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itAssisi
3nights
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3nights
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Tour by cities: Rome; Assisi; Montepulciano; Florence;
Private tour
Price per person
10 days, 9 nights
Private tour
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Rome
1day
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Rome Itinerary

Day 1: Arrival
Buongiorno and welcome to the capital of Italy, Rome*! Upon arrival, you are met by your private driver at the airport, who transfers you to the hotel in Assisi for check-in.

Please, note: alternatively, you may have a transfer to Assisi from Florence.

Included services
Included services
Want to add more experiences
Rome car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Car
Rome
2 hours
Assisi
Assisi
3nights
Italyit
Castello di Petrata
Close
Standard Double Room Breakfast Included x 2
3nights
Standard Double Room Breakfast Included
2 Rooms
4 Guests
Schedule
Close
Assisi Itinerary

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.

Included services
1
Assisi City Tour & Trip to GubbioAssisi City Tour & Trip to Gubbio
Full day
2
Exploring Umbria CountrysideExploring Umbria Countryside
Full day
Included services
Assisi City Tour & Trip to Gubbio
Full day
Assisi City Tour & Trip to Gubbio
Exploring Umbria Countryside
Full day
Exploring Umbria Countryside
Want to add more experiences
Assisi car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Car
Assisi
8 hours
Montepulciano
Montepulciano
3nights
Italyit
La Corte Segreta
Close
Standard Double Room Breakfast Included x 2
3nights
Standard Double Room Breakfast Included
2 Rooms
4 Guests
Schedule
Collections
Close
Montepulciano Itinerary

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.

Included services
1
Pienza Cheese Farm Group Tour & Montepulciano Winery VisitPienza Cheese Farm Group Tour & Montepulciano Winery Visit
Full day
2
Cooking Class and Wine Tasting in MontalcinoCooking Class and Wine Tasting in Montalcino
Full day
Included services
Pienza Cheese Farm Group Tour & Montepulciano Winery Visit
Full day
Pienza Cheese Farm Group Tour & Montepulciano Winery Visit
Cooking Class and Wine Tasting in Montalcino
Full day
Cooking Class and Wine Tasting in Montalcino
Want to add more experiences
Montepulciano car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Car
Montepulciano
8 hours
Florence
Florence
3nights
Italyit
Hotel De La Ville
Close
Standard Double Room Breakfast Included x 2
3nights
Standard Double Room Breakfast Included
2 Rooms
4 Guests
Schedule
Collections
Programs
Close
Florence Itinerary

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 in 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.

Your ticket to the Grande Museo del Duomo allows you to visit the other magnificent monuments of Piazza del Duomo in your free time within 72 hours: the Cathedral itself, the Dome and its famous Bell Tower.

As you proceed to the main square of the city - Piazza della Repubblica - you pass by the touristic area of the Strozzi Palace a bustling shopping street, via Tornabuoni.

Then you enter in Oltrarno where you see numerous local craftsmen shops and beautiful Santo Spirito Church and Convent, built for the Agostinian monks. In this very part of the city you can find the first official work of Michelangelo dating back to the age when he was 17 years old.

We also visit the Galleria dell'Accademia to see the famous Michelangelo's statue David as well before ending the tour on the Ponte Vecchio.

After the tour you return to your hotel and enjoy 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.

Included services
1
Comprehensive Guided Walking TourComprehensive Guided Walking Tour
Half day
2
Pisa and Lucca by TrainsPisa and Lucca by Trains
Full day
Included services
Comprehensive Guided Walking Tour
Half day
Comprehensive Guided Walking Tour
Pisa and Lucca by Trains
Full day
Pisa and Lucca by Trains
Want to add more experiences
Florence car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Departure
Private Transfer Minivan
Included
Useful information:

What is an itinerary

This is a trip planner, which allows you to design your trip as you want it. You can add destinations, edit the number of days at each destination, move things around. You can choose what to include in the program from our inventory or you can add your own reservations. It’s up to you!

What’s included and what’s not

Everything that is listed in the itinerary is included. You are welcome to choose which services you want to book with us and which services you will book yourself. The total price on the itinerary will show the price of all services that you added from our inventory. The price of services that you are arranging somewhere else is not included in the total.

Flights and transportation

International flights are not included, but all transportation between destinations on the itinerary is included if you have selected our transport connections. For example, if you see a train connection on the itinerary it is included in the price. In general, everything you see on the itinerary is included in the price (unless you added your own inventory).

Hotels

If you selected our hotels, they are included. In the case of experiences, there are free and paid experiences. When adding experiences to the program, you decide what to add, simply tickets or a professional guide. You can also create your own list of top things to do and do them on your own.

How to book

When you have finished putting together your perfect trip, you can click the Book button on top of the page, and complete your booking. Depending on how far in advance you are booking, we will ask you to pay a deposit or full payment.

How to change your plans after booking

If you would like to modify your itinerary after you booked it, you can do that by creating a new trip version by clicking Unlock button. Our system will create a new version of your trip, transfer all paid balance (if any) and open this new version for editing. Please note, there is a cut-off period for modifications, typically 30 days before the beginning of the trip. If there are supplier cancelation fees arising from your modifications, we will do our best to minimize them, but ultimately you will be responsible for paying them.

If you have any questions, we are happy to assist you. Please send an email to [email protected] and we will respond within one business day or less.

Price per person
10 days, 9 nights
Private tour
Travelers
Itinerary is not saved! Please save this program
Home
Tour by cities: Rome; Assisi; Montepulciano; Florence;
Private tour
Rome
1day
Italyit
Recommended hotels
Schedule
Collections
Programs
Rome Itinerary

Day 1: Arrival
Buongiorno and welcome to the capital of Italy, Rome*! Upon arrival, you are met by your private driver at the airport, who transfers you to the hotel in Assisi for check-in.

Please, note: alternatively, you may have a transfer to Assisi from Florence.

Included services
Included services
Want to add more experiences
Rome car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Rome, Rome hotel / airport
Car2 hours / Private Transfer Minivan
Assisi, Assisi hotel
Assisi
3nights
Italyit
Castello di Petrata
Castello di Petrata
Standard Double Room Breakfast Included
2 Rooms
4 Guests
3nights
Schedule
Assisi Itinerary

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.

Included services
1
Assisi City Tour & Trip to GubbioAssisi City Tour & Trip to Gubbio
Full day
2
Exploring Umbria CountrysideExploring Umbria Countryside
Full day
Included services
Assisi City Tour & Trip to Gubbio
Full day
Assisi City Tour & Trip to Gubbio
Exploring Umbria Countryside
Full day
Exploring Umbria Countryside
Want to add more experiences
Assisi car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Assisi, Assisi hotel
Car8 hours / Private Transfer Minivan & Tour of Perugia and Cortona
Montepulciano, Montepulciano hotel
Montepulciano
3nights
Italyit
La Corte Segreta
La Corte Segreta
Standard Double Room Breakfast Included
2 Rooms
4 Guests
3nights
Schedule
Collections
Montepulciano Itinerary

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.

Included services
1
Pienza Cheese Farm Group Tour & Montepulciano Winery VisitPienza Cheese Farm Group Tour & Montepulciano Winery Visit
Full day
2
Cooking Class and Wine Tasting in MontalcinoCooking Class and Wine Tasting in Montalcino
Full day
Included services
Pienza Cheese Farm Group Tour & Montepulciano Winery Visit
Full day
Pienza Cheese Farm Group Tour & Montepulciano Winery Visit
Cooking Class and Wine Tasting in Montalcino
Full day
Cooking Class and Wine Tasting in Montalcino
Want to add more experiences
Montepulciano car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Montepulciano, Montepulciano hotel
Car8 hours / Private Transfer & Tour of Siena
Florence, Florence hotel
Florence
3nights
Italyit
Hotel De La Ville
Hotel De La Ville
Standard Double Room Breakfast Included
2 Rooms
4 Guests
3nights
Schedule
Collections
Programs
Florence Itinerary

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 in 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.

Your ticket to the Grande Museo del Duomo allows you to visit the other magnificent monuments of Piazza del Duomo in your free time within 72 hours: the Cathedral itself, the Dome and its famous Bell Tower.

As you proceed to the main square of the city - Piazza della Repubblica - you pass by the touristic area of the Strozzi Palace a bustling shopping street, via Tornabuoni.

Then you enter in Oltrarno where you see numerous local craftsmen shops and beautiful Santo Spirito Church and Convent, built for the Agostinian monks. In this very part of the city you can find the first official work of Michelangelo dating back to the age when he was 17 years old.

We also visit the Galleria dell'Accademia to see the famous Michelangelo's statue David as well before ending the tour on the Ponte Vecchio.

After the tour you return to your hotel and enjoy 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.

Included services
1
Comprehensive Guided Walking TourComprehensive Guided Walking Tour
Half day
2
Pisa and Lucca by TrainsPisa and Lucca by Trains
Full day
Included services
Comprehensive Guided Walking Tour
Half day
Comprehensive Guided Walking Tour
Pisa and Lucca by Trains
Full day
Pisa and Lucca by Trains
Want to add more experiences
Florence car services
Here you can add your arrival & departure car transfers, meet-and-greet services
Departure
Private Transfer Minivan
Included
Itinerary is not saved! Please save this program