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From Cortona to the Apennines Between Umbria and Le Marche: A Scenic Road Trip
With this fifth itinerary, our series “From Cortona by Car: Summer Itineraries Between the Sea, Villages and Cool Mountain Escapes” comes to an end. After traveling towards Maremma, the Romagna Riviera, Casentino and the Tuscan Apennines, we now go beyond Tuscany’s borders to discover the Apennines between Umbria and Le Marche. This route is designed for travelers looking for a more original journey, away from the most crowded itineraries and immersed in the authentic landsca
nicola boninsegni
Sep 44 min read


Tuscan Apennines from Cortona: The Cooler Side of Tuscany
Our summer series “From Cortona by Car: Itineraries Between the Sea, Villages and Cool Mountain Escapes” continues by climbing higher. After the sea of Maremma and the Romagna Riviera, and after the green landscapes of Casentino, it is time to discover a lesser-known side of Tuscany: the Tuscan Apennines. This is a different Tuscany from the one usually seen on postcards. It is not only rolling hills, vineyards and art cities, but also forests, abbeys, mountain villages, pano
nicola boninsegni
Aug 284 min read


Escape the Heat in Casentino: A Road Trip from Cortona to Forests, Castles and Monasteries
After two itineraries dedicated to the sea, our series “From Cortona by Car: Summer Itineraries Between the Sea, Villages and Cool Mountain Escapes” continues towards a closer, greener destination that is perfect for escaping the summer heat: Casentino. When summer in the Valdichiana becomes intense, you do not always need to drive all the way to the coast to find relief. Not far from Cortona and Arezzo, there is an Apennine valley made of forests, castles, monasteries, medie
nicola boninsegni
Aug 233 min read


From Cortona to the Romagna Riviera: A Weekend on the Adriatic
Vista di Anghiari
nicola boninsegni
Aug 74 min read


From Cortona by Car: Summer Itineraries Between the Sea, Villages and Cool Mountain Escapes Ep. 1: From Cortona to the Maremma Coast: A Scenic Road Trip to the Sea
Summer in Cortona has a special charm: the stone streets of the historic center, the hills of the Valdichiana, the sunsets over Lake Trasimeno and the authentic atmosphere of Tuscany that travelers love so much. But when temperatures rise, it is also the perfect time to get on the road, look for the sea, head towards the mountains or discover new places where the air feels cooler. This is why we have created our series “From Cortona by Car: Summer Itineraries Between the Sea,
nicola boninsegni
Aug 14 min read
Ai analyzes our Blog
We fed all the articles from our blog into AI, allowing it to analyse our itineraries, travel stories, tips, favourite places and the impressions we have collected over time. The result is this article: a thoughtful and creative synthesis of what emerges from our way of telling the story of Arezzo and its valleys. It is not simply a summary, but a new interpretation of the territory, woven together from the experiences, atmospheres and ideas already present in our content. In
nicola boninsegni
Jun 174 min read
Explore Arezzo and Valdichiana: Unmissable Events in June 2026
June is the perfect month to hit the road and discover the wonders of Tuscany. As the days grow longer and the weather warms up, the province of Arezzo and the beautiful Valdichiana come alive with historical festivals, open-air markets, and traditional food fairs. Having a rental car at your disposal allows you to travel comfortably between medieval villages and city squares without missing a single event. Here is our curated selection of the most fascinating events to make
nicola boninsegni
Jun 12 min read
Discover December Events in Arezzo and Valdichiana!
December turns our area into a true wonderland, blending tradition, art, and holiday atmosphere for visitors of all ages. Here’s a selection of the month’s top events: Arezzo City of Christmas (15 November 2025 – 6 January 2026) Arezzo’s historic center is filled with magic: Tyrolean Christmas markets in Piazza Grande, unique light installations, an ice skating rink, panoramic wheel, and the “Forest of Emotions.” Also not to miss are Santa’s House at the Medici Fortress and l
nicola boninsegni
Nov 29, 20252 min read
OCTOBER EVENTS IN AREZZO AND SURROUNDINGS
1. Flavors of Casentino (Pratovecchio, first weekend of October) This food festival celebrates the culinary heritage and typical products...
nicola boninsegni
Sep 28, 20252 min read
The 4 Valleys of Arezzo – 48 Hours in Casentino
Casentino, land of Etruscan roots, ancient monasteries and green forests. Day 1: Morning: Visit Bibbiena (Piazza Tarlati, Santa Maria...
nicola boninsegni
Aug 31, 20251 min read
Arezzo in Celebration: History, Tradition, and Art at the September Joust of the Saracen and Antiques Fair
September is when Arezzo reveals its most authentic and lively soul, transforming into a vibrant stage of events blending history,...
nicola boninsegni
Aug 29, 20254 min read
The 4 Valleys of Arezzo – 48 Hours in Valtiberina
A journey into Renaissance art, spirituality and scenic beauty along the Tiber Valley. Day 1: Morning: Visit Anghiari and the Battle...
nicola boninsegni
Aug 17, 20251 min read
The 4 Valleys of Arezzo – 48 Hours in Valdarno
Valdarno offers scenic views, medieval villages and stories from the heart of Tuscany. Day 1: Morning: Discover San Giovanni Valdarno...
nicola boninsegni
Aug 3, 20251 min read
The 4 Valleys of Arezzo
“The 4 Valleys of Arezzo” invites you to explore the most authentic soul of the Arezzo province through its four valleys: Valdichiana,...
nicola boninsegni
Jul 21, 20251 min read
The Rhythm of Blues Invades Torrita di Siena: Don't Miss the Torrita Blues Festival!
Dear music lovers and fans of vibrant atmospheres, Get ready for a weekend dedicated to great blues music! From June 26th to 28th,...
nicola boninsegni
Jun 22, 20251 min read
Experience the Thrill of the Giostra del Saracino in Arezzo!
Dear friends and travelers, Get ready for an unforgettable experience in the heart of Tuscany! Next Saturday, June 21st, Arezzo will dive...
nicola boninsegni
Jun 14, 20251 min read
First Seaside Trips: Maremma or Romagna? Double Short Distance Choiche From Cortona
--- As June arrives, the desire for sunshine, sea, and relaxation becomes irresistible. From Arezzo, in just over 2 hours, you can reach...
nicola boninsegni
May 25, 20252 min read
How to Choose the Right Car for Your Tuscan Holiday
Number of Passengers 1-2 people: compact car 3-4 people: medium sedan 5+ people: minivan or SUV Groups: van or minibus Luggage Type Large...
nicola boninsegni
May 23, 20251 min read
Farmers' Markets: A Journey Through Authentic Flavors of Valdichiana
Spring transforms Valdichiana's farmers' markets into a kaleidoscope of colors and flavors. These markets are not just trading places,...
nicola boninsegni
May 10, 20251 min read
Seasonal Events in Valdichiana: A Complete Guide
Spring (March-May) Flower Fair - Foiano della Chiana When: April Highlight: Floral exhibitions, local crafts Activities: Gardening...
nicola boninsegni
May 9, 20251 min read
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