User
Edit your trip as you want. Save it to see the price
Incredible Umbria & Tuscany: Journey by Car
Add destination
Map editor

Incredible Umbria & Tuscany: Journey by Car

Private tour
10 days
5 cities
1day

Florence, Italy

Cradle of the Renaissance, Florence, is among the most outstanding cities in Italy, rich in historic architecture and some the world's finest museums. When visiting Florence, make sure to save enough time to view not only the symbol of the city, the red-domed Florence Cathedral, and but also visit outstanding galleries. As such, the iconic Uffizi Gallery, the Leonardo da Vinci Museum, and the Galleria dell'Accademia, home to Michelangelo's masterpiece "David", are must-visit sites....
  • Day By Day

    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.

    Edit
  • Included in your trip
    Included Experiences
    Show Experiences
    Included Transfers
    Show Transfers
CarCar
Connection | Florence - Assisi
Journey by car. The distance from Florence airport to Assisi hotel is 118 miles (approximately 2 hours 30 minutes).
Florence airport
Florence
2.5
Assisi hotel
Assisi
3nights

Assisi, Italy

Nested in the central part of Italy in Umbria region, Assisi is a historical and cultural gem that is well worth visiting. Being a birthplace of St. Francis, the founding father of the Franciscan religious order, Assisi attracts many pilgrims every year. The town's main landmark, the Basilica of San Francesco d'Assisi, is also home to numerous masterpieces by Giotto, Pietro Lorenzetti, and Simone Martini....
  • Day By Day

    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. 


    Edit
  • Included in your trip
    Castello di Petrata
    4-star hotel
    Via Petrata, 25, Assisi, Italy, 06081
    Castello di Petrata
    Standard Double Room Breakfast Included
    Nested in a restored 14th-century fortress, this rustic hotel offers modern amenities and stylish coziness to its guests. All rooms and suites feature free WiFi and satellite TV, while upgraded rooms add sofas and/ or kitchenettes. A spa and an outdoor pool are among other amenities.... show more
    4 days / 3 nights
    Included Experiences
    • Guide Services for Umbria Countryside Tour
    • Guide Services for Perugia and Cortona Tours
    • Guide Services for Assisi and Gubbio Tour
    Hide Experiences
    Included Transfers
    Transfers can be added here
    Hide Transfers
CarCar
Connection | Assisi - Montepulciano
Journey by car. The distance from Cortona to Montepulciano hotel is 19 miles (approximately 40 minutes).
Cortona
Assisi
1
Montepulciano
Montepulciano
3nights

Montepulciano, Italy

Montepulciano is a medieval town in Tuscany, famous for its vineyards and red wine. Apart from select wines, the place is admired for its pork, cheese, special pasta, and honey. Another distinctive feature of Montepulciano is a "green" approach and car-free parts of the city....
  • Day By Day

    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.

    Edit
  • Included in your trip
    Il Palazzetto
    3-star hotel
    Via di Voltaia Nel Corso, 26, Montepulciano, Italy, 53045
    Il Palazzetto
    Deluxe Double Room Breakfast Included
    Set in the central part of the city, the hotel offers excellent sightseeing opportunities. Cozy and airy rooms include complimentary Wi-Fi.... show more
    4 days / 3 nights
    Included Experiences
    • Half Day Small Group Cooking Class on the Farm
    • Pecorino Cheese Farm Visit with Tastings
    • Half Day Private Montepulciano Walking Tour
    • Montalcino Winery Visit
    • Wine Tasting at Boscarelli Estate Winery
    Hide Experiences
    Included Transfers
    Transfers can be added here
    Hide Transfers
CarCar
Connection | Montepulciano - Siena
Journey by car. The distance from Montepulciano hotel to Siena is 35 miles (approximately 1 hour).
Montepulciano hotel
Montepulciano
1
Siena
Siena
1day

Siena, Italy

Resting in the heart of Tuscany, Siena is probably the most famous town in the area after Florence. In contrast to the latter though, Siena represents the Medieval part of Italy's history and brings to its visitors serenity and the comforting feel of a smaller traditional place. Being a convenient hub for exploring Tuscany, Siena offers excellent opportunities for wine-lovers too. For example, you can take a trip to Pienza and try traditional Italian cheese before you carry on to Montepulciano, the birthplace of Tuscany's best wines. ...
  • Day By Day

    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.

    Edit
  • Included in your trip
    Included Experiences
    • Half Day Guided City Tour
    Hide Experiences
    Included Transfers
    Transfers can be added here
    Hide Transfers
CarCar
Connection | Siena - Florence
Journey by car. The distance from Siena to Florence hotel is 50 miles (approximately 1 hour 20 minutes).
Siena
Siena
1.5
Florence hotel
Florence
3nights

Florence, Italy

Cradle of the Renaissance, Florence, is among the most outstanding cities in Italy, rich in historic architecture and some the world's finest museums. When visiting Florence, make sure to save enough time to view not only the symbol of the city, the red-domed Florence Cathedral, and but also visit outstanding galleries. As such, the iconic Uffizi Gallery, the Leonardo da Vinci Museum, and the Galleria dell'Accademia, home to Michelangelo's masterpiece "David", are must-visit sites....
  • Day By Day

    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.   

    Edit
  • Included in your trip
    Hotel De La Ville
    4-star hotel
    Piazza degli Antinori, 1/r, 50123, Florence, Italy
    Hotel De La Ville
    Standard Double Room Breakfast and Parking Included
    Hotel De La Ville is centrally located on a pedestrian high-fashion street of Via Tornabuoni in Florence and is within a walking distance of the Florence Cathedral and the Uffizi Gallery. All hotel Florentine-style decorated rooms come with LCD TVs, air-conditioning and free Wi-Fi. The hotel also has a breakfast room offering an American-style buffet and a bar open for coffee and drinks throughout the day.... show more
    4 days / 3 nights
    Included Experiences
    • Half Day Comprehensive Guided Walking Tour
    • Guide Services in Lucca
    Hide Experiences
    Included Transfers
    Transfers can be added here
    Hide Transfers
Add destination
What’s included:
  • Accommodation with parking for the rental car included at remarkable centrally located 4-star hotels in Florence, Assisi and country house hotel in Montepulciano; 
  • Delicious breakfasts;
  • Sightseeing tours with private professional English-speaking guides;
  • Entrance tickets to Florence Duomo, Galleria dell'Accademia, Siena Duomo;
  • Wine tastings in Montalcino and Montepulciano wineries;
  • Cooking class in the farm restaurant in Tuscany;
  • Cheese tasting at Pienza farm;
  • All tourist fees & taxes, including tourist city taxes;
  • Support line during the trip.

Not included:international flights, multiple arrival/departure transfers, other meals not mentioned in the program, optional tours and services, all personal expenses. 

Note: 

  1. Hotels availability is subject to change. In case current hotels are booked out we will provide alternative hotels of an equal value for you. 
  2. We include 1 vehicle for your arrival and departure transfers. If multiple vehicles are required additional transfer costs will apply.

Stress-free Booking Book your journey without stress and at convenient pace. You can pay a deposit of 20% to book any tour in any major currency; the final balance will be due 90 days before start date. In event if you decide to change or postpone your trip, you can transfer your deposit to any other packages we offer. Cruise bookings and special offers may be subject to different booking terms. 

Trip Assurance If you need our assistance during your trip, you can call our support line available from 6 a.m. to 8 p.m. (CET) on weekdays and weekends. 

Firebird tour policies & FAQs