Arrive in Florence and transfer to your hotel.
The rest of the day is free to settle in and explore at your own pace.
Overnight in Florence at Hotel Plaza Lucchesi.
Colle Val D'Elsa, Tuscany
Peace of Mind
Exclusive Packages
Central Italy Winter Escape - Florence, Tuscany & Umbria
Colle Val D'Elsa, Tuscany
Florence
Hand-on Pasta making
Perugia
Piazza del Campo, Siena
In partnership
Overview
Experience Italy at a slower, more authentic pace on this self-drive winter journey through Florence, Tuscany and Umbria. Begin in Florence, where Renaissance landmarks, historic streets and local cafés set the scene for your journey. From here, take the wheel and explore the countryside at your own pace, following scenic routes through Chianti’s rolling vineyards, olive groves and charming hilltop villages.
Along the way, enjoy a series of curated local experiences, from hands-on cooking and regional tastings to private guided tours that bring each destination to life. Discover Siena’s medieval character, explore Perugia’s historic centre with a chocolate tasting, and visit Assisi and nearby villages where traditions remain part of everyday life.
Travelling in winter offers a quieter and more atmospheric side of Italy, with fewer crowds, festive Christmas markets, twinkling lights and a more relaxed rhythm in both cities and countryside. It’s the perfect time to connect more deeply with the destination, from local food to small-town charm, often missed in peak season.
This itinerary is designed as a flexible journey, allowing you to tailor the pace, experiences and accommodation to suit your travel style, while still enjoying the ease and freedom of a self-drive journey.
Itinerary
Day 1 Florence
Day 2 Florence
Florence Walking Tour & Local Tasting
In Piazza della Repubblica, trace the city’s origins back to its days as a Roman settlement, then follow the narrow medieval streets as they weave between ancient tower-houses and echoes of guilds, merchants, and artisans. These winding alleys suddenly open onto Piazza della Signoria, the stage of Florence’s political life since the Middle Ages. From here, the city’s icons unfold one after another: the Duomo with its magnificent dome rising above the rooftops, and the Ponte Vecchio arching gracefully over the Arno. You’ll end your walk on a softer note: a cappuccino tasting in one of the city’s finest pastry shops, where Florentine tradition lingers in every aroma and every sip, a small, delicious pause at the end of a journey through centuries. Duration: 3 hours.
The rest of the day is at leisure in Florence.
✨ Seasonal highlight (Nov–Dec) During the winter season, Florence is enhanced by elegant Christmas markets and festive light installations, creating a warm and atmospheric setting throughout the historic centre.
Overnight in Florence at Hotel Plaza Lucchesi.
Breakfast
Day 3 Florence
Market Visit & Tuscan Cooking Class
Accompanied by a local chef, explore a traditional Florentine market where seasonal ingredients, local produce and regional specialties reveal the flavours of the territory. The experience continues in the kitchen with a hands-on cooking class, where you will learn how to prepare traditional dishes, including homemade pasta, guided by simple gestures passed down through generations. Afterwards, sit down to enjoy the meal you have created ,a convivial moment that captures the essence of Italian hospitality.
The rest of the day is free to continue exploring Florence at your own pace or to enjoy the city’s atmosphere in a more relaxed and personal way.
Overnight in Florence at Hotel Plaza Lucchesi or similar.
Breakfast, Lunch
Day 4 Florence Chianti countryside Siena
Chianti Countryside & Olive Oil Experience
After breakfast, pick up your car rental and drive into the rolling Tuscan countryside,passing vineyards and olive groves.
Along the way, stop for a visit to a local olive oil producer in the Chianti area and learn about the process. Enjoy a relaxed tasting lunch featuring regional products.
✨ Seasonal note During winter, the Tuscan countryside reveals a quieter and more authentic side, far from peak-season crowds, ideal for a relaxed self-drive experience.
Overnight in Siena at Hotel Athena or similar.
Breakfast, Lunch
Day 5 Siena
Siena’s Medieval Charm walking tour
Discover Siena with a private guided walking tour that brings its medieval identity to life.
Explore the magnificent Piazza del Campo, one of Europe’s most iconic squares, before visiting the striking Duomo, a masterpiece of Italian Gothic architecture. Along the way, learn about local traditions that still shape daily life, including the historic Palio. Pause in a traditional café to taste ricciarelli, Siena’s almond biscuits, paired with a cappuccino, a simple yet authentic moment of local life. Duration: 2 hours.
The rest of the day is at leisure to wander through Siena’s narrow streets, browse artisan boutiques or simply enjoy the peaceful rhythm of the Tuscan countryside.
Overnight stay in Siena at Hotel Athena or similar.
Breakfast
Day 6 Siena Perugia
Into Umbria & Perugia Walking Tour
Continue your journey into Umbria, often referred to as Italy’s green heart.
Upon arrival, enjoy a private walking tour of Perugia, where medieval streets, layered architecture and panoramic views reveal the city’s rich character. The experience is enriched by a chocolate tasting, celebrating one of Perugia’s most enduring traditions.
✨ Seasonal highlight (Nov–Jan) During the festive season, Perugia’s Rocca Paolina hosts a unique underground Christmas market, creating a particularly evocative atmosphere.
Overnight in Perugia at UNA Posta Donini or similar.
Breakfast
Day 7 Perugia Assisi & Umbrian countryside Perugia
Assisi & Umbrian Hill Towns
Today is time to drive to Assisi, drive through the Umbrian countryside.
Explore Assisi with a private guided walking tour, discovering one of Italy’s most spiritual and evocative towns. Walking through its quiet stone streets, you will encounter its most significant landmarks, including the Basilica of Saint Francis, while experiencing the serene atmosphere that defines the town.
Later, continue through some of Umbria’s most charming villages, where artisan traditions remain deeply rooted in daily life. Stops may include towns such as Deruta, renowned for its hand-painted ceramics (suggestion) and you can consider to visit the Ceramics Museum (not included). Duration: 2,5 hours.
Return to your hotel and enjoy a final evening immersed in the tranquil atmosphere of Perugia.
Overnight in Perugia at UNA Posta Donini or similar.
Breakfast
Day 8 Perugia
After breakfast, check out of your hotel and return your car before continuing your journey.
Breakfast
Accommodation
Hotel Athena
Siena
Located just outside Siena’s historic walls, Hotel Athena combines convenience with a more relaxed setting.
The hotel offers easy access to the old town on foot, while providing additional space, views and on-site parking ideal for a self-drive itinerary. Rooms are spacious and comfortable, and the panoramic terrace opens onto sweeping views of the Tuscan countryside, creating a calm and easy base to explore Siena.
UNA Posta Donini
San Martino in Campo
Set within a historic estate just outside Perugia, UNA Posta Donini offers a peaceful countryside stay surrounded by landscaped gardens. The property blends historic character with a more refined, tranquil atmosphere, making it an ideal retreat after time in the cities. Rooms are spacious and quiet, with a mix of classic and modern elements, while facilities include a restaurant focused on regional cuisine, a wellness area and generous outdoor spaces that invite a slower pace.
Central Italy Winter Escape - Florence, Tuscany & Umbria
Italy
From AUD 6,795pp
stars, 89 reviews
From AUD 6,795pp