Tuscany Tour 2027

After breakfast, the first big day of riding begins. From the Bologna area, the route leads into the northern Apennines—a landscape that is often underestimated and, for that very reason, full of surprises. The roads here are varied yet pleasantly unspoiled. Forests, mountain ranges, and small villages alternate, making the journey toward Tuscany an experience in itself.

A special highlight of the day is a visit to Rocchetta Mattei. This fairytale castle was built in the 19th century by Cesare Mattei, a flamboyant Italian naturopath and founder of so-called electrohomeopathy. Architecturally, the estate seems almost like a dream, blending elements of the Orient, the Middle Ages, and the Romantic era—full of towers, arches, and surprising vistas.

As the day progresses, the route gradually opens up toward Florence and Chianti. The landscape becomes softer, sunnier, and more typically Tuscan: vineyards, tree-lined avenues, country estates, and rolling hills now dominate the scene. The day’s destination is the Fattoria Torre a Cona, an elegant 4-star hotel set on a historic estate in the heart of the wine-growing region just outside Florence. Over dinner on the terrace overlooking the vineyards, Tuscany reveals for the very first time why it has become a place of longing for so many.

The day begins in the heart of the Chianti wine region. Even the first few kilometers wind through a landscape familiar from movies and picture books: winding roads, solitary cypress trees, stone houses, and sweeping views across golden-green hills.

The highlight of the day is Lake Trasimeno, one of Italy’s largest lakes. Unlike many of the country’s better-known bodies of water, it feels calmer, more unspoiled, and almost timeless. From there, we take a boat across to Isola Maggiore, the lake’s second-largest island. It’s small, charming, and sparsely populated—which is exactly what gives it its special charm.

Dinner on the island offers a moment that stands out distinctly from the typical day of driving: quieter, more intimate, and almost a bit ethereal. This is followed by the final leg of the journey to Perugia, the capital of Umbria. Overnight accommodations are at Le Cappuccinelle Suites & SPA, a stylish property with historic character that combines modern tranquility with the charm of a former monastery estate. A fitting place to wind down the day in relaxation.

Today, the route continues through the heart of central Italy. The drive from Umbria toward Siena combines quiet country roads with landscapes that constantly draw the eye outward: fields, olive groves, cypress trees, and rolling hills that, bathed in soft light, seem almost unreal. This section, in particular, is defined less by dramatic scenery and more by elegance, vastness, and an almost meditative driving experience.

Castel Monastero awaits as a very special destination for the day. The 5-star resort is located in a carefully restored medieval hamlet and combines historic character with exclusive discretion. Simply arriving among the natural stone walls, courtyards, and Tuscan tranquility makes this place an experience in itself.

The highlight of the day then literally takes off: a helicopter sightseeing flight over Siena and the Tuscan hills. From above, you can see the features for which the region is known worldwide—winding roads, orderly fields, scattered estates, and the characteristic harmony of a cultural landscape that has evolved over centuries. We then land at a renowned winery in the region. During a wine tasting paired with regional specialties, it quickly becomes clear just how closely the landscape, cuisine, and way of life are intertwined in Tuscany.

The last big day of riding offers another welcome change of scenery. From the hills surrounding Siena, the route heads northwest, gradually moving away from the classic postcard view of Tuscany.

At lunchtime, a special stop awaits in Montecatini Terme. This historic spa town was already a gathering place for those seeking relaxation, artists, and affluent travelers in the 19th and early 20th centuries. From here, the historic Funicolare di Montecatini Terme takes you up to Montecatini Alto. The funicular is considered the oldest of its kind still in operation in Italy and has connected the spa town to the higher-lying district for over a century. Once at the top, you’ll find not only lunch with sweeping panoramic views but also a beautiful slice of authentic Italy: narrow alleys, small squares, and the feeling that time passes a little more slowly here.

In the afternoon, the journey continues to Viareggio on the coast. There, the Grand Hotel Principe di Piemonte—one of the most famous grand hotels on the Tuscan Riviera—awaits you: a 5-star hotel right on the beach promenade, elegant, steeped in tradition, and exuding the charm of classic seaside resorts. Before the final evening, there’s time for a stroll along the promenade with its boutiques, cafés, and the city’s sophisticated coastal atmosphere. The group dinner at the hotel’s beach restaurant, right by the sea, provides the perfect finale: relaxed, special, and with a view of the water.

After breakfast, it’s time to say goodbye. Perhaps there’s still time for one last glimpse of the sea, a coffee on the terrace, or a brief chat about the best moment of the trip. Behind you lie days full of contrasts: the green hills near Bologna, the fairytale Rocchetta Mattei Castle, the vineyards around Florence, the tranquil Lake Trasimeno, the view of Siena from a helicopter, a historic mountain village, and finally, the grand finale on the coast. A journey that doesn’t have to be loud to leave a lasting impression.