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Incredible Umbria & Tuscany
10 days9 nights
Trip Type
Private tour
Private tour
Travelers
Price options
Please select date
Assisi
3nights
Italyit
Le Silve di Armenzano
Superior Double Room, Ensuite
Included
Superior Double Room, Ensuite
Superior Double Room, Ensuite
Up to 2 guests
1 Double Bed
30 m²
Breakfast included
Plans for Assisi

Day 1: Arrival
Welcome to Umbria! Upon arrival, you are transferred you to the hotel for check-in.

The rest of the day is at your own leisure to relax after the trip.

Day 2: Assisi City Tour & Trip to Gubbio
After breakfast you meet your guide and start a walking tour of Assisi which is described as the cradle of Romanesque art and design. UNESCO-listed Basilica of San Francesco with traces of the most famous artists of the period and the other Franciscan Sites in Assisi definitely make you immerse into the atmosphere of the Middle Ages.

Following break for lunch you are transferred to Gubbio set on the slope of Mt. Ingino. Beautiful Piazza Grande with the public palaces on it, Palazzo dei Consoli, a magnificent Gothic building completed around 1340, Palazzo del Podestà which holds the Town Hall and Ruins of Roman amphitheatre are among the sights you see here.

After the tour you return back to your Assisi hotel.

Day 3: Exploring Umbria Countryside
In the morning you meet your driver in the hotel lobby and start an exciting tour of Umbria countryside.

Your first stop for today is the medieval fortress city of Spoleto. Here you enjoy a private guided walk of the town covering its numerous Roman temples, theatres and arches.

The next on your list is Bevagna. The town excites its visitors with half a dozen medieval churches, two of Roman temples and the remains of a Roman theatre.

You continue to Spello. Its Roman origins can be seen in the stone gates and the ancient walls surrounding the village.

After the tour you are driven back to Assisi.

Day 4: Departure
After breakfast you check out and depart from Assisi.

map
Included experiences2 Experiences
Assisi City Tour & Trip to Gubbio
Included
Full day
Assisi City Tour & Trip to Gubbio
Exploring Umbria Countryside
Included
Full day
Exploring Umbria Countryside
Want to add more experiences
Assisi car services
Arrival transfer is included in your trip
Assisi car services
Arrival transfer is included in your trip
Arrival
Private Rail Station Transfer
Included
Departure
Departure transfer
Not selected
Included
Assisi
Assisi hotel
Assisi, Italy
8 h
Montepulciano
Montepulciano hotel
Montepulciano, Italy
Montepulciano
3nights
Italyit
Borgo San Vincenzo
Signature Suite
Included
Signature Suite
Signature Suite
Up to 2 guests
1 King Bed
37 m²
Breakfast included
Plans for Montepulciano

Day 4: Arrival
Upon arrival, you check in to your hotel and have a good rest.

Day 5: Tour to Cheese Farm and Winery in Pienza & Montepulciano
In the morning after breakfast you have another amazing experience as today you visit a Pecorino cheese farm.

Your driver-guide takes you to Pienza, the area known for the wonderful Pecorino di Pienza cheese, which gets its name from the word pecora, Italian for "sheep". This delicious "sheep" cheese is made exclusively in and around the town of Pienza from sheep’s milk. In the beginning, you have a tour of the historical center of Pienza, included into the list of UNESCO World Heritage Sites. You enjoy the views of wonderful Renaissance Palazzo Piccolomini, the beautiful Cathedral of Pienza and Palazzo Comunale.

You are then driven to a gorgeous rustic organic cheese farm that sits on top of a hill overlooking the entire Val d’Orcia and even Pienza itself. Here the local cheese producer shows you how the pecorino sheep cheese is made and the many stages of aging from soft and fresh to hard and complex.

You proceed with a visit to a traditional winery on a small farm near Montepulciano. Here you enjoy tasting one of the most famous Italian wines: Vino Nobile di Montepulciano*. The Nobile wines of Montepulciano were the first to be given the ultimate quality level of DOCG certification.

You have a guided tour of the Montepulciano historical center before you finally return to your hotel.

*Please note: there are 255 wineries in the region so if there is any particular that you wish to visit - let us know and we will modify program accordingly.

Day 6: Cooking Class in Montalcino
Today following breakfast your private driver-guide picks you up from the hotel and drives you first to Montalcino. The ancient village is best known for its red Brunello di Montalcino wines, made with Sangiovese Grosso grapes.

Upon arrival, you have a cooking class in a local farm restaurant located just few kilometers outside of the village. Here you learn how to cook a traditional Italian meal and about Italian dining traditions. Your experience starts from picking spices and vegetables and collecting the eggs. After about 3 hours of the workshop, you enjoy a full Italian lunch which includes starters, home-made fresh pasta with sauce, the main course and a dessert.

Later you have a private visit to an amazing winery located inside a historical castle. At the winery you have a tour of the cellars, the vineyards, take in the gorgeous views and taste Brunello "Riserva" and also Rosso di Montalcino.

After the tour, you are transferred back to your hotel and have the evening on your own.

Day 7: Departure
In the morning you check out from the hotel and depart from Montepulciano.

map
Want to add more experiences
Montepulciano car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Montepulciano car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Included
Montepulciano
Montepulciano hotel
Montepulciano, Italy
8 h
Florence
Florence hotel
Florence, Italy
Florence
3nights
Italyit
Hotel Cerretani Mgallery Collection
Superior Room, 2 Twin Beds
Included
Superior Room, 2 Twin Beds
Superior Room, 2 Twin Beds
Up to 2 guests
2 Twin Beds
23 m²
Breakfast included
Plans for Florence

Day 7: Arrival in Florence
Welcome to Florence! Upon arrival, your private driver transfers you to the hotel for check-in. The rest of the day is at your own leisure to relax after the trip.

Day 8: Florence Sightseeing 
After breakfast at your hotel, meet with your private guide and go on a comprehensive walking tour of Florence's highlights.

Today's program includes exploration of the Piazza del Duomo with a visit to the Baptistery dedicated to St. John the Baptist.

As you proceed to the main square of the city - Piazza della Signoria - you pass through the heart of the historical center with its landmark sites like Piazza della Repubblica and the Strozzi Palace. Stroll down via Tornabuoni, one of the most beautiful streets of the city, famous for its fine shops.

During the tour we also visit the Galleria dell'Accademia to see Michelangelo's famous colossal statue of David, a must-see in Florence.

After the tour return to your hotel and enjoy an evening at your own leisure.

Day 9: Day at Leisure in Florence 
Today is reserved for you to explore and enjoy Florence on your own. After breakfast you can do some independent sightseeing, shop for souvenirs or have a good rest. We suggest visiting the Uffizi Gallery, the Pitti Palace or joining one of our carefully planned optional tours.

Day 10: Departure
Following breakfast in your hotel, you check out and meet your private driver for the transfer.

map
Included experiences1 Experience
Comprehensive Guided Walking Tour
Included
Half day
Comprehensive Guided Walking Tour
Want to add more experiences
Florence car services
Departure transfer is included in your trip
Florence car services
Departure transfer is included in your trip
Departure
Private Transfer Sedan
Included
Useful information:

About Triptile

Triptile empowers you to plan trips better and enables you to book all services in one place. You can be your own travel expert and access valuable insights on the best hotels, experiences, and transportation options to create the perfect itinerary. Our platform not only provides information, but also allows you to book all your travel services in one place, so you can focus on enjoying your trip while Triptile handles the details.

What’s included in the price

Unless otherwise stated, everything listed in the itinerary is included. You can also add your own services to the itinerary, even if they are booked outside of Triptile. Please note that international flights are not included, but transportation between destinations listed in the itinerary is included if you choose to use Triptile transport connections.

Could not find something?

We are constantly improving Triptile. If you could not find something that you needed, please drop us a note at [email protected]  

How to book

To book, all you need to do is to make a deposit of 20% of trip price. The 20% deposit is non-refundable, but you can always transfer it to another trip if your plans change.  Just click on the red button in the top right corner that will take you to the Payment page. After you make your deposit, we will book all things that you chose.

Can I modify my trip after I booked

Of course! You can continue planning and even changing your trip to your heart's content up to 90 days before departure. Just keep in mind that all non-refundable hotels are set in stone. Oh, before we forget, your final balance will be due 90 days before beginning of your trip. If you have any questions, please don't hesitate to contact us at [email protected]

Incredible Umbria & Tuscany
Private tour
Assisi
3nights
Italyit
Le Silve di Armenzano
Superior Double Room, Ensuite
Le Silve di Armenzano
Included
Superior Double Room, Ensuite
Superior Double Room, Ensuite
Up to 2 guests
1 Double Bed
30 m²
Breakfast included
Plans for Assisi
Plans for Assisi

Day 1: Arrival
Welcome to Umbria! Upon arrival, you are transferred you to the hotel for check-in.

The rest of the day is at your own leisure to relax after the trip.

Day 2: Assisi City Tour & Trip to Gubbio
After breakfast you meet your guide and start a walking tour of Assisi which is described as the cradle of Romanesque art and design. UNESCO-listed Basilica of San Francesco with traces of the most famous artists of the period and the other Franciscan Sites in Assisi definitely make you immerse into the atmosphere of the Middle Ages.

Following break for lunch you are transferred to Gubbio set on the slope of Mt. Ingino. Beautiful Piazza Grande with the public palaces on it, Palazzo dei Consoli, a magnificent Gothic building completed around 1340, Palazzo del Podestà which holds the Town Hall and Ruins of Roman amphitheatre are among the sights you see here.

After the tour you return back to your Assisi hotel.

Day 3: Exploring Umbria Countryside
In the morning you meet your driver in the hotel lobby and start an exciting tour of Umbria countryside.

Your first stop for today is the medieval fortress city of Spoleto. Here you enjoy a private guided walk of the town covering its numerous Roman temples, theatres and arches.

The next on your list is Bevagna. The town excites its visitors with half a dozen medieval churches, two of Roman temples and the remains of a Roman theatre.

You continue to Spello. Its Roman origins can be seen in the stone gates and the ancient walls surrounding the village.

After the tour you are driven back to Assisi.

Day 4: Departure
After breakfast you check out and depart from Assisi.

map
Included experiences2 Experiences
Assisi City Tour & Trip to Gubbio
Included
Full day
Assisi City Tour & Trip to Gubbio
Exploring Umbria Countryside
Included
Full day
Exploring Umbria Countryside
Want to add more experiences
Assisi car services
Arrival transfer is included in your trip
Assisi car services
Arrival transfer is included in your trip
Arrival
Private Rail Station Transfer
Included
Departure
Departure transfer
Not selected
Included
Assisi, Assisi hotel
8 h / Private Transfer Sedan & Tour of Perugia and Cortona
Montepulciano, Montepulciano hotel
Montepulciano
3nights
Italyit
Borgo San Vincenzo
Signature Suite
Borgo San Vincenzo
Included
Signature Suite
Signature Suite
Up to 2 guests
1 King Bed
37 m²
Breakfast included
Plans for Montepulciano
Plans for Montepulciano

Day 4: Arrival
Upon arrival, you check in to your hotel and have a good rest.

Day 5: Tour to Cheese Farm and Winery in Pienza & Montepulciano
In the morning after breakfast you have another amazing experience as today you visit a Pecorino cheese farm.

Your driver-guide takes you to Pienza, the area known for the wonderful Pecorino di Pienza cheese, which gets its name from the word pecora, Italian for "sheep". This delicious "sheep" cheese is made exclusively in and around the town of Pienza from sheep’s milk. In the beginning, you have a tour of the historical center of Pienza, included into the list of UNESCO World Heritage Sites. You enjoy the views of wonderful Renaissance Palazzo Piccolomini, the beautiful Cathedral of Pienza and Palazzo Comunale.

You are then driven to a gorgeous rustic organic cheese farm that sits on top of a hill overlooking the entire Val d’Orcia and even Pienza itself. Here the local cheese producer shows you how the pecorino sheep cheese is made and the many stages of aging from soft and fresh to hard and complex.

You proceed with a visit to a traditional winery on a small farm near Montepulciano. Here you enjoy tasting one of the most famous Italian wines: Vino Nobile di Montepulciano*. The Nobile wines of Montepulciano were the first to be given the ultimate quality level of DOCG certification.

You have a guided tour of the Montepulciano historical center before you finally return to your hotel.

*Please note: there are 255 wineries in the region so if there is any particular that you wish to visit - let us know and we will modify program accordingly.

Day 6: Cooking Class in Montalcino
Today following breakfast your private driver-guide picks you up from the hotel and drives you first to Montalcino. The ancient village is best known for its red Brunello di Montalcino wines, made with Sangiovese Grosso grapes.

Upon arrival, you have a cooking class in a local farm restaurant located just few kilometers outside of the village. Here you learn how to cook a traditional Italian meal and about Italian dining traditions. Your experience starts from picking spices and vegetables and collecting the eggs. After about 3 hours of the workshop, you enjoy a full Italian lunch which includes starters, home-made fresh pasta with sauce, the main course and a dessert.

Later you have a private visit to an amazing winery located inside a historical castle. At the winery you have a tour of the cellars, the vineyards, take in the gorgeous views and taste Brunello "Riserva" and also Rosso di Montalcino.

After the tour, you are transferred back to your hotel and have the evening on your own.

Day 7: Departure
In the morning you check out from the hotel and depart from Montepulciano.

map
Want to add more experiences
Montepulciano car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Montepulciano car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Included
Montepulciano, Montepulciano hotel
8 h / Private Transfer & Tour of Siena
Florence, Florence hotel
Florence
3nights
Italyit
Hotel Cerretani Mgallery Collection
Superior Room, 2 Twin Beds
Hotel Cerretani Mgallery Collection
Included
Superior Room, 2 Twin Beds
Superior Room, 2 Twin Beds
Up to 2 guests
2 Twin Beds
23 m²
Breakfast included
Plans for Florence
Plans for Florence

Day 7: Arrival in Florence
Welcome to Florence! Upon arrival, your private driver transfers you to the hotel for check-in. The rest of the day is at your own leisure to relax after the trip.

Day 8: Florence Sightseeing 
After breakfast at your hotel, meet with your private guide and go on a comprehensive walking tour of Florence's highlights.

Today's program includes exploration of the Piazza del Duomo with a visit to the Baptistery dedicated to St. John the Baptist.

As you proceed to the main square of the city - Piazza della Signoria - you pass through the heart of the historical center with its landmark sites like Piazza della Repubblica and the Strozzi Palace. Stroll down via Tornabuoni, one of the most beautiful streets of the city, famous for its fine shops.

During the tour we also visit the Galleria dell'Accademia to see Michelangelo's famous colossal statue of David, a must-see in Florence.

After the tour return to your hotel and enjoy an evening at your own leisure.

Day 9: Day at Leisure in Florence 
Today is reserved for you to explore and enjoy Florence on your own. After breakfast you can do some independent sightseeing, shop for souvenirs or have a good rest. We suggest visiting the Uffizi Gallery, the Pitti Palace or joining one of our carefully planned optional tours.

Day 10: Departure
Following breakfast in your hotel, you check out and meet your private driver for the transfer.

map
Included experiences1 Experience
Comprehensive Guided Walking Tour
Included
Half day
Comprehensive Guided Walking Tour
Want to add more experiences
Florence car services
Departure transfer is included in your trip
Florence car services
Departure transfer is included in your trip
Departure
Private Transfer Sedan
Included
Please select date
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