Tuscany is made for road trips. Its sun-drenched hills, medieval villages, vineyard-dotted valleys, and hilltop towns are best explored with the freedom of your own car.

Whether you land in Florence or Pisa, this guide gives you two magical one-week road trip routes that skip Florence (you can come back for that later!) and dive straight into the heart of Tuscany’s countryside.

On our travels through the region, we found ourselves drawn again and again to these ancient towns. Some  like Siena, with its proud palazzos and famous piazza. Others, like Monteriggioni or Volterra, feel almost untouched, their cobbled streets winding through centuries of history and local life. What they all share is that unmistakable sense of the past—alive, tangible, and beautifully worn.

Florence, the birthplace of the Renaissance, is more than just a city—it’s a living museum, a culinary paradise, and a cultural treasure trove. Choosing where to stay here isn’t just about star ratings—it’s about discovering the neighborhood that matches your travel style.

Whether you’re coming for the art, the shopping, the food, or the views, Florence’s compact layout makes it ideal for exploring by foot, but each district brings something different.

Tuscany’s landscape is dotted with enchanting hilltop towns where history, culture, and spectacular views converge in a perfect landscape.

If you’re dreaming of wandering through medieval streets, tasting world-class wines, and savoring authentic Tuscan cuisine—all framed by rolling vineyards and golden sunsets—then the hilltop towns of San Gimignano, Montepulciano, Cortona, Pienza, and Volterra should be at the top of your itinerary.

Each of these towns offers a unique window into Tuscany’s rich heritage and vibrant presence, making them essential stops on any Tuscan journey.

Tuscany is a region filled with timeless charm, rolling hills, and cultural gems. While Florence is the crown jewel, taking a day trip to nearby Pisa and Lucca offers a deeper glimpse into Tuscany’s diversity.
This guide will walk you through the perfect itinerary—how to get there, what to do in each city, where to enjoy authentic Tuscan cuisine in Lucca, and tips to make the most of your time. Whether you’re a first-time visitor or a seasoned traveller, this one-day adventure blends history, food, and scenery into one seamless experience.