If you love wine and travelling, few getaways compare to a weekend in Tuscany. Think rolling hills, medieval villages and endless vineyards where time slows down just enough for you to sip, savour and explore.
The Heart of Tuscan Wine
Tuscany is one of Italy’s most celebrated wine regions, famed for Sangiovese, the grape behind Chianti, Brunello di Montalcino and Vino Nobile di Montepulciano. Each area offers a unique expression: from Chianti’s bright cherry notes to Brunello’s full-bodied complexity. Along the coast, Super Tuscans blend Sangiovese with Cabernet or Merlot for bold, modern reds, while whites like Vernaccia di San Gimignano and Vermentino bring a refreshing contrast. The region’s variety makes it ideal for short trips, each valley and hillside reveals a different flavour of Tuscany.
Where to Stay & How to Get Around
For easy exploring, stay somewhere central like Greve in Chianti or Castellina in Chianti, both perfectly placed for day trips across the wine trail. If you prefer a southern base, Pienza or Montepulciano offer postcard-perfect scenery and access to Val d’Orcia’s renowned wineries.
When it comes to transport, Tuscany is best enjoyed by car, allowing you to stop at small vineyards and scenic viewpoints along the way. Car rental is straightforward from Florence, Pisa, or Siena, and driving through the countryside is part of the charm. For a more adventurous option, you can rent a Vespa or motorbike for shorter routes around Chianti.
If you’d rather not drive, regional trains connect major towns (Florence, Siena, Arezzo), and many guided wine tours include transport directly from the city — perfect for a carefree weekend without worrying about navigation or tastings.
Weekend Highlights
Friday evening: Arrive and ease into Tuscan time. Wander through cobbled streets, enjoy your first glass of Chianti Classico at a cosy enoteca and a simple dinner of handmade pasta or crostini.
Saturday: Dedicate the day to wine tasting. Many wineries welcome visitors by reservation — combine two or three visits with a long vineyard lunch featuring local olive oil and Pecorino Toscano. Spend the afternoon discovering a nearby town like Radda or Gaiole, then return for dinner paired with Brunello or a Super Tuscan.
Sunday: Enjoy a relaxed morning at a local market or one final tasting before heading home. For organised experiences, check Tuscan Escapes or Grape Tours, which offer small-group trips from Florence and Siena.
Food to Savour
Tuscan cuisine is rustic and generous, think pappardelle al cinghiale (wild boar ragu), bistecca alla Fiorentina, or a hearty ribollita are all must-tries. Finish with cantucci & Vin Santo, the region’s classic dessert pairing.
If You Had More Time…
With a few extra days, explore the Maremma coast for Morellino di Scansano wines, visit Lucca or Carmignano for smaller DOCG producers, or venture into Umbria for a different take on Sangiovese. Add a cultural stop in Florence, Siena, or San Gimignano to balance wine with art and history.
Continue the Journey
If you enjoyed this guide, don’t miss our articles “Vineyard-Hopping by Train” and “A Wine Lover’s Weekend in Portugal: Exploring the Douro Valley” both perfect for planning your next wine-filled adventure.
Tuscany’s magic lies in its simplicity: good food, honest wines and timeless landscapes. Even a weekend here feels like stepping into a postcard you’ll never want to leave.