Val d'Orcia at the Wheel: A Tuscan Road Story
Imagine the scent of wild herbs through an open car window, cypress rows casting long shadows across the Val d'Orcia, a gravel road bending toward a stone chapel. This is Tuscany by car, at your own pace, on a fully planned route with fully insured car hire, private guides included, and the option to hand over the wheel to a chauffeur. Your Destination Expert curates every detail.
- Duration
- 8 days, 7 nights
- Route
- Florence · Castellina in Chianti · San Gimignano · Siena · Montalcino
- Style
- Private and tailor-made: your own guide and driver throughout
- From
- $6,920 per person, hotels, guides and transfers included
- Take the wheel through Tuscany's vine-covered hills and cypress-lined roads at your own pace.
- Walk Siena and Florence with your private guide, from Gothic duomos to Uffizi masterpieces.
- Climb San Gimignano's medieval towers and explore its UNESCO-listed streets at leisure.
- Set off with fully insured, premium car hire and the option to upgrade to a chauffeur.
- Ask your Destination Expert about wine tastings, dining reservations, and curated routes.
Every day, already yours.
The Golden Hills of Tuscany
Begin your journey behind the wheel and prepare for the open road. A premium category vehicle has been reserved in your name, offering comfort and style as you travel between hilltop towns, vineyards, and historic countryside estates. Should you wish to upgrade, your Destination Expert will be happy to assist.
- Premium Car Rental from Florence Airport
- Road Trip: Florence to Castellina in Chianti
- Road Trip: Castellina in Chianti to San Gimignano
Quiet Roads & Walled Villages
Rising above the Tuscan hills with its striking skyline of medieval towers, San Gimignano, often called the “Manhattan of the Middle Ages”, is one of Tuscany’s most iconic destinations. Today's experience invites you to stroll through the town's cobbled streets with a private guide, uncovering centuries of art, history, and tradition in this UNESCO World Heritage Site.
- San Gimignano Walking Tour (2 hrs) - Private
- Road Trip: San Gimignano to Siena via Monteriggioni
Siena After Hours
Perched across three hills, Siena is one of Italy’s most enchanting medieval cities. Meet your private guide at your hotel and set out on a 3-hour walking tour through its atmospheric historic center. Discover the magnificent Piazza del Campo, one of Europe’s most beautiful medieval squares, framed by the Gothic Palazzo Pubblico and the soaring Torre del Mangia.
- Siena Walking Tour (3 hrs) - Private
- Evening in Chianti (with Dinner & Wine Tasting, 6 hrs) - Private
Through Cypress-Lined Roads
Enjoy a beautiful scenic drive through the rolling landscapes of the Val d’Orcia, one of Tuscany’s most celebrated regions. Along the way, stop at the iconic Cappella della Madonna di Vitaleta, a small stone chapel set among cypress trees and open fields that has become one of the most photographed scenes in Tuscany.
- Road Trip: Siena to Montalcino
- Self-Guided: Exploring Montalcino
The Journey Continues…
Drive to the historic center of Pienza, a perfectly preserved Renaissance town overlooking the rolling landscapes of the Val d’Orcia. Wander its harmonious streets and quiet piazzas, pause at panoramic viewpoints across the Tuscan countryside, and visit the elegant Pienza Cathedral that anchors the town’s beautifully designed square.
- Road Trip: Montalcino to Pienza
- Road Trip: Pienza to Montepulciano
Across the Silvery Crete Senesi
Depart Montepulciano and drive through the Crete Senesi, a striking landscape of rolling clay hills known for its soft grey tones, sculpted ridgelines, and dramatic, almost lunar scenery. Pause at scenic viewpoints along the way for memorable photos of this uniquely beautiful corner of Tuscany.
- Road Trip: Montepulciano to Florence
- Florence at Leisure - Independent Discovery
Art and Atmosphere
Renaissance Florence unfolds in a seamless journey through art, architecture, and everyday life. Meet your private, licensed English-speaking guide at your hotel and set out on foot through the historic center, taking in the Ponte Vecchio, Piazza della Signoria, and Cathedral Square crowned by Brunelleschi’s dome. Along the way, uncover the stories behind the city that shaped generations of artists.
- Walking Tour with Uffizi & Accademia (6 hrs) - Private
- Dining Reservation at Enoteca Pinchiorri
Arrivederci Tuscany
Your journey winds down as you make your way to the designated rental car drop-off point and return your vehicle, marking a smooth and easy end to your self-drive experience.
- Car Rental Drop Off at Florence Airport
Where you will wake up.
Agriturismo Mormoraia
Set in the rolling hills just minutes from San Gimignano, La Mormoraia welcomes guests to an elegant estate that was once an ancient convent, now lovingly transformed into a celebrated Tuscan agriturismo where history and hospitality meet.
Grand Hotel Continental
The Grand Hotel Continental is located in the heart of Siena, in the center of the pedestrian shopping area, within walking distance to the Piazza del Campo, the Duomo and all major sites/attractions. This 17th century palace treasures many magnificent frescoes both in public areas as in several rooms.
Castello di Velona Resort
Perched atop a hill overlooking the UNESCO-listed Val d'Orcia, just outside Montalcino, Castello di Velona Resort is an exceptional countryside retreat set within a beautifully restored 11th-century fortress surrounded by the vineyards of Brunello di Montalcino.
Poggio alla Sala
Precise Tale Poggio Alla Sala, located near the historic town of Montepulciano, offers a luxurious escape amidst the serene Tuscan countryside. This historic estate features 60 refined rooms and suites, each designed with sophistication and boasting panoramic views of vineyards and rolling hills.
Grand Hotel Minerva
Experience a luxurious retreat in the heart of Florence at the Grand Hotel Minerva where dreams weave seamlessly with reality. Steps away, the majestic facade of Santa Maria Novella stands as a true gem against the backdrop of the city.