Top 5 Wine Tasting Experiences in San Gimignano (2025 Edition)

San Gimignano isn’t just famous for its medieval towers — it’s also one of the most charming places in Tuscany to enjoy authentic wine tasting experiences. Whether you’re a curious traveler, a wine lover, or simply looking for a memorable activity, these five tastings offer something special for everyone.

From organic vineyards to truffle-paired lunches, here are the top 5 wine tasting experiences in San Gimignano you can’t miss:

1. Private Wine, Olive Oil & Balsamic Tasting with Tuscan Lunch

What to expect: Begin with a tour of the vineyard, followed by a private tasting of 4–5 organic wines, extra virgin olive oils, and aged balsamic vinegars. The experience ends with a traditional four-course Tuscan lunch, all with a panoramic view.

👉 Book this experience

2. Maxi Wine Tour at Agriturismo Poderi Arcangelo

What to expect: A 90-minute experience combining a vineyard and cellar tour with an extended tasting session. Learn about the estate’s wine production and sample multiple local varietals in a peaceful Tuscan setting.

👉 See the full experience

3. Wine Tasting with Truffle Lunch & Vineyard Tour

What to expect: For something truly unique, pair wine with fresh truffles. Start with a guided tour of the vineyard, followed by a truffle-based lunch and private tasting of wines, oils, and balsamic vinegars.

👉 Learn more

4. Vernaccia di San Gimignano Tasting

What to expect: Taste the region’s most historic white wine — Vernaccia — at its source. Often accompanied by local cheese and olive oil tastings, this is a must-do for wine history buffs.

👉 Explore more options

5. Romantic Wine & Food Tour in a Vintage Beetle

What to expect: Cruise through the Chianti countryside in a vintage Beetle, visit a boutique winery, and enjoy a vineyard lunch paired with wine, olive oil, and balsamic tastings. Ideal for couples.

👉 Book a wine tasting with food in San Gimignano

Want to see more?

👉 Browse all wine tasting experiences in San Gimignano

Book your favorite and get ready to sip, swirl, and fall in love with Tuscany!