Slow Tuscany: vineyards, valleys, and hill towns
Embark on a slow 5-day journey through Tuscany’s famous landscapes. With a private driver, you’ll see vineyards and medieval villages between key cities.
Visit Tuscany at your own pace with a private driver
Vineyards
Visit wineries and vineyards like Podere Le Ripi for a taste of Tuscany’s iconic wines.
Medieval villages
Explore Certaldo, Monteriggioni, and Montalcino, hilltop villages boasting rich histories and valley views.
Art hotspots
See Impruneta for terracotta production, Colle di Val d’Elsa for blown glass, and the historic art collections of Siena.
How it works
Choose your pickup and drop-off locations, and add optional sightseeing stops.
Your driver will meet you at your door and begin day one of your trip.
On the way to your first destination, your driver will stop at the sightseeing sites you booked and wait while you explore.
After a relaxing drive and optional sightseeing stops, you’ll arrive at your first overnight destination.
The next morning, you’ll meet your driver for day two and start the adventure again.
Choose your pickup and drop-off locations, and add optional sightseeing stops.
Your driver will meet you at your door and begin day one of your trip.
On the way to your first destination, your driver will stop at the sightseeing sites you booked and wait while you explore.
After a relaxing drive and optional sightseeing stops, you’ll arrive at your first overnight destination.
The next morning, you’ll meet your driver for day two and start the adventure again.
Day 1: Florence to San Gimignano
Stop 1: Impruneta 
Explore Tuscany’s terracotta capital and watch local artists uphold centuries-old traditions.
- Visit a multi-generational kiln and watch artists handmake clay products
- Wander the Piazza Buondelmonti, stopping at the Basilica of Santa Maria
- Try peposos beef stew, a peppery specialty born in this quiet town
Stop 2: Certaldo
Stop in this hilltop medieval village, the birthplace of the writer Boccaccio.
- Take the funicular from the lower town to the red-walled fortress
- Visit Casa Boccaccio, former home of the Decameron author
- See the Church of San Tommaso and Prospero for its Renaissance art
Arrival in San Gimignano
Spend the night in this iconic town, its skyline dominated by 14 medieval towers.
- Wander the cobblestone lanes and find the Piazza della Cisterna
- Climb the highest remaining tower, Torre Grossa, for panoramic views
- See the vibrant frescoes of the Duomo di San Gimignano
Day 2: San Gimignano to Siena
Stop 1: Colle di Val d’Elsa
Start your day in Italy’s “crystal capital,” known for its blown glass and multi-level layout.
- Visit the Museo del Cristallo for glassblowing history
- Hike the SentierElsa trail to see waterfalls and cross wooden bridges
- Head to the upper old town and explore cobblestone streets
Stop 2: Monteriggioni
Feel like you’re stepping into a fantasy novel as you enter Monteriggioni, a town surrounded by a defensive wall, famously appearing in Dante’s Inferno.
- Walk along the ramparts for views across the Tuscan hills
- Visit Piazza Roma, the village center, for coffee and people-watching
- See the bell tower of the Romanesque Church of Santa Maria Assunta
Arrival in Siena
Stay for a night in historic Siena, boasting Gothic architecture and a rich collection of art.
- Begin at the Piazza del Campo, the city’s medieval heart
- Tour the Siena Cathedral, especially the Piccolomini Library
- Climb Torre del Mangia for unmatched views, doubly magical at sunset
Day 3: Siena to Montalcino
Stop 1: Territorial Abbey of Monte Oliveto Maggiore
Kick off the day at this active Benedictine Monastery hidden in a cypress forest.
- See the detailed frescoes in the Great Cloister
- Enter the Abbey Church, spotting the 16th-century carved choir
- Visit the wine cellar and browse monk-made wine, honey, and oil
Stop 2: Buonconvento
Stroll through a walled medieval village, a quiet retreat packed with mud-brick buildings and flowering alleys.
- Walk along the Via Soccini, the picturesque center street
- Explore along the red mud-brick walls, dating back to 1379
- See the Church of San Pietro and San Paolo
Stop 3: Podere Le Ripi
Just before reaching Montalcino, stop at this biodynamic (“beyond organic”) wine estate.
- Tour the unique “bonsai” vineyard, the densest in the world
- Visit the spiral-shaped golden ratio cellar
- Taste the winery’s favorite vintages paired with local cheeses
Arrival in Montalcino
End your day in Montalcino, perched on a hilltop and known around the world for its Brunello wine.
- See the Fortezza, the 1361 fortress that crowns the town
- Head to the Piazza del Popolo for dinner or people-watching
- Spot the clock tower on the Palazzo dei Priori in the main square
Day 4: Montalcino to Pienza
Stop 1: San Quirico d'Orcia
Be mesmerized by this walled, Etruscan town tucked into the rolling Val D’Orcia landscape.
- Visit the 12th-century Collegiata di Santi Quirico e Giulitta church
- Explore the symmetrical Horti Leonini, a classical, relaxing garden
- Head to Cappella Madonna di Vitaleta, a solitary chapel in the hills
Stop 2: Bagno Vignoni
Unwind in this thermal village, built around a central square of steaming volcanic water.
- Stroll ancient stone channels historically walked by popes and royals
- Hike down the hill to see the ancient Park of the Mills
- Enjoy coffee or Bagno Vignoni wine at a Bohemian cafe in town
Stop 3: Podere Il Casale
Indulge in a farm-to-table lunch at this organic farm just outside of Pienza.
- Tour the dairy farm to see the dairy sheep
- Sample raw-milk pecorino cheeses and learn about their production
- Dig into fresh pasta dishes with romantic valley views
Stop 4: Pienza
Stay the night in an elegant town remodeled at the behest of Pope Pius II.
- Start in the central trapezoidal Piazza Pio II; visit the cathedral
- See the hanging garden of the Palazzo Piccolomini
- Stroll the Via dell’Amore, one of the town’s romantic streets
Day 5: Pienza to Florence
Stop 1: Montepulciano
Visit this iconic Renaissance town, home to cathedral-like wine cellars and elaborate palaces.
- Explore the Piazza Grande, appearing in the Twilight series
- Climb the Torre di Pulcinella for panoramic views
- Sample the famous local wine, Vino Nobile
Stop 2: Castellina in Chianti
Enjoy one last stop on your way to Florence at this fortified medieval town and wine hotspot.
- Visit the 15th-century Rocca fortress, featuring square-cut towers
- Stroll the Via delle Volte, a covered medieval street circling the town
- See the Church of San Salvatore, with its 15th-century frescoes
Return to Florence
Return to Florence, Tuscany’s crowning gem and the heart of the Renaissance.
- Visit the iconic red-roofed Duomo; climb inside the dome for panoramas
- See art by Michelangelo and da Vinci in the Uffizi Gallery
- Visit the Galleria dell’Accademia to see Michelangelo’s David
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