Montalcino Wine Tastings at a glance
- Our pick: Montalcino Brunello Wine Tasting & Lunch in a Castle, € 62 per person (1h 30m, 4.69★ · 137).
- Top rated: Montalcino & Montepulciano: Brunello Wine Tour from Florence, € 776 per group (9h, 4.94★ · 102).
- Also recommended: Montalcino Brunello Wine Tasting & Tuscan Dinner in Vineyards, € 165 per person (3h, 4.80★ · only 5 reviews).
Price per person across the 6 options priced per person: € 62–€ 380 (median € 165). With 100+ reviews: 3 of 7.
Of the 7 options: 7 with live guides in English, 7 with free cancellation, 5 with instant confirmation, 1 with hotel pickup, 2 kid-friendly, 4 private and 5 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Prices are per person, except options priced per group: that price is for the whole group, and the per-person figure assumes the group is full. “Top rated” = the highest score among options with at least 100 reviews.
Montalcino Wine Tastings
Based on each operator's calendar. Confirmed when you book.
7 options
Siena: Brunello di Montalcino Wine Tour & Tuscan Lunch Full-day Brunello wine tour from Siena with three tastings, family winery lunch, and Sant'Antimo Abbey. Small groups of eight, air-conditioned transport, local guide included. Tue, Fri and Sun · 09:30 · From age 8 ★ 4.92 (1,056 reviews) Duration: 9h Live guide: EN ✓ Free cancellation. from € 190 per person
Montalcino Brunello Wine Tasting & Lunch in a Castle Taste three Tuscan wines with a sommelier in a medieval castle in Montalcino, then sit down to a three-course lunch of handmade pasta, local cheeses and cold cuts. Mon–Fri · 11:45 and 13:00 · From age 4 ★ 4.69 (137 reviews) Duration: 1h 30m Live guide: EN · IT ✓ Free cancellation. from € 62 per person
Montalcino & Montepulciano: Brunello Wine Tour from Florence Full-day Brunello and Nobile wine tour from Florence through Val d'Orcia. Includes winery visits, tastings, Pienza cheese tasting, and hotel pickup with private guide. Every day · 09:00 · Hotel pickup ★ 4.94 (102 reviews) Duration: 9h Live guide: EN · IT · ES ✓ Free cancellation. from € 776 per group
Florence: Chianti Wine Tasting & Montalcino Day Trip Full-day Chianti wine tour from Florence with tastings at a farmhouse, visits to Montalcino and Montepulciano, lunch included, small groups, minivan with WiFi. Tue, Thu and Sun · 08:30 · All ages ★ 4.77 (44 reviews) Duration: 10h Live guide: EN · IT ✓ Free cancellation. from € 290 per person
Montalcino Brunello Wine Tasting & Tuscan Dinner in Vineyards Taste 7 Tuscan wines including Brunello Riserva at Paradiso di Cacuci vineyard estate, paired with handmade pasta and beef tagliata at a private dinner. Tue, Thu and Sat · 18:30 · From age 18 ★ 4.80 (5 reviews) Duration: 3h Live guide: EN · IT ✓ Free cancellation. from € 165 per person
Brunello di Montalcino Wine Tour: Vineyard Tasting & Lunch in Siena Visit a Brunello vineyard near Siena for organic wine tasting and a three-course Tuscan lunch with vineyard views, including hotel pickup and dropoff. Next departure: 22 Mar 2027 · From age 6 ★ 5.00 (1 review) Duration: 4h Live guide: EN · IT ✓ Free cancellation. from € 149 per person
Montalcino & Chianti: Private Wine Tasting Small Group Tour Private Montalcino wine tour with two tastings at boutique wineries, Brunello di Montalcino education, and medieval fortress walk. Small groups only. Mon–Sat · No fixed time · Ages 18–90 Duration: 6h Live guide: EN · IT ✓ Free cancellation. from € 380 per person
All 7 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Montalcino Brunello Wine Tasting & Lunch in a CastleOur pickPrivate | € 62 per person | 1h 30m | 4.69★ · 137 | Mon–Fri · 11:45 and 13:00 | English, Italian |
| Montalcino & Montepulciano: Brunello Wine Tour from FlorenceTop ratedPrivate · Pickup offered | € 776 per group up to 8 people · ≈ € 97 per person if 8 go | 9h | 4.94★ · 102 | Every day · 09:00 | English, Spanish, Italian |
| Montalcino Brunello Wine Tasting & Tuscan Dinner in VineyardsAlso recommendedPrivate | € 165 per person | 3h | 4.80★ only 5 reviews | Tue, Thu and Sat · 18:30 | English, Italian |
| Siena: Brunello di Montalcino Wine Tour & Tuscan LunchGroup of up to 8 | € 190 per person | 9h | 4.92★ · 1,056 | Tue, Fri and Sun · 09:30 | English |
| Florence: Chianti Wine Tasting & Montalcino Day TripGroup of up to 8 | € 290 per person | 10h | 4.77★ · 44 | Tue, Thu and Sun · 08:30 | English, Italian |
| Brunello di Montalcino Wine Tour: Vineyard Tasting & Lunch in SienaGroup of up to 4 | € 149 per person | 4h | 5.00★ only 1 review | Next departure: 22 Mar 2027 | English, Italian |
| Montalcino & Chianti: Private Wine Tasting Small Group TourPrivate | € 380 per person | 6h | — | Mon–Sat · No fixed time | English, Italian |
By what you need
- Small groups (up to 15) (3): Siena: Brunello di Montalcino Wine Tour & Tuscan Lunch (€ 190 per person) · Florence: Chianti Wine Tasting & Montalcino Day Trip (€ 290 per person) · Brunello di Montalcino Wine Tour: Vineyard Tasting & Lunch in Siena (€ 149 per person)
- With pickup (1): Montalcino & Montepulciano: Brunello Wine Tour from Florence (€ 776 per group)