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.

Set out on your first scenic drive into the rolling hills of Chianti, arriving in Castellina in Chianti, a charming hill town surrounded by vineyards and olive groves. Take time for a leisurely stroll through the historic center, wander along its medieval streets and stone arcades, and pause for a relaxed coffee in the piazza before continuing on to lunch.

After lunch, continue on to San Gimignano, one of Tuscany’s most iconic and beautifully preserved medieval towns. Famous for its skyline of ancient stone towers rising above the surrounding countryside, the town offers a wonderful glimpse into medieval Tuscany. Wander through its cobbled streets and lively piazzas, browse artisan shops and gelaterias, and soak in the atmosphere of this UNESCO-listed hill town before returning to the countryside.

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. Explore artisan shops, savor the town’s celebrated Vernaccia wine, and soak in sweeping views of the surrounding countryside.

Depart San Gimignano and drive toward Siena, pausing along the way to visit Monteriggioni, one of Tuscany’s most remarkable walled towns. Encircled by perfectly preserved medieval walls and watchtowers, the village offers sweeping views over the surrounding Chianti countryside. Enter through the historic Porta Franca gate to explore the quiet stone streets, the 13th-century Church of Santa Maria, and small museums showcasing medieval arms and local history before continuing on your journey.

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. Admire landmarks including Palazzo Sansedoni and the Gaia Fountain before continuing to the striking Siena Cathedral and Baptistery, celebrated for their Gothic architecture and artistic treasures. After the guided visit, enjoy time at leisure before returning to your accommodation independently.

Savor the flavors and scenery of the Tuscan countryside on a private evening of wine, village charm, and regional cuisine. Depart your hotel with a private English-speaking driver and journey through Chianti’s rolling vineyards to Setriolo Winery, where you’ll tour the estate and sample its locally produced wines. Continue to the medieval village of Radda in Chianti for a stroll along its ancient walls before settling in for a delightful dinner at Restaurant Le Panzanelle, celebrated for its authentic Tuscan dishes. After dinner, relax on the scenic drive back to your hotel.

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. Explore the famous “Gladiator Road,” the winding cypress-lined track featured in the film Gladiator, where sweeping views of the countryside capture the timeless beauty of this UNESCO-listed landscape.

Wander through Montalcino, a beautiful hilltop town at the heart of one of Tuscany’s most celebrated wine regions. Explore the impressive 14th-century fortress, which offers sweeping views over the surrounding vineyards and countryside. Stroll the charming streets of the historic center, lined with stone buildings, small cafÉs, and artisan shops, and browse the many wine boutiques showcasing the region’s world-famous Brunello di Montalcino.

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.

Head to the historic center of Montepulciano, where Renaissance palaces line the winding streets leading to Piazza Grande. Explore the town’s atmospheric wine cellars and elegant tasting rooms, sampling the celebrated Vino Nobile produced in the surrounding vineyards.

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.

Enjoy some time at leisure in the heart of Florence, soaking up the city's timeless charm at your own pace. Start by exploring the bustling Central Market, where fresh produce, local delicacies, and vibrant stalls offer a true taste of Tuscan life. Consider venturing into the vibrant Santo Spirito neighborhood, known for its bohemian flair, artisan shops, and charming cafes. Don’t miss the chance to indulge in a scoop of gelato from a nearby gelateria, perfect for savoring as you wander through the picturesque streets. If you’re feeling more energetic, stroll up to Piazzale Michelangelo for breathtaking panoramic views of the city’s iconic skyline. Whether savoring a cappuccino in a quiet piazza or browsing artisan shops, the time is yours to relish.

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. The experience includes guided visits to the Uffizi Gallery and the Accademia, home to masterpieces by Leonardo, Michelangelo, and Raphael, all at a relaxed and well-paced rhythm.

An icon of Italian gastronomy set in the heart of Florence, Enoteca Pinchiorri offers an extraordinary dining experience where culinary artistry meets one of the world’s most celebrated wine collections. Within its elegant, Renaissance-era setting, each course is a refined expression of Italian tradition, reimagined with precision, creativity, and impeccable technique. Paired with exceptional service and a cellar of global renown, an evening here promises to be a true highlight of your time in Florence. Kindly note this is a confirmed reservation only; all food and beverage charges are payable directly at the restaurant.

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.

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. Surrounded by vineyards and olive groves with panoramic views of the medieval towers, this tranquil retreat features around 30 individually styled rooms and suites that blend original Tuscan charm with modern comforts and countryside vistas. Guests can unwind by the seasonal outdoor pool with jacuzzi corner, indulge in rejuvenating spa experiences, or savor authentic regional cuisine at the on-site restaurant paired with the estate’s own organic wines and olive oils. Beyond the property enjoy wine tastings, scenic walks, cycling or horseback riding through nature, all while soaking in the peace of rural Tuscany.

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. The rooms and suites are unique and all offer the services and comforts of a top level hotel. The rooms have been restored and furbished with elegance, antique or contemporary furniture, precious fabrics and unique dÉcor. Guests can dine at SaporDivino restaurant, offering a seasonal-inspired menu featuring traditional Tucson cuisine.

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. This intimate luxury resort features 45 rooms and suites, seamlessly blending historic castle charm with contemporary accommodations, many showcasing sweeping vineyard views and natural thermal water amenities. Ideal for couples, honeymooners, wine enthusiasts, and wellness-focused travelers seeking a peaceful escape, the resort offers a refined base for exploring southern Tuscany while indulging in one of the region's most celebrated spa experiences.

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. Experience exceptional dining with a menu inspired by Italy’s diverse regions, crafted from the freshest seasonal ingredients. The bar offers an inviting space to enjoy global flavors in the serene poolside atmosphere, perfect for unwinding. The spa provides unique treatments and tailored fitness programs, fostering a profound sense of well-being. Three pools, including an adults-only option and an indoor spa pool, create a tranquil oasis for relaxation. The sauna and steam bath enhance the experience with their therapeutic benefits. Precise Tale Poggio Alla Sala combines Tuscan charm and contemporary luxury, offering an unforgettable retreat in one of Italy’s most enchanting regions.

The Hotel Brunelleschi is located in the historical center of Florence, a stone’s throw from the Uffizi Gallery, the Piazza della Signoria, and one of the world’s most famous shopping streets. The Brunelleschi was included as one of Travel & Leisure’s 500 Best Hotels as selected by their readers and offers rooms and suites, spectacular views of the Duomo, a restaurant, and a gym. The hotel was created within a circular Byzantine tower and a medieval church, entirely reconstructed, but keeping the original characteristics of the buildings. Inside you can find a private museum that has conserved the architectural ruins discovered during the restoration of the buildings. This hotel is also featured at the end of Dan Brown’s The Da Vinci Code.