A long weekend in Tuscany's wine country
Enjoy three relaxing days in Tuscany. Begin and end in Florence, visiting world-renowned wineries and small wine towns while overnighting in Siena.
Spend a long weekend indulging in classic Tuscan wines
Relaxing vineyards
Tour the scenic estate of famous producer Antinori nel Chianti Classico.
Hilltop Views
Enjoy peaceful hilltop villages like Montalcino and Montepulciano.
Iconic wines
Sample famous wines in their birthplace, including Brunello di Montalcino and Chianti Classico.
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 Siena
Stop 1: Castello di Verrazzano (1 hour)
Sample organic Chianti Classico wines surrounded by pristine Renaissance gardens at Castello di Verrazzano.
- Tour the historic cellars and gardens
- Enjoy a guided tasting of the estate’s organic wines paired with local olive oils, vinegars, and cheeses
- Enjoy a classic Tuscan lunch using ingredients fresh from the estate and nearby farms
Arrival in Siena
Your private driver will safely transport you back to your accommodation in Siena, wrapping up your deep dive into Tuscan wines.
Day 2: Siena to Montepulciano day trip
Stop 1: Montalcino (2 hours)
Sip on globally renowned Brunello di Montalcino while admiring medieval architecture.
- Explore the imposing Fortezza di Montalcino and enjoy a wine tasting sitting on the ramparts
- Wander the Piazza del Popolo and stop into small local wine shops
- Visit the neoclassical Cathedral of the Holy Savior
Stop 2: Montepulciano (2 hours)
Marvel at hilltop vistas and sample Vino Nobile di Montepulciano in this historic town.
- Enjoy a guided tasting in De’ Ricci Cantine Storiche and explore its “wine cathedral”
- Visit the Piazza Grande and climb the Palazzo Comunale tower
- See the fortress’s pristine gardens and valley views
Return to Siena
Relax on the private ride back to Siena after a full day of sightseeing.
- Head to a traditional osteria for local pastas and one last glass of wine
- Catch the sunset at the Basilica of San Domenico terrace, or the Fortezza Medicea ramparts
- Stop for a Sienese sweet treat at a bakery in the Piazza del Campo
Day 3: Siena to Florence
Stop 1: Antinori nel Chianti Classico (2 hours)
This contemporary estate highlights the six centuries of viticulture behind every glass of Chianti Classico.
- Tour the iconic spiral staircase, rooftop vineyard, and gravity-flow cellars
- Sample Chianti Classico Riserva and Tignanello at a guided tasting
- Dine on classic Tuscan fare in the rooftop restaurant
Return to Florence, stay for 2-3 days
See Renaissance masterpieces and enjoy classic Tuscan wines in vibrant Florence.
- Explore the Duomo complex; climb the dome or bell tower for sweeping views
- Pop into a local wine bar or enoteca (“wine library”) for a cozy local experience
- Visit the Uffizi Gallery’s collection of world-famous Renaissance art
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