Tuscany’s love affair with wine stretches back to the Etruscans, who first cultivated these sun-kissed hills over 3,000 years ago. Since then, generations of winemakers have perfected their craft, creating world-famous wines such as Chianti Classico, Brunello di Montalcino and the modern Super Tuscans.
Today, that rich tradition lives on in rolling vineyards and family-run estates. With over 30 years of expertise behind us, we work closely with villa owners to offer guests an immersive, insider experience. Naturally, in Tuscany, wine experiences take centre stage. Armed with insider tips and knowledge, our local concierge experts go above and beyond to offer bespoke experiences that enrich your villa experience.
With that in mind, we’ve curated a selection of our top rentals located on and around Tuscany’s most extraordinary estates. Sample small-batch, biodynamic wine from a historic winery, take part in a private tour with a local winemaker, or experience a bespoke tasting from the comfort of your villa.
Discover our best villas in Tuscany for wine tasting
1. Palazzo Nelle
With Florence, Siena, San Gimignano and the region’s famed wineries all within easy reach, Palazzo Nelle is ideally located for wine tasting in Tuscany.
Among the highlights is a trip to the Poggione Winery in Tignano. Stroll through the 12th-century Castle of Tignano, wander ancient olive groves and biodynamic vineyards, then step inside the boutique cellar to uncover native grapes and heritage vines. The day ends back at Palazzo Nelle, where Chef Giuseppe prepares a gourmet feast paired with four of Poggione’s finest wines and Matteo’s award-winning olive oil.
Bespoke, in-villa tastings can be personally tailored and arranged for Palazzo Nelle guests through our expert concierge team. Matteo, the owner’s son, will share his local expertise and recommendations in an intimate and elegant atmosphere.
Location: Palazzo Nelle is just 4km from Tavarnelle Val di Pesa, located in the heart of Chianti between Florence and Siena.
Sleeps: 10
Local Tip: Be sure to sample Palazzo Nelle’s very own rare wine, produced exclusively for guests.
2. Santa Dieci
Located a few kilometres southeast of Siena’s centre, Santa Dieci is an 8.5-hectare hamlet and family-run organic farm offering immersive wine experiences.
Join the owners on a private tour of the gardens before an informative but friendly wine tasting session to learn all about Santa10’s sustainable winemaking processes. Part of the tour includes a look at the estate’s ancient Etruscan cave. Now used as a wine cellar, the cave is carved into a tufa rock beneath an eleventh-century watchtower.
For easy access to the winery, Santa Dieci guesthouse sits within Santa10’s immaculate estate. Days here begin with gentle morning swims in the private pool and end with gourmet meals made from seasonal, local ingredients.
Location: A 10-15 minute drive from Siena’s historic centre.
Sleeps: 10
Local Tip: Don’t miss out on Siena’s bustling Wednesday market with in-villa chef, Orsa.
3. Gugliaie
Gugliaie is a beautiful restored farmhouse set amidst the rolling hills of Villa Le Corti Estate. This award-winning wine estate dates as far back as the 14th century, when the Tuscan Corsini family swept in to purchase the land. Since then, it has been transformed into a vibrant vineyard and olive grove, producing some of Chianti’s most celebrated wines and extra-virgin olive oils.
Guests at Gugliaie can enjoy sweeping views of the estate’s meticulously tended vineyards, aromatic gardens and sun-dappled olive groves, all framed by the gentle undulations of the Tuscan countryside.
Tailored experiences include a private wine tasting in the estate’s historic cellars. The journey continues with a guided tour of the vineyards and optional cooking classes. Whether exploring the nearby villages of Radda and Greve or relaxing with a glass of Chianti by the pool, Gugliaie and the wider estate are sure to impress.
Location: 2km from San Casciano in Val di Pesa in Chianti Classico, a short drive from Florence and Siena.
Sleeps: 10
Local Tip: Don’t miss a private tasting in the estate’s historic cellars. Pair their award-winning Chianti with fresh bruschetta.
4. VignaSassa
Wine is intrinsic to a stay at VignaSassa, a fantastic family-sized villa set on a sweeping organic wine estate just 2.5km from San Gimignano. Inside, you can expect a classic Tuscan farmhouse aesthetic, with wood-beamed ceilings and traditional terracotta floors.
A gentle stroll through the estate leads to the serene winery, while a short walk further brings you to a charming local trattoria – perfect for tasting and savouring the estate’s Vernaccia di San Gimignano wines. The menu champions local produce, with most ingredients being picked right on the estate.
For those keen to explore further, the iconic Chianti hill towns are within easy reach: Barberino Val d’Elsa (21km) in under half an hour, and Castellina-in-Chianti (28km) in around 40 minutes.
Location: VignaSassa is set on an organic wine estate just 2.5 km from San Gimignano, surrounded by vineyards, cypress trees and rolling Tuscan hills.
Sleeps: 8
Local Tip: Visit San Gimignano’s weekly food and local goods market every Thursday from 8:30am to 1:30pm to stock up on Tuscan specialities such as Val d’Orcia pecorino and porchetta sandwiches.
5. Ca’ di Lista
Ca’ di Lista is a spectacular 16th-century Venetian villa set within the grounds of the award-winning Count Emo Capodilista Estate. The estate has been in the noble Capodilista family for centuries, preserving an unwavering devotion to tradition and craftsmanship. A short drive takes you through the rolling vineyards to the winery for an afternoon of expert-led wine tasting.
Learn about the estate’s rich history and high-quality wines in a private tasting with a sommelier. Tasting sessions are thorough but friendly, held in the heart of the Colli Euganei DOC wine region. Beyond wine tasting, the villa’s frescoes, sprawling gardens and award-winning 27-hole golf course will keep you entertained throughout the season.
Location: Ca’ di Lista sits on the Montecchia Hill amidst the Euganean hills, just a short drive from Padua in the Veneto region. Located in northeast Italy, Veneto is equally renowned for its wines, including Prosecco, Valpolicella and Soave.
Sleeps: 10
Local Tip: Don’t miss out on a chilled glass of the winery’s very own prosecco. It’s gentle and approachable on the palate, even for those who usually shy away from sparkling wine.
When is the best time to visit Tuscany for wine tasting?
Autumn is a particularly magical time to visit, as the vendemmia -– the annual grape harvest — brings the vineyards to life. The landscapes glow yellow and orange, villages celebrate with harvest festivals and wineries open their doors for tastings straight from the barrel. Salute!