Private Tuscany wine tasting in a historic cellar — Brunello di Montalcino and Chianti Classico estate visit
Chianti & Montalcino, Tuscany

The Tuscan Vintage Journey

Private cellars, legendary producers, and the families behind Italy's most celebrated wines.

The wines of Tuscany — Brunello di Montalcino, Chianti Classico, Vino Nobile di Montepulciano, the great Super Tuscans of Bolgheri — are among the most admired in the world. Yet the estates that produce them are largely private, their best cellars and oldest vintages accessible only through relationship and introduction. Italy Spotlight has spent years cultivating the connections that open these doors.

A Tuscan Vintage Journey is a bespoke expedition designed around your palate and your interests. It may take you to a centuries-old Benedictine abbey whose monks have tended the same Sangiovese vines since the 12th century. It may include a private tasting of library vintages — bottles that never appear on auction lists — guided by the estate's own oenologist. It will almost certainly include a long lunch on a terrace overlooking vines, with the producer's family present, in the unhurried Tuscan manner.

Italy Spotlight's wine director curates each itinerary individually, selecting producers whose philosophy and character match those of the guests. No two journeys are identical. We handle all bookings, private transfers between estates, accommodation at selected agriturismi and boutique hotels, and any dietary requirements. The only thing required of you is an open mind and a willing glass.

Every Tuscany wine tasting can include a dedicated chauffeur for hotel pick-up, travel between estates, and your return journey. This private driver wine tasting format lets every guest enjoy the tastings while we manage the route, timings, and reservations.

Palio di Siena 2027 Packages

Palio di Siena Ticket and Hospitality Packages

Half-Day Estate Visit

  • Private visit to one selected estate (Chianti or Montalcino)
  • Cellar tour and guided tasting of 4–6 wines with the estate oenologist
  • Light lunch or antipasto pairing
  • Private transfer from Florence or Siena

From €380 per person

Full-Day Grand Tour

  • Private visits to two estates across Chianti Classico and Montalcino
  • Guided tastings at each, including reserve and aged library wines
  • Three-course lunch at one of the estates
  • Italy Spotlight wine director accompaniment
  • Private transfers throughout

From €780 per person

Two-Day Connoisseur Journey

  • Full-Day Grand Tour inclusions across two days
  • Three estates selected to represent different appellations
  • Overnight at a 5-star agriturismo or boutique hotel in the Crete Senesi
  • Private dinner with one of the producers
  • Curated case of wines shipped to your home address

From €1,900 per person

Historic wine cellar on a Tuscan estate — Brunello di Montalcino barrels
Vineyard landscape in Chianti Classico at harvest time, Tuscany
Private sommelier-guided tasting on a terrace overlooking Tuscan vines
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