Discover the gentle rhythms of Tuscan and Umbrian village life on a journey through vine-clad hills, medieval towns, and timeless countryside. From the Chianti wine region to Siena, Pienza, Bagno Vignoni, Perugia and Assisi, explore UNESCO treasures, evocative contrade, and serene piazzas. Savour hands-on cooking, artisan traditions, and curated wine tastings, alongside visits to abbeys and hilltop hamlets. With ample leisure time to wander cobbled lanes and panoramic roads, this itinerary blends culture, gastronomy and breathtaking landscapes for an immersive and unhurried Italian escape.
Upon arrival at Florence airport, pick up your rental car and drive to your accommodation in the Chianti Wine Region. Take the rest of the day at leisure.
Overnight stay in Colle di Val d'Elsa at Palazzo San Lorenzo Hotel & Spa or similar.
*Please note: The driver must hold a valid driver's license.
In the morning, reach the walled hilltop gem of San Gimignano, a UNESCO World Heritage site famed for its skyline of 14 medieval towers. Stroll through its remarkably preserved historic center, where cobbled alleys, Romanesque and Gothic architecture, and artisan shops evoke the charm of Tuscany’s medieval past.
Lunch at leisure and rest of the day free.
Overnight stay in Colle di Val d'Elsa at Palazzo San Lorenzo Hotel & Spa or similar.
Please note: The driver must hold a valid driver's license.
In the morning, enjoy a hands-on cooking class at a traditional Tuscan farm, where you’ll learn to prepare regional recipes using fresh, local ingredients. Then sit down to savour your creations over a relaxed lunch and wine tasting, surrounded by the charm of the countryside.
Rest of the day at leisure.
Overnight stay in Colle di Val d'Elsa at Palazzo San Lorenzo Hotel & Spa or similar.
Breakfast and check out. Drive to your next accommodation near Siena and leave your luggage at the hotel.
Explore one of Siena’s historic contrade—the city’s ancient districts that form the beating heart of its social and cultural identity. Each contrada is a close-knit community with its own emblem, museum, and centuries-old traditions tied to the famed Palio horse race.
On this immersive walk, you’ll discover quiet but significant corners, where the spirit of the neighbourhood endures through rituals, oral history, and strong local pride. Surrounded by timeless charm, experience the slower rhythm that reveals Siena’s most authentic soul.
Lunch at leisure and rest of the day free.
Overnight stay in Siena at Hotel NH Siena or similar.
In the morning, experience the prestige of Castello di Brolio, an icon of Chianti Classico and the cradle of Ricasoli winemaking. Enjoy privileged access to the castle’s private gardens, chapel, and family collection before continuing to the state-of-the-art winery for a curated tasting of three refined labels. A sophisticated immersion into one of Tuscany’s most historic and influential estates.
Take the afternoon at leisure to discover on your own pace the local villages such as Radda in Chianti and Gaiole in Chianti.
Overnight stay in Siena at Hotel NH Siena or similar.
After breakfast, enjoy your day at leisure.
Overnight stay in Siena at Hotel NH Siena or similar.
Check out and private transfer to your next accommodation. Drop off your luggage and reach Pienza.
Set out on a walking tour to discover the “perfect city” - an architectural gem worth the UNESCO site designation. Step into the stunning Palazzo Piccolomini, its Renaissance style hanging garden and the breathtaking view of the Val d’Orcia. Reach Rocca d’Orcia, a tiny hilltop medieval village dominated by the ruins of the Medieval Tower of Tentennano. Then enjoy a delightful lunch (reservation included - lunch à la carte to be paid on spot).
Finally, drive along winding country roads studded with vineyards, olive groves, green hills, and reach the Romanesque Abbey of Sant’Antimo, a beautiful and evocative Benedictine Monastery dating back to the 8th century.
Return to your accommodation for the check in and rest of the day at leisure.
Overnight stay in Castiglione d'Orcia at Relais Osteria dell'Orcia or similar.
In the morning, meet a local pecorino cheese maker and discover all the secrets of traditional cheese making in Pienza. Enjoy a tasting of local products and sheep cheese on a light lunch accompanied by local red wine.
Rest of the day at leisure.
Overnight stay in Castiglione d'Orcia at Relais Osteria dell'Orcia or similar.
Enjoy breakfast at the hotel, and the rest of the day is at leisure.
Overnight stay in Castiglione d'Orcia at Relais Osteria dell'Orcia or similar.
Breakfast and check out. Drive to your next accommodation.
En route Discover Viandante del Cielo winery (pending confirmation) an exclusive estate on the panoramic terraces above Lake Trasimeno, founded by George Lucas’s Skywalker Vineyards. Your private tour guides you through the vineyards, winery, and barrel cellar, ending with a terrace tasting of three wines and extra-virgin olive oil — an authentic and refined experience.
Continue to your accommodation in Perugia and rest of the day at leisure.
Overnight stay in Perugia at Realis dell'Olmo or similar.
In the morning, enjoy a walking tour of Perugia and visit Moretti‑Caselli Studio and Museum. Nestled in the historic centre of Perugia, the Moretti‑Caselli Studio and Museum is a living testament to five generations of master glass painters. Housed in a 15th‑century building that has preserved its original layout and period frescoes, the site invites visitors into an extraordinary world where artistry, history, and science meet.
Lunch at leisure and rest of the day free.
Overnight stay in Perugia at Realis dell'Olmo or similar.
After your breakfast, spend the day to discover the city on your own.
Overnight stay in Perugia at Realis dell'Olmo or similar.
In the morning, discover the charm and spirituality of Assisi on a guided walking tour through its cobblestone streets. Explore the town’s historic squares, medieval alleys, and charming piazzas, while visiting iconic landmarks such as the Basilica of San Francesco, Santa Chiara, and the Roman Temple of Minerva. Immerse yourself in the town’s rich history, art, and serene atmosphere, and enjoy stunning views over the Umbrian hills that have inspired pilgrims and travellers for centuries.
Lunch at leisure and rest of the day at leisure.
Overnight stay in Perugia at Realis dell'Olmo or similar.
Breakfast and check-out. Then, drive to Rome Airport to drop off your car and prepare for your journey home. Alternatively, you may return your car rental in Florence, depending on your departure arrangements.
Colle Val d'Elsa
Palazzo San Lorenzo is a wonderful ancient Tuscan residence with unique charm. It is in a perfect location, Colle Val d'Elsa, near the most interesting resorts of Tuscany.
Siena
Centrally located in Siena, within walking distance of Piazza del Campo and the Duomo. Offers stylish rooms, some with city views or Jacuzzi showers, plus a restaurant, bar, gym, meeting rooms, and bike-friendly facilities. Ideal for exploring the historic city.
Castiglione d'Orcia
Set in the Val d’Orcia countryside near Bagno Vignoni, this 16th‑century relais features elegant Tuscan-style rooms, an outdoor pool, restaurant serving local cuisine, bar, and garden. Guests enjoy scenic views, peaceful surroundings, and easy access to thermal spas and villages.
Perugia
Located near Perugia’s business district, this 43-room hotel offers allergy-friendly rooms with free Wi-Fi, a pool, spa, gym, and sauna. Guests enjoy on-site dining, a bar, meeting rooms, and easy access to city attractions and transport.
