Wine Tastings in Siena at a glance
- Our pick: Montalcino Brunello Wine Tasting & Lunch in a Castle, € 62 per person (1h 30m, 4.69★ · 137).
- Top rated: Siena: Underground Wine Tasting in Private Medieval Cave, € 75 per person (1h, 4.98★ · 62).
- Best value: Wine tasting in Siena's historic center: Bubbles and reds, € 40 per person (1h 30m, 5.00★ · only 5 reviews).
Price per person across the 14 options priced per person: € 40–€ 190 (median € 70). With 100+ reviews: 4 of 15.
Of the 15 options: 15 with live guides in English, 15 with free cancellation, 14 with instant confirmation, 1 with hotel pickup, 9 kid-friendly, 5 private and 13 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 50 reviews.
Wine Tastings in Siena
Based on each operator's calendar. Confirmed when you book.
15 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
Florence / Tuscan Wine School: Tasting Class with Local Pairings Next departure: 29 Oct 2027 · From age 18 ★ 4.94 (267 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from € 60 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
Siena: Underground Wine Tasting in Private Medieval Cave Step into Siena’s medieval underworld for a private wine tasting with a sommelier, exclusive access to an Etruscan cave, and top Tuscan wines. Limited spots daily. Every day except Wednesday and Sunday · 11:30 and 15:00 · From age 3 ★ 4.98 (62 reviews) Duration: 1h Live guide: EN ✓ Free cancellation. from € 75 per person
Siena walking tour with lunch & Chianti wine tasting Walk through Siena's medieval squares and hidden alleys with a licensed guide, tasting gelato, local wine and a full lunch at a traditional osteria: all in 2.5 hours. Next departure: 16 Mar 2027 · From age 3 ★ 4.81 (101 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from € 85 per person
Chianti Wine Tasting Lunch: Eight Wines with Tuscan Cuisine Taste eight Chianti wines paired with a three-course Tuscan lunch at Poggio ai Laghi winery, led by a sommelier in English, Spanish or Italian. Every day · Every 30 min, 10:30 to 17:00 · All ages ★ 4.25 (16 reviews) Duration: 1h 45m Live guide: EN · IT · ES ✓ Free cancellation. from € 70 per person
Wine tasting in Siena's historic center: Bubbles and reds Taste 4 glasses of Tuscan wine in Siena's historic center with a guide who teaches you to read aromas and structure, moving between two wine bars in 90 minutes. Mon–Sat · 11:00, 12:30, 14:30, 16:00 and 17:30 · From age 18 ★ 5.00 (5 reviews) Duration: 1h 30m Live guide: EN · IT · FR ✓ Free cancellation. from € 40 per person
Dinner with wine tasting at Poggio ai Laghi winery in Chianti Taste five wines, three oils and two vinegars at Poggio ai Laghi winery in Chianti, then sit down to a four-course Tuscan dinner with a live guide. Every day · Every 30 min, 18:00 to 21:00 · All ages ★ 5.00 (7 reviews) Duration: 2h Live guide: EN · IT · ES ✓ Free cancellation. from € 56 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
Chianti Vineyard Jeep Tour: Wine Tasting & Tuscan Lunch Off-road Jeep tour through Chianti vineyards with wine expert guide, wine and oil tastings, and a Tuscan lunch featuring grilled beef paired with local flavors. Every day · Every 30 min, 10:00 to 17:00 · All ages ★ 4.20 (5 reviews) Duration: 2h Live guide: EN · IT ✓ Free cancellation. from € 70 per person
Poggio ai Laghi vineyard golf cart tour: Wine tasting and lunch Golf cart tour through Poggio ai Laghi vineyards with tastings of six wines, oils and vinegars, plus a three-course Tuscan lunch. Every day · Every 30 min, 10:00 to 17:00 · All ages ★ 5.00 (2 reviews) Duration: 2h 30m Live guide: EN · IT · ES ✓ Free cancellation. from € 70 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
Cooking class: Tuscan lasagna with wine tasting in Chianti Learn to make Tuscan lasagna from an Italian chef, then taste four wines paired with your meal in a working vineyard kitchen near Chianti. Every day · 10:30 · All ages ★ 5.00 (1 review) Duration: 3h Live guide: EN · IT ✓ Free cancellation. from € 77 per person
Truffle hunting near Siena with wine tasting and Tuscan lunch Hunt truffles with a trained dog in Tuscan woodland, then taste wines and oils from Poggio ai Laghi before a truffle lunch with a live guide. Every day · 10:30 and 16:00 · All ages ★ 5.00 (1 review) Duration: 2h 45m Live guide: EN · IT ✓ Free cancellation. from € 105 per person
Saturnia Hot Springs & Sovana tour: Private Maremma wine tasting Private tour of Saturnia Hot Springs and the Etruscan city of Sovana with winery visit, wine tasting, archaeological park entry and licensed guide. Pickup included, 8 hours. Every day · 08:30 · Pickup available Duration: 8h Live guide: EN · DE · IT · ES ✓ Free cancellation. from € 650 per group
The top 12 of 15 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 |
| Siena: Underground Wine Tasting in Private Medieval CaveTop ratedGroup of up to 13 | € 75 per person | 1h | 4.98★ · 62 | Every day except Wednesday and Sunday · 11:30 and 15:00 | English |
| Wine tasting in Siena's historic center: Bubbles and redsBest valueGroup of up to 8 | € 40 per person | 1h 30m | 5.00★ only 5 reviews | Mon–Sat · 11:00, 12:30, 14:30, 16:00 and 17:30 | English, French, 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 / Tuscan Wine School: Tasting Class with Local PairingsGroup of up to 14 | € 60 per person | 2h | 4.94★ · 267 | Next departure: 29 Oct 2027 | English |
| Siena walking tour with lunch & Chianti wine tastingGroup of up to 12 | € 85 per person | 2h 30m | 4.81★ · 101 | Next departure: 16 Mar 2027 | English |
| Chianti Wine Tasting Lunch: Eight Wines with Tuscan CuisineGroup of up to 15 | € 70 per person | 1h 45m | 4.25★ · 16 | Every day · Every 30 min, 10:30 to 17:00 | English, Spanish, Italian |
| Dinner with wine tasting at Poggio ai Laghi winery in ChiantiGroup of up to 15 | € 56 per person | 2h | 5.00★ only 7 reviews | Every day · Every 30 min, 18:00 to 21:00 | English, Spanish, Italian |
| Montalcino Brunello Wine Tasting & Tuscan Dinner in VineyardsPrivate | € 165 per person | 3h | 4.80★ only 5 reviews | Tue, Thu and Sat · 18:30 | English, Italian |
| Chianti Vineyard Jeep Tour: Wine Tasting & Tuscan LunchPrivate | € 70 per person | 2h | 4.20★ only 5 reviews | Every day · Every 30 min, 10:00 to 17:00 | English, Italian |
| Poggio ai Laghi vineyard golf cart tour: Wine tasting and lunchGroup of up to 15 | € 70 per person | 2h 30m | 5.00★ only 2 reviews | Every day · Every 30 min, 10:00 to 17:00 | English, Spanish, 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 |
By what you need
- Private (5): Montalcino Brunello Wine Tasting & Lunch in a Castle (€ 62 per person) · Montalcino Brunello Wine Tasting & Tuscan Dinner in Vineyards (€ 165 per person) · Chianti Vineyard Jeep Tour: Wine Tasting & Tuscan Lunch (€ 70 per person)
- With pickup (1): Saturnia Hot Springs & Sovana tour: Private Maremma wine tasting (€ 650 per group)