Florence & Tuscany

Discover the best of Tuscany on this unforgettable luxury self-drive tour through Florence, Chianti, and the UNESCO-listed Val d’Orcia. Start in Florence, the Renaissance capital of Italy, where iconic art, grand architecture, and timeless charm set the tone for your journey. From there, hop into your car for a thrilling drive along the famed SR222—part of the historic Mille Miglia route—into the heart of the Chianti wine region. Meander through olive groves and medieval hill towns like Greve, Castellina, and Radda, pausing at legendary wineries and estates for tastings and breathtaking views.

Continue south into the postcard-perfect landscapes of Val d’Orcia, with its cypress-lined roads, golden fields, and world-class vineyards. Explore Montepulciano and Montalcino, sampling iconic Tuscan reds like Vino Nobile and Brunello di Montalcino, and make optional visits to monasteries and thermal spa towns. Wind your way back through San Gimignano and Monteriggioni, soaking in Tuscany’s rich history and natural beauty before returning to Florence for a final evening of Italian elegance. This Tuscany driving holiday is the perfect blend of culture, scenery, fine wine, and driving pleasure.

Prices from: €7900

Tour Availability: May – October

Tour Highlights

Sights and Stops

Antinori nel Chianti Classico

A striking modern architectural masterpiece set into the hillside, this innovative winery offers panoramic views and a wine shop to explore.

Badia a Coltibuono Monastery

A serene olive oil estate nestled in the hills of Chianti, where you can enjoy a relaxing lunch and olive oil tasting amid historic monastery grounds.

Montepulciano

A medieval hilltop town famous for Vino Nobile di Montepulciano, with cobblestone streets, Renaissance architecture, and artisan shops to explore on foot.

San Gimignano

Known for its iconic medieval towers, San Gimignano is the best-preserved walled city in Tuscany and a must-stop for history, views, and local shopping.

Drive Highlights

SR222 – Strada Chiantigiana

One of the most scenic roads in Tuscany, this historic Mille Miglia route winds through vineyards, olive groves, and picturesque villages in the Chianti region.

Val d’Orcia Loop Drive

A stunning circular route through UNESCO-listed landscapes, featuring rolling hills, cypress-lined roads, and views straight out of a Tuscan postcard.

Brunello Wine Region

Drive through the heart of Montalcino to enjoy a private tasting of Brunello, one of Italy’s most prestigious wines, at a hand-picked estate.

Tuscan Hill Town Circuit

A relaxed drive linking the iconic towns of Monteriggioni, San Gimignano, and Certaldo.

Itinerary

Day 1 – Arrive in Florence

Begin your journey in Florence, the cradle of the Renaissance and one of the most beautiful cities in Italy. Stroll across the Ponte Vecchio, admire Michelangelo’s David, and soak in panoramic views from Piazzale Michelangelo. With time to explore world-renowned art, architecture, and cuisine, Florence sets the stage for your luxury Tuscany road trip. Enjoy seamless arrival with private airport transfer and settle into your hotel before the adventure begins.

Overnight Stay: 5-Star Villa Cora

Day 2 – Florence to Tuscany

Kick off your scenic Tuscany driving tour with a thrilling ride along the iconic SR222, once part of the Mille Miglia race route. Wind through the Chianti region’s rolling vineyards, olive groves, and medieval towns like Greve, Castellina, and Radda. Highlights include a visit to the stunning Antinori nel Chianti Classico winery, a gourmet lunch and olive oil tasting at Badia a Coltibuono monastery, and optional stops at Castel di Brolio and the Felsina wine shop before arriving at your countryside retreat.

Overnight Stay: 5-Star Hotel Le Fontanelle

Day 3 – Val d’Orcia Loop

Embark on a spectacular drive through Val d’Orcia, a UNESCO World Heritage site known for its cypress-lined roads and golden hills. Visit Montepulciano to sample Vino Nobile, then head to Montalcino for a private Brunello wine tasting experience. Optional stops include thermal spa towns and the serene Benedictine monastery of Monte Oliveto Maggiore. This unforgettable day pairs world-class driving with Tuscany’s most iconic scenery and flavors.

Overnight Stay: 5-Star Hotel Le Fontanelle

Day 4 – Pianella to Florence

Enjoy a more relaxed day exploring Tuscany’s medieval gems. Stop in the walled village of Monteriggioni, wander the ancient towers of San Gimignano, and savor a laid-back lunch in Certaldo. Your final drive back to Florence follows the legendary Strada Chiantigiana (SR222), offering one last sweep through the rolling vineyards of Chianti, with a charming stop in Greve before returning to the Renaissance city.

Overnight Stay: 5-Star Villa Cora

Day 5 – Departures from Florence

Wrap up your luxury driving tour with a final morning in Florence. Stroll through the old town, visit hidden gems, or simply relax in one of the city’s sun-drenched piazzas. Your vehicle will be collected seamlessly from your hotel, and transfer options to the city or airport are readily available. Depart with memories of Tuscan wine roads, hilltop towns, and the artistic heart of Italy.

Package Includes

Luxury Car Rental & Insurance
Ample KM
4 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

Porsche 911 Carrera GTS Cab

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0-62 mph in 3.1 secs

Max power 473 hp

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Lamborghini EVO Spyder

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Ask a Question

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