Top 10 Hill Towns of Maremma
Skyward Maremma: Best Hill Towns to Explore from Agriturismo Lo Scalandrino
From our olive-grove sanctuary at Agriturismo Lo Scalandrino, each of these ten medieval towns is a day-trip dream. Picture winding stone alleys, volcanic cliffs, sunlit vineyards, and centuries of history etched into every wall. Lace up your walking shoes and ready your camera—adventure awaits at every summit.
(1) Pitigliano - The Little Jerusalem
Pitigliano’s golden tuff houses cascade down a volcanic ridge, creating one of Tuscany’s most dramatic panoramas. Its Jewish quarter, kosher bakery, and beautifully restored synagogue offer a cultural tapestry you won’t soon forget.
Highlights:
- Sunset panorama from the belvedere
- Guided tour of the Vie Cave rock-cut roads
- Tasting local wines in a historic cantina
(2) Sorano - Fortress in Stone
Nestled on a sheer cliff, Sorano feels suspended between earth and sky. The Orsini Fortress crowns the town, while hidden grotto-chapels and frescoed caverns evoke medieval mystery.
Highlights:
- Rampart walk atop Orsini Castle
- Exploration of frescoed cliff-side chapels
- Viewpoint over the Lente Valley
(3) Sovana - Sacred Serenity
Sovana’s hushed lanes open onto one of the Maremma’s most serene piazzas. Here, a Romanesque cathedral and nearby Etruscan necropolis create an atmosphere of timeless reverence.
Highlights:
- Tomb of Ildebrando carved in tuff
- Cathedral of San Pietro's intricately sculpted portal
- Quiet reflection in Piazza del Pretorio
(4) Massa Marittima - Gothic Splendour
Massa Marittima enchants with its perfectly preserved medieval core. Piazza del Duomo, framed by the striped marble of San Cerbone Cathedral, is a masterpiece of Tuscan Gothic art.
Highlights:
- Climbing Torre del Candeliere for 360° views
- Discovering the Mining Museum's subterranean exhibits
- Espresso under arched porticoes
(5) Montemerano - Fairytale in Stone
With ivy-clad walls and pastel shutters, Montemerano looks like a scene from a storybook. Inside San Giorgio Church, Renaissance frescoes whisper tales of faith and artistry.
Highlights:
- Admiring San Giorgio's vibrant fresco cycle
- Dinner by candlelight in the central piazza
- Evening stroll along fortified ramparts
(6) Capalbio - Artistic Ramparts
Capalbio marries medieval architecture with contemporary creativity. After wandering its ancient walls, lose yourself in Niki de Saint Phalle's whimsical Tarot Garden just outside town.
Highlights:
- Dawn walk along the town walls
- Colour-soaked sculptures in the Tarot Garden
- Sunset Vermentino tasting at a hilltop café
(7) Scansano - Wine on the Ridge
Scansano reigns over Morellino di Scansano country, where vineyards ripple down the hillsides. Cosy enoteche invite you to sample robust reds and hear stories of local winemakers.
Highlights:
- Private tasting at a family-run cantina
- Picnic among fragrant vines at dusk
- Tour of the Wine Museum's vintage collection
(8) Magliano in Toscana - Legends Among Olives
Encircled by ancient walls, Magliano whispers legends at every corner. Giant olive trees stand sentinel over cobblestone lanes, and the mysterious "Tree of Witches" adds a touch of myth.
Highlights:
- Olive grove picnic at dusk
- Seeking out the fabled Tree of Witches
- Aperitivo with locals in Piazza Roma
(9) Campagnatico - Dante's Muse
This tranquil village once inspired Dante's poetry and still radiates creative calm. Its medieval bastions frame sweeping vistas over the Ombrone Valley, perfect for sunrise reflections.
Highlights:
- Early-morning terrace views at dawn
- Quiet moments in Santa Maria delle Grazie
- Wandering the ancient town walls
(10) Roccalbegna - Rugged Majesty
Dramatically carved into a cliffside, Roccalbegna wears Aldobrandeschi ramparts like a crown. Just beyond, Bosco dei Rocconi offers woodland trails alive with wildflowers and bird song.
Highlights:
- Hiking to the cliff-top Rocca fortress
- Exploring trails in Bosco dei Rocconi
- Sunset dinner overlooking rugged stone walls
Each of these hilltop jewels reveals a different facet of the Tuscan Maremma, and Agriturismo Lo Scalandrino is the serene home-base where every adventure begins and ends. As dusk settles, meander back through our sunlit olive groves and onto your favourite terrace with a glass of local wine. Let the day's discoveries linger in the twilight glow. Here at Lo Scalandrino, you're not just witnessing Tuscany's soul; you're living it.
Agritourism in Maremma, Authentic Tuscan experiences, Hidden gems in Maremma, Maremma hill towns, Maremma magic
