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.
Exploring Chianti through its wineries is one of the most rewarding ways to experience Tuscany. In this guide, we share five of our best wineries to visit in Chianti—each offering a unique blend of tradition, wine making, and breathtaking scenery.
You’ll find practical travel tips, detailed introductions, and honest pros and cons for each winery, along with advice on where to stay and the best times to visit.
Welcome to Timeless Wanderers – Our Travel Story Begins Here Hello fellow wanderer, We’re Gary and Sally—two Aussies who traded routine for the road,
Tuscany is known the world over for its rolling hills, cypress-lined roads, and historic towns—but it’s the wine that often leaves the most lasting impression.
From bold reds aged in ancient cellars to crisp whites enjoyed on sun-drenched terraces, Tuscany offers a wine experience like no other.
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.
When we first explored Tuscany, we realized that the magic wasn’t only in the iconic cities, but in the quiet backstreets of tiny towns, the early mornings on hilltop piazzas, and the simple joy of a shared bottle of wine overlooking a valley. That’s why we created this guide—to help you experience Tuscany the way we fell in love with it: slowly, personally, and with open eyes.
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.
From its central location, you can venture out to medieval towns, vineyard-covered hills, or even the sparkling Ligurian coast—and be back in time for aperitivo.
With fast train links, guided tours, and day-trip itineraries offered through sites like GetYourGuide and Viator, day-tripping from Florence has never been easier. Here are 10 incredible destinations that you can explore in a day.
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.
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.
Florence is the perfect base for discovering the best of Tuscany’s world-renowned wine regions. With its central location, the city gives easy access to everything from the rolling vineyards of Chianti Classico to the coastal estates of Bolgheri. Wine lovers will find an incredible range of tasting experiences just a short drive away, with each region offering its own distinctive grape varietals, traditions, and scenery.
When it comes to dressing for an Italian summer, the goal is to balance comfort with effortless style. Italians are known for their fashion sense, even in the heat, so this is your chance to pack light—but thoughtfully.
Lightweight, breathable fabrics like linen, cotton, and rayon are your best friends. Think flowy dresses, midi skirts, or tailored shorts paired with breezy blouses. A neutral palette with a few pops of color tends to blend in beautifully, whether you’re sipping espresso in Florence or wandering the Amalfi Coast.
