For one Singapore traveller, wine was not just something to enjoy after a long day — it became the reason to build an entire holiday around Tuscany.
When she and her husband planned their annual trip to Italy, she deliberately set aside three and a half days to explore Tuscany’s wine country, travelling through Chianti and Val d’Orcia and visiting wineries along the way.
Rather than relying entirely on organised tours from Florence, the couple rented a car and drove through the countryside, visiting places including Siena, San Gimignano, Pienza, Bagno Vignoni and Montalcino.
The decision gave them more flexibility, particularly because many wineries are located away from major towns. The winding roads through the Tuscan countryside also became part of the experience.
For travellers planning a similar trip, an International Driving Permit is recommended when renting a car in Italy. The traveller also found that luggage size mattered when choosing a rental vehicle, after discovering that a large suitcase could push the need for a bigger car.
Where they stayed was just as important.
The couple split their accommodation between two agriturismos — traditional farm stays that offer a more rural experience — in Chianti and Val d’Orcia. One overlooked vineyards and olive groves, while the other offered views of the rolling Tuscan landscape and an on-site restaurant.
The trip also highlighted an important point for wine lovers: Tuscany is not one single wine destination.
Chianti Classico is closely associated with Sangiovese-based wines and areas such as Greve, Radda and Castellina in Chianti. Val d’Orcia and Montalcino are better known for Brunello di Montalcino, another Sangiovese wine generally associated with a fuller style and longer ageing. Montepulciano, meanwhile, is famous for Vino Nobile di Montepulciano.
That means choosing a base according to the wines you want to explore can save considerable driving time.
Two winery visits stood out during the journey.
Cantalici L’Antica Fornace Di Ridolfo in Chianti offered a more intimate tasting experience, with the couple learning about the connection between the wine, grapes, land and winemaking process.
Vallepicciola provided a very different experience, combining a large estate and modern production facilities with a guided tour before the tasting.
For the traveller, seeing how the wine was produced made the tasting more meaningful because there was greater context behind every bottle.
And then came the question many Singapore wine lovers may eventually face: how to bring the bottles home.
Some wineries can arrange international shipping to Singapore, but imported wine is subject to Singapore duties and GST. Shipping costs also need to be factored into the final price.
For just one or two bottles, transporting them in checked luggage with proper wine protectors may be more economical, although travellers should check the latest Singapore Customs rules on alcohol allowances before returning home.
The biggest lesson from the trip was that a Tuscany wine holiday does not have to be a rushed checklist of vineyards.
With at least three days, a rental car and the right base, wine lovers can combine tastings with countryside drives, historic towns, farm stays and long meals — turning the search for the perfect bottle into the centrepiece of an entire Italian getaway.
And for anyone who loves wine enough to plan a holiday around it, Tuscany may offer something even better than the next great bottle: the chance to understand where it came from.
