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.
Viareggio is Tuscany’s elegant seaside escape, known for its Art Deco architecture, palm-lined promenade, and vibrant beach clubs. Located on the Versilia coast, it blends classic Italian beach culture with charming cafés, shopping, and its famous carnival. It’s a perfect spot for sun, sea, and stylish relaxation.
Monteriggioni is a beautifully preserved medieval town in the heart of Tuscany that seems frozen in time. Perched atop a gently sloping hill, it overlooks the rolling countryside of Siena and offers one of the most historic experiences in the region.
The town was founded in the early 13th century by the Republic of Siena as a defensive outpost against Florence, and its circular walls with 14 imposing towers have remained remarkably intact, creating a striking appearance against the Tuscan landscape.
Val d’Orcia is the postcard-perfect heart of Tuscany, known for its rolling hills, cypress-lined roads, and golden fields. This UNESCO-listed valley is dotted with charming towns like Pienza and Montalcino. It’s a dream destination for slow travel, scenic drives, fine wine, and the timeless beauty of rural Italy countryside.
Chianti is Tuscany’s iconic wine region, famous for its rolling vineyards, hilltop villages, and rustic charm. Stretching between Florence and Siena, it’s the perfect place to sip world-class wine, enjoy scenic drives, and explore medieval towns. Chianti offers a classic Tuscan experience rich in flavor, beauty, and tradition.
Elba Island is Tuscany’s island escape, known for its crystal-clear waters, scenic beaches, and rich history. Just a ferry ride from the mainland, it offers hiking, snorkeling, charming port towns, and Napoleon’s historic exile home. Elba blends natural beauty with laid-back coastal vibes—perfect for a peaceful Italian getaway
Montalcino is a picturesque hilltop town in Tuscany, world-renowned for its Brunello wine. Surrounded by vineyards and olive groves, it offers stunning views, medieval charm, and a relaxed pace. Wander cobbled streets, visit historic fortresses, and enjoy tastings in local wineries—Montalcino is a true gem for wine and culture lovers.
Pitigliano is a dramatic hilltop town in southern Tuscany, carved from volcanic tufa rock. Known as “Little Jerusalem” for its historic Jewish quarter, it offers a unique blend of history, culture, and stunning views. Its cliffside setting, winding alleys, and ancient charm make Pitigliano a captivating and unforgettable destination.
Saturnia’s hot springs are a natural wonder in southern Tuscany, where warm, mineral-rich waters flow over terraced rock pools. Free and open year-round, these cascading thermal baths offer a relaxing, spa-like experience in the wild. Surrounded by countryside, Saturnia is perfect for unwinding and soaking in nature’s healing waters.
