Siena and Southern Tuscany Private Wine Tour

This morning, you will arrive at either Florence or Pisa airport, where your private driver-guide and elegant Mercedes will be waiting. Your first stop on this tour is a winery, naturally! You will drive into the romantic Chianti Classico, the “ultimate” Italian wine region. This is the wine country of postcards, with its medieval hilltop villages, lush woodlands, cypress-lined country roads, and valleys blanketed in vineyards and olive groves.

Arrive at a top winery such as Badia a Coltibuono, one of our favorites. This historic winemaking estate was founded by Vallombrosan monks when they built their impressive abbey here in the 11th century. Badia Coltibuono translates as “Good Harvest Abbey.” These days, it is one of Italy’s most prestigious wineries, making not only wines but also balsamic vinegar and olive oil. On a private VIP tour, you will explore the extensive grounds, including the manicured Renaissance garden (aromatic with its lavender and lemons) and the ancient wine caves. Taste their best wines, including the Super Tuscan Sangioveto and historical vintages of Chianti Classico Riserva Badia a Coltibuono, followed by an elegant lunch right at the estate.

In the afternoon, carry on to Siena and check into your gorgeous hotel with the best location in town. Settle in, and your friendly and knowledgeable art guide will meet you in the lobby, and you will embark on a private walking tour of Siena’s most cherished sites and monuments. Learn all about the medieval Palio, which captures the world’s attention every summer when colorful riders on decked-out horses bearing the family coat of arms dating back for centuries compete in the “Campo” (the scallop-shaped main square). Visit the cathedral, one of the most spectacular buildings in Italy (and this says quite a lot!), which took hundreds of years to complete.

Your guide will entertain you with anecdotes and plenty of local legends, bringing Siena’s fascinating history to life. The rest of the evening is yours. In your luxurious room, you will find a welcome pack and wine and a keepsake itinerary with plenty of suggestions for dining, shopping, and exploring. Welcome to Siena!

After a leisurely breakfast in your beautiful hotel, your driver will meet you, and you will head southeast for about one hour to Montalcino this morning. The scenery is supremely picturesque and contrasts with the landscapes of Chianti Classico. Montalcino is where Brunello di Montalcino, one of Italy’s most exceptional wines, is made, and today you are going to visit the best estates. Begin with a private tour at Luce della Vite estate, created by the Mondavi and Frescobaldi families, and blossomed under the Frescobaldi ownership. You will see the lush vineyards, tour the wine cellar and follow with a tasting of different vintages of Luce (Sangiovese and Merlot), Lux Vitis (Cabernet Sauvignon and Sangiovese) and Luce Brunello, the tribute to Montalcino wine region.

Next is Massimo Ferragamo’s Castiglion del Bosco, where you will have a complete tour and taste six great vintages of their cru Brunello Campo del Drago and Brunello Riserva Millecento. A real delight!

You will almost certainly be ready for lunch by the time your tasting finishes. We will have a special traditional menu planned for you at Nardi estate; mama’s cooking paired with their top wines, such as single-vineyard Brunello di Montalcino Manachiara, an excellent wine for aging, but smooth enough to drink now.

Your last winery tour and tasting in Montalcino is at boutique winery Il Palazzone, a project by US businessman Richard Parsons, locally managed by Laura Gray. You will taste some of the five-stars vintages, including 2010, “the vintage of the millennium in Montalcino.”

Explore Montalcino on your own, to stretch your legs, get some photos of the fortress and dramatic views below or pick up some excellent Brunellos in an enoteca (wine shop), before returning to Siena and relax at the hotel.

The morning is yours to sleep in, relax, or have a leisurely breakfast. Your friendly driver will meet you and transfer to Pienza countryside, to one of the best producers of sheep cheese, Pecorino di Pienza. Ulisse will guide you through the farms, before tasting his divine products, like fresh raw milk Pecorino with pink pepper, Pecorino aged in pomace, organic Pecorino blue cheese, Pecorino Riserva, and more.

Just a few minutes away from this cheese paradise, you will have an unforgettable experience at organic winery Fabbrica, founded and designed by Philippe and Tonie Bertherat. You will visit the vineyards on a 4-wheel ride, visit the cellar, and enjoy a vertical wine tasting. Bonus for the art lovers: Mr. Bertherat is an art collector and president of Mamco (Geneva Museum of Modern and Contemporary Art), and the estate is scattered with artworks, starting from Ugo Rondinone’s Seven Magic Mountains.

After a fantastic tour, you will sit down to a traditional lunch in a quaint trattoria in the heart of lovely Monticchiello hamlet. Taste local dishes like spelt salad, Pici pasta with a Chianina beef ragu, local Cinta Senese breed pork loin, and homemade almondy cantucci polished off with a glass of nutty Vin Santo.

In the afternoon, your driver will take you on a sightseeing tour of the most beautiful villages in Val d’Orcia. You will visit the romantic town of Pienza including the whimsically named streets “Via del Bacio” (Kiss street) and “Via dell’Amore” (Love street).. Next to San Quirico d’Orcia, where you cannot miss the stunning Collegiata and the Italian garden Horti Leonini; Bagno Vignoni, where you have a large medieval thermal water pool, instead of the main square.

On the way back to Siena, you will admire Crete Senesi (literally Sienese clays), the perfect image of Tuscany, and the magic Accona desert.

The evening is yours with our suggestions.

This morning or afternoon at your preferred time, your driver will take you to Florence or Pisa’s airport for your departure flight. And this concludes your luxurious and highly enjoyable short stay in Siena. We look forward to seeing you again!