Tuscany Food and Wine Tour

Sample the culinary treasures of Tuscany with winery visits, tastings, a cooking class, meals, and full-service villa accommodations.

  • Visit cities of art, charming medieval villages and local food producers in the rolling countryside of Chianti and the Val D’Orcia.
  • Taste artisanal, small production wines including Chianti Classico, Vino Nobile di Montepulciano and Brunello di Montalcino.
  • Take a hands-on cooking class in a private home just steps from the ancient Roman baths of Bagno Vignoni.
  • Enjoy a cheesemaking demo and tour an organic olive oil estate while taking in breathtaking views of the rolling countryside.
  • Meet artisans at an alabaster workshop and terracotta factory practicing their centuries-old craft.
  • Stay in charming, historic, villas on wine-producing estates with full-service amenities.

  • Food allergies and special dietary requests can be accommodated with advance notice.
  • R/T Group airport transfers and transportation in mini bus is provided for all activities.

What to expect?

Cities of art, overflowing with culture, breathtaking vistas across the unspoiled countryside, medieval villages oozing with charm—Tuscany epitomizes the romantic notion of Italy. And best of all there are world-famous wines and a delightful meal around every corner of ancient stone. Step off the beaten tourist past and meet the locals on this eight-night food and wine tour from Chianti to Maremma.

Day to Day Itinerary

Day 1: Chianti & Siena

Our tour begins with a transfer to our villa in Chianti located in the heart of the Chianti wine region about a half hour from the historic center of Siena. Meet your fellow travelers over a light lunch at this meticulously restored wine property nestled amidst acres of rolling hills before a late afternoon of sightseeing in Siena, a UNESCO world heritage city filled with images of pre-Renaissance Italy. A guided walking tour of the city
includes the Piazza del Campo, site of the famed Palio race, and a visit to the Duomo with free time before dinner back at the villa.

Day 2: Monteriggioni & Radda in Chianti

After breakfast we’ll stop in the ancient walled village of Monteriggioni. We’ll lunch today at a family run winery in the Chianti Classico region before an afternoon stop in Radda in Chianti with free time to shop or sip a spritz in the piazza. Later in the day, we’ll return to our villa to relax before a traditional Tuscan dinner including wine.

Day 3: San Gimignano & Volterra

Today we visit San Gimignano, a Tuscan gem whose 12th-century towers are visible from afar. We’ll have free time to shop the many boutiques or sip a cappuccino as you watch the lineup of elderly locals gossiping under a shady loggia. We’ll have lunch and a wine tasting at a restored aristocratic residence along the Via Francigena before heading to Volterra for a visit with an alabaster craftsman. The working of alabaster is an ancient tradition here, with numerous shops and museums dedicated to the art form. After our visit, we’ll have free time in Volterra before “apericena” in the piazza.

Day 4: Pienza & Val D’Orcia

After breakfast, we’ll spend our morning at an organic farm near Pienza. We’ll meet the colorful owner for a tour and a cheesemaking demo followed by lunch on this gorgeous property immersed in nature. Next, we’ll head to Pienza, the beautiful UNESCO world heritage town widely known as the “ideal city of the Renaissance.” There will be free time to stroll and shop or sip a glass of wine while enjoying the gorgeous views of Monte Amiata in the distance. Afterward, we’ll check into our charming, historic villa just outside the city with time to relax before dinner.

Day 5: Montepulciano

After breakfast, we’ll visit Montepulciano. The home of Vino Nobile and a former Etruscan settlement, this medieval town of rare beauty boasts panoramic views over the wonderful Val d’Orcia and Val di Chiana valleys. We’ll have free time to meander before a wine tasting tour with lunch at one of the town’s historic cellars. Later on, we’ll have a wine pairing dinner at our

Day 6: Montichiello, San Quirico & Bagno Vignoni

Today we’ll stop in Monticchiello, a tiny, walled medieval village that was the subject of the film, “Spettacolo,” which tells the story of the Teatro Povero, a yearly play where the town becomes a stage and all its citizens, the actors. Later we’ll have lunch at a nearby organic olive oil estate with a fascinating history. Next, we head to Bagno Vignoni for a walk around town and a look at the ancient Roman baths before our aperitivo, “Pici” making and cooking class with Daniela followed by dinner made with the fruits of our labor.

Day 7: Montalcino

Today we visit a Brunello wine estate that has become the subject of a very unusual scientific experiment whereby music therapy, not chemicals are used to treat the vines. You’ll visit the vineyards and taste top-rated wines, surrounded by the music of Mozart. After our visit, we’ll have free time in Montalcino with lunch on your own. Our last stop will be a short visit to Sant’Antimo Abbey. Nestled amidst the vines and olive groves, the abbey is still used daily by monks chanting their prayers. In the late afternoon, we’ll check in to our resort in Sovana with free time to relax before dinner

Day 8: Sovana & Pitigliano

This morning we visit the 2500-year old Etruscan archeological site in Sovana and the Vie Cave, a network of ancient, canyon-like roads carved by hand into the tufa rock. We then head to Pitigliano, a town that is also known as Piccola Gerusalemme (Little Jerusalem) due to the long-standing presence of a thriving Jewish community here. We’ll have time to stroll the Jewish Quarter and visit its artisan shops or take an optional tour of the town’s synagogue, followed by lunch. Later in the day, our tour ends with a farewell dinner at our 4-star hotel near Rome Airport.


Although every effort is made to adhere to the stated tour, itineraries are subject to change at any time due to unforeseen circumstances beyond the control of Via del Vino, LLC and its travel providers. A 25% deposit is due at the time of booking. The deposit is non-refundable. For full terms & Conditions, visit: https://viadelvino.com/return-policy/ and reference the section on group culinary tours. A day-by-day tour schedule with contacts, transfer information, and additional details is provided before your departure.

Duration: 8 Nights
Location: Siena, San Gimignano, Volterra, Montepulciano, Pienza, Montalcino, Bagno Vignoni, Sovana, Pitigliano



Pricing is per person in a shared room and is based on a minimum of 12 participants. Single supplement is €450 (Limited QTY available). Airfare is not included.

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