We Love —
- Immersing through Tuscany’s golden fields, cypress-lined roads, and rustic hilltop villages with your included car hire.
- Sipping on velvety reds and crisp whites from local vineyards, all while enjoying panoramic views of rolling vineyards and medieval towers.
- Sampling a slice of ribollita, a hearty Tuscan soup made with seasonal vegetables and beans, ideal after a day of exploration.
Customer reviews —
Your itinerary in brief —
Embark on an unforgettable road trip in Tuscany, through hills, vineyards and towns steeped in history.
Discover the majesty of Florence, the medieval beauty of Siena and the charm of San Gimignano. Stroll through Lucca, admire the leaning Tower of Pisa and savour the finest wines in the heart of Chianti. Discover the essence of Italy and enjoy its art, food, and culture around every corner.
Your 5-night itinerary:
Day 1: Greve in Chianti - Siena
Day 2: Siena
Day 3: San Gimignano - Monteriggioni
Day 4: Montalcino - Montepulciano
Day 5: San Galgano
Day 6: Departure
Your 7-night itinerary :
Day 1: Pisa - Montecatini
Day 2: Lucca - Pisa
Day 3: Florence
Day 4: San Gimignano
Day 5: Monteriggioni - Siena
Day 6: San Galgano
Day 7: Montalcino - Pienza - Montepulciano
Day 8: Departure
Please note: your itinerary may have minor adjustments, but your overall trip experience will remain the same.
Please note that your hotels may be located inside or outside cities and towns. You may park your car inside or outside the hotels (subject to availability). Additional charges may apply on-site.
Your itinerary in detail —
Suggested 5-night itinerary
Day 1: Chianti - Siena
- Arrive in the heart of Tuscany, where the picturesque town of Greve in Chianti welcomes you, sitting strategically between Florence and Siena.
- Explore the charming, rustic atmosphere of this small town, where the town square remains the vibrant focal point, hosting the traditional weekly market every Saturday.
- We recommend immersing yourself in the rich history of Greve by visiting a historic castle.
- Breathe in the fresh country air and soak up the tranquil beauty of the Chianti region, famed for its rolling hills, vineyards, and timeless charm.
Day 2: Siena
- Explore the medieval masterpiece of Siena, where Gothic architecture tells the story of centuries past.
- Wander through winding streets lined with narrow, red-brown brick palaces made from Sienese clay, creating a timeless atmosphere. We recommend:
- Discovering the historic centre, perched on three hills, shaped in a star formation, with the iconic Palazzo Pubblico at its heart.
- Climbing the Torre del Mangia, standing 88 metres tall, for breathtaking views over the stunning Piazza del Campo.
Day 3: San Gimignano - Monteriggioni
- Step back in time with a visit to the medieval town of San Gimignano, a UNESCO World Heritage site that has preserved its charm since the 14th century.
- Wander through its enchanting streets, where history comes alive in the well-preserved towers and buildings that make it one of Tuscany’s most iconic destinations.
- Enjoy an included wine-tasting experience accompanied by homemade bread and organic extra virgin olive oil.
- Why not join a cooking course in San Gimignano to master the art of Tuscan cuisine, followed by a delightful lunch or dinner to savour your creations?
- Continue to Monteriggioni, a beautifully preserved medieval town encircled by a 600-metre-long wall, offering a true sense of stepping into the past with its quaint houses and narrow, cobbled streets.
Day 4: Montalcino - Montepulciano
- Start your day with a scenic drive to Montalcino, which is world-renowned for its exceptional "Brunello" wine and steeped in history dating back to Etruscan times.
- Discover this charming town, once fiercely contested by Florence and Siena, and soak in its rich heritage and picturesque streets.
- Continue to Montepulciano, perched atop a high tufa plateau, famous for its "Vino Nobile" wine, offering stunning views and a vibrant town centre.
- We recommend enjoying a wine-tasting session in an ancient cellar in Montepulciano, paired with homemade bread and organic extra virgin olive oil—an authentic taste of the region’s rich culinary heritage.
Day 5: San Galgano Abbey
- After breakfast, set off to discover one of Tuscany’s most enchanting viewpoints, where history and legend intertwine. We suggest:
- Visiting the stunning monastery, which includes an enormous roofless church that evokes a sense of timeless beauty.
- Exploring the Hermitage of Monte Siepi, a sacred site where the legend of San Galgano unfolds – it is said he retired here in 1170 to live as a hermit, embedding his sword into the stone as a symbol of peace. This legendary "sword in the stone" is still visible today.
- Discovering the mystical round of Montesiepi transports you into the world of Arthurian legend, while the grand Abbey reveals its own "musical" and "Egyptian" surprises, all shrouded in the secrets of sacred geometry.
Day 6: Departure
- Enjoy your final hearty breakfast at the hotel before heading to the airport for your return flight.
Suggested 7-night itinerary
Day 1: Pisa - Montecatini
- Arrive in the charming town of Montecatini, a serene gem nestled in Tuscany.
- Check in to your hotel, where comfort and relaxation await.
Day 2: Lucca - Pisa
- Drive to Lucca, known as the city of a hundred churches, surrounded by its stunning medieval city walls.
- Enter the historic centre through one of the seven gates and wander through charming streets and squares. We suggest:
- Exploring the Amphitheatre Square, a circular marketplace with origins dating back to Roman times.
- Visiting San Michele Square, home to the Church of San Michele in Foro and the impressive Palazzo Pretorio.
- In the afternoon, head to Pisa, where the world-renowned Leaning Tower awaits. Then, we would recommend:
- Discovering the Square of Miracles, a UNESCO World Heritage site, and admire the Cathedral, Baptistery, Leaning Tower, and Campo Santo.
- Stepping inside the Cathedral of Santa Maria Assunta, a masterpiece of Italian architecture.
- Visiting the hexagonal pulpit by Nicola Pisano inside the Baptistery, and taking in the unique beauty of the monumental Cemetery cloister.
Day 3: Florence
- Immerse yourself in Florence, the world’s art capital, where a third of Italy’s art treasures are housed. How about:
- Visiting Santa Croce, Italy’s largest Franciscan church, which serves as the burial place for famous figures from history, art, and literature.
- Exploring the Palazzo Vecchio in Piazza della Signoria, home to a replica of Michelangelo’s iconic David.
- Discovering the octagonal Baptistery dedicated to San Giovanni, a stunning example of Florence’s architectural heritage.
- Visiting the Palazzo Medici-Riccardi, the first palace of the early Renaissance.
Day 4: Florence
- Spend the day immersed in the beauty of Florence.
- We would highly recommend starting with a visit to the renowned Uffizi Gallery, home to European paintings from the 13th to 18th centuries.
- Enjoy a delicious pizza lunch at a traditional Florence restaurant, complete with refreshing ice cream and a soft drink or beer (not included)
- Take your time to explore the art and culture of one of the world’s most celebrated cities, where masterpieces await at every turn.
Day 5: Chianti and Siena
- After checking out of your hotel, venture into the picturesque Chianti region, nestled between Siena and Florence and renowned for producing the iconic Chianti wine.
- Be enchanted by the stunning landscape of rolling hills, lush fields, and sprawling vineyards and olive groves.
- Arrive in the medieval city of Siena, a true Gothic masterpiece with its winding streets and red-brown palaces made from Sienese clay.
- Explore the historic centre, perched on three hills, and marvel at the famous Palazzo Pubblico and Torre del Mangia, standing at 88 metres high.
- From here, take in the breathtaking views of the beautiful Piazza del Campo, one of Italy’s most renowned squares.
Day 6: Monteriggioni - San Gimignano
- Today's journey takes you through narrow streets flanked by towering palaces and fortifications.
- Visit the medieval town of Monteriggioni, founded in the 13th century, perched on a small hill and enclosed by a formidable 600-metre wall.
- Continue to San Gimignano, famous for its soaring towers visible from miles around, offering a striking skyline.
- We suggest exploring the Basilica of Santa Maria Assunta, the Palazzo del Popolo housing the Museum Civico, and the charming Piazza della Cisterna, home to a picturesque fountain.
- End your day with a wine tasting at a renowned winery near San Gimignano, where you can savour the region's fine wines.
Day 7: Montalcino - Montepulciano
- After breakfast, set off for Montalcino, renowned worldwide for its prestigious Brunello wine.
- With Etruscan origins, Montalcino has a rich history, having been fiercely contested between Florence and Siena for centuries.
- Continue to Montepulciano, perched on a volcanic tuff plateau, and celebrated for its Vino Nobile di Montepulciano.
- Explore the charming town, where history and fine wine blend seamlessly, offering a perfect opportunity to discover the essence of Tuscany.
Day 8: Departure
- Check out of your hotel and drive to the airport, bringing your unforgettable Tuscan experience to a close.
Important information about your tour and visits: The hotels, which comply with local standards, are indicative and may be changed locally for hotels of a similar category. The itinerary is subject to changes due to compelling reasons such as delayed flights, weather conditions or other cases of force majeure. The order of visits is also subject to change without affecting the overall experience of the itinerary.
Your hotels —
Hand-picked just for you
At each of your stops, you will be staying in comfortable rooms in thoughtfully chosen 4* hotels:
In Montecatini: Minerva Palace Hotel (or similar)
In Arezzo: Etrusco Hotel (or similar)
If the hotels listed above are unavailable, you will be provided with comfortable accommodation in similar hotels. Local standards apply.
Single rooms are available at an extra cost.
Your dining choices
This is a bed and breakfast stay.
Your included services —
Wine tasting in San Gimignano (ages 18+)
Savour an authentic wine-tasting experience in the heart of San Gimignano, surrounded by rolling Tuscan vineyards.
Pecorino di Pienza cheese and wine tasting
Indulge in a tasting of Pecorino di Pienza paired with fine wines, a true expression of Tuscan tradition.
Your journey to Italy —
Flights:
You will be able to choose your airline and flight times when you make your booking, in either Economy, Premium, or Business class, depending on the destination and carrier. This flight may include one or more stopovers. Please review your flight options carefully as departure and arrival airports may differ, in order to offer the best price.
Luggage information
Luggage, meals and other services on board may be subject to an additional fee on certain airlines. It is possible to view details of luggage allowances when you choose your flights at the next stage of the booking process. If luggage is not included with your flight, please go to the airline's website before your departure to purchase your luggage for an additional fee.
For domestic flights, airlines do not always offer the option of reserving luggage. In this case, you will need to pay for it at the airport counter.
You will receive all the information you need to check in for your flights after you have made your reservation.
Your destination —
Tuscany
Overflowing with artistic treasures, Tuscany is a timeless haven where ancient history meets rolling landscapes. From Etruscan origins to Roman marvels and Renaissance brilliance, this region is a journey through the ages. Beyond its celebrated cities, Tuscany invites you to explore serene vineyards, sun-dappled olive groves, and quaint villages that define its rustic charm.
Must-sees:
- Florence's Oltrarno District: Venture beyond the Arno River to discover artisan workshops, hidden gardens, and authentic trattorias.
- San Gimignano’s Towers: A medieval skyline framed by Tuscany’s picturesque countryside.
- Etruscan Legacy in Volterra: Wander ancient walls and explore artefacts in the Guarnacci Etruscan Museum.
Culinary culture:
Tuscany's culinary heritage is as rich as its landscapes. Indulge in seasonal Tuscan produce, from creamy pecorino cheeses to fragrant white truffles. Pair these delicacies with Chianti or Brunello di Montalcino wines from the region's renowned vineyards. Don’t miss rustic panzanella salads or ribollita, a hearty vegetable soup traditionally prepared with stale bread. For a sweeter note, try cantucci biscuits dipped in local Vin Santo.
Dive deeper:
Beyond Florence and Siena, Tuscany’s smaller towns reveal unique stories. In Pienza, you’ll find a Renaissance utopia shaped by Pope Pius II’s vision, while the Carrara marble quarries offer a glimpse into the artistry that crafted Michelangelo’s David. For a different perspective, take a cycling tour through the Val d’Orcia, a UNESCO World Heritage Site famed for its cinematic beauty.
Good to know:
The local currency is the euro (€), and Tuscany enjoys a mild Mediterranean climate, with spring and autumn being the ideal seasons to visit. Regional trains and buses connect towns efficiently, but renting a car offers the best flexibility for exploring the countryside’s hidden gems.
