Your journey starts in Palermo. After arrival you are transferred to the centrally located NH Palazzo Sitano. First impressions are intense: baroque facades, market stalls scented with citrus and espresso, voices echoing through the narrow lanes. In the afternoon you discover the city on a guided walking tour, including access to the cathedral’s rooftop with its spectacular view over the old town and the sea. An aperitivo is the perfect moment to meet your fellow travelers. For the welcome dinner you stroll through Palermo’s lively streets to the restaurant “La Galleria” – an atmospheric introduction to Sicily and a fitting prelude to the driving days ahead.

After breakfast you head along the coast to Cefalù and onward to the Costa Verde Resort. Here you meet the Nostalgic fleet for the first time: classic Alfa Romeo Spiders, polished bodywork, interiors with patina – every detail carefully prepared. Following a thorough technical briefing and driver’s meeting, you set off on your first major loop on the historic Targa Florio routes in the Madonie mountains. The road winds through dense woods and open high plateaus, past small villages where time seems to move more slowly. Lunch is served at “Casale Drinzi”, where you enjoy generous Sicilian cuisine. In the afternoon you roll back toward the sea. A visit to the picturesque town of Cefalù with its cathedral, beach and tight medieval alleys makes for an ideal ending to this first, memorable driving day.

Today the route leads east along the north coast via Santo Stefano di Camastra, where brightly colored ceramics fill the shop windows. The road traces the shoreline again and again before climbing into the interior. Around each bend a new view opens up – deep blue bays, quiet valleys, distant ridgelines. Around midday you reach Relais Villa Muraglia and pause over regional specialties. In the afternoon the scenery shifts as you head toward Etna: the closer you come, the more the volcano shapes the landscape. Black lava fields, chestnut forests and vineyards create a striking backdrop. Your destination is the Picciolo Golf & Spa Resort – a green and tranquil retreat where you can unwind at the end of the day.

After breakfast you head up toward Rifugio Sapienza on the southern slope of Mount Etna. As you gain altitude, the landscape changes: lush vegetation gives way to lava fields and craters until you find yourself in an almost surreal volcanic world. You have time to take in the views and feel the unique atmosphere of this active volcano. Then you ease the Spider back down the mountain roads to Gambino Winery, where Etna wines, local cuisine, and sweeping panoramas combine into one of the highlights of the journey. After lunch and a tasting, you continue via Castiglione and Francavilla di Sicilia back to the hotel. In the evening, a gourmet dinner in Linguaglossa rounds off the day.

The morning drive takes you once more into the Sicilian hills to Savoca – an authentic mountain village with quiet lanes, stone houses and a small bar on the main square. An espresso with a view, a short stroll, a quick photo – these are the little moments that stay with you. After a final look across the hills you return the classic cars and drive back to Taormina. Some free time remains: perhaps a last walk through town, a lunch with sea view or a swim in the bay. Later you transfer to Catania Airport and fly to Rome (flight not included). In the capital you check into a centrally located hotel; the evening is yours – for a first stroll or a relaxed dinner in the neighborhood.

This day belongs to Rome. After an unhurried breakfast, you have time to explore on your own: a visit to Campo de’ Fiori, a caffè on Piazza Navona, or browsing small boutiques around the Spanish Steps. In the afternoon you discover Rome on a guided tour, for example with a focus on the Vatican and St. Peter’s Basilica. Here, history, art and modern city life blend at every corner. In the evening a typical Roman dinner awaits at the traditional “Checco er Carrettiere”, where you experience the city’s cuisine in convivial surroundings – complete with trattoria bustle and warm evening light.

After check-out, the morning in Rome is again at leisure. You might return to a favorite lookout, pay a last visit to a museum or simply enjoy one more cappuccino at a local bar. Around midday an executive transfer collects you and brings you north into Tuscany. Your destination is Hotel Il Piccolo Castello near Monteriggioni – an elegant hideaway framed by cypress trees, olive groves and vineyards. In the late afternoon you visit the winery Rocca delle Macìe: a guided tour, cellar visit and tasting provide insight into Tuscan wine culture. The day ends with dinner at “Osteria Passo dopo Passo”, where regional cuisine and atmosphere align perfectly.

Today marks the start of the Tuscan driving section of your Grand Tour. After an introduction to Alfa Romeo history and a detailed driver briefing, you select “your” Spider for the day. The route leads through the Colline Metallifere via Pievescola, Radicondoli and San Dalmazio – a landscape of rolling hills, forests and scattered villages straight from a coffee-table book. Around lunchtime you pause in Sassetta. In the afternoon you head toward Piombino. Driving the classic cars onto the ferry is one of those special images that stays in the mind. From the deck you watch the mainland recede and the island of Elba grow larger. By late afternoon you reach Portoferraio and continue to Villa Ottone – an elegant waterfront hotel that will be your base for the coming days.

After breakfast it’s time for a full island loop in the classic Alfa. The western coastline of Elba unfolds as a sequence of panoramas – cliffs dropping steeply into the sea, coves with turquoise water, small places like Marciana Marina with its promenade and cafés right on the harbor. Lunch is at your own discretion in Marina di Campo – perhaps fresh fish or pasta with seafood. In the afternoon more winding roads lead you back to Villa Ottone. In the evening you drive up to the agriturismo “Montefabrello”. Under the open sky, with home-made products and local wines, you experience a side of Elba far from the bustle and very personal in character.

The day begins with a short driver briefing before you set off toward Porto Azzurro. This small harbor town with its piazza right on the water invites you to a coffee stop and a stroll. Next the road climbs to Capoliveri, a picturesque hilltop village with stairways, narrow alleys and wide views over the coast – a perfect setting for an individual lunch. In the afternoon you enjoy the finest roads of eastern Elba once again. The mix of driving pleasure, sea and Mediterranean light seems to amplify every impression. Back at Villa Ottone there is time for a swim or a drink on the terrace. In the evening you return to Porto Azzurro, this time to the “Sapereta” winery, where you end the day over dinner among the vines.

On your final day you set off early. After breakfast you drive to the ferry and watch Elba slowly fade into the haze behind you. Back on the mainland, a last, particularly atmospheric stage begins via Mensano and Colle Val d’Elsa – Tuscany’s parting greeting with gentle hills, cypress trees and small villages. In the trattoria “La Fornace” you enjoy a farewell lunch together before returning the cars at Casone. The many impressions, conversations and pictures of this Grand Tour accompany you on the transfer to Florence Airport (FLR). From here you commence your individual journey home – taking with you the feeling of having experienced Italy from some of its most beautiful island and coastal roads.