If you love wine and travel, few escapes rival a weekend in Tuscany. The region offers rolling hills, medieval villages and vineyards that seem to stretch forever. Most importantly, life slows down here. You sip, savour and explore at a gentler pace.
Whether you are planning your first visit or returning for more, a weekend in Tuscany is always a good idea.
Wine Regions to Explore on a Weekend in Tuscany
Tuscany is one of Italy’s most celebrated wine regions. It is best known for Sangiovese, the grape behind Chianti, Brunello di Montalcino and Vino Nobile di Montepulciano.
Each sub-region tells a different story. Chianti offers bright cherry notes and fresh acidity. In contrast, Brunello delivers depth, structure and long ageing potential. Meanwhile, along the coast, Super Tuscans blend Sangiovese with Cabernet Sauvignon or Merlot, creating bold and modern styles.
White wines also shine here. Vernaccia di San Gimignano brings freshness and minerality, while Vermentino adds a coastal touch.
Because of this diversity, Tuscany is ideal for short breaks. Every valley reveals a new expression, even during a short weekend in Tuscany.
Where to Stay & How to Get Around
To truly enjoy a weekend in Tuscany, renting a car is the easiest option. It allows spontaneous stops at vineyards, viewpoints and small villages.
Car hire is simple from Florence, Pisa or Siena. Plus, driving through the countryside is part of the experience.
For shorter routes, consider renting a Vespa or motorbike, especially in Chianti. However, if you prefer not to drive, trains connect major towns like Florence, Siena and Arezzo. In addition, many guided wine tours include transport and tastings, making weekends stress-free.
A Perfect Weekend in Tuscany: Day-by-Day Itinerary
Friday evening
Arrive and slow down. Wander through cobbled streets and enjoy your first glass of Chianti Classico at a cosy enoteca. Afterwards, opt for a simple dinner of handmade pasta or crostini.
Saturday
Focus on wine tasting. Book two or three wineries in advance. Then, enjoy a long vineyard lunch with local olive oil and Pecorino Toscano. Later, explore towns like Radda or Gaiole. End the day with Brunello or a Super Tuscan at dinner.
Sunday
Enjoy a relaxed morning at a local market or one final tasting before heading home. Visit a local market or enjoy one last tasting before heading home.
Tuscan Food to Taste on a Weekend Getaway
Tuscan cuisine is simple and generous. Try pappardelle al cinghiale, rich ribollita, or the iconic bistecca alla Fiorentina.
To finish, enjoy cantucci with Vin Santo. It is the perfect sweet ending to a wine-filled weekend.
If You Have More Than a Weekend in Tuscany
With extra days, explore the Maremma coast for Morellino di Scansano. Alternatively, visit Lucca or Carmignano for smaller DOCG producers.
You could also cross into Umbria for a different take on Sangiovese. Finally, balance wine with culture by visiting Florence, Siena or San Gimignano.
Continue Your Wine Travel Journey
If this guide inspired you, explore our articles “Vineyard-Hopping by Train” and “A Wine Lover’s Weekend in Portugal: Exploring the Douro Valley”.Both are ideal for planning your next escape.
In the end, Tuscany’s magic lies in its simplicity. Honest wines, comforting food and timeless landscapes define every weekend in Tuscany. Even a short stay feels unforgettable.