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Exploring Chianti through its wineries is one of the most rewarding ways to experience Tuscany. In this guide, we share five of our best wineries to visit in Chianti—each offering a unique blend of tradition, wine making, and breathtaking scenery.
You’ll find practical travel tips, detailed introductions, and honest pros and cons for each winery, along with advice on where to stay and the best times to visit.
Few places on Earth capture the timeless romance of Tuscany quite like Val d’Orcia. A UNESCO World Heritage Site, this sweeping valley of golden hills, cypress-lined lanes, and storybook villages is also home to some of Italy’s most celebrated wineries.
Framed by medieval towns such as Montalcino, Pienza, and San Quirico d’Orcia, the region’s unique terroir and centuries-old winemaking traditions have produced wines that are not only rich in character but deeply connected to the landscape.
Tuscany is known the world over for its rolling hills, cypress-lined roads, and historic towns—but it’s the wine that often leaves the most lasting impression.
From bold reds aged in ancient cellars to crisp whites enjoyed on sun-drenched terraces, Tuscany offers a wine experience like no other.
On our travels through the region, we found ourselves drawn again and again to these ancient towns. Some like Siena, with its proud palazzos and famous piazza. Others, like Monteriggioni or Volterra, feel almost untouched, their cobbled streets winding through centuries of history and local life. What they all share is that unmistakable sense of the past—alive, tangible, and beautifully worn.
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Florence is the perfect base for discovering the best of Tuscany’s world-renowned wine regions. With its central location, the city gives easy access to everything from the rolling vineyards of Chianti Classico to the coastal estates of Bolgheri. Wine lovers will find an incredible range of tasting experiences just a short drive away, with each region offering its own distinctive grape varietals, traditions, and scenery.
Viareggio is Tuscany’s elegant seaside escape, known for its Art Deco architecture, palm-lined promenade, and vibrant beach clubs. Located on the Versilia coast, it blends classic Italian beach culture with charming cafés, shopping, and its famous carnival. It’s a perfect spot for sun, sea, and stylish relaxation
Monteriggioni is a perfectly preserved medieval walled village in Tuscany, perched on a hilltop near Siena. Its circular walls and 14 towers create a fairytale-like silhouette. Steeped in history and charm, it’s ideal for leisurely strolls, scenic views, and a quiet taste of Tuscany’s ancient past
Val d’Orcia is the postcard-perfect heart of Tuscany, known for its rolling hills, cypress-lined roads, and golden fields. This UNESCO-listed valley is dotted with charming towns like Pienza and Montalcino. It’s a dream destination for slow travel, scenic drives, fine wine, and the timeless beauty of rural Italy
Chianti is Tuscany’s iconic wine region, famous for its rolling vineyards, hilltop villages, and rustic charm. Stretching between Florence and Siena, it’s the perfect place to sip world-class wine, enjoy scenic drives, and explore medieval towns. Chianti offers a classic Tuscan experience rich in flavor, beauty, and tradition.
Elba Island is Tuscany’s island escape, known for its crystal-clear waters, scenic beaches, and rich history. Just a ferry ride from the mainland, it offers hiking, snorkeling, charming port towns, and Napoleon’s historic exile home. Elba blends natural beauty with laid-back coastal vibes—perfect for a peaceful Italian getaway
Montalcino is a picturesque hilltop town in Tuscany, world-renowned for its Brunello wine. Surrounded by vineyards and olive groves, it offers stunning views, medieval charm, and a relaxed pace. Wander cobbled streets, visit historic fortresses, and enjoy tastings in local wineries—Montalcino is a true gem for wine and culture lovers.
Pitigliano is a dramatic hilltop town in southern Tuscany, carved from volcanic tufa rock. Known as “Little Jerusalem” for its historic Jewish quarter, it offers a unique blend of history, culture, and stunning views. Its cliffside setting, winding alleys, and ancient charm make Pitigliano a captivating and unforgettable destination.
Saturnia’s hot springs are a natural wonder in southern Tuscany, where warm, mineral-rich waters flow over terraced rock pools. Free and open year-round, these cascading thermal baths offer a relaxing, spa-like experience in the wild. Surrounded by countryside, Saturnia is perfect for unwinding and soaking in nature’s healing waters.
Arezzo is a charming Tuscan city rich in art, history, and local life. Known for its medieval architecture and antique markets, it was once home to artist Piero della Francesca. Explore elegant piazzas, Roman ruins, and vibrant cafes—Arezzo offers an authentic, less-crowded glimpse into Tuscany’s cultural and historical heart
3 Day to 10 Day Planned Itinerary trips in Tuscany offer endless possibilities—charming hilltop towns, vineyard visits, historic cities, and scenic drives. From Florence to the Val d’Orcia, each stop reveals timeless beauty and rich culture. Whether you’re into food, wine, art, or nature, Tuscany’s diverse landscapes make every journey unforgettable and uniquely Italian
Tuscany’s diverse day trips from Florence offer everything from medieval hilltop towns and Renaissance masterpieces to world-renowned wine regions and stunning countryside vistas. Explore iconic destinations like Siena’s Palio traditions, Pisa’s architectural marvels, and San Gimignano’s towering skyline, alongside hidden gems including ancient Etruscan Volterra and peaceful Lucca’s tree-topped towers. Wine enthusiasts can savor Chianti’s rolling vineyards, Montepulciano’s noble cellars, and Montalcino’s prestigious Brunello estates, while culture seekers discover Arezzo’s Renaissance frescoes, Pienza’s perfect urban planning, and Val d’Orcia’s UNESCO landscapes.
Pienza is a stunning Renaissance town located in the heart of the most picturesque part of Tuscany – Val da Orcia. Just like most smaller towns and villages in Tuscany. Pienza was built high on the hill.
Cortona is one of the absolute highlights of Tuscany. We love this romantic Hilltop town in Southern Tuscany. Famous for the movie “Under The Tuscan Sun’
Lucca the hidden gem of Tuscany “We Love you, “Renaissance walls completely encircle this perfectly preserved medieval city, creating ideal cycling and walking paths with panoramic countryside views. Famous tree-topped Guinigi Tower, the unique oval Piazza dell’Anfiteatro built on Roman amphitheater ruins, and charming cobblestone streets offer intimate Tuscan charm without overwhelming crowds.
Montepulciano in Italy is a popular tourist destination in Tuscany and a true paradise for connoisseurs and wine lovers. This medieval town offers exceptionally charming scenery and is beautiful on a hill in the Val d’Orcia region, surrounded by green vineyards and olive groves. Walking through the old town you will be amazed by the abundance of historic buildings, impressive churches and picturesque squares. A real highlight is that Vino Nobile di Montepulciano and Rosso di Montepulciano are two amazing red wines that are famous worldwide and can be tasted locally.
With its incredible Duomo picturesque main square and medieval streets to explore. It’s no wonder Siena is one of the highlights of Tuscany, and for many the historic Old Town is one of the most beautiful in Italy.
Florence is one of the most beautiful cities in Europe. It’s the perfect city to jump-start your time in Tuscany. Renaissance birthplace and Tuscany’s cultural capital, Florence houses world-famous art treasures including Michelangelo’s David, Botticelli’s masterpieces, and Brunelleschi’s magnificent cathedral dome. The Uffizi Gallery, Ponte Vecchio bridge, and Palazzo Pitti showcase centuries of artistic genius while charming neighborhoods offer authentic Tuscan cuisine and artisan craftsmanship.
We often say Volterra is our favorite Italian hillside town. It ticks all the boxes for us, beautifully preserved, with just enough tourism. Far enough away. Not to be overrun by crowds. There are plenty of good restaurants, cafes, bars and traffic free.
Pisa is a city that effortlessly blends in a rich medieval past with a vibrant present. Nestled in the heart of Tuscany, Italy, is a city that charms visitors with iconic landmarks, and lively ambience. While the leaning tower remains the star attraction, the city offers so much more.
San Gimignano, known as the “Medieval Manhattan,” is famous for its striking skyline of ancient towers. This hilltop town in Tuscany enchants visitors with cobbled streets, artisan shops, and the crisp white wine Vernaccia. Its UNESCO-listed charm and panoramic views make it a must-visit for history and wine lovers.
Italy’s most celebrated region combines Renaissance art treasures, world-renowned wines, and breathtaking landscapes of rolling hills dotted with cypress trees. From Florence’s cultural masterpieces to Chianti’s vineyards, medieval hilltop towns, and Val d’Orcia’s golden countryside, Tuscany epitomizes Italian beauty, cuisine, and timeless charm.
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Please email us with any questions to Gary and Sally at timelesswanders@gmail.com