Florence & Tuscany - 5 Days

Florence & Tuscany Luxury Driving Tour

Our Florence & Tuscany Luxury Driving Tour takes you on a journey through the most beautiful regions of Tuscany, sampling gourmet highlights, visiting medieval hilltop towns, and driving the most scenic driving routes.

This fully-planned 4-night trip starts in the historic city of Florence and includes 3 full days touring on the best roads in Tuscany. The first tour takes you around the wine regions of Chianti, with time to stop for a pasta cooking master class in the heart of Chianti. The second tour takes you south on a loop across the spectacular Tuscan vistas of the Crete, or Val d'Orcia, with its sweeping Cyprus tree-lined roads. The final tour takes you around the hilltop fortified towns that make up the "borderlands of Florence" including San Gimignano, Certaldo, and Monteriggioni. This Tuscany trip truly combines the best driving routes and fantastic cultural sights to create a well-rounded luxury road trip.

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Florence & Tuscany Luxury Driving Tour

Day 1 - Arrive in Florence & Michelin Dinner

From the airport, your limo pick-up awaits for your short transfer to downtown Florence. Your updated boutique hotel and spa is just minutes from the city center and provides tasteful luxury and privacy with just the right amount of Italian flare.

Overnight Hotel: LHW 5-Star Relais Santa Croce, Florence 

Day 2 - Tour of Chianti Country & Wine Tasting 

In the morning, the car handover will take place and you'll be on your way! Your first drive starts from Florence via the super scenic SR222, a famous part of the legendary Mille Miglia road race route. The road will take you directly into the rolling hills and vineyards of the Chianti region, dotted with wineries and olive groves, one of the most beautiful landscapes you can find in the whole of Italy. You will then make a loop of the most beautiful hilltop towns in the region, including Greve, Castellina, and Radda, with optional stops at our select wineries, taking lunch in the heart of the Chianti region. Next, head directly to your hotel for the evening. After settling in, take a short 5 minute stroll through the hotel's gardens, and up to the adjacent Chianti winery Azienda Agricola Vallepicciola. Later that evening, dine at the hotel's beautiful panorama restaurant, with views across the Chianti vineyards to Castelo di Brolio in the distance.

Overnight Hotel: 5-Star Hotel Le Fontanelle

Day 3 - Le Crete and Val d'Orcia & Cooking Class

On Day 3, you will head to the beautiful Val D'orcia / La Crete region, famous for its rolling hills, unique vistas, and Cyprus tree-lined roads - the iconic Tuscan landscape. This region of Tuscany also has some of the best thermal waters and spas. Take in the beautiful hilltop village of Montepulciano, where wines by the same name are made, before stopping at the spa town of Bagno Vignoni. Continue south, and stop at a wonderful farmhouse where a master class in pasta-making will be arranged for you so that you can prepare and cook your own pasta, then enjoy it with a glass of local wine. We will highlight several great vineyards in the Brunello region for you to explore, including Poggio di Sotto. Loop back through Val d'Oricia to Chianti for a second evening. Visit the nearby village of Castelnuovo Berardenga, and dine at one of our favorite restaurants in the region where you can enjoy some local Tuscan cuisine.

Overnight Hotel: 5-Star Hotel Le Fontanelle

Day 4 - Borderlands of Florence & Route Mille Miglia

The last drive takes you through the rolling Tuscan hills west of Florence, visiting some of the most beautiful and well-preserved towns in the region, including the hilltop towns of Monteriggioni, Certaldo, and San Gimignano. This tour is very much about a combination of sightseeing and drives. After lunch in San Gimigiano, spend some time exploring on foot and shop for the best local produce and wines from the region. The final drive back takes you along the SP 222 (Strada Chiantigiana), which is arguably the most scenic route in central Tuscany as it cuts its way through Chianti then back into the city of Florence where your drive ends.

Overnight Hotel: LHW 5-Star Relais Santa Croce, Florence 

Day 5 - Morning at Leisure in Florence

On your final day, spend some more time enjoying the beautiful city of Florence. The hotel will be delighted to hold your luggage whilst you explore. When you're ready, shuttle back to the hotel and continue your onward plans.

For even more details, choose your desired car and click "Continue" to fill out our inquiry form. Or, send us an email at info@ultimatedrives.net

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