Guides4 Days Tuscan Wine Tours through the Best DOCG Regions
A day-by-day itinerary through Chianti Classico, Vernaccia di San Gimignano, Brunello di Montalcino, and Vino Nobile di Montepulciano — Tuscany's four most prestigious DOCG regions in one trip.
Discover the best Tuscan wine with this exclusive 4-day wine tour for true wine lovers. Together with our team of expert local guides, you'll visit the four most prestigious DOCG wine regions of Tuscany: Chianti Classico, Vernaccia di San Gimignano, Brunello di Montalcino, and Vino Nobile di Montepulciano — a journey through breathtaking landscapes, boutique wineries, charming hilltop towns, and authentic Tuscan flavors, with private tastings, meetings with winemakers, traditional lunches, and overnight stays in charming 4-star countryside hotels.
Day 1 — Chianti Classico. Begin at Tenuta Poggio Casciano for a guided cellar tour and tasting, then continue to San Polo in Chianti for lunch and a private tasting at a small, family-run winery. In the afternoon, visit a second winery and enjoy local specialties like extra virgin olive oil, balsamic vinegar, and cured meats, before checking into your countryside hotel.
Day 2 — Vernaccia di San Gimignano. Follow the scenic Strada della Vernaccia, starting with a morning stop at a historic Chianti-hills winery for wine and olive oil tastings, then on to San Gimignano, where a young winemaking couple welcomes you for a homemade lunch paired with their white wines. Explore the medieval town at your leisure before continuing to Siena for the night.
Day 3 — Brunello di Montalcino. A full day on the Brunello wine road, visiting two carefully selected wineries tucked into the peaceful countryside of Montalcino, with private tours, tastings, and a traditional Tuscan lunch served at a winery in the heart of the Val d'Orcia.
Day 4 — Nobile di Montepulciano. The journey ends in Montepulciano, home of Vino Nobile, with exclusive tours and tastings at two estates, a walk through the vineyards, and lunch featuring local products and wines — followed by a stroll through the historic center, made famous by films like Under the Tuscan Sun and Twilight.
Frequently asked questions
How many wines are served at each winery?
The number of wines varies according to the winery and the selected program.
Each tasting normally includes a selection of wines representing the winery's production. Tastings may also be accompanied by extra virgin olive oil, cheese, cured meats or other local products.
The exact number and selection of wines may change according to the season, availability and the winery's current tasting program.
What's the difference between Chianti Classico and a Super Tuscan?
Chianti Classico must follow strict DOCG rules based mainly on Sangiovese, while Super Tuscans are made outside those rules — often blending in Cabernet Sauvignon or Merlot — giving winemakers more freedom to experiment with style.
How long is the drive from Florence?
Our tours depart from Florence at the meeting point on Lungarno Cellini. From there, the minivan journey to the truffle hunting area in the Tuscan countryside takes approximately one hour each way.
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