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Private tour

Incredible Umbria & Tuscany

itItaly
3 cities
10 days, 9 nights
Day by day
Places you explore
Recommended hotels
Landmarks & Experiences
Day 1 Assisi

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.

Breakfast included
Le Silve di Armenzano
Le Silve di Armenzano
Loc. Armenzano di Assisi, 89, Assisi, PG, IT, 6081
Superior Double Room, Ensuite
1 room
Up to 2 guests
1 Double Bed
30 m²
Breakfast included
More amenities
Arrival: Private Rail Station Transfer
Day 2 Assisi

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.

Full day
Assisi City Tour & Trip to Gubbio
Assisi City Tour & Trip to Gubbio
Day 3 Assisi

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.

Full day
Exploring Umbria Countryside
Exploring Umbria Countryside
Day 4 Assisi

Departure
After breakfast you check out and depart from Assisi.

Le Silve di Armenzano
Address
Loc. Armenzano di Assisi, 89, Assisi, PG, IT, 6081
Car from Assisi to Montepulciano
Departure
Assisi, ItalyAssisi hotel...
8 h
Arrival
Montepulciano, ItalyMontepulciano hotel...

Description for connection

Your private driver takes you to Perugia, the capital of Umbria. Together with your local guide you walk along the streets dating back to the Etruscan age, admire the 13th century Fontana Maggiore and the Palazzo dei Priori.

After sightseeing in Perugia you leave Umbria for another marvelous Italian region - Tuscany. The first Tuscan city on your list is Cortona, a small charming town in Chiana Valley. Here you start exploration from Republic Square - the heart of Cortona and home to the elegant 13th century Town Hall. You also get inspired by a scenic view from the town of the surrounding valley and even Lake Trasimeno.

Later afternoon you continue your way to Montepulciano.

Day 4 Montepulciano

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

Breakfast included
Borgo San Vincenzo
Borgo San Vincenzo
Via di Montenero 18, Montepulciano, Provincia di Siena, IT, 53045
Signature Suite
1 room
Up to 2 guests
1 King Bed
37 m²
Breakfast included
More amenities
Day 5 Montepulciano

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 Montepulciano

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 Montepulciano

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

Borgo San Vincenzo
Address
Via di Montenero 18, Montepulciano, Provincia di Siena, IT, 53045
Car from Montepulciano to Florence
Departure
Montepulciano, ItalyMontepulciano hotel...
8 h
Arrival
Florence, ItalyFlorence hotel...

Description for connection

After check-out, your private driver takes you on a sightseeing tour.

The first destination on your route today is Siena, Italy's loveliest medieval city. During
a 3-hour walking tour with a local guide, you visit all of the major sights including the Cathedral of the Duomo, which houses the works of artists like Nicola Pisano, Ghirlandaio, Ghiberti, Donatello and Jacopo della Quercia. You then see the Piazza del Campo - a shell-shaped structure, which is also a major attraction famous for hosting horse races.

Then you continue to San Gimignano where you have some free time for independent sightseeing. San Gimignano is often called the town of towers as it is home to 14 well-preserved towers from the medieval times. These towers vary in height and form the international identity of the town. San Gimignano boasts many churches, such as the Collegiata and the Sant' Agostino. Moreover, the heart of the town contains 4 Piazzas - Cisterna, Duomo, Pecori and Erbe.

After the tour you continue the trip to Florence.

Day 7 Florence

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.

Breakfast included
Hotel Cerretani Mgallery Collection
Hotel Cerretani Mgallery Collection
Via De' Cerretani 68, Florence, FI, IT, 50123
Superior Room, 2 Twin Beds
1 room
Up to 2 guests
2 Twin Beds
23 m²
Breakfast included
More amenities
Day 8 Florence

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.

4h
Comprehensive Guided Walking Tour
Comprehensive Guided Walking Tour
Day 9 Florence

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 Florence

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

Hotel Cerretani Mgallery Collection
Address
Via De' Cerretani 68, Florence, FI, IT, 50123
Departure: Private Transfer Sedan

What's included

Exceptional downtown hotel accommodations
Guided sightseeing tours with expert English-speaking guides
Delicious breakfasts at your hotels
Entrances to Galleria dell'Accademia, Piazza della Repubblica and more
Tickets and intercity transportation as per itinerary
Professional meeting services at the airport
Dedicated support team before and during your trip

Reviews

As you prepare for your travels, we proudly highlight our 99.8% customer satisfaction rate. Below are reviews from travelers who have enjoyed our award-winning service. Thank you for choosing us—your extraordinary journey awaits!
4.9 / 5
Excellent
962 Reviews
This was a dream trip for me, and they helped make it a dream come true.
The guides they work with are top-notch.
We had a “trip of a lifetime,” thanks to them.
I was extremely pleased with the personalized service.
itAssisi
3 nights
itMontepulciano
3 nights
itFlorence
3 nights
App ID
FT-255202
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