CLASSIC TUSCANY
Chianti Vacation Rentals
Chianti is the classic area of Tuscany that many dream of visiting. Renting a villa in Chianti positions you at the epicenter of Italy’s most famous wine region amidst heartbreakingly beautiful scenery. Charming medieval hill towns reveal ancient churches and castles, surrounded by the classic Tuscan landscape of rustic farmhouses tucked among its hills. Visit Siena, Florence, San Gimignano, Volterra, Greve or Panzano. Follow the ancient wine road that runs between Florence and Siena — stopping at vineyards along the way for tours and tastings. From your Chianti villa, you’ll instantly appreciate how the region today epitomizes all that Tuscany represents as a land of inexhaustible culinary, cultural and historical fascination—along with jaw-dropping natural beauty.
Villa Amarika
7 bed, 7 bath, from €30,715/week
Villa Amarika is a great choice for large groups who want to get a glimpse of true Tuscan life. The villa is jsut 50 minutes from Florence and 25 minutes from Siena, the iconic views of Tuscany.
Villa La Tavernaccia
8 bed, 7.5 bath, from €34,300/week
Dream Renaissance villa in heart of Tuscany. Luminous, luxurious, and relaxing. The setting is picture perfect — a classic Renaissance villa set on a hill and commanding an impressive view over the gorgeous Tuscan countryside.
Villa Colli
7 bed, 7 bath, from €18,985/week
I Colli is the perfect vacation villa for families and groups of friends. The villa has many gathering spaces, outdoor and indoor, perfect for hosting dinners and parties, and the heated pool makes it a great off-season retreat.
Villa Trionfante
7 bed, 7 bath, from €28,570/week
The layout with two separate annexes gives space to the group without the risk of overcrowding. Enjoy the privacy of the estate, including a private access to the nearby river. Florence is just 25 minutes away.
Villa Giunia
14 bed, 14 bath, from €23,400/week
Villa Giunia is a restored three story villa, designed as resort-like home. The estate includes a massive infinity pool with sundeck area, idyllic walking trails that run inside the expansive estate, and it also features its own farm, horse stables and organic garden.
Villa Danica
5 bed, 5 bath, from €10,935/week
Surrounded by soft rolling hills and glorious views, Danica has been meticulously restored to create the perfect scenario for a vacation you will never forget.The villa, with an eclectic and relaxed design, offers a true respite from everyday life.
Villa Morea
6 bed, 5 bath, from €9,445/week
Villa Morea offers high-end interiors, landscaped gardens, furnished outdoor spaces and enchanting views from its stone-paved pool. This villa is ideal for multi-generational reunions in Tuscany.
Villa La Fontenella
5 bed, 7 bath, from €10,780/week
Villa La Fontenella is located in the heart of Tuscany's Chianti region, with expansive views over the olive groves. The location couldn’t be better: private, tranquil position on hillside just 15 minutes south of Florence.
Villa La Novellina
5 bed, 5 bath, from €9,040/week
La Novellina is a wonderfully renovated farmhouse built around a central 11th-century tower and located halfway between Florence and Siena, overlooking the Chianti hills.This typical Tuscan house has been respectfully restored.
Villa Certaldo
13 bed, 13 bath, rates on request
Villa Certaldo is a beautiful estate overlooking the vast hills of Tuscany. The estate consists of ten apartments (six of which are air conditioned), and is perfect for large groups. Many beautiful weddings have been held at the villa over the years.
Villa Hortus
5 bed, 5 bath, rates on request
Enjoy the unspoiled Tuscan countryside in this authentic yet modern villa. While retaining its original structure, Villa Hortus offers contemporary amenities that cater to modern comforts. This impeccably designed home offers lush surroundings, an infinity pool, and plenty of common spaces
Villa Poggio delle Rose
11 bed, 11 bath, rates on request
Poggio delle Rose is an elegant hilltop farmstead, strategically positioned in the center of the Golden Triangle between Florence, Siena and Pisa. The property sits on top of a hill, surrounded by 24 acres or vineyards, olive groves and woods.
When is the best time of year to Chianti Tuscany?
Each season in Chianti has its charm. If you prefer mild weather and fewer tourists, the spring months of April to June are ideal as the Tuscan countryside begins to bloom with vibrant colors. For those interested in wine tourism, visit in September and October for an inside look at the grape harvest, with many local festivals celebrating the region's famed Chianti wines. Summer, specifically July and August, brings warm weather and bustling tourism, making it perfect for those who enjoy lively atmospheres and outdoor activities. Lastly, winter, from November to February, sees fewer visitors, making it an excellent time for a peaceful and intimate exploration of the region, complete with cozy stays at charming local inns and indulging in hearty Tuscan cuisine.
Jan
38°
Feb
40°
March
46°
April
52°
May
60°
June
67°
July
73°
August
73°
Sep
65°
Oct
56°
Nov
46°
Dec
40°
Why visit Chianti?
Chianti is special because it offers an authentic Tuscan experience rooted in history, culture, and natural beauty.
Legendary Wine: Chianti is the birthplace of Chianti Classico, a wine tradition dating back to the 13th century. Taste this wine in the region where it’s made and connect to centuries of winemaking heritage.
Medieval Villages: Towns like Castellina, Greve, and Panzano are steeped in history, with ancient buildings and cobblestone streets that offer a glimpse into the past.
Culinary Excellence: The region is known for its farm-to-table cuisine, featuring fresh, local ingredients like Tuscan olive oil, wild boar, and pecorino cheese. Meals here are a true reflection of the land.
Deep Connection to Nature: The rolling hills, vineyards, and olive groves of Chianti aren’t just scenic; they’re a vital part of the local way of life, cultivated with care over generations.
Cultural Richness: Chianti’s festivals and traditions celebrate its rich heritage, offering a chance to experience local culture in an authentic setting.
Chianti isn’t just a destination; it’s a place where history, culture, and nature come together in a uniquely Tuscan way.
Culinary delights in Tuscany
Enjoy fine wine and savor the endless culinary delights that Tuscany has to offer. Tuscan cuisine revolves around fresh, seasonal ingredients like legumes, cheeses, vegetables, and fruits. Treat yourself to typical dishes such as pappardelle, a fresh egg noodle pasta often served with a rich hare or wild boar sauce.
After exploring Florence, build up an appetite and choose between dining at one of the city’s many Michelin-starred restaurants or experiencing a more local flavor at the indoor food market of San Lorenzo. Be sure to try lampredotto, a traditional dish that’s a key part of Florence’s culinary heritage.
For meat lovers, tasting the famous bistecca alla fiorentina is a must. This thick, juicy steak comes from the Chianina breed of cattle and is typically served rare, accompanied by roasted potatoes, beans, or spinach.
End your meal with cantucci, crunchy almond cookies traditionally paired with Vinsanto dessert wine, perfect for dipping. To deepen your experience, consider taking a cooking class to learn the secrets behind Tuscan recipes.
Top wineries in Tuscany
Tuscany is home to some of the world’s most renowned wine regions. Visiting a Tuscan winery offers more than just a chance to taste exceptional wines—it’s an opportunity to delve into the passion, history, and traditions behind their creation, all while enjoying the stunning Tuscan landscape.
Cantina Antinori: Located in San Casciano Val di Pesa, this winery is not only known for its excellent wines but also its striking architecture. Their specialties include the dessert wine Muffato and the famous Brunello di Montalcino.
Tenuta Fanti: Situated in the Montalcino area, this family-run winery offers fantastic wine tasting experiences, pairing exquisite wines with seasonal local foods.
Cantina Salcheto: Found in Montepulciano, this winery is celebrated for its biodynamic and sustainable winegrowing practices. It’s especially known for producing Vino Nobile di Montepulciano, a wine with a soft texture and rich flavor.
Tenuta Avignonesi: One of Italy’s oldest wineries, dating back to the mid-16th century, Avignonesi offers a diverse selection of wines, including the famed Vin Santo and Vino Nobile.
Badia a Coltibuono: Located in the Chianti region, this estate, once a monastery, is surrounded by elegant gardens. It’s renowned for producing prestigious Chianti Classico and high-quality olive oil.
Things to do in Tuscany
Explore Florence: Start with the capital city, Florence, the birthplace of the Renaissance. Visit the Uffizi Gallery to see masterpieces by Michelangelo, Botticelli, and Leonardo da Vinci. Don’t miss the iconic Duomo with its stunning dome, and take a stroll across the Ponte Vecchio, a medieval stone bridge lined with shops.
Visit the Hilltop Towns: Tuscany is famous for its charming hilltop towns, each with its own unique character. Siena is known for its stunning Piazza del Campo and the annual Palio horse race. In San Gimignano, explore the medieval towers that define its skyline. Montepulciano and Montalcino are perfect for wine lovers, offering picturesque views and some of the best wines in Italy.
Wine Tasting in Chianti: The Chianti region is synonymous with wine. Take a scenic drive through its rolling hills and stop at local wineries to sample Chianti Classico. Many wineries offer tours where you can learn about the winemaking process and enjoy tastings paired with local cheeses and cured meats.
Relax in the Tuscan Countryside: Tuscany’s countryside is ideal for relaxation. Stay in a rustic farmhouse or villa and take in the serene landscape of vineyards, olive groves, and cypress trees. Enjoy leisurely walks, bike rides, or simply relax by the pool with a glass of wine.
Discover Pisa: No visit to Tuscany is complete without seeing the Leaning Tower of Pisa. While the tower is the main attraction, the city also boasts a beautiful cathedral and the Campo dei Miracoli, a UNESCO World Heritage site.
Experience the Tuscan Coast: The Tuscan coastline, known as the Etruscan Coast, offers beautiful beaches and charming seaside towns. Visit the island of Elba, where Napoleon was exiled, or explore the natural beauty of the Maremma region, which combines rugged coastline with rolling hills.
Indulge in Tuscan Cuisine: Tuscany is a food lover’s paradise. Try local specialties like ribollita, a hearty vegetable soup, or bistecca alla fiorentina, a thick, juicy steak. Pair your meals with local wines, and don’t forget to finish with cantucci and Vinsanto for dessert.
Visit Thermal Baths: Tuscany is home to several natural hot springs. The thermal baths in Saturnia are particularly famous, offering a relaxing experience in mineral-rich waters that have been used since Roman times.
Art and Architecture in Lucca: Lucca is known for its well-preserved Renaissance walls and charming historic center. Explore its narrow streets, visit the stunning Lucca Cathedral, and walk or bike along the tree-lined walls for panoramic views of the city.
Attend Local Festivals: Tuscany hosts many festivals throughout the year, celebrating everything from food and wine to medieval history. The Palio di Siena, a thrilling horse race held twice a year, is one of the most famous. Other notable events include the Chianti Classico Wine Festival and the Luminara di San Ranieri in Pisa.
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