We begin our tour in true Tuscan style: at Rocca delle Macìe, an iconic Chianti winery nestled among rolling hills and old stone walls. Here, a private wine tasting sets the tone – relaxed, refined, and full of character. In the evening, we dine at Passo dopo Passo, a true insider’s tip among local gourmets. Set on a panoramic terrace surrounded by olive groves and vineyards, it’s the perfect place to savor your first evening under the Tuscan sky.

This morning, the engines roar to life: we head west in our classic Alfa Romeo Spiders, following winding roads through the heart of the Maremma – a land of cypress-lined lanes, medieval villages and the scent of wild herbs in the air. Our destination is Piombino, a bustling ferry port and gateway to the Tuscan Archipelago. From here, we set sail for Elba – no longer a secret, but still one of the most enchanting islands in the Mediterranean, and once Napoleon’s place of exile. We arrive at our home for the next few days: the Villa Ottone, a five-star residence set right on the coast, with a private beach and timeless Mediterranean elegance.

After breakfast, we set off for a full island tour – and today, the road itself is the star. Elba’s legendary coastal drive twists and turns above the sea, revealing one spectacular view after another: turquoise coves, remote beaches, pine-covered cliffs and sailboats dancing on the horizon. We pass through picturesque villages like Marciana Marina, where elegant promenades invite a pause.

Today, there is no group route and no fixed itinerary. After breakfast, choose your Alfa Romeo and set off to discover Elba at your own pace. We provide a selection of suggested drives, leaving you free to decide how the day unfolds. Follow the coast in search of a quiet beach and stop for a swim, explore the island’s Napoleonic history with a visit to one of his former residences, browse a local market or simply enjoy the pleasure of driving with nowhere you need to be. Elba is compact enough to explore easily, yet its winding roads, mountain scenery and hidden bays offer plenty to discover. By late afternoon, we meet back at Villa Ottone. That evening, we leave the cars behind and transfer to Porto Azzurro for dinner together at Sapereta; a relaxed finale to our time on the island.

After breakfast and check-out, we choose our Alfa Romeos one last time and drive to the harbour for the morning ferry back to mainland Italy. As Elba disappears behind us, there is still plenty of driving ahead. From Piombino, we turn inland and leave the Mediterranean coast behind for one final journey through the Tuscan countryside. The route takes us towards Mensano and Colle Val d’Elsa, through rolling hills and quiet country roads that provide a fitting final chapter behind the wheel. By early afternoon, we arrive back at Piccolo Castello near Monteriggioni, where it is time to return the Alfa Romeos. We sit down for one last lunch together before the transfer to Florence Airport (FLR) and the journey home.