-see attraction on any vacation in Tuscany. If you’re looking for places to stay in Tuscany that are close to historical landmarks, Montepulciano offers an ideal choice.
Montepulciano is a true paradise for wine aficionados. Local wine cellars, particularly the famous Contucci winery, offer tastings of fine Vino Nobile di Montepulciano, providing a unique experience for visitors. This region not only delivers wine enjoyment at the highest level but also offers insight into the centuries-old tradition of Tuscan viticulture. If you’re searching for the best places to stay in Tuscany Italy that highlight Tuscan wine culture, Montepulciano is undoubtedly one of the top destinations.
The hotels in Montepulciano are scattered across the picturesque countryside, offering luxurious accommodation surrounded by olive groves and serene landscapes. These tranquil villas and vacation homes serve as perfect retreats for those seeking a luxurious and peaceful Tuscany vacation. Whether you’re seeking a farm stay in Tuscany or one of the best luxury places to stay in Tuscany, you will find the perfect spot to unwind in Montepulciano 🌟.
Things to do in Montepulciano:
- Visit Piazza Grande and explore the historical landmarks, such as the Palazzo Comunale 🏰.
- Take a wine tour at the Contucci winery, tasting some of the finest Vino Nobile di Montepulciano 🍷.
- Discover the stunning Church of Madonna di San Biagio, a peaceful retreat just outside town 🏞️.
- Stay in one of the best villas to stay in Tuscany, nestled among olive groves 🌿.
- Explore the best places to stay in Tuscany, including luxurious vacation homes with scenic views 🌄.
Is Montepulciano Neighborhood Safe?
In my experience, Montepulciano is a safe and welcoming destination. The town’s quiet, historic streets and the peaceful countryside offer a secure atmosphere for travelers. Whether you’re staying in a farm stay in Tuscany or a luxury hotel in Tuscany, you can expect a calm and inviting environment. The village’s small size and tight-knit community contribute to a sense of safety, making Montepulciano an ideal place to stay in Tuscany for families and couples alike 🌟.
Where to stay in Montepulciano?
10. Pisa: A beautiful city, famous for the Leaning Tower
Pisa, located on the west coast of Italy, is a city full of charm, rich history, and iconic landmarks. Most famous for its Leaning Tower, Pisa is an unmissable part of any Tuscany vacation. The tower, constructed in the 12th century in Piazza dei Miracoli, stands as a testament to medieval engineering, its distinctive tilt caused by unstable foundations. Visitors can climb to the top for a breathtaking panoramic view of the city and the surrounding region—truly a once-in-a-lifetime experience that should not be missed when considering where to stay in Tuscany. 🌍
Beyond the Leaning Tower, Pisa boasts several other must-see attractions, such as:
- The Cathedral of Santa Maria Assunta: A stunning cathedral featuring magnificent mosaics and an ornate façade, showcasing the city’s rich architectural heritage. 🏰
- The Baptistery of Pisa: With its 54-meter-high dome covered in orange tiles, this structure is renowned for its excellent acoustics, making it a must-visit for music enthusiasts. 🎶
- The National Museum of Pisa: Home to valuable collections of art and sculptures, this museum highlights the city’s historical significance in the artistic world. 📚
- The Church of Santa Maria della Spina: A Gothic masterpiece located on the banks of the River Arno, famous for its delicate architecture and stunning detail. 🌐
Pisa also offers an exciting blend of culture and leisure. As a base for exploring Tuscany, this city offers convenient access to other remarkable towns and cities across the region. Whether you’re planning a vacation in Tuscany countryside or seeking the best places to stay in Tuscany Italy, Pisa is perfectly positioned.
For those who enjoy vibrant nightlife, Pisa has a lively nightlife scene with nightclubs, pubs, and wine bars where you can unwind and soak up the local atmosphere. Whether you’re relaxing after a day of sightseeing or socializing in the evenings, Pisa has something for everyone. 🍸
As for accommodations, Pisa caters to all preferences, offering a variety of options from luxury hotels to more budget-friendly places to stay in Tuscany. Whether you’re visiting for a few days or making it your base for exploring the region, there’s a perfect place for you to stay in this historical city. 🌆
Things to Do in Pisa 🗺️:
- Climb the Leaning Tower of Pisa for an unforgettable view of the city and surrounding area. 📸
- Visit the Cathedral of Santa Maria Assunta and marvel at its intricate mosaics and architecture. ✨
- Explore the Baptistery of Pisa and its awe-inspiring acoustics. 🌟
- Discover the treasures of the National Museum of Pisa, from art to ancient sculptures. 🔖
- Wander the River Arno and stop by the Church of Santa Maria della Spina for a peaceful and picturesque experience. 🌄
- Enjoy a lively evening at one of Pisa’s wine bars or nightclubs. 🎉
Is Pisa Neighborhood Safe? 🛎️
Pisa is a generally safe city for travelers, offering a welcoming atmosphere for those exploring its historical sites and lively nightlife. With well-patrolled streets and friendly locals, I always feel comfortable exploring the city’s charming squares, enjoying a peaceful evening along the River Arno, or walking through its medieval lanes. For a city that attracts millions of tourists every year, Pisa is a great destination for a Tuscany vacation filled with culture and adventure. 🌍
Where to stay in Pisa?
- (€€€) Pisa Tower Plaza
- (€€) Grand Hotel Duomo
- (€) Hotel Pisa Tower
11. Livorno: A harbor town in Tuscany for families and children
Livorno, an often-overlooked gem on the Tuscan coast, offers a tranquil escape from Italy’s more famous cities. For travelers seeking serenity and authentic Tuscan experiences, Livorno provides the perfect blend of natural beauty and historical charm. The city’s coastal views and rich cultural heritage make it one of the most unique places to stay in Tuscany, especially for those looking for a quieter vacation in Tuscany. 🏞️
One of the city’s most striking landmarks is Fortezza Nuova, a 16th-century fortress originally built to defend the harbor. Surrounded by lush greenery, this historic site offers a peaceful retreat in the heart of the city. The active port area is still bustling with life, where you can watch cruise liners and ships dock along the shore, creating an enchanting atmosphere. ⚓
The Nuova Venezia district is another highlight of Livorno. This area, which resembles Venice with its winding canals and quaint boats, offers picturesque views and a slice of Tuscan charm. Whether you’re strolling the narrow alleyways or enjoying a boat ride, this district showcases the city’s unique atmosphere. 🌍
Another must-see spot is the Mercato Centrale, a vibrant market with over 200 stalls selling everything from fresh produce to handmade goods. Seafood lovers will be particularly delighted by Livorno’s reputation for serving up some of the finest seafood dishes along the Tyrrhenian coast. For an authentic taste of Tuscany, this is the place to be. 🍴
Livorno offers a range of accommodation options, from cozy hotels to scenic villas with breathtaking views of the coastline. It is ideal for couples, families, and anyone looking to experience the quieter side of Tuscany. Whether you prefer a relaxing retreat by the sea or a cultural adventure, Livorno has something for everyone. It is also conveniently reachable by train from Florence or Pisa, making it the perfect stopover on any Italian adventure. 🚶♂️
Things to Do in Livorno 🗺️:
- Visit the Fortezza Nuova, a historic fortress offering views and lush green surroundings. 🌿
- Explore the Nuova Venezia district and wander the charming canals and narrow streets. 🌆
- Discover the bustling Mercato Centrale, where you can shop for fresh produce and unique goods. 🛍️
- Enjoy a relaxing day by the Tyrrhenian coast, savoring the delicious seafood the city is famous for. 🍣
- Take a scenic walk along the harbor and watch the ships dock. 🚢
Is Livorno Neighborhood Safe? 🛎️
Livorno is a safe and welcoming city, perfect for those looking for a peaceful vacation in Tuscany. The areas near the harbor and Nuova Venezia district are especially charming and well-maintained, with locals and tourists alike enjoying the relaxed pace of life. I always feel comfortable exploring Livorno’s narrow streets, soaking in the historical sights and enjoying the coastal ambiance. Whether you’re strolling along the canals or dining in one of the quaint restaurants, you can rest assured that Livorno offers a safe and enjoyable experience for visitors. 🌠
Where to stay in Livorno?
- (€€€) Grand Hotel Palazzo Livorno
- (€€) Max Hotel Livorno
- (€) B&B Ricci
12. Viareggio: Where to stay in Tuscany for beach life
Viareggio, often hailed as the “Pearl of the Tyrrhenian Sea,” is a vibrant seaside resort on the Tuscan coast that ranks among Italy’s most popular vacation spots. Blending cultural attractions, lively nightlife, and one of Tuscany’s most stunning sandy beaches, Viareggio offers something for everyone—whether you’re looking to relax or engage in an active holiday. It’s certainly one of the best places to stay in Tuscany if you enjoy a blend of sun, sea, and culture. 🌞🌊
The city’s 10-kilometer-long sandy beach is a must-see, extending along the renowned La Passeggiata—an elegant promenade dotted with charming cafés, restaurants, and boutiques. Strolling here, you can soak in the refreshing sea air and enjoy authentic Tuscan cuisine at one of the many seaside restaurants. Viareggio’s beaches, like Plage Maurizio and Bagno Irene, are perfect for sunbathing or indulging in water sports, including sailing, surfing, and jet skiing. For those wondering where to stay in Tuscany, the best area to stay in Tuscany would surely be somewhere near these serene shores. 🌊🍴
A standout attraction is the famous Viareggio Carnival, celebrated annually from late January through early March. Known for its vibrant parades featuring giant papier-mâché figures, this festival draws thousands of visitors worldwide. If you plan to visit during carnival season, early accommodation booking is a must, as Viareggio is a prime destination during the festivities. The best places to stay in Tuscany during this time would include luxury hotels in Tuscany or best hotels in Tuscany Italy, which offer both comfort and a front-row view of the action. 🎭✨
Viareggio combines beach relaxation, cultural excursions, and exciting events, creating an unforgettable experience for travelers of all kinds. Whether you choose to stay in a vineyard in Tuscany or are looking for places to stay in Tuscany Italy by the coast, Viareggio offers an ideal balance of relaxation and excitement. 🏖️🏙️
Things to do in Viareggio:
- Take a leisurely stroll along La Passeggiata to enjoy the promenade’s cafes and boutiques. 🍷
- Visit Plage Maurizio or Bagno Irene for sunbathing and water sports like surfing and sailing. 🏄♀️🚤
- Don’t miss the Viareggio Carnival, with its famous giant papier-mâché floats and parades. 🎉
- Enjoy delicious seafood at one of Viareggio’s many seaside restaurants. 🍣🍴
- Explore the Forte dei Marmi area for high-end shopping and luxurious villas. 🛍️✨
Is Viareggio Neighborhood Safe?
From my experience, Viareggio is a very safe and welcoming destination. The best places to stay in Tuscany like hotels near the beach or in the town center are well-lit and bustling with activity. The vibrant nightlife makes it a lively but secure location, especially along the promenade. Whether you are enjoying a farm stay in Tuscany or staying in one of the luxury places to stay in Tuscany, the area is family-friendly, and I have always felt comfortable walking around at night. 🌆🔒
Where to stay in Viareggio?
- (€€€) Grand Hotel Principe Di Piemonte
- (€€) Palace Hotel
- (€) Hotel I 4 Assi
13. San Gimignano: A small walled medieval town in Tuscany
San Gimignano, a picturesque medieval town embraced by ancient walls, is celebrated for its iconic medieval towers. While 72 towers once graced the skyline, today 14 towers still stand proudly, a testament to the town’s rich heritage. This historical charm has earned San Gimignano UNESCO World Heritage status, making it an unmissable stop on a vacation in Tuscany. It’s one of the best places to stay in Tuscany if you’re looking to immerse yourself in history while enjoying the local culture. 🏰🌍
Not-to-miss highlights in San Gimignano include:
- The triangular, cobbled Piazza della Cisterna 🌆
- The impressive Palazzo Razzi 🏰
- The historic Piazza del Duomo ⛪
- The 12th-century Collegiata church adorned with captivating frescoes 📚
- The renowned Torri Gemelle or twin towers 🗺️
San Gimignano is also known for its traditional Tuscan cuisine and exquisite wines. For wine lovers, tasting Vernaccia di San Gimignano—one of Italy’s best wines—is a must. The region is also one of the best places to stay in Tuscany for wine tasting, with vineyard stays in Tuscany offering an authentic experience of the local vineyards. 🍷🍇
This charming town is an irresistible blend of historic architecture and culinary excellence. If you’re planning a Tuscany vacation, be sure to include San Gimignano on your itinerary to experience its unique charm. Whether you’re interested in staying at luxury places to stay in Tuscany or seeking out unique places to stay in Tuscany, San Gimignano is sure to offer the perfect backdrop for a memorable stay. 🌟📍
Things to do in San Gimignano:
- Wander through Piazza della Cisterna and soak in the medieval atmosphere. 🏙️
- Explore the stunning Collegiata Church and admire the beautiful frescoes. ✍️
- Visit the famous Torri Gemelle to take in panoramic views of the surrounding countryside. 🌄
- Sample the world-renowned Vernaccia di San Gimignano wine at a local vineyard. 🍷
- Discover the historic Palazzo Razzi and learn about the town’s fascinating past. 🗿
Is San Gimignano Neighborhood Safe?
From my perspective, San Gimignano is a very safe and peaceful destination. The town, with its well-preserved medieval charm, is a great place to explore on foot. Whether you’re enjoying a farm stay in Tuscany or staying in one of the best hotels in Tuscany Italy, the streets are welcoming and secure, even at night. As a popular spot for tourists, the area has a relaxed vibe that makes it ideal for a family or romantic getaway. 🌠
Where to stay in San Gimignano?
- (€€) Cappuccina Country Resort
- (€€) Hotel Bel Soggiorno
- (€) Leon Bianco
14. Crete Senesi: A magical area in Tuscany
The Crete Senesi, situated southwest of Siena, stands out as one of Tuscany’s most unique landscapes. Known for its clay-rich terrain that creates a moon-like setting of rolling hills and sparse forests, the Crete Senesi is an ideal destination for a peaceful Tuscan vacation. Unlike the more tourist-centric regions of Tuscany, Crete Senesi offers a serene escape, making it perfect for those seeking tranquility and natural beauty. It’s one of the best places to stay in Tuscany for a quiet, immersive experience. 🌄🏞️
A visit to the village of Asciano is a must; its distinct architecture reflects the essence of this one-of-a-kind region. Also noteworthy is Buonconvento, regarded as one of Italy’s most beautiful villages. The main street, Via Soccini, is lined with charming restaurants and cafés, as well as the Museum of Sacred Art and the historic Chiesa dei Santi Pietro e Paolo. Nearby, the Monte Oliveto Maggiore Abbey, a 14th-century treasure, is home to captivating Renaissance artworks. This area truly offers some of the best places to stay in Tuscany region if you’re looking for a getaway immersed in history and culture. ✨🍴
For those planning a vacation in Tuscany away from the usual tourist bustle, Crete Senesi offers an inviting atmosphere of calm and culture, set against the stunning, surreal landscapes of rural Tuscany. Whether you’re looking for luxury places to stay in Tuscany or a farm stay in Tuscany, this area is sure to provide the perfect retreat. 🏡🌿
Things to do in Crete Senesi:
- Take a scenic drive or walk through the rolling hills to experience the surreal landscapes of Tuscany’s countryside. 🌅
- Visit the charming village of Asciano, known for its distinct architecture. 🏙️
- Explore Buonconvento and its charming cafés and restaurants. 🍽️
- Admire Renaissance artworks at the Monte Oliveto Maggiore Abbey. 📸
- Taste local wines and cuisine while enjoying the peaceful atmosphere of the region. 🍷🌟
Is Crete Senesi Neighborhood Safe?
From my experience, Crete Senesi is incredibly safe and peaceful. The region is more off the beaten path compared to popular tourist areas, making it a great spot for those seeking a tranquil Tuscany vacation. The village of Asciano and Buonconvento are both charming and welcoming, with friendly locals and well-maintained streets. Whether you’re staying in a farm stay Tuscany or a luxurious villa, you can expect a relaxed and secure environment, perfect for unwinding in the beautiful Tuscan countryside. 🏡🌍
Where to stay in Crete Senesi?
15. Cortona: A charming little town in Tuscany
Cortona, famous for its picturesque setting in the movie “Under the Tuscan Sun,” is a charming town in southern Tuscany with Etruscan roots. Perched on a hill and surrounded by ancient stone walls, it offers breathtaking panoramic views of the valley and Lake Trasimeno, making it one of the best places to stay in Tuscany for a vacation. 🏞️✨
Despite its small size, Cortona is rich in museums, fortresses, and archaeological sites that should not be missed during a vacation in Tuscany. Be sure to visit the Piazza della Repubblica, the heart of Cortona, and the Piazza Signorelli, famous for its lively Sunday market and the historic Palazzo del Capitano with its town hall and bell tower. The town blends culture, history, and stunning landscapes, making it one of the best places to stay in Tuscany for couples. 🌿📚
A highlight is a visit to the Museum of the Etruscan Academy, where artifacts from the tombs of Camucia and Sodo are on display. The city is a treasure trove of Etruscan tombs and an extensive Roman road network that offers a unique insight into ancient history. If you’re interested in the best vineyards to stay in Tuscany, Cortona is nearby some of the most iconic wine regions of the area, ideal for wine tasting and discovering local flavors. 🍷📸
If you visit the city in summer, don’t miss the Festival of the Tuscan Sun. It’s a popular event, so I recommend booking your places to stay in Tuscany well in advance so you don’t miss this cultural spectacle in this stunning Tuscan city. This vibrant festival, combined with the stunning atmosphere of the town, is the perfect way to enjoy all that Cortona has to offer. 🌞🎒
Things to do in Cortona:
- Explore the Piazza della Repubblica, the heart of Cortona, and the lively Sunday market at Piazza Signorelli. 🗺️🌟
- Visit the Museum of the Etruscan Academy and see fascinating Etruscan and Roman artifacts. 🏺📚
- Take in the breathtaking panoramic views of Lake Trasimeno and the surrounding valley. 🌄📸
- Attend the Festival of the Tuscan Sun in summer, a unique cultural event. 🎉🍷
- Wander through the charming streets of Cortona to soak in the medieval atmosphere and picturesque views. 🚶♂️🌍
Is Cortona Neighborhood Safe?
From my experience, Cortona is an incredibly safe town. The atmosphere is relaxed, and the streets are quiet, with friendly locals. Whether you’re staying in a luxury hotel in Tuscany or a cozy farm stay in Tuscany, the town offers a secure and peaceful environment, perfect for a family vacation or a romantic getaway. With its ancient history, panoramic views, and warm hospitality, Cortona truly embodies the charm and safety that makes it one of the best places to stay in Tuscany. 🏡✨
Where to stay in Cortona?
You can read more about Tuscany on Wikipedia.
Websites that I use to book my trips
- 👉 Agoda is my favourite site for booking hotels and unique stays.
- 👉 GetYourGuide is my top pick for booking tours and activities worldwide.
Questions about where to stay in Tuscany Italy:
Where is the best place to stay in Tuscany if you are visiting for the first time?
For first-time visitors, Florence is often recommended as the best place to stay in Tuscany. The city is a cultural center with numerous attractions, including the Duomo and the Uffizi Gallery. The extensive range of accommodation on offer ranges from luxury hotels to budget hostels and makes the city an ideal base for exploring not only Florence, but also nearby cities such as Pisa and Siena.
Which city is the best for wine lovers?
Chianti is the ultimate destination for wine lovers. Known for its picturesque vineyards and world-famous Chianti wine, a stay in this region offers the opportunity to visit local wineries and enjoy wine tastings. The charming villages of Greve and Radda offer excellent accommodation amidst stunning scenery and guarantee a wonderful experience for wine lovers.
Is Tuscany suitable for families?
Absolutely! Tuscany offers plenty of family-friendly accommodation and activities. Cities such as Lucca and Livorno have parks, beaches and historical sites that are suitable for all ages. In addition, many agriturismos (farms) offer hands-on experiences with farm animals and cooking classes, making them an educational and fun day out for families.
When is the best time to visit Tuscany?
The ideal time to visit Tuscany is spring (April to June) or fall (September to October). During these months, the weather is pleasant and the crowds are less numerous than in high season. In addition, these seasons coincide with local festivals and harvests and offer travelers a taste of authentic Tuscan culture.
How do I find cheap accommodation in Tuscany?
If you are looking for cheap accommodation in Tuscany, you should look for options such as agriturismos or smaller boutique hotels. Websites that specialize in local accommodation often offer great rates. Booking in advance can also help to get better prices, especially in the peak travel season when demand is high.
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