About this tour
Spend eight hours exploring Chianti's countryside in a private car, visiting the hilltop towers of San Gimignano and the fortified village of Monteriggioni. Lunch happens at a family winery where you'll eat homemade pasta and regional charcuterie, paired with tastings of Chianti and Super Tuscan wines. Your driver navigates vine-covered slopes and cypress-lined roads, stopping at a second winery on the return journey to sample Chianti Classico Gallo Nero before heading back by early evening.
Highlights
- San Gimignano's medieval towers rising above the Tuscan hills
- Lunch at a working family farm with six wine tastings included
- Homemade pasta, cured meats, and Pecorino cheese from Pienza
- Monteriggioni's ancient castle walls and village centre
- Two separate winery visits featuring Chianti and Super Tuscan varieties
- Private transport through olive groves and vineyard landscapes
What to expect
Your driver collects you from your accommodation and drives south into rolling vineyards. The landscape shifts from cultivated slopes to medieval settlements perched on hilltops. At San Gimignano, you'll walk the cobbled streets past artisan workshops and tower houses. By midday you reach a family-run winery where lunch unfolds over several courses—fresh pasta, cured meats, cheese—each paired with wines from their cellars. The afternoon includes Monteriggioni's compact fortified village, then a final winery stop for tasting Gallo Nero before the return drive. Expect gentle walking in villages and time sitting at tables rather than hiking.
Good to know
Air-conditioned vehicle throughout the day. Bottled water provided. If you need a knowledgeable guide (rather than just a driver), arrange this a week ahead for an additional fee. Prams and infant seats available. Return by 5 pm.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.