From Siena you will explore its near by Wine Country & gastro delights

Siena is one of Tuscany’s most delightful and beautiful cities and a fantastic destination for a wine tour as it is in easy reach of top wine regions like Montalcino and Chianti Classico, as well as the airports of Florence and Pisa. So, for wine lovers looking for a short and luxurious break in Italy, we have organized this fabulous tour! Dining is just as important as wine on our tours, and you can look forward to a range of gastronomic experiences from Michelin starred restaurants to rustic and warm meals at historic wineries. Apart from food and wine, you will take on a privately guided tour of Siena’s “Centro Storico” along with, chauffeured sightseeing tours of the beautiful Tuscan towns of Val d’Orcia towns including Pienza, Bagno Vignoni, San Quirico d’Orcia, and hidden gems like Crete Senesi and Accona desert. This is an ultra-luxury short break, and you will have a private chauffeured Mercedes for all the touring, meet the owners and winemakers themselves at the wine estates, and enjoy VIP treatment everywhere you go.

Explore Tuscany, the beautiful Italian region birthplace of Renaissance, where the powerful Medici family ruled, and where many great artists such as Michelangelo, Donatello, and Botticelli found their inspiration. Siena houses a wealth of Renaissance architecture and paintings which you will discover with your private art guide. Taste top Brunello wines and Sangiovese based velvety Chianti. Try traditional Tuscan products like “Pecorino alla erbe aromatiche” (cheese with aromatic herbs), “Olio extravirgine di oliva Chianti Classico Dop” (extra virgin olive oil from a designated and protected appellation), “Funghi Porcini Toscani” (Porcini mushrooms) and “Pici” pasta (a delicious traditional pasta from the area south of Siena). And sleep in a breathtaking palace dating back to the 17th century. If you love Italian food and wine and would like to visit Siena and its wine country like a savvy & glamorous local, then contact us today for more information on this unforgettable wine tour.

Siena Wine Tours Highlights:

  • Siena Wine Tour Excursions to Tuscan Wine Country
  • Private guided walking tour of Siena
  • Michelin starred dining in Tuscany
  • Sightseeing in Val d'Orcia San Gimignano & Monteriggioni
  • Privately Chauffeured Mercedes

Below is a suggested Itinerary for your private Siena Wine Tours

  1. Arrival airport – Chianti Classico - Siena

    Arrive Siena & Badia a Coltibuono Wine Tasting

    Stunning Chianti countryside
    Stunning Chianti countryside
    • 5* Luxury Hotel
    • Traditional Lunch with wine pairings, private wine tasting
    • Private Chauffeured Mercedes

    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 Balsamic Vinegar, and Olive Oils. 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 for you. The rest of the evening is yours. You will find a welcome pack and wine in your luxurious room and a keepsake itinerary with plenty of suggestions for dining, shopping, and exploring. Welcome to Siena!

  2. Siena – Montalcino - Siena

    Vertical Brunello di Montalcino Wine Tastings

    The mythically Luce della Vite winery
    • 5* Luxury Hotel
    • Full Breakfast, Traditional Lunch with wines, private wine tasting
    • Private Chauffeured Mercedes

    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.

  3. Siena- Val'Orcia – Crete Senesi - Siena

    Cheese and wine experience in Pienza, and sightseeing in UNESCO site Val d'Orcia and Crete Senesi

    Pici pasta
    Pici pasta
    • 5* Luxury Hotel
    • Full Breakfast, Traditional Lunch with wines, private cheese tasting, private wine tasting
    • Private Chauffeured Mercedes

    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.

  4. Siena – departure airport

    Depart Siena

    Buon Viaggio!
    Buon Viaggio!
    • None
    • Full breakfast
    • Private Chauffeured Mercedes

    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!

More information

If you would like us to customize an exclusive, luxury tour for you, get in touch with us and let us know your travel plans. We offer luxury food and wine tours for private groups of minimum 2 guests. All of our private, chauffeured tours are available year round upon request.

Contact us for your personalized quote!
Cellar Tours Private Luxury Food & Wine Tours

Cellar Tours

Cellar Tours is a Luxury Travel Specialist, operating since 2003 and offering exclusive Mercedes chauffeured Gourmet Vacations in Chile, France, Italy, Ireland, Portugal, South Africa, and Spain. We specialize in luxurious custom designed vacations, events and incentives related to food and wine. We are proud members of Slow Food, UNAV (Travel Agency Association in Spain), and the IACP (International Association of Culinary Professionals).

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