Tour guides Italy > Tuscany

5 ideas for guided tours in Tuscany

• Montalcino

  

  Montalcino is best known for its wine, Brunello di Montalcino. But beyond the cellars and tasting glasses, the town surprises with its atmosphere. Perched on a hill, it keeps its cobbled streets, stone houses, and above all, those sudden views opening onto the Tuscan countryside.

  Around it, the hills stretch gently. You walk among vineyards and olive groves, sometimes in shade, sometimes under full sun. The paths are never very long, but every turn changes the scene—a field, a valley, a shift in light. The pace slows, and you go along with it.

  The town also preserves traces of its past. The Fortezza di Montalcino, built in the 14th century, still overlooks the city and houses a small museum. Lower down, the Church of Sant’Agostino offers ancient frescoes striking in their intensity. A mix of wine, history, and silence—that’s what defines Montalcino.

• Pisa

  

  Pisa, in Tuscany, instantly brings to mind its famous Leaning Tower. Yet the city is far more than this monument. Its history stretches back to a Roman port that grew into one of the most powerful merchant cities of the Mediterranean during the Middle Ages. Many buildings from that prosperous era still shape the landscape today.

  The Leaning Tower of Pisa, begun in the 12th century, was meant to stand straight. The ground decided otherwise. Rising 56 meters high, it continues to intrigue, and climbing its 294 steps gives an uncanny, slightly dizzying sensation. From the top, the view sweeps over the city’s rooftops and out toward the Tuscan hills.

  Beside it lies the Piazza dei Miracoli. Here stand the cathedral with its white-and-black marble, elegant facades, and an interior adorned with frescoes and sculptures. The whole ensemble surprises with its balance of grandeur and simplicity. Pisa, in the end, is this blend: a world-famous monument surrounded by a city worth lingering in.

• San Gimignano

  

  San Gimignano traces its origins back to the Etruscans, but it was in the Middle Ages that the town reached its peak. Set along the old Silk Road, it became a thriving trading center. Wealthy families built towers to display their power and protect their property. More than sixty once stood, and about fifteen still rise today, shaping the skyline.

  Walking through the cobbled lanes, you encounter signs of this prosperity at every turn. The Palazzo del Popolo, the Church of Sant’Agostino with its 14th-century frescoes, and the facades lining the Piazza della Cisterna together form a remarkably preserved medieval setting. Sitting for a while on this square, surrounded by towers, you sense a calm atmosphere that contrasts with the liveliness of the streets.

  San Gimignano’s fame also rests on its wine. Vernaccia di San Gimignano, a dry and aromatic white, has been produced on these hills for centuries. The surrounding vineyards paint landscapes that shift with the light, and many cellars welcome travelers to share both their craft and their bottles.

• Siena

  

  Siena still carries the character of a medieval city perched on its hill. At its center, the Piazza del Campo unfolds like an open shell, framed by brick facades that all seem to lean toward the square. Each summer in July and August, the Palio di Siena fills it with pounding hooves and the passion of the locals, a moment outside of time.

  Above it all, the Torre del Mangia rises over the rooftops. The climb is steep, but at the top the view stretches across rolling hills dotted with cypresses and tiny villages. Then comes the Duomo di Siena, built between the 13th and 14th centuries. Its black-and-white marble facade, adorned with mosaics and sculptures, catches the light in an almost unreal way.

  Inside, the eye wanders between frescoed vaults and intricate marble floors. Tucked away in one wing lies the Piccolomini Library. Its walls, painted by Pinturicchio, burst with color—a striking contrast to the silence of the space. It’s often here, more than in the crowds of the square, that you grasp Siena’s true artistic wealth.

• The island of Elba

  

  Off the Tuscan coast lies the island of Elba. A small land, yet one that changes its face at every turn—bright beaches, hidden coves, hills draped in pines. It’s easy to see why travelers keep coming back. The Fetovaia Beach, often ranked among the most beautiful in Italy, sums up the island’s spirit: golden sand against a sea that’s almost transparent.

  But to reduce the island to its shores would be unfair. History is everywhere. Romans, Genoese, Lombards—all left their mark. In Populonia, Etruscan remains recall an ancient presence. In Portoferraio, fortifications still circle the town, their towers once keeping watch over the sea. Walking through these lanes, you can almost feel the weight of the past in the stones.

  And then there’s Napoleon Bonaparte. Exiled here in 1814, he turned the island into a forced residence, but left behind palaces, stories, and legends. Today, Elba blends it all—the sea, the vineyards, the villages, the history. A miniature Tuscany, but wilder, more raw, that stays with you long after you leave.