Inspiration for your own tailor-made trip
Vineyards, Food and Frescoes Italian Road Trip in Tuscany and Umbria
Italy – Florence – Chianti – Cortona – Perugia
Your journey begins in Florence, straddling the tranquil waters of the Arno. Palaces, museums and grand piazzas set the scene, and we’ll arrange tickets to the dazzling Grand Duomo Museum for an immersive introduction to the city’s artistic legacy. From here, it’s time to hit the road and head into the Tuscan countryside, spending time in Chianti amid vineyards and gentle hills, with opportunities for wine tastings and excursions to Siena.
The route then leads east to Cortona, a lovely hill town surrounded by vines and olive groves, and on to Arezzo, celebrated for its food and frescoes. Finally, you’ll head to Perugia, Umbria’s vibrant capital full of Etruscan, Roman and Gothic architecture, before journeying home.
Itinerary
100% customisable for you
Your Italian adventure begins with a two-hour flight to Florence. On arrival, you’ll be privately transferred to your accommodation for the first two nights, ideally located in the historic heart of the city and perfectly placed for exploring its museums, churches and cafés.
Today, we’ll arrange skip-the-line tickets to the Grand Duomo Museum, the largest museum complex in Florence. Your visit includes access to Brunelleschi's dome, the Cathedral, Campanile, Baptistery, Crypt and the museum itself. Inside, you’ll find original and reconstructed architecture and sculptures from some of Florence’s most iconic buildings, including the Florence Duomo, the Baptistery of Saint John and Giotto's Campanile.
The grandeur of these historic buildings is clear to see, whether in Lorenzo Ghiberti’s Gates of Paradise – a gleaming set of doors created for the Baptistry – or the reconstructed facade of the Duomo itself, which contains 40 exact replicas of the sculptures on the original façade. You’ll also find a poignant, unfinished Michelangelo sculpture here, which he carved for his own tomb. If you’d like to see more of Michelangelo’s work, we can arrange a private tour of the Accademia Gallery.
Today, you’ll pick up your rental car and drive south into the heart of Chianti, around 35 minutes from Florence. You’ll spend two nights here, so be sure to carve out some time to visit a vineyard and sample their creations. The remainder of your stay here can be spent visiting the Romanesque churches and fortresses, or admiring the frescoes of Cosimo Gheri's studio.
If you like, we can also arrange guided experiences in Siena, including walking tours focused on the city’s history and traditions, such as the famous Palio horse race.
Continue east through the countryside to Cortona, a scenic drive of around an hour and a half. En route, we can arrange a wine tasting and leisurely lunch at a local vineyard.
Your home for the next two nights is a historic villa where the beautiful garden converges on fields of vines and tobacco. Sunny days can be spent cooling off in the swimming pool, and when you get peckish, tuck into inventive seasonal cuisine in the hotel restaurant.
Far from the hustle and bustle of Florence, Arezzo is a small country town that’s known for its artistic heritage and fabulous food. Specifically, this town owes its reputation as a city of art to Piero della Francesca and his frescoes in the Basílica de San Francisco. We’ll arrange for you to visit Arezzo with a private guide today, taking in highlights such as the Basílica de San Francisco along with the church of Santa Maria della Pieve, the Piazza Grande, the Duomo and the Basilica of San Domenico.
If you’d prefer to continue discovering Tuscany’s wine regions, we can arrange a visit to the hilltop town of Montepulciano for a private wine tasting.
You’ll swap Tuscany for Umbria today, driving for just under an hour until you reach its capital, Perugia.
This lively university city blends Etruscan, Roman and Medieval influences, with cobbled alleyways and panoramic viewpoints. The next two days here are yours to spend as you please, whether that means shopping for traditional ceramics or sipping Aperol spritz with a view across the rooftops.
If you’d like to explore further, we can arrange a private guided visit to Assisi and the Basilica of San Francesco.
It’s time to say arrivederci to Italy today. Drive to Perugia airport, return your rental car and board your flight back to the UK, bringing your Italian road trip to a close.
Suggestions
Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included
DISCOVER MICHELANGELO'S WORK IN FLORENCE'S ACCADEMIA GALLERY
At just 26 years old, the genius sculptor Michelangelo began work on his Florentine masterpiece: ‘David’. He would go on to play a central role in many of the city’s important artistic projects, including the façade of the San Lorenzo church and the Medici Chapel. During this private tour of the Accademia Gallery, you’ll come face-to-face with some of his incredible pieces including ‘Prisoners’ (also known as ‘Slaves’) and ‘David’, his most famous work.OFF-THE-BEATEN-TRACK TOUR OF SIENA
Built across three clay hillsides, Siena’s Medieval streets wind inside impressive walls before opening out onto the Piazza del Campo, the beating heart of the city. Each summer, this famous square hosts the Palio di Siena, a historic horse race between the city’s 17 districts. During this private tour, you’ll step away from the main thoroughfares to explore Siena’s quieter alleyways, gaining an insight into daily life in this fascinating city.WINE TASTING AND TOUR OF MONTEPULCIANO
Set high on a hill between the valleys of Chiana and Orcia, Montepulciano is a small Renaissance town with a Medieval soul. It is best known as the home of vino nobile, one of Tuscany’s most celebrated wines. During this private tour of the old town, you’ll see the Piazza Grande, the cathedral, the Palazzo Comunale, the Contucci and Nobili-Tarugi Palaces and the San Biagio church. Afterwards, you’ll head to a local wine cellar for a tasting at a family-run estate, traditionally overseen by the women of the household.TOUR OF ASSISI
Listed as a UNESCO World Heritage site, the small Medieval town of Assisi is the birthplace of Saint Francis and closely linked to the Franciscan Order. During this private tour, you’ll learn more about the masterpieces it contains, and why it’s a benchmark for the artistic and architectural development of Italy and Europe.
Why visit Italy with Original Travel ?
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
Enquire nowA few of the benefits of travelling with us to Italy
- Our local Concierges
- The Original Travel app
- Destination Dossier
- 24-hour helpline
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