Tuscany & the Italian Riviera

Florence6 Nights4 Drives

Highlights
Itinerary
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Experience the ultimate Italian road trip as you cruise through the rolling hills of Tuscany, the dramatic mountain passes of Emilia-Romagna, and the sun-soaked coastlines of the Italian Riviera. Starting and ending in Florence, this six-night journey blends high-performance driving with some of Italy’s most iconic landscapes and destinations. From the legendary Mille Miglia route and the supercar heritage of Motor Valley to the cliffside villages of Cinque Terre and the timeless charm of Chianti, every day brings a new and unforgettable setting.

This curated self-drive tour features thrilling scenic routes, world-class cuisine, and handpicked luxury stays. Stop in medieval hill towns like San Gimignano and Montepulciano, take in sweeping views along the Apennine passes, and unwind with optional coastal boat charters near Portofino. Whether you’re sipping Brunello in Montalcino or coasting along Tuscany’s cypress-lined roads, this tour offers the perfect blend of driving excitement, cultural immersion, and effortless Italian elegance.

Prices from: €11400

Tour Availability: May – October

Tour Highlights

Sights & Stops

Mugello Race Circuit

A famous Italian motorsport venue known for hosting MotoGP, with a massive helmet sculpture at the entrance that has become a popular photo stop.

Bardi Castle

A striking medieval fortress set high on a rocky outcrop, offering panoramic views and rich history in the heart of the Apennines.

Leaning Tower of Pisa

One of Italy’s most iconic landmarks, this freestanding bell tower is known worldwide for its unintended tilt and photogenic location in Piazza dei Miracoli.

San Gimignano

A walled hill town in Tuscany renowned for its skyline of medieval towers, preserved architecture, and traditional local products like saffron and white wine.

Drive Highlights

Futa and Giogo Passes

A pair of winding mountain roads through Tuscany that were once part of the Mille Miglia rally, offering a blend of smooth curves and elevated views.

Passo del Tomarlo & Passo della Scoglina

Remote and exhilarating mountain passes with tight turns, forested stretches, and minimal traffic — ideal for spirited driving.

Chianti Wine Road

A picturesque route through the vineyards and olive groves of central Tuscany, dotted with historic villages and panoramic hilltop views.

Val d’Orcia & Crete Senesi

Classic Tuscan landscapes with rolling hills, cypress-lined roads, and golden fields, frequently featured in travel photography and films.

Itinerary

Day 1 – Arrive in Florence

Touch down in the cultural heart of Tuscany and settle into a five-star villa nestled in the hills above Florence. With its Renaissance treasures, cobbled streets, and world-class cuisine, Florence offers the perfect backdrop to begin your Italian self-drive adventure in style.

Overnight Stay: 5-Star Villa Cora

Day 2 – Florence to Maranello

Start your engines and hit the legendary Mille Miglia route through Tuscany’s sweeping passes and hillside villages. Cross the Giogo and Futa Passes en route to Italy’s Motor Valley, where you can explore world-famous supercar museums before arriving at a tranquil vineyard estate near Maranello.

Overnight Stay: 5-Star Relais Roncolo 1888

Day 3 – Maranello to Ligurian Coast

Take the scenic route into the Apennines, where lush valleys and twisty mountain passes like Tomarlo and Scoglina offer pure driving joy. After a stop in the fortress town of Bardi, descend to the Ligurian coastline and arrive at your cliffside retreat, with an optional evening in iconic Portofino.

Overnight Stay: 5-Star Villa Riviera Resort

Day 4 – Down Day: Portofino and Cinque Terre

Spend your day soaking up the Italian Riviera’s coastal magic. Choose a boat charter to Portofino, a scenic trip to the Cinque Terre, or simply relax poolside at your luxury resort. This is your time to slow down and savor the Mediterranean in ultimate style.

Overnight Stay: 5-Star Villa Riviera Resort

Day 5 – Ligurian Coast to Tuscany

Cruise down the coast to Pisa for a quick visit to the Leaning Tower, then wind inland to the hilltop town of San Gimignano for lunch. The afternoon delivers a picture-perfect drive through Chianti’s wine roads and villages, ending at a peaceful Tuscan estate among olive groves and vineyards.

Overnight Stay: 5-Star Hotel Le Fontanelle

Day 6 – Tuscany to Florence

Today’s drive takes you deep into the postcard landscapes of Val d’Orcia and Crete Senesi. Visit Montalcino and Montepulciano, enjoy optional wine tastings, and navigate some of Tuscany’s most iconic rally roads before returning to Florence for a final night of luxury.

Overnight Stay: 5-Star Villa Cora

Day 7 – Departures from Florence

Enjoy a relaxed morning, then take your private transfer to the airport. With unforgettable roads, luxury stays, and the essence of Italy behind the wheel, this self-drive tour wraps up as the ultimate Italian road trip experience.

Package Includes

Luxury Car Rental & Insurance
Arrival Transfer
Ample KM
6 Nights in Luxury Accommodation
Daily Breakfasts
Curated Driving Itinerary
eRoadbook & Navigation Links
CarPlay & Android Auto Integration
On-Call Support
Car delivery & pick up directly at your hotel

Recommended Cars

Mini Cooper JCW Cab

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Ferrari Roma Spider

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Max power 612 hp

Max speed 199 mph

Ask a Question

If you have any questions about our ‘Tuscany & the Italian Riviera’ Driving Vacation, simply fill out the form below. One of out experienced team members will get back to you within 24 hours.