Your journey begins in the heart of Chianti at the renowned Rocca delle Macìe winery, surrounded by rolling vineyards, cypress-lined hills, and medieval stone villages. After meeting the group, enjoy an exclusive wine tasting featuring some of Tuscany’s best-known wines.

Later, settle into your charming countryside hotel before joining the group for dinner at Passo dopo Passo, a hidden gem loved for its panoramic terrace, refined Tuscan cuisine, and relaxed atmosphere beneath the Tuscan sky.

Today the classic Alfa Romeo Spiders come to life. Leaving Chianti behind, you follow scenic roads through the wild landscapes of the Maremma — one of Tuscany’s most beautiful and untouched regions.

The route winds past olive groves, hill towns, and quiet country lanes before reaching the ferry port of Piombino. From here, you cross the Tyrrhenian Sea to Elba Island, once Napoleon’s place of exile and now one of Italy’s most exclusive island escapes.

Your home for the next days is the elegant five-star Villa Ottone near Portoferraio, complete with private beach access and classic Mediterranean charm.

Today is all about the drive. Elba’s legendary coastal road delivers endless curves, dramatic cliffs, turquoise bays, and sweeping sea views — ideal terrain for a vintage Alfa Romeo Spider.

You pass through charming seaside villages including Marciana Marina, where elegant promenades and waterfront cafés invite a relaxed stop. Along the route, pine forests, hidden coves, and panoramic viewpoints showcase the island’s incredible variety..

Today, we hand you the keys and Elba is yours. There is no group drive and no schedule to follow. Choose your Alfa Romeo, pick one of our suggested routes and spend the day exploring the island exactly the way you want to.

Maybe that means following the coast until you find the right beach for a swim. Maybe you dive into Elba’s fascinating Napoleonic history and visit one of his former residences, stop at a local market or simply keep driving through the mountains and along the sea. With its twisting roads, secluded bays and constantly changing views, Elba rewards taking your time – and occasionally taking the road you hadn’t planned on.

By late afternoon, we meet back at Villa Ottone and leave the classics behind for the evening. A transfer takes us to Porto Azzurro, where we come together for dinner at Sapereta and our final night on the island.

After breakfast and check-out, pick your Alfa Romeo one last time and head for the harbor. We board the morning ferry together, classics included, and watch Elba fade into the distance as we cross back to mainland Italy. But the road trip isn’t over yet.

From Piombino, we turn away from the Mediterranean and head back into the heart of Tuscany. Our final route takes us toward Mensano and Colle Val d’Elsa, trading island roads and sea views for rolling hills, medieval villages and the quiet backroads that make Tuscany such a rewarding place to drive.

By early afternoon, we arrive back at Piccolo Castello near Monteriggioni. Here, after four days on the road and a journey that has taken our Alfa Romeos from Tuscany across the sea to Elba and back again, it is finally time to hand over the keys. We finish with lunch together before transferring to Florence Airport (FLR) for the journey home.