Day 1: Arrival in Florence and Departure to Assisi
Welcome to Florence! Upon arrival, you pick up your rental car and proceed to Assisi.

If you are full of energy you may visit The Mall Luxury Outlets and take advantage of great deals for premium and luxury brands as it is located on our route today.

Arrival to Assisi
Welcome to Umbria! Upon arrival you have a check-in, and the rest of the day is at leisure.

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 allow you to immerse into the atmosphere of the Middle Ages.

Following a break for lunch you continue your journey by car to Gubbio and have a tour there as well.

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.

Journey by car: the total distance to be covered for the round trip is 60 miles (approximately 1 hour 30 minutes pure driving).

Day 3: Exploring Umbria Countryside
In the morning you meet your guide and start a journey by car to Umbria countryside.

Your first stop for today is the medieval fortress city of Spoleto. Here you enjoy a  guided walk around 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 drive back to Assisi.

Journey by car: the total distance to be covered for the round trip is 63 miles (approximately 1 hour 30 minutes pure driving).

Day 4: Departure from Assisi
After breakfast you check out from the hotel. Meet your private guide and start your journey by car to Perugia and Cortona. 

Walk along Perugia's streets, dating back to the Etruscan age, admire the 13th century Fontana Maggiore, and the Palazzo dei Priori.

After sightseeing in Perugia, you proceed to another marvellous Italian region, Tuscany. The first Tuscan city on your list is Cortona, a small charming town in the Chiana Valley. 

Here you start your exploration from the Republic Square, the heart of Cortona and home to the elegant 13th-century Town Hall. You also get to enjoy the scenic view from the town of the surrounding valley and even of Lake Trasimeno.

Journey by car: the total distance to be covered for the trip is 90 miles (approximately 2 hour  20 minutes pure driving).

Later this afternoon you continue your journey by car without the guide to Montepulciano, a small village of Etruscan origin and one of the most beautiful hill towns in Tuscany. 

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

Day 5: Tour to Cheese Farm in Pienza & Montepulciano Winery
Following breakfast in your hotel, meet your local guide for a 2-hour walking tour in the city. 

You explore Palazzo Comunale, Palazzo Tarugi, Duomo of Montepulciano and learn more about its picturesque neighborhoods.

Following the tour you start a journey by car to try local specialties.

You head to Pienza, the area known for the wonderful Pecorino di Pienza cheese, which gets its name from the word pecora, Italian for "sheep".  Here you visit the rustic organic cheese farm that sits on top of a hill overlooking the entire Val d’Orcia and even Pienza itself. The local cheese producer shows you how the pecorino sheep cheese is made and the many stages of ageing from soft and fresh to hard and complex.

Continue to a traditional winery in 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.

Journey by car: the total distance to be covered for the round trip is 20 miles (approximately 1 hour pure driving).

Tuscany is also famous for its hot springs and we recommend you to visit hot springs of San Filippo which is just 30 minutes away from Montepulciano.

You may also devote your time to a hike with a guide. Hillside nature of Val D'Orcia is included in the UNESCO World Heritage list, and along with this picturesque Tuscan landscape you have a chance to discover the Church of Vitaleta which is perfect if you want to take some beautiful pictures.

Day 6: Cooking Class in a Local Farmhouse
Following breakfast in the hotel, a local chef is waiting for you to start the cooking class in a local farm restaurant. Here you learn how to cook a traditional Italian meal and about Italian dining traditions.

Your experience starts with picking spices and vegetables and collecting 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 planned visit to an amazing winery located inside a historical castle in Montalcino.

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 have an evening at leisure.

Journey by car: the total distance to be covered for the round trip is 46 miles (approximately 1 hour 30 minutes pure driving).

Day 7: Departure to Florence and Tour in Siena
In the morning you check out from the hotel and drive north.

Walking Tour in Siena
Upon arrival meet your guide and start an exploration of Siena, Italy's loveliest medieval city.

During the walking tour, 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.

After the tour, you head to your hotel in Florence.

Before arrival in Florence you may visit San Gimignano - the town of towers as it is home to 14 well-preserved towers from the medieval times. They 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.  San Gimignano is just 15 miles extra (approximately 20 minutes) to your journey by car to Florence.

One extra place which we recommend you to see is  Vignamaggio Winery which is one of Tuscany's oldest farming estates since 1404. We can organize a wine tasting with a tour in the vineyards for you. Vignamaggio Winery is 37 miles extra (approximately 1 hour 20 minutes) to your journey by car to Florence.  

Arrival in Florence
Upon arrival, you have a check-in and the rest of the day at leisure.

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.

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 famous Dome, the Bell Tower, and the Cathedral Museum with works by Michelangelo and Donatello.

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.

You also cross over the Arno River on the Ponte Vecchio to enter the Oltrarno district where you see numerous local craftsmen shops and the beautiful Santo Spirito Church and Convent, built for the Agostinians. In this very part of the city you can find an early work of Michelangelo dating back to when he was just 17 years old.

During the tour you 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.

You may highlight your stay in Florence with a pasta cooking class and a local market tour.  

If you are fond of art and history take a chance to visit Uffizi Gallery to see masterpieces by Michelangelo, Leonardo da Vinci, Raffaello, Botticelli.

Day 9: Day Trip to Lucca and Pisa
Following breakfast in the hotel, start your journey by car to charming town Lucca and iconic Pisa. 

Upon arrival in Lucca, meet your private guide and start a 2-hour tour. Lucca is a town encircled by an unspoiled Renaissance wall and during the tour, you witness the Anfiteatro Square, Guingi Tower, San Martino Cathedral, and the town's many antique shops.

Continue to Pisa to witness one of the most recognized symbols of Italy - Pisa Tower and Baptistery. 

Journey by car: the total distance to be covered for the round trip is 114 miles (approximately 3 hours pure driving).

To enhance your stay in Florence you may treat yourself with a wine tasting at one of the local restaurants,  or even take a chance in Truffle hunting as it is just 1 hour drive from Florence.

Day 10: Departure
This is the final day of your amazing journey! After breakfast you chec out and depart from your hotel to Florence Amerigo Vespucci airport where you drop off your rental car.