Italy · Wine Tours
Italian Wine Tours by Region — Chianti, Tuscany & Beyond
Day-trip from Florence into the Chianti hills — cellar tastings, vineyard walks, San Gimignano's towers, and a long Tuscan lunch. Compare the best wine tours by region.
Why a Wine Tour
Sangiovese Between the Cypresses
Italian wine tourism centers on Tuscany, and almost every great tour leaves from Florence: a day-trip into the Chianti hills with two or three cellar tastings, a farmhouse lunch overlooking the vineyards, and often a stop in San Gimignano or Siena. The Chianti and broader Tuscany tours overlap heavily — Chianti is the region, Florence is the departure city — so we list both. Beyond Chianti, Montepulciano and Montalcino (Brunello) and Piedmont’s Barolo round out Italy’s wine map. Below, compare the regions, then pick your spoke for the top-rated tour and full booking details.
Compare by City
Italian Wine Tours — Compare the Regions
Both leave from Florence; here's how they differ.
By the Numbers
Italian Wine Tours by Region — Compare & Book — The Data Behind the Choice
We pulled every bookable tour in this category from GetYourGuide. Here's what 6 cities · 52 experiences · 50,967+ traveler reviews actually tell you.
Where the scene is deepest — by traveler reviews · tap a city
Across the category, prices run $34–$299 per person (median $103). What you pay for: hands-on time, ingredients and tastings, group size, and whether wine or a full meal is included — check each tour's inclusions.
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Choose Your City
Each city page has the top-rated tour, a full comparison, FAQ, and booking.
Wine Tour Florence — Chianti & Tuscany Day Trips
Best wine tours from Florence — Chianti & Tuscany day-trips with cellar tastings, vineyard lunch, Siena & San Gimignano, top-rated 4.8/5, from $157. Free cancellation.
Browse Florence →Tuscany Wine Tour — Chianti Vineyard Day Trips 2026
Best Tuscany wine tours — small-group Chianti vineyard day-trips from Florence with cellar tastings & lunch, top-rated 4.9/5, from $103. Free cancellation.
Browse Tuscany →Wine Tour Chianti — From Florence, Tastings & Lunch
Best Chianti wine tours from Florence — San Gimignano, Siena & Chianti cellar tastings with Tuscan lunch, top-rated 4.6/5 from 3,500+ reviews, from $92. Free cancellation.
Browse Chianti →Montepulciano Wine Tour — Vino Nobile Tastings 2026
Best Montepulciano wine tours — Vino Nobile cellar tastings & Val d'Orcia vineyard day-trips with lunch, top-rated 4.7/5, from $99. Free cancellation.
Browse Montepulciano →Wine Tour Barolo — Langhe Tastings 2026
Best Barolo wine tours — small-group Langhe cellar tastings of Barolo, Italy's 'king of wines', with lunch, 4.9/5, from $243. Free cancellation.
Browse Barolo →Wine Tour Montalcino — Brunello Tastings 2026
Best Brunello di Montalcino wine tours — Val d'Orcia winery tastings of Brunello & Rosso with Tuscan lunch, 4.7/5, from $107. Free cancellation.
Browse Montalcino →Pick the Right Fit
Best For…
Best for first-timers
Wine Tour Florence — a full-day loop through Siena, San Gimignano, and a winery lunch covers Tuscany's greatest hits in one trip.
Best for wine focus
Wine Tour Chianti — fewer sightseeing stops, more time in the cellar tasting Sangiovese where it's grown.
Best for couples
Either — a vineyard lunch overlooking the Tuscan hills is one of Italy's most romantic afternoons.
Italian Wine Tours by Region — Compare & Book — FAQ
Common questions about wine tours in Italy.
Most Tuscan wine tours depart from Florence by minivan or coach. Some smaller-group tours also leave from Siena.
Full-day tours run 8–10 hours including transport, 2–3 cellar tastings, and lunch. Half-day options (4–5 hours) focus on Chianti.
Chianti is a specific region within Tuscany. 'Tuscany' tours often add San Gimignano, Siena, or Montepulciano; 'Chianti' tours stay closer to the Chianti hills and cellars.
Most full-day tours include a farmhouse or winery lunch paired with the wines. Check each tour's inclusions.
Typically 6–12 wines across 2–3 wineries, often paired with olive oil, cheese, and cured meats.
Yes — guided tours include transport, so no one in your group has to drive. That's the main reason to book a tour rather than self-drive.
Spring and autumn are ideal — mild weather and, in September–October, the grape harvest. Summer is hot but scenic.
1–2 weeks in peak season; harvest-season (September–October) tours sell out earlier.
Browse Every Option
All tours below include free cancellation and instant confirmation.