Chianti Wine Tour: 3 Wineries with Cellar Tours, Tastings and Tuscan Snacks

Explore three Chianti wineries in one guided tour with cellar visits, premium tastings, and Tuscan food pairings.

Getting started

Begin your Tuscany Wine Experience by checking in for your selected variant: departure from Tuscany on Wheels, from Florence, or from San Gimignano. Meet your dedicated local expert tour leader and join your group. After a brief overview of the route through the Chianti countryside, board your private air-conditioned minivan and set off toward the first of three handpicked wineries.

What to expect

Chianti winery one: traditional cellar and first tastings

Your first stop introduces you to a family-run style of Chianti winemaking, starting in the working cellar.

Features

• A guided cellar tour at this first of the three handpicked wineries shows you how Chianti is produced and aged, with your local expert tour leader explaining regional methods and traditions.
• Multiple premium wine tastings are served here, giving you an initial comparison of Chianti labels and styles in a calm, dedicated tasting space.
• Tuscan food and snacks are paired with your glasses at this stop, so you can see how regional flavors interact with the wines right from the start.

Chianti winery two: boutique estate and paired samplings

The second winery highlights a different side of Chianti, shifting from traditional cellars to a more boutique estate setting.

Features

• Another guided cellar tour takes you through this estate’s production areas, so you can contrast scale, layout, and barrel rooms with the first winery.
• Premium tastings continue here, curated to show how terroir and winemaking choices shape aroma and structure across several pours.
• Olive oil and balsamic tastings with tasting pairings are introduced at this stop, letting you sample estate products side by side with selected Chianti wines.

Chianti winery three: vineyard time and regional pairings

Your third winery balances tasting with unhurried time among the vineyards that define the Chianti landscape.

Features

• At this final handpicked winery, you round off your premium tastings while your tour leader ties together what you have learned about grape varieties, cellars, and regional styles.
• Additional Tuscan food, olive oil, and balsamic tastings with tasting pairings are served here, completing the food-focused part of the experience.
• Free time to relax in vineyards is built into this stop, so you can wander short paths, capture photos of the rolling Tuscan countryside, or simply sit and take in the Chianti views before rejoining the group.
• The private air-conditioned minivan brings you back to your original departure city at the end of the circuit, with the ride used to recap key details and ask any final questions to your dedicated local expert tour leader. Return in the afternoon filled with new wine knowledge—and perhaps a bit of wine snobbery.