Discover the quieter side of Italy behind the wheel of a classic Alfa Romeo Spider. This boutique driving tour leads through the rolling vineyards of Chianti, the Renaissance towns of southern Tuscany, and the hidden roads of Umbria — Italy’s “green heart.”
From Montepulciano and Orvieto to Lake Bolsena and the Val d’Orcia, every day combines scenic driving, authentic cuisine, wine culture, and elegant small hotels. Designed for travelers who appreciate classic cars, beautiful roads, and understated luxury, this journey captures the timeless charm of central Italy at a relaxed and sophisticated pace.
After arrival at Florence Airport, you are transferred into the Tuscan countryside to the charming Villa Curina hotel near Siena. Following a welcome briefing and introduction to your classic Alfa Romeo Spider, your first drive begins through the legendary Chianti wine region.
Winding country roads, cypress-lined lanes, vineyards, and medieval villages provide the perfect introduction to Italian grand touring. Back at the hotel, relax by the pool or enjoy a glass of local wine overlooking the hills before gathering for a traditional Tuscan dinner in a small village hidden among the vineyards.
Today’s route leads south through the beautiful Crete Senesi landscape — one of Tuscany’s most iconic driving regions. Rolling hills, quiet backroads, and postcard scenery make this an unforgettable day behind the wheel.
By late morning you arrive in Montepulciano, the elegant Renaissance hill town famous for its world-renowned red wines. After lunch, the journey continues into Umbria via gentle countryside roads and historic villages before reaching the Altarocca Wine Resort near Orvieto.
Surrounded by vineyards and olive groves, the resort offers panoramic views across the Umbrian hills. The evening includes wine tasting followed by dinner at the hotel.
Today you explore Umbria’s quieter interior along scenic secondary roads inspired by the legendary Mille Miglia route. Forests, river valleys, rolling farmland, and mountain views create a completely different side of Italy.
At midday you arrive in the beautifully preserved town of Todi for a guided visit and free time to explore its medieval lanes, Roman heritage, boutiques, and cafés. The afternoon route follows the Tiber Valley through oak forests and peaceful countryside before returning to Orvieto.
Built dramatically atop volcanic cliffs, Orvieto is one of Italy’s most remarkable hill towns, known for its Gothic cathedral and underground history. A guided evening walk reveals the town’s timeless atmosphere.
After breakfast, the route turns west toward Lake Bolsena before joining stretches of the ancient Via Cassia — one of Italy’s great historic roads. Passing through Radicofani and San Quirico d’Orcia, today’s drive delivers some of Tuscany’s most cinematic scenery.
The roads through the Val d’Orcia and Crete Senesi seem tailor-made for classic Alfa Romeo touring: endless curves, golden hills, cypress trees, and quiet medieval villages. By early afternoon you reach Monteriggioni, where the journey concludes with transfer service back toward Florence.
Central Italy offers some of Europe’s finest roads for classic car travel. Tuscany and Umbria combine rolling landscapes, historic towns, wine culture, and quiet scenic routes ideally suited for Alfa Romeo grand touring.
Tuscany is defined by vineyard-covered hills, cypress-lined roads, Renaissance architecture, and world-famous wine regions such as Chianti and Montepulciano. Roads wind naturally through valleys and hill towns, creating an effortless rhythm behind the wheel of a vintage Alfa Romeo Spider.
Beyond Tuscany lies Umbria — often called Italy’s “green heart.” Less visited and more authentic, the region is known for medieval towns, forested valleys, Roman roads, olive groves, and exceptional cuisine. Orvieto, Todi, Perugia, and Assisi preserve centuries of Italian history while offering a slower, more intimate atmosphere than larger tourist centers.
Together, Tuscany and Umbria create the ideal setting for a luxury classic car tour through Italy: relaxed driving days, beautiful hotels, exceptional food and wine, and roads that seem designed for the golden age of motoring.
Discover what our guests say about this tour. Real experiences from drivers and travelers who have explored Europe’s most beautiful roads with us.
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