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Incredible Umbria & Tuscany

10 days3 cities
Italy1 country
Tour rating: 4.89 / 5, Based on 247 Reviews
Private tour to Italy

Make your way to the historic heart of Italy and explore off the beaten track destinations of the Umbria region. Then set out to glorious Tuscany and enjoy both the hilly countryside with endless vineyards, included tastings as well as guided tours of Lucca, Florence, and even see the Leaning Tower of Pisa.
 

10 days3 cities
Italy1 country
From
 $4,295 
Assisi, Italy
3
days
Italy

Located in the central part of the country, Assisi is the jaw-dropping gem of the Umbria region, which has actually earned the status of a UNESCO World Heritage site.

Day by day
Hotel
Day-by-day program
1
day
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.

2
day
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.

3
day
Exploring the 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.

Your choice of hotels

We carefully select hotels to ensure your amazing stay. We will recommend the best available properties for your travel dates.

4-star hotel

Enhance your travel with staying in a remarkable 4-star property. As always, the location near all top landmarks, excellent quality service, and top-notch amenities are an indispensable part of your stay. The gallery demonstrates the examples of 4-star hotels we offer to our guests.

car
Assisi
Montepulciano
8 hrs

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.

Montepulciano, Italy
3
days
Italy

Situated on a hilltop in the region of Tuscany, Montepulciano is the perfect place to visit for an ultimate Italian experience and sampling the exceptional wines.

Day by day
Hotel
Day-by-day program
4
day
Arrival

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

5
day
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.

6
day
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.

Your choice of hotels

We carefully select hotels to ensure your amazing stay. We will recommend the best available properties for your travel dates.

4-star hotel

Enhance your travel with staying in a remarkable 4-star property. As always, the location near all top landmarks, excellent quality service, and top-notch amenities are an indispensable part of your stay. The gallery demonstrates the examples of 4-star hotels we offer to our guests.

car
Montepulciano
Florence
8 hrs

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.

Florence, Italy
4
days
Italy

One of the brightest gems of the Tuscany region, Florence, is the treasure trove, birthplace and cradle of the Renaissance.

Day by day
Hotel
Day-by-day program
7
day
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.

8
day
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.

9
day
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.

10
day
Departure

This is the last day of your amazing Umbria & Tuscany exploration! Following breakfast in your hotel, you check out and meet your private driver for the transfer.

Your choice of hotels

We carefully select hotels to ensure your amazing stay. We will recommend the best available properties for your travel dates.

Hotel De La Ville, Florence

Set near the magnificent Florence Cathedral and the amazing Uffizi Gallery, the Hotel De La Ville is a great place to stay during your Italy getaway. The stylish property boasts excellent service and top-notch amenities.

What's included

  • Accommodation at remarkable 4-star or 5-star centrally located hotels in Assisi, Montepulciano, and Florence;
  • Delicious breakfasts at your hotels;
  • Airport transfers and all transportation according to the itinerary with private drivers;
  • Regular class train tickets Florence - Lucca, Lucca - Pisa, Pisa - Florence;
  • Sightseeing tours with private professional English-speaking guides according to the itinerary;
  • Entrances to Duomo and Galleria dell'Accademia in Florence and Duomo in Siena;
  • Tours to Tuscany wineries with tasting;
  • Tour to a cheese farm in Montepulciano and cooking class at a farm restaurant in Montalcino;
  • All tourist fees & taxes, including tourist city taxes;
  • Support line during the trip.

Note: we include 1 vehicle for your arrival and departure transfers. If multiple vehicles are required additional transfer costs will apply.

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

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Tour Highlights

  • Fully tailor-made program according to your interest;
  • Your own professional local guides and drivers;
  • Full flexibility of hotel options;
  • Touring off the beaten track Italy destinations in Umbria and Tuscany like Gubbio, Bevagna, Perugia and Cortona;
  • Tastings of cheese in Montepulciano and cooking class in Montalcino;
  • Day trip to the Leaning Tower of Pisa and Lucca;
  • Exploring the Baptistery in Florence and Duomo in Siena.

What To Know

  • You can expect to find some shops and restaurants closed from 1-4 p.m. as it is "Riposo" time, Italy’s midday siesta. Most places will be also closed on Sundays
  • Tipping in restaurants is included in the bill, the cover charge is called ”coperto”. A charge from $1 to $3 will be noted on the menu
  • Make sure you have coins, in Italy you will be typically charged from 1 to 2 Euros to enter a public restroom