The journey begins at the Palazzo di Varignana, a stylish 4-star hotel in the hills south of Bologna. The property combines historic architecture with modern elegance and is nestled within expansive parks and gardens offering sweeping views across Emilia-Romagna. After check-in, there will be time to settle in, get to know one another, and relax as you prepare for what lies ahead. During dinner together at the hotel, anticipation quickly takes center stage: for Italian country roads, sweeping views, and charming towns.

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-like castle was built in the 19th century by Cesare Mattei, a colorful Italian naturopath and founder of what is known as 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 journey continues, the route gradually opens up toward Florence and Chianti. The landscape becomes gentler, sunnier, and more typically Tuscan: vineyards, tree-lined avenues, country estates, and rolling hills now dominate the view. Today’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 take you through a landscape straight out of movies and coffee-table books: winding roads, solitary cypress trees, stone houses, and sweeping views of golden-green hills.

The highlight of the day is at 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’ll take a boat across to Isola Maggiore, the lake’s second-largest island. It’s small, charming, and sparsely populated—and that’s exactly what gives it its special charm.

Dinner on the island offers a moment that stands out distinctly from a typical day of driving: quieter, more intimate, and almost a little otherworldly. This is followed by the final leg of the journey to Perugia, the capital of Umbria. We’ll spend the night at Le Cappuccinelle Suites & SPA, a stylish property with historic character that combines modern tranquility with the charm of a former monastery. It’s the perfect place to wind down and relax at the end of the day.

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 less about dramatic scenery and more about elegance, vastness, and an almost meditative driving experience.

Castel Monastero promises a truly special stay at today’s destination. This 5-star resort is located in a carefully restored medieval hamlet and combines historic charm with exclusive discretion. Just arriving here, surrounded by natural stone walls, courtyards, and the tranquility of Tuscany, makes this place an experience in itself.

The highlight of the day then takes off—in the truest sense of the word: 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, neatly arranged 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 pace. From the hills around 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 with 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 closing 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 look at 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-like 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.

With an optional rental car, you can enjoy Italy flexibly, independently, and exactly as you’d like. Transportation between the airport or train station and the rental car location is already included, ensuring a stress-free start to your trip. You can also choose a specific car model upon request—ideal for perhaps fulfilling your dream of driving a car you’ve always wanted to try.

If you’d like to start this special trip in an even more relaxed way or bring it to a stylish close, you can book additional nights at the respective hotels before the trip begins and after it ends. This gives you more time to enjoy the unique atmosphere of the hotels at your leisure, explore the surrounding area on your own, and immerse yourself even more deeply in the Italian way of life. Whether it’s an early start in the hills near Bologna or an extended stay by the sea in Viareggio—additional nights turn a special trip into an even more immersive experience.

For maximum planning security, you can take out suitable travel cancellation insurance through us. This means you are covered if something unexpected happens before you start your trip.