A Tuscan Table: Florence to Siena
Savor Tuscany through vineyard feasts, olive oil tastings, and hands-on cooking in a medieval hilltop village, where the scent of herbs and slow-simmered sauces fills the air. Explore Renaissance Florence, stroll Lucca’s sun-warmed walls, uncover Montepulciano’s candlelit wine cellars, and wander Siena’s Gothic streets. Each moment unfolds at a relaxed pace, thoughtfully tailored by your Destination Expert and rich with the flavors and textures of the region.
- Duration
- 10 days, 9 nights
- Route
- Florence · Montepulciano · Siena
- Style
- Private and tailor-made: your own guide and driver throughout
- From
- $6,670 per person, hotels, guides and transfers included
- Trace Florence’s Renaissance gems with an expert, ending with Michelangelo’s famed "David".
- Savor Montepulciano’s farm-to-table bounty with Pecorino cheese, meats, and organic wines.
- Cook Italian classics in a quaint village with a chef, savoring each dish with Tuscan wines.
- Tour olive groves in Assisi’s countryside, learning EVOO secrets before a tasting and lunch.
- Ask your Destination Expert for ideas to enhance your trip, like a hot air balloon ride.
Every day, already yours.
Here we Go!
Meet your private English-speaking assistant outside of airport customs. Waiting with a sign with your name on it, they will direct you to your awaiting private transfer, and accompany you to your hotel for check-in.
- Airport with Meet & Greet - Private Transfer
- Italy Welcome Package
- Evening Aperitivo in Florence, On Your Own
Strolling the Magical Streets
Explore Florence on a privately guided walk through its UNESCO-listed historic center, where your guide weaves stories and local insight into the city’s squares, bridges, and everyday streets. Move through Cathedral Square, Piazza della Signoria, and across the Ponte Vecchio as your guide draws attention to details and viewpoints many visitors miss, before entering the Accademia Gallery with included tickets.
- Walking Tour of Florence’s Historic Center and Accademia Gallery (3 hrs) - Private Tour
- Insider Dining Suggestions: Florence
See the Signature Sights in Style
Step into the timeless charm of Tuscany with a journey from Florence to Lucca, a perfectly preserved medieval gem encircled by Renaissance walls and alive with history, artistry, and atmosphere. Your private driver will take you west across the Tuscan countryside to the banks of the River Serchio, where you’ll meet your local guide for a two-hour exploration.
- Journey to Medieval Lucca (6 hrs) - Private Tour
En Route
Meet your private driver and vehicle for a transfer to Montepulciano. Approximate travel time is two hours.
- Florence to Montepulciano (2 hrs) - Private Transfer
- Garden & Pool Leisure at Villa Cicolina
A Festive Feast
Taste Tuscany from pasture to cellar on a gourmet day with your private guide and driver. Begin at a family pecorino producer, where heritage methods shape every wheel. Enjoy a flight of six pecorini paired with a glass of Rosso di Montepulciano. Continue into the Val di Chiana to a working farmhouse that raises Chianina cattle and Cinta Senese pigs.
- Signature Tuscany Gourmet Experience (with Tastings & Lunch, 6.5 hrs) - Semi-Private
Tastes and Traditions
Go beneath Montepulciano’s streets with your private guide into a hidden world of Etruscan-carved cellars, silent chapels, and barrels of Nobile quietly aging. Stroll the historic center, then slip through a discreet wine shop and descend about 40 feet into sandstone tunnels that open into a main gallery, vaults and passageways shaped by 16th-century winemakers and used for centuries since.
- Historic Cellar Tour (with Wine Tasting, 2.5 hrs) - Private
The Journey Continues…
Meet your private driver and vehicle for a transfer to Siena. Approximate travel time is 1 hour and 15 minutes.
- Montepulciano to Siena (75 mins) - Private Transfer
- Siena Discovery Walking Tour (2 hrs) - Private
Creative Cuisine
Indulge in a day of culinary enchantment as you depart your hotel to the 12th-century hillside haven of Castello di Volpaia. Unlike others, this is a terra murata, a walled village, preserving its medieval charm. The well-preserved layout within unveils a culinary treasure trove. Engage in an intimate cooking class, unraveling the secrets of crafting perfect Italian dishes with a private chef.
- Cooking Class & Wine Tasting at Castello di Volpaia (with Lunch, 6.5 hrs) - Private Tour
Hidden Gems
Follow the scent of crushed olives into Umbria’s hills on a private estate visit near Assisi. Arrive at a stone farmhouse surrounded by nine hectares of silvery trees and meet a local expert for a gentle walk through the groves. Learn how the land is tended, when olives are harvested, and how extra virgin olive oil is produced from fruit to mill.
- Olive Oil Tasting in the Umbrian Hills (with Lunch, 5 hrs) - Private
Jet Off
Meet your private driver and vehicle for a transfer to Florence Airport. Approximate travel time is 1 hour and 15 minutes.
- Siena to Florence Airport (75 mins) - Private Transfer
Where you will wake up.
Brunelleschi
The Hotel Brunelleschi is located in the historical center of Florence, a stone’s throw from the Uffizi Gallery, the Piazza della Signoria, and one of the world’s most famous shopping streets.
Villa Cicolina
Villa Cicolina is an enchanting hideaway that was once home to a noble family of Montepulciano. Originally built in the late 16th century, secret gardens, romantic characteristics and sun-kissed hues fill every corner of this charming villa.
Hotel Athena
Surrounded by great ancient walls and breathtaking panoramic views of Tuscany lies Hotel Athena. Located in the heart of Siena, Duomo and Piazza del Campo are just walking distance away. The Hotel Athena provides rooms fitted with all the comforts you require for a relaxing stay.