The Tuscan Hill Towns No One Talks About (but You’ll Love More Than Florence)

Barga (Renaissance Tuscany Il Ciocco Resort & Spa)

Barga is often called the “most Scottish town in Italy” because of its long history of Scottish emigration, giving it a unique cultural blend. It’s tucked in the Garfagnana valley, surrounded by the dramatic Apuan Alps, making it more rugged and less touristy than the rolling Chianti hills. The town itself is full of narrow cobbled streets and is dominated by a beautiful Romanesque Duomo with panoramic views over the mountains.

Climb to the Duomo di San Cristoforo

The climb to the Duomo di San Cristoforo is often described as one of Barga’s most rewarding experiences. What draws me in is how locals talk about the silence at the top, the way the Garfagnana valley stretches out in layers of deep green, and how the view invites you to pause. It’s not just a photo op; it sounds like a moment to reset.

The Fish & Chips Festival

And then there’s the Fish & Chips Festival. I haven’t been, but I can’t stop thinking about it. A Tuscan hill town throwing a full-blown celebration of its Scottish heritage with kilts, pipers, and golden fried fish? That kind of cultural mashup doesn’t show up in typical Tuscany itineraries, which is exactly why it’s on mine.

Casole d’Elsa (Castello di Casole, A Belmond Hotel)

Casole d’Elsa is a quieter medieval hill town compared to nearby San Gimignano or Volterra, offering a more serene experience. It’s perched with sweeping views over vineyards and olive groves, right in the heart of Tuscany’s golden triangle between Siena, Volterra, and San Gimignano. The town is known for its thriving community of artists and sculptors, giving it a creative, lived-in charm.

Walk the ancient city walls

Walking the ancient city walls at sunset sounds like the kind of low-key magic that makes Tuscany unforgettable. Travelers say the views stretch endlessly over soft hills and olive groves, and because Casole d’Elsa is more under-the-radar, you’re likely to have the place mostly to yourself. I’m drawn to that quiet stillness as not every Tuscan town gives you space to just breathe.

Visit local art studios and galleries

The town’s art scene is what really piqued my interest. Casole has a long tradition of sculpture and painting, and visitors often stumble into studios tucked into medieval buildings. It’s not curated for tourists but a town where art is part of everyday life, and that’s something I’d love to experience firsthand.

Artimino (Tenuta di Artimino – Meliá Collection)

Artimino is a tiny borgo famous for the Medici Villa “La Ferdinanda,” a UNESCO World Heritage Site with legendary “100 chimneys.” Unlike many hill towns, Artimino feels like a preserved Renaissance retreat, with deep ties to Florentine nobility and history. It’s also in the Carmignano wine region, one of Tuscany’s oldest and most prestigious but lesser-known DOCGs, making it a hidden gem for wine lovers.

Visit Villa La Ferdinanda: “Villa of 100 Chimneys”

The Medici “Villa of 100 Chimneys” almost sounds mythical, but it’s real, and a UNESCO World Heritage Site at that. I haven’t stepped inside yet, but I’m fascinated by how it’s described: a place that blends grandeur with historical mystery. The idea of standing in the same rooms where the Medici once lived, with views stretching over the Carmignano vineyards, has firmly placed this spot on my list.

Enjoy a Carmignano DOCG wine tasting

Wine lovers often say Carmignano is one of Tuscany’s best-kept secrets. I love the idea of tasting wines that are locally beloved but less internationally hyped. Visiting a family-run vineyard here where the winemaker likely knows every vine by name feels like the kind of authentic experience that still flies under the radar.

Radda in Chianti (Pieve Aldina – Fontenille Collection)

Radda is a quintessential Chianti hill town but feels more authentic and less commercial than nearby Castellina or Greve. Its position along the scenic Chiantigiana road makes it a perfect hub for wine touring. The medieval walls and narrow streets give it a cozy, timeless feel, and it has a deep winemaking tradition that stretches back centuries.

Chianti Classico Wine Consortium

I’m drawn to Radda because it seems to offer the best of Chianti without the crowds. The Chianti Classico Wine Consortium isn’t just a tasting stop—it’s where you can really understand what makes this wine region so historic and respected. For someone who wants more than just a pour in a glass, it sounds like an essential stop.

Explore the medieval center

What I find most charming, though, is the layout of the village itself. Radda’s medieval core is elliptical, with narrow cobblestone streets and a walkable rhythm that feels timeless. Travelers say it’s one of those places where you wander aimlessly and still discover something lovely, like a tucked-away trattoria or a quiet square with blooming geraniums.

Pienza (La Bandita Townhouse)

Pienza is called the “ideal Renaissance city” because it was redesigned by Pope Pius II to embody perfect urban harmony. Unlike other Tuscan hill towns, its streets and piazzas were laid out in a planned way, making it feel open and elegant rather than medieval and winding. It’s also world-famous for pecorino cheese and offers some of the most stunning views of the Val d’Orcia’s rolling landscapes.

Stroll through Piazza Pio II

Pienza is often described as the “ideal city” of the Renaissance, and it’s one of those places I’ve mentally bookmarked for years. The layout is said to be surprisingly open and balanced, a refreshing contrast to the maze-like alleys of most hill towns. Just sitting in Piazza Pio II with a coffee, watching the town go about its quiet business, sounds like a deeply grounding moment.

Pecorino di Pienza

And then there’s the pecorino. This is what Pienza is famous for, and from everything I’ve read and heard, it’s not just a single cheese. It’s an entire spectrum of flavors. Some shops age it in hay, some with truffle, others with walnut leaves. I’m already planning my route between cheese shops.

Barga (Renaissance Tuscany Il Ciocco Resort & Spa)

• L’Altana: Elegant restaurant in the heart of town with creative takes on Tuscan dishes and a great wine selection. Guests rave about the truffle macaroni at L’Altana. Delicately infused with local Garfagnana truffles, it’s rich, earthy, and beautifully balanced. It’s a luxurious reflection of Barga’s rugged, forested setting.

• Scacciaguai: Stylish yet rustic spot with creative Tuscan plates and a great local wine list, loved by both locals and visitors. Scacciaguai’s taglioni is a standout, often served with wild mushrooms or a silky truffle cream. The thin pasta soaks up every drop of flavor, delivering a dish that feels both elevated and warmly rustic.

Casole d’Elsa (Castello di Casole, Belmond Hotel, Tuscany)

• Il Colombaio: Family-run restaurant in a farmhouse setting, known for authentic Tuscan classics and seasonal ingredients. The bistecca alla fiorentina at Il Colombaio is a showstopper. Thick-cut, flame-grilled, and seasoned with restraint to let the quality of the meat shine. Paired with a glass of red and views over the rolling countryside, it’s a must-try.

• Caffè Casolani: A casual but excellent osteria right in the center, great for pasta, grilled meats, and regional wines. Slow-simmered and deeply flavorful, the ragu here, often made with wild boar or beef, is a local favorite. Served over handmade pappardelle, it captures the heart of Tuscan home cooking.

Artimino (Tenuta di Artimino, Meliá Collection)

• Biagio Pignatta: The elegant restaurant of the estate, offering refined Tuscan cuisine with Carmignano wine pairings. The gamberini antipasti at Biagio Pignatta is a bright, zesty beginning to any meal. Typically featuring marinated shrimp with citrus, herbs, and a subtle hint of chili, it’s a refreshing contrast to the estate’s richer offerings.

• Ristorante Da Delfina: Historic trattoria near the Medici villa with panoramic terrace views and traditional dishes. A true taste of tradition, the rabbit at Da Delfina is usually stewed with olives, herbs, and white wine. Guests love its tenderness and robust flavor, calling it a rustic classic that still feels special.

Radda in Chianti (Pieve Aldina – Fontenille Collection)

• La Perla del Palazzo: Upscale restaurant in Radda’s historic center, with refined Tuscan cuisine and an intimate atmosphere. This spot serves ravioli that feels like comfort food with a refined edge. Often filled with ricotta and herbs, then finished with sage butter or a Chianti wine reduction, it’s an elegant nod to Tuscan simplicity.

• La Bottega di Volpaia: Scenic restaurant in the nearby hamlet of Volpaia, with rustic dishes and spectacular vineyard views. Chianti is more than a pairing here—it’s the star. Guests enjoy tasting local vintages alongside rustic seasonal dishes, all while taking in postcard-perfect vineyard views from this hilltop hamlet.

Pienza (La Bandita Townhouse)

• Trattoria Latte di Luna: Famous for handmade pici pasta and roasted meats, a must-visit for a true Pienza experience. From warm pecorino baked with honey to pecorino-stuffed pasta, this cheese shines at Latte di Luna. Guests describe every bite as a celebration of Pienza’s most famous export.

• Sette di Vino: Tiny, character-filled spot serving local cheeses, salumi, and simple but delicious Tuscan specialties. Sette di Vino’s fagiola bean soup is pure Tuscan soul. It’s simple, hearty, and comforting. Made with local beans, olive oil, garlic, and fresh herbs, it’s the kind of dish that lingers in your memory long after the trip ends.