Italy experiences
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3 Wine & Tapas Tours in Italy
Supercar, Wine Tasting & Castello di Brolio Experience
5.0
(125)
A private afternoon and evening supercar experience through the Chianti countryside, combining scenic driving, wine tasting and Tuscan hospitality. The experience starts from Villa Ermellina in Siena
7 Hours
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Supercar & Wine Tasting Experience at Casanova di Neri
4.9
(132)
A private one-day experience combining the emotion of driving a supercar through the Tuscan countryside with a guided wine tasting at Casanova di Neri, one of the most renowned wineries in Montalcino.
7 Hours
Classic Car, Wine Tasting & Castello di Brolio Experience
4.9
(145)
A private afternoon and evening classic car experience through the Chianti countryside, combining scenic driving, Tuscan heritage, wine tasting and refined hospitality.
8 Hours
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Few experiences capture Italy better than a day among its vineyards. Our wine and food tours lead you into the heart of Tuscany, where historic estates produce some of the country's most celebrated wines against a backdrop of cypress trees and rolling hills.
Travel by private car from tasting to tasting around Siena and the Val d'Orcia, meeting winemakers, sampling regional vintages and pairing them with local cheeses, cured meats and countryside cooking. It is a relaxed, delicious way to understand Tuscan life.
About Italy
Tuscany is Italy's most famous wine region, and the countryside around Siena and the Val d'Orcia is dotted with historic estates and family-run wineries. Rolling vineyards, medieval villages and long lunches define the local rhythm here. Because the best cellars sit deep in the countryside, private car tours are the ideal way to visit several estates in a day while enjoying the tastings without worrying about driving.
What to expect on a Italy experience
- Guided tastings at Tuscan wineries and historic estates
- Private car travel between vineyards near Siena and the Val d'Orcia
- Local food pairings such as cheeses, cured meats and regional dishes
- Scenic drives through cypress-lined Tuscan countryside
- A relaxed, full-day pace with expert wine guidance
Best time to visit
April to June and September to October are ideal, with warm weather, harvest season in the vineyards and fewer crowds than midsummer. July and August are hot and busy, and many locals leave the cities in mid-August (Ferragosto). Winter is quieter and atmospheric, great for cities and lower prices, though some coastal and rural spots wind down.
Getting around
Italy's high-speed trains (Frecciarossa and Italo) link Rome, Florence, Venice, Milan and Naples in a few comfortable hours; book ahead for the best fares. Regional trains reach smaller towns. Within cities, walking is best, supplemented by metros in Rome and Milan and vaporetto water buses in Venice. Renting a car suits Tuscany and the countryside, but avoid driving in historic city centres (ZTL zones carry fines).
Frequently asked questions
Our wine experiences focus on Tuscany, particularly the countryside around Siena and the Val d'Orcia. This region is home to historic estates and family-run wineries producing some of Italy's most respected wines.
Yes. Tastings are typically paired with local Tuscan food such as cheeses, cured meats, olive oil and regional dishes, so you experience the wines the way locals enjoy them, alongside good food.
No. Most wine tours include private car travel with a driver, so you can relax and enjoy the tastings while moving comfortably between estates in the Tuscan countryside.
A typical full-day tour visits two to three wineries or estates, allowing enough time for tastings, a cellar visit and a leisurely lunch without feeling rushed.
Absolutely. Guides explain each wine, the region and the production process in an approachable way, making these tours enjoyable whether you are a seasoned enthusiast or simply curious to learn.