A Taste of Tuscany

Experience Tuscany at its most indulgent on this gourmet road trip through rolling vineyards, historic hill towns, and world-renowned wine regions. This 6-day journey blends scenic driving routes with immersive culinary experiences, from olive oil tastings at ancient monasteries to cooking classes in sun-drenched farmhouses. Wind your way through Chianti and Val d’Orcia, explore medieval gems like Montepulciano and San Gimignano, and enjoy private tastings of Brunello and Chianti Classico straight from the source.

Designed for lovers of fine food, stunning drives, and timeless Italian landscapes, this tour offers the perfect balance of adventure and relaxation. You’ll drive hand-picked scenic routes—including iconic sections of the Mille Miglia—stay in luxurious countryside estates, and savor long Tuscan lunches with vineyard views. Whether you’re uncorking a bold Brunello or rolling fresh pasta by hand, every moment is a taste of the good life in Tuscany.

Prices from: €9900

Tour Availability: May – October

Tour Highlights

Sights & Stops

Antinori nel Chianti Classico

A striking architectural landmark and wine estate blending modern design with centuries of winemaking heritage; perfect for a pre-dinner browse and tasting inspiration.

Badia a Coltibuono

A peaceful 11th-century monastery and olive oil estate where you’ll enjoy a leisurely lunch and guided olive oil tasting in the heart of the Chianti hills.

Montepulciano

A classic Tuscan hilltop town known for Renaissance architecture and Vino Nobile di Montepulciano; ideal for strolling, shopping, and wine tasting.

Brunello Wine Region (Montalcino area)

Home of the legendary Brunello di Montalcino wines, this region offers a private tasting experience amid rolling hills and historic estates.

Drive Highlights

SR222 (Strada Chiantigiana)

Tuscany’s most scenic road, weaving through vineyards and medieval villages in Chianti, with panoramic views at every turn.

Val d’Orcia Loop

A stunning UNESCO-listed route with cypress-lined roads, golden hills, and timeless vistas—quintessential postcard Tuscany.

Mille Miglia Route

A historic racing route that adds a touch of thrill to the journey, especially the section leading back to Florence through Chianti.

Monteriggioni to San Gimignano Stretch

A cultural corridor connecting a perfectly preserved medieval fortress town with Tuscany’s “Manhattan” of towers, rich in views and history.

Itinerary

Day 1 – Arrive in Florence

Begin your Tuscan journey in the Renaissance heart of Florence, where world-class art, culture, and cuisine converge. After your airport transfer, take time to explore iconic sights like the Uffizi Gallery, Ponte Vecchio, and Michelangelo’s David. Enjoy an optional pre-tour evening savoring authentic Tuscan dishes and fine Chianti in this UNESCO-listed city steeped in history and culinary heritage.

Overnight Stay: 5-Star Villa Cora

Day 2 – Florence to Tuscany

Today’s drive follows the famed SR222 into the heart of Chianti wine country, weaving through Greve, Castellina, and Radda. Discover rolling vineyards, olive groves, and medieval hill towns. Highlights include a stop at Antinori nel Chianti Classico, olive oil tasting at Badia a Coltibuono, and a visit to Castel di Brolio. End the day with a Chianti tasting near your countryside retreat, surrounded by views straight out of a postcard.

Overnight Stay: 5-Star Hotel Le Fontanelle

Day 3 – Val d’Orcia Loop

Venture into the UNESCO-listed Val d’Orcia, a land of cinematic beauty and prestigious wines. Visit Montepulciano, famed for Vino Nobile, then head into the Brunello di Montalcino region for a private tasting. The drive features cypress-lined lanes, hilltop villages, and optional stops at thermal spas or the serene Monte Oliveto Maggiore Abbey—offering a full sensory dive into Tuscany’s food, wine, and landscapes.

Overnight Stay: 5-Star Hotel Le Fontanelle

Day 4 – Down Day

Slow the pace with a hands-on Tuscan cooking class at a local farmhouse or winery. Learn to prepare fresh pasta and traditional sauces, then enjoy your meal paired with regional wines overlooking the vines. In the afternoon, enjoy a curated tasting at a boutique estate producing Chianti Classico or Brunello, then unwind at your villa with time to relax or explore nearby hill towns.

If you fancy a hot air balloon ride over the romantic Tuscan landscape, we can help arrange this for you. These balloons are very weather-dependent, but if everything aligns, it will easily create a lifelong memory.

Overnight Stay: 5-Star Hotel Le Fontanelle

Day 5 – Pianella to Florence

Your final drive winds through Monteriggioni, San Gimignano, and Certaldo—famed for their towers, artisan shops, and Tuscan charm. Enjoy lunch and shopping in Certaldo before returning to Florence via the scenic Strada Chiantigiana, one of Tuscany’s most beautiful routes. Pause for coffee in Greve before closing the loop on this unforgettable journey through Tuscany’s cultural and culinary heart.

Overnight Stay: 5-Star Villa Cora

Day 6 – Departures from Florence

Spend your final morning soaking up Florence at your own pace—perhaps a last cappuccino near the Duomo or a stroll through the Boboli Gardens to end your luxurious escape through the rolling hills and vineyard-covered valleys of Tuscany.

Package Includes

Luxury Car Rental & Insurance
Ample KM
Arrival Transfers
5 Nights in Luxury Accommodation
Daily Breakfasts
Curated Driving Itinerary
eRoadbook & Navigation Links
CarPlay and Android Auto
On-Call Support
Pasta Cooking Class
Wine Tasting

Recommended Cars

Ferrari Portofino M

€15399.98

0-62 mph in 3.4 secs

Max power 612 hp

Max speed 199 mph

Ferrari 296 GTS

€17900

0-62 mph in 2.9 secs

Max power 819 hp

Max speed 205 mph

Ask a Question

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