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We will spend the week in the Umbrian hills, between the beauty of the Italian countryside and Lake Trasimeno, while we explore Umbria and Tuscany together.
Private only to us, this estate holds an 18th century farmhouse beautifully restored with modern comforts, an apartment and a stand alone house with epic views.
Pool
Air Conditioning
Private to only us
Welcome to Di Colle in Colle
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Our Week in Tuscany
We pick you up via private transport at the Rome FCO airport.
You arrive at the sprawling property and get settled in your room.
Enjoy welcome snacks and wine as all our friends roll in.
Dinner will be a home made Italian meal cooked by our private chef at the villa.
*order of events subject to change
After breakfast at the villa, we head to tour an olive oil mill before heading to Cortona for a private tour of the city. After the tour, we will have some free time to grab lunch and explore the streets of this medieval town.
Private transportation to and from the villa is provided.
When we return to the villa, relax by the pool before dinner provided by our private chef.
After breakfast at the villa, a private transfer will take us to Florence for the day. We will start the day with a private tour hitting the famous food market for cheese tasting, gelato in a historical artisanal gelato shop, wine from an iconic wine window and a stop at the Accademia Gallery to see the incredible David by Michelangelo.
You will have some time to wonder the city on your own before we return to the villa in time for dinner prepared by our private chef.
Following breakfast at the villa, we will travel 15 minutes to the property's very own winery where we will have a private wine tasting while enjoying the expansive views of Umbria.
We will head back to the estate for a private cooking class, lunch and free time to relax by the pool and wonder the property.
Dinner will be prepared by our own private chef at the villa.
After breakfast at the villa, a private driver will take us to Siena where we will have a private guided tour of the history of the city, the contrades and the famous Palio di Siena.
After the tour, you will have time to explore the city on your own and grab some lunch.
We will head back to the villa for dinner prepared by our private chef.
Today, after breakfast at the villa, we will visit a small family run chocolate factory for a tasting before heading to Assisi for the day.
We will take a guided tour of Santa Maria degli Angeli church where Saint Frances is buried, see the Basilica and the historical centre of Assisi. You will also have free time to explore.
We will return to the villa in time for our private dinner.
Today after breakfast, we will travel to Pienza, known as the Renaissance Utopia. We will stop for a tasting of the famous local pecorino in a small family run cheese shop.
After lunch, we will head to Montopluciano. You will have time to explore on our own and grab some lunch. This is the best Tuscan town for purchasing your Tuscan leather so there will be more than enough time for shopping.
We will return to the villa for dinner.
It's been a beautiful week. It's not goodbye - but see you again soon.
After breakfast at the villa, your private transfer will take you to the Rome airport.
M: Lemon Always
B: Caffe
Spending time in the Tuscan countryside is life changing. The expansive views, the gothic, medieval architecture, the fascinating stories of the locals - it's a place that never leaves you.
Which is why we are so excited to be hosting our first Tuscan Group Trip in June 2027.
If Tuscany is on your vision board - this is your chance to soak in the beauty, energy and inspiration of Italy, without the overwhelm of planning it all yourself.
All you have to do is say yes. We'll take care of the rest.
We will provide transportation to/ from the villa from the Rome FCO airport. Please note that Tuscany is fairly remote so the drive from Rome is approx. 3 hours. The drive is mostly highway and in air conditioned vehicles.
Breakfast every morning will be provided at the villa. Lunch will be on your own every day (we will be exploring every day so you can grab lunch at whatever town we are in that day). On the day of the winery / cooking class - we will provide lunch that day. Dinner and wine will be provided every night.
Yes! A deposit of $1000 per person is needed to secure your room.
Half the remaining balance will be due in October 2026 and the remaining balance due January 2027.
You also can pay in full if you prefer.
All excursions are included in the cost of the trip.
Click HERE to check out the available rooms. Choose the room you would like to book and fill out the contact form at the bottom of the page. Just drop us a note letting us know what room you would like to reserve and we will be in touch within 24 hours with a link to pay your deposit.
Please note - requesting a room does not lock in your reservation, making your deposit does.