Weekend in Tuscany: What to See and Where to Go

Tuscany offers a wealth of possibilities for an unforgettable weekend getaway. Here are some ideas and suggestions, organized by type of experience, on what to see and where to go.

Weekend in Tuscany: scenic itinerary through Val d’Orcia and Chianti

What landscape comes to mind when you think of Tuscany? For us, the answer is almost immediate: golden wheat fields stretching as far as the eye can see, interrupted only by rows of solitary cypress trees and medieval villages that look like they were painted on a canvas. This place truly exists—it's Val d'Orcia, a UNESCO World Heritage Site. Here, towns like Pienza, the “ideal Renaissance city,” will welcome you with the aroma of its famous pecorino cheese, while Montepulciano and Montalcino invite you to discover the secrets of their renowned wines, Vino Nobile and Brunello, perhaps right inside a historic cellar. Renting a car is almost a rite of passage—it's the best way to get lost among scenic roads and uncover hidden corners.

Not far away, Chianti awaits, with its rolling hills dotted with vineyards and olive groves. Charming villages like Greve in Chianti, with its distinctive square, or the picturesque Castellina, Radda, and Gaiole in Chianti, are ready to reveal the region’s most authentic soul. Here, life moves at a pace defined by the pleasure of good living: Chianti Classico tastings, dinners made with local products, and stays in cozy farmhouses that offer warm, genuine hospitality. And don’t forget a stop in Monteriggioni, the fortified village whose perfectly preserved walls will transport you straight back in time.

Weekend in Tuscany: what to see and where to go for art and history lovers

If you’re drawn to art, Tuscany never disappoints. A weekend is the perfect opportunity to soak in the Renaissance elegance of Florence. Even in just a few days, you can pack in a lot: admire the imposing Cathedral with its iconic Brunelleschi Dome, maybe even climb Giotto’s Bell Tower, get lost among the masterpieces in the Uffizi Gallery, or encounter Michelangelo’s David at the Accademia Gallery. Don’t miss a stroll along the Ponte Vecchio at sunset, or the climb up to Piazzale Michelangelo for a stunning panoramic view of the city.

But Tuscany is also Siena, with its majestic Piazza del Campo, stage of the famous Palio, and the enchantment of its Cathedral, a true Gothic masterpiece. If you love dramatic architecture, San Gimignano, with its soaring towers, will leave you speechless, offering unforgettable views from the Torre Grossa. And for a walk atop city walls, there’s no better place than Lucca, a city that has preserved its ancient fortifications intact—perfect for exploring by bike through a green, tree-lined path.

To make the most of your Tuscan adventure, especially in the countryside and smaller villages, renting a car is highly recommended. While major cities are well connected by public transport, having a car gives you greater freedom for a more complete itinerary. Contact one of Locauto’s rental offices in Tuscany to book the car that best suits your travel needs!