Rolling hills and patchwork fields of Crete Senesi landscape near Buonconvento in Tuscany

Best Places to Visit in Tuscany From Hilltowns to the Sea

by Tom

There’s far more to Tuscany than its famous leaning tower. Beyond Pisa’s crowds, the region gradually reveals dramatic hilltowns, medieval landmarks, and quiet coastal villages. Indeed, the best places to visit in Tuscany show a slower pace of life, shaped by wine harvests, morning markets, and stories carved in stone. Moreover, each destination offers a unique glimpse into the region’s rich history and culture.

Cathedral Stillness and Golden Stone

In Massa Marittima, the Cattedrale di San Cerbone overlooks a sloped piazza with calm authority. Its Romanesque façade glows under late sunlight. Inside, columns stretch skyward while narrow windows send threads of light across the floor. Because few visitors make it here, the cathedral feels untouched and sacred. Every detail holds centuries of craft and care.

Romanesque façade of Cattedrale di San Cerbone in Massa Marittima, one of the best places to visit in Tuscany
Cattedrale di San Cerbone, Massa Marittima – ENIT SpA

Stone Towers and Wide Horizons

East of there, Volterra sits high above the valley. Its skyline is shaped by the towers of the Fortezza Medicea, built during Florence’s expansion in the 15th century. From the fortress walls, the view is endless—cypress trees, olive groves, and golden hills roll far into the distance. As a result, this spot offers one of the most peaceful and expansive vistas in Tuscany.

Fortezza Medicea di Volterra seen from Parco Archeologico Enrico Fiumi surrounded by trees and ancient ruins
Fortezza Medicea di Volterra vista dal Parco Archeologico Enrico Fiumi – Simone Antonazzo / ENIT SpA

Salt Air and Fishing Boats

Down on the coast, Porto Santo Stefano stretches along the edge of the Argentario Peninsula. Fishing boats bob in the harbor, and painted homes rise in narrow stacks up the hill. Although tourism exists, the village still belongs to its locals. Children play in the streets while elders chat near open cafés. At sunset, the sky and sea melt together in soft pinks and oranges.

Colorful hillside buildings and fishing boats in the harbor of Porto Santo Stefano on the Argentario coast
Porto Santo Stefano – Simone Antonazzo / ENIT SpA

Shadows and Towers at Sunrise

Back inland, San Gimignano greets visitors with stone towers and winding alleys. While the town is well known, early walks along Via San Giovanni offer rare calm. The street climbs gently through shops, bakeries, and quiet doorways. Even with its fame, San Gimignano retains a lived-in feeling. Families here still open shutters each morning, as they’ve done for generations.

Medieval towers and stone buildings along Via San Giovanni in San Gimignano, among the best places to visit in Tuscany
San Gimignano, via San Giovanni – Simone Antonazzo / ENIT SpA

Explore More of the Best Places to Visit in Tuscany and Beyond

The best places to visit in Tuscany are more than postcard views. They hold layers of life that blend past and present. From peaceful hilltowns to working harbors, Tuscany rewards those who look past the obvious. For more journeys beyond the mainstream, see the Abruzzo travel guide, explore Liguria’s dramatic coastline, or step into Sicily’s blend of cultures. To plan a route through Tuscany, visit the official Tuscany travel site or explore its shores with this seaside guide.

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