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Join Wine History Tours for this once in a lifetime Italian wine travel trip through Southern Tuscany and Florence.

This professionally curated wine tasting vacation features beautiful countrysides, iconic wineries, historic chapels and pilgrim roads, and expert local tour guides. Get ready to learn about the cuisine, culture and countryside of one of the most renowned places on earth!

As a bonus, you will learn about the Renaissance & Reformation as we journey through Tuscany and into Florence. Your host will also help connect the fascinating story of this famous region to larger important historic themes in art and religion.

Space is limited for our Italian wine travel trip so register soon*

(Pictured at right: Fattoria di Fugnano winemaker, Laura Dell’Aira, and tour host, Ken Wytsma).

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Building in Italy at night


italy tour scenery


building in Italy


Italian Wine Vacation
September 22-29, 2024

Cost: $ 3,979 per person

(Single add on $899)

Deposit: $1000 

For more information, contact

Included in Price

  • accommodation with breakfast for 7 nights (taxes included)
  • transportation by private luxury minibus
  • all the activities as described
  • tour guides and tours (no expectation of gratuity)
  • lunches
  • all the reservations for dinner (order
    a la carte and pay directly on spot)

Not included

  • airfare
  • anything that is not included in the
    “Included” section

Italy Wine Tour Itinerary


DAY 1 - SUNDAY, September 22

  • Arrival and transfer to San Gimignano, check in the hotel
  • H 20.00 - reservation for dinner at Cum Quibus
San Gimignano tour picture

DAY 2 - MONDAY 23rd

  • H 10.00 - meet the guide by the hotel
  • H 10.00 - 13.00 - Guided tour of San Gimignano with the guide
  • H 13.30 - Food & Wine pairing lunch @ Fugnano
  • H 15.30 - wine tasting @ Santa Chiara
  • H 20.00 - reservation for dinner at San Martino
Italy wine tour


  • H 9.30 - Check-out
  • H 11.00 - private visit & tasting @ Ciacci Piccolomini winery in Montalcino with the guide
  • H 13.00 - stop at S. Antimo abbey for a free visit of this beautiful place
  • H 13.30 - pairing lunch @ Tenuta Fanti winery in Montalcino
  • H 15.30 - private visit & tasting @ La Fornace winery
  • H 18.00 - check in the locanda Franci in Montalcino
  • H 20.00 - reservation for dinner at Drogheria Franci
elderly enjoying Italy


  • H 10.00 - 13.00 - private cooking class @ Locanda Demetra
  • H 15.00 - stop in San Quirico for a mini guided tour with the guide
  • H 16.00 - stop in Bagno Vignoni for a mini guided tour with the guide
  • H 20.00 - reservation for dinner at Il Giglio or Il Giardino
Italy architecture


  • check out
  • H 9.00 -13.00 Guided tour of Pienza and Montepulciano with the guide
  • H 13.30 - private visit & tasting @ Nobile winery with lunch on site
  • H 16.00 - transfer to Florence, check in the hotel in Piazza Santa Maria Novella
  • H 20.00 - reservation for dinner at TBD restaurant
Florence Duomo tour image


  • H 10.00 -16.00 - Guided tour of Florence with the guide including the Uffizi and stop for lunch
  • H 20.00 - reservation for dinner at TBD restaurant
beautiful architecture of the Florence Cathedral


  • H 10.00 -16.00 - Guided tour of Florence with the guide including the Accademia and stop for lunch
  • H 20.00 - reservation for dinner at TBD restaurant
vineyard near Montalcino, Tuscany

DAY 8 - SUNDAY, September 29th

  • check out and transfer to the airport

A History of Winemaking in Central Italy

When it comes to winemaking, few regions in Italy can compare to the richness and diversity of Tuscany. Located in Central Italy, this region has been producing wines for thousands of years, and is home to some of the world’s most famous wine styles, like Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano. Whether you’re a seasoned wine enthusiast or a curious wine traveler who enjoys exploring new tastes and traditions, a journey to Tuscany is a must-do experience. 

Italy tour countryside view
wine tour of Montalcino

Early Italian Wine

Tuscany’s wine story began with the Ancient Etruscan Civilization, which flourished between the 8th and 3rd centuries BC, in what is now Central Italy. The Etruscans were skilled winemakers, and they cultivated vineyards all over their territory, using innovative techniques like trellising, pruning, and grafting. They also developed a deep cultural and religious connection to wine, seeing it as a gift from the gods and an essential part of their social life. The Middle Ages and Renaissance were also important periods for Tuscan wine, as the region became a center of trade and commerce, and a hub of artistic and intellectual ferment. Many aristocratic families of the time, such as the Medici, became passionate wine lovers and patrons, commissioning new vineyards and cellars, and experimenting with blends and techniques. In fact, the Renaissance that the Medici family helped birth through their native Florence is one of the main themes we’ll get to explore as we venture through the cities of Tuscany during the Wine History Tours Italian Wine Travel Trip. 

Modern Italian Winemaking

The 20th century marked a period of challenges and opportunities for Tuscan wine, as it faced the aftermaths of the two World Wars, the rise of industrialization, and the emergence of new wine regions in Italy and abroad. However, thanks to the resilience, passion, and innovation of many Tuscan winemakers and grape growers, the region was able to thrive and evolve, meeting the changing tastes and demands of consumers, and reinforcing its reputation as a top-quality wine destination. It was during this time that a new kind of Tuscan wine became famous, the Super Tuscan. These wines defied long standing regional traditions in favor of new grape varieties and winemaking styles. Today, some of the most exciting trends in Tuscan wine include the rediscovery of indigenous grape varieties, the experimentation with biodynamic and organic farming methods, and the influence of global trends like natural wine and low-alcohol wines. The fine wine movement has also helped bring renewed passion for winemakers in Tuscany to produce the best Chianti, Brunello di Montalcino, and Nobile di Montepulciano wines of recent decades. These fine expressions also cater to the growing global movement for wine tasting tourism and wine travel trips. 

Nobile de Montepulciano

Italian Wine Travel Trips 

A trip to discover the wines and history of Tuscany is much more than a wine tour, it’s a journey through history, culture, and nature. While visiting these family owned boutique Italian wineries and cellars, you will discover the stories, traditions, and personalities behind each bottle, immersing yourself in the mesmerizing landscapes and flavors of this unique region. From the rolling hills and cypress trees of Chianti to the majestic castles and steep slopes of Montalcino, from the medieval towns and villages to the bustling cities like Florence and Siena, Tuscany offers an endless source of inspiration, discovery, and enjoyment. So grab a glass of Sangiovese or Vernaccia, and let yourself be carried away by the magic of Tuscan wine. And make sure to join us on our next unforgettable Italian wine travel trip. Salute!

We are pleased to plan, advise, and lead custom wine travel trips for you!