5 Wine Tastings for Two in Italy for the Trip of a Lifetime

1.San Gimignano: Romantic Vineyard Dinner

★★★★★★★★★★4.3 · 47 reviews · from $141Our pick

You’ll dine among the vines at Tenuta Torciano near San Gimignano, tasting Tuscan foods, wines, and extra virgin olive oil with a wine expert. Hosts such as Alberto, Gabriel, Elena, and Donato help make the evening personal, while garden time gives you room for photos.

“An absolutely amazing experience. This was our first wine tasting and our sommelier Alberto gave a good introduction and information regarding the estate, background, tasting and the wine making process and the Family's traditions. Food and wine was top notch. The estate itself is very beautiful and we were given a tour of the yard. Alberto was also very outgoing and humorous which made it a nice evening.”

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2.ROMANTIC WINE TOUR FOR 2 – Wine Tour in Chianti (Tuscany)

★★★★★★★★★★5.0 · 27 reviews · 99 days Top rated

Spend a private day with an English or Italian-speaking driver-guide in Chianti. Visit two wineries, taste more than 10 Tuscan wines, enjoy a traditional lunch, stroll through San Gimignano, and stop at Michelangelo Square. Guides named Andrew, Andrea, Florian, and Andrei have received especially warm praise.

“Both vineyards were amazing and different in their respective ways. Our meal was terrific and the explanation around the 7 different wines was informative. The second stop included a tour of the process and a glimpse back in time 700 years, to the original cellar on the property. Very special time spent at each property.”

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3.Wine tasting in a romantic castle with archaeologist guide

★★★★★★★★★★4.7 · 25 reviews · 2 hours · from $73Best value

Meet in Bibbona and follow a scenic road to a private medieval castle. Archaeologist Fabio leads a 30-minute visit to the church, courtyard, and old barrel cellar, followed by five wines, olive oil, and an optional cheese and cold-cut platter.

“Fabio is a great guide and the whole trip was very interesting and unique. We were very satisfied.”

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4.Romantic Dinner and Wine Tasting in San Gimignano Winery

★★★★★★★★★★4.5 · 21 reviews · 2 hours 30 minutes (approx.) · from $90

Meet at Tenuta Torciano near San Gimignano for a 2.5-hour Italian-style dinner with Tuscan meats, cheeses, truffle lasagna, roast meat, dessert, wine, and olive oil tastings. You will sample DOCG wines, Super Tuscans, vintage reserves, and local specialties without hotel transport.

“An awesome experience, staff, food and wine were all exceptional. Would definetly reccomend and return”

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5.Romantic Escape in Tuscany with Overnight and Wine Tasting

★★★★★★★★★★5.0 · 6 reviews · from $133

You’ll stay one night in a classic room at Torciano Hotel, enjoy breakfast, then taste Tenuta Torciano wines, olive oils, and Tuscan appetizers with an English or Italian sommelier. The small group is limited to 10, with free parking and no estate tour included.

“wonderful experience, the room is finely furnished and is located in a very quiet and relaxing context. the tasting is truly unmissable, breakfast could be improved.”

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