Name: Autumn in Italy: Tuscany & Umbria
Start: 2025-10-25T00:00:00.000Z
End: 2025-11-01T00:00:00.000Z
Location: 52044 Cortona, Province of Arezzo, Italy

Cross Cultural Journeys

Email address verified

12 reviews

Oct 25 - Nov 1, 2025

Group size: 10 - 14

Autumn in Italy: Tuscany & Umbria

52044 Cortona, Province of Arezzo, Italy

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Cross Cultural Journeys

Email address verified

12 reviews

$3,995

Deposit: $500

Oct 25 - Nov 1, 2025

Group size: 10 - 14

Join Cross Cultural Journeys for an opportunity to experience the beauty of Italy on a 7-night journey through Tuscany and Umbria, staying in a charming agriturismo villa nestled in the rolling Tuscan hills. Enjoy authentic Tuscan meals made from local, seasonal ingredients, and savor the rich flavors of the region. Explore medieval towns with private guided tours of Assisi, Orvieto, and Montepulciano, and immerse yourself in the region's culture with a hands-on Italian cooking class, where you'll learn to make traditional dishes.

Your adventure also includes wine tastings at local vineyards, where you'll sample renowned wines such as Chianti and Vino Nobile di Montepulciano. This fall journey offers a perfect blend of culinary delights, stunning landscapes, and cultural exploration, providing you with an unforgettable Italian escape.

Your trip will include:

* 7-night stay in a charming Tuscan agriturismo villa

* Authentic Tuscan meals (breakfast + lunch or dinner daily)

* Private guided tours

* Traditional Italian cooking class
* Montepulciano wine tasting

* Olive oil experience

* Transport to/from Florence train station

INCLUDED:

In-country transportation per itinerary; best available agriturismo accommodations; meals while on-site at the villa; one Cross Cultural Journeys trip manager; English-speaking local guides; all excursions & entrance fees on itinerary; preparation materials.

NOT INCLUDED: Airfare from the United States to and from Italy. Meals not on itinerary; alcoholic drinks; add-on excursions & entrance fees not on the itinerary; tips for local guide(s) and driver; travel insurance.

TRAVEL PROTECTION: Cross Cultural Journeys is not responsible for cancellation expenses that you might incur before or during our trip. You may want to check first to see if your current insurance policy covers travel abroad, but we have found that most do not. We strongly encourage considering taking out travel interruption and evacuation insurance to cover any emergencies abroad such as evacuation, or reimbursement for cancellation due to your own illness or an illness in your family. We encourage you to choose a plan covers travel interruption before you depart, as well as during the trip. CCJ is not responsible for events beyond our control in this regard.

This itinerary is a living document and subject to change based on local schedule changes and circumstances beyond our control. Hotels, events and restaurants may have to change, sometimes at the last minute, to a similar category. We take this as an opportunity to perhaps meet someone new while we are on our journey, or to engage in an activity we could not have foreseen/planned.

Jesus Noguera resides in Palermo, Sicily, where he spends half the year immersing himself in the vibrant Italian culture, history, and lifestyle. His time in Italy allows him to savor the rich cuisine, picturesque landscapes, and warm community, adding depth to his already broad perspective of the world. Whether enjoying the charm of Sicily or exploring the local traditions, Italy has become a second home for him.

When he’s not in Italy, Jesus is based in Havana, Cuba, where he’s a sought-after guide with over 20 years of experience. A graduate of the Higher Institute for International Relations (ISRI), he combines his deep knowledge of Cuba’s culture with an insatiable curiosity for the world. Fluent in several languages and having visited over 30 countries, Jesus is passionate about sharing his expertise with travelers. A proud father of two daughters and a grandfather to a young granddaughter, he thrives in balancing his Cuban heritage with his Italian lifestyle, offering a unique perspective to those who cross his path.

Day 1
Day 1
Florence >> Cortona
Your guide will meet you at the train station in Florence to begin your trip. The drive from Florence to Cortona is a picturesque journey through the heart of Tuscany, covering about 110 kilometers (68 miles). The trip takes approximately 1.5 to 2 hours by car.

We'll pass through the rolling hills of the Chianti region, famous for its vineyards and charming towns like Greve in Chianti. Further along, we might stop in Arezzo, a beautiful city known for its medieval architecture and the Piazza Grande.

Check in at our Agriturismo, a charming countryside villa located near Cortona, offering guests an authentic Tuscan experience. Set amidst the rolling hills, vineyards, and olive groves typical of the region, this villa provides a peaceful escape with rustic yet comfortable accommodations.

Evening welcome dinner.

Meals: D
Sleep: Agriturismo Villa, Cortona
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Day 2
Day 2
Cortona & Surroundings
Today's activities will be filled with exploration of the area's incredible history.
We will visit the MAEC Parco, also known as the Archaeological Park of Sodo, which features two monumental Etruscan burial mounds, known as meloni, dating back to the 6th century BC. We will explore the ancient tombs and admire the impressive funerary architecture, including stone carvings and remnants of burial chambers.

We will also visit the Basilica e Santuario di Santa Margherita, a church perched on a hill overlooking Cortona and the Eremo Francescano Le Celle, a peaceful Franciscan hermitage located just outside Cortona, nestled in a wooded valley.

After lunch we will have a guided walking tour of the town of Cortona, before returning to the villa. We will enjoy dinner at our lovely accommodations.

Meals: B/D
Sleep: Agriturismo Villa, Cortona
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Day 3
Day 3
Orvieto
Orvieto is a historic city renowned for its striking cathedral, medieval architecture, and strategic location atop a volcanic plateau. Today, it remains an important destination for its artistic treasures, historical sites, and unique architectural features. We will take the funicular in Orvieto, a cable car system that connects the medieval city, perched on a hill, with the modern town below.

We will visit the Fortezza Albornoz, as well as one of Italy’s most celebrated cathedrals, Il Duomo di Orvieto, a magnificent Gothic cathedral renowned for its stunning façade and intricate artwork.

Before lunch we will also get a chance to explore Il Pozzo della Cava, an ancient underground well and archaeological site.
Later in the afternoon we will visit the Chiesa di Sant'Andrea e San Bartolomeo, a prominent Romanesque church founded in the 12th century.

Meals: B/L
Sleep: Agriturismo Villa, Cortona
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Day 4
Day 4
Assisi
Today we visit Assisi, an important and historic city in central Italy, renowned for its medieval architecture and its association with Saint Francis of Assisi. The historical center is a UNESCO World Heritage Site, characterized by narrow, winding streets, ancient stone buildings, and significant religious landmarks. We will visit key sites including the Basilica of Saint Francis, which houses frescoes by Giotto, and the Basilica of Saint Clare. The city's architecture and layout reflect its rich history and its role as a center of spirituality and art.

In between site visits, we will enjoy lunch at a well-regarded eatery known for its traditional Umbrian cuisine.

Meals: B/L
Sleep: Agriturismo Villa, Cortona
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Day 5
Day 5
Castiglione del Lago
Today our adventures take us to Castiglione del Lago, a charming town located on the western shore of Lake Trasimeno. Known for its well-preserved medieval architecture, it features a historic fortress, picturesque lakeside views, and narrow, winding streets. The town is renowned for its scenic beauty and historic sites, making it a popular destination for visitors exploring the region.

You will also have time to enjoy La Merangola, a popular beach located near Castiglione del Lago on the shores of Lake Trasimeno.

We will return to our hotel for a cooking class with our host Giusi, followed by dinner.

Meals: B/D
Sleep: Agriturismo Villa, Cortona
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Day 6
Day 6
Montepulciano & Pienza
Today is a full day of explorations and wine tastings!
We will start in Montepulciano a historic hilltop town in Tuscany, renowned for its medieval and Renaissance architecture. We will visit the Piazza Grande and the Church of San Biagio. Montepulciano is also famous for its Vino Nobile di Montepulciano, a distinguished red wine, and its charming narrow streets, which offer picturesque views and a rich cultural experience.

We will enjoy an immersive wine tasting experience focused on Vino Nobile di Montepulciano. The visit will begin with a guided tour of the winery, where guests learn about the winemaking process and the history of the region. The tour includes a walk through the vineyards and cellars. Following the tour, we will partake in a tasting session accompanied by local cheeses and other regional delicacies.

We will also visit Pienza, a picturesque Tuscan town, known for its Renaissance architecture and stunning views of the Val d'Orcia.

Meals: B/L
Sleep: Agriturismo Villa, Cortona
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Day 7
Day 7
Final Day - Cortona
On our last day in Cortina we will visit the Frantoio Molitura Tradizionale that produces high-quality, locally made olive oil using traditional methods.

We will also visit the Fortezza di Girifalco, a significant military fortification originally built in the late 16th century during the Renaissance. We will explore the historic ramparts and enjoy the panoramic vistas. We will end our adventures with a walk around the town in Cortona.

This evening we will have our farewell dinner.

Meals: B/D
Sleep: Agriturismo Villa, Cortona
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Day 8
Day 8
Departure Day
After breakfast we will check out of our lovely accommodations and make our way back to the central train station in Florence for our journeys back home or beyond!

Meals: B
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Day 1

Florence >> Cortona

Your guide will meet you at the train station in Florence to begin your trip. The drive from Florence to Cortona is a picturesque journey through the heart of Tuscany, covering about 110 kilometers (68 miles). The trip takes approximately 1.5 to 2 hours by car.

We'll pass through the rolling hills of the Chianti region, famous for its vineyards and charming towns like Greve in Chianti. Further along, we might stop in Arezzo, a beautiful city known for its medieval architecture and the Piazza Grande.

Check in at our Agriturismo, a charming countryside villa located near Cortona, offering guests an authentic Tuscan experience. Set amidst the rolling hills, vineyards, and olive groves typical of the region, this villa provides a peaceful escape with rustic yet comfortable accommodations.

Evening welcome dinner.

Meals: D

Sleep: Agriturismo Villa, Cortona

I enjoyed this trip very much. It was very well organized with timely communication and updates. The hotels were very clean and the meals provided offered great variety & were delicious.

By Catherine A for Momentum Music School on Jul 17, 2024

We loved our trip! Our tour guide Kat was amazing, she was so personable and on top of everything (and special bonus, she offered yoga on the beach at sunrise - one of my trip highlights). We also loved the Spanish tour guides! I would definitely use Kat and Cross Cultural Journeys for future travel plans!

By Rachel B for Momentum Music School on Jul 17, 2024

THANK YOU for the most amazing tour to Barcelona and Tossa de Mar imaginable!! I've heard back from all of the families and everyone had a spectacular time. Several of the families with younger children specifically said that the tour organization and community allowed them to do much more than they would have been able to had they been on their own. For me, it was a wonderful example of the potential of teamanship. We had 6 age groups on this tour: 4-5 year olds, 6-8 year olds, 10-12 year olds, 13-16 year olds, parents, and grandparents (Kat, do I have those ages correct?). The tour appealed to each age group for different reasons. The pool time at each hotel was a huge key to success. The flexibility to step in and step out of activities was also very important. The discussion we had at Marrakesh back in December helped guide important decisions about the activities we participated in. Everyone loved the boat tour, and the guided tours of Picasso and Gaudi were really important as well. It was terrific to have down time for the pool or for shopping (making the teens very happy!). Montserrat was incredible. Pol and his guides were very approachable, interesting, and personable. Kat was an incredible master tour guide. She was so adept at herding us all around, solving problems in the background so that everyone (especially me) could focus on the music and on making the activities relevant and right for their family. There was time and opportunity for serendipitous concerts, and Kat was so supportive of this. She was incredibly supportive of everyone. AND, she turned from master tour guide into master yogi and led us in two 5:45 a.m. yoga sessions on the beach - true highlights for me and for everyone that participated. The proof of the success of the tour was in the final dinner. I've never seen such joy and camaraderie, and this at the end of a very demanding 8 days! I put a day by day post with photos on Facebook. I'll put photos on my website and on the shared google drive as well. Please feel free to use anything to promote your incredible tour company! I sincerely hope that we can work together for the next studio tour. I'd love to offer one every three years. I hope that Kat will help us plan and guide us once again next time. Lots of love and gratitude, Tracy

By Tracy W for Momentum Music School on Jul 17, 2024

Vi hade en bra resa. Bra boende och god mat. Intressant att möta andra halvan av släkten.

By Mirja H for Dubbelman Family Reunion on Jun 26, 2024

Everything was well planned and the hotel choices were spot on. We had several wonderful guides to show us around and give us insights into their country, history and culture. Well done Kat !