Trip Overview

Incredible Umbria & Tuscany

Tour rating: 4.89 / 5, Based on 20 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.
 

Incredible Umbria & Tuscany

10 days3 cities
Italy1 country
Private tour to Italy
From
$4,295
Tour rating: 4.89 / 5, Based on 20 Reviews

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.
 

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Day-By-Day

Assisi

first destination
4 days in the city
Detailed itinerary
3 nights in a centrally located hotel
Day 1
Arrival & Transfer to Assisi
Transfer
Transfer

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.

The rest of the day is at your own leisure to relax after the trip.

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

No meals included.

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Day 2
Assisi City Tour & Trip to Gubbio
City tour
City tour

After breakfast, you meet your guide and start a walking tour of Assisi, the Umbrian city often described as the cradle of Romanesque art and design. The UNESCO-listed Basilica of San Francesco with traces of the most famous artists of the period and the other Franciscan sites in Assisi are surely going to make you immerse into the atmosphere of the Middle Ages.

Following a break for lunch, you are transferred to Gubbio set on the slope of Mt. Ingino. Among the places you see is the beautiful Piazza Grande, home to public palaces like Palazzo dei Consoli (a magnificent Gothic building completed around 1340) as well as Palazzo del Podestà which holds the Town Hall and the ruins of the Roman amphitheater.

After the tour you return to your Assisi hotel and have the remaining part of the day free.

Breakfast is included.

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Day 3
Exploring the Umbria Countryside
Day tour
Day tour

In the morning you meet your driver in the hotel lobby and start an exciting tour of the 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.

Next on your list is Bevagna, the town excites its visitors with a half a dozen medieval churches, two Roman temples, and the remains of a Roman theatre.

Then 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, the rest of the day is at leisure.

Breakfast is included.

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Day 4
Touring Perugia & Cortona
Day tour
Day tour

After breakfast, you check out, meet your private driver, and head for Perugia, the capital of Umbria.

Together with your local guide, you 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 leave Umbria for another marvelous 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.

Later this afternoon you continue your way to Montepulciano, a small village of Etruscan origin and one of the most beautiful hill towns in Tuscany. Upon arrival, you check in to your hotel and have a good rest.

Breakfast is included.

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4-star hotel
4

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.

Welcome to Assisi

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.

car
Assisi
Montepulciano
1 hr 10 min

Marvel at the jaw-droppingly beautiful Italian landscapes while our trusted driver takes you from Assisi to Montepulciano. The short drive will undoubtedly be a memorable one. 

Montepulciano

second destination
3 days in the city
Detailed itinerary
3 nights in a centrally located hotel
Day 5
Tour to Cheese Farm and Winery in Pienza & Montepulciano Sightseeing
Day tour
Day tour
Tasting
Tasting

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.

Later you carry on to Montepulciano, a small village of Etruscan origin and one of the most beautiful hill towns in Tuscany. After the guided tour of the Montepulciano historical center, you visit a traditional winery on a small farm. 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.

Breakfast and wine-tasting included.

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Day 6
Cooking Class in Montalcino
Day tour
Day tour
Tasting
Tasting

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 a few kilometers outside of the village. 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 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.

Breakfast, lunch, and wine tasting included.

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Day 7
Siena & San Gimignano Sightseeing
Day tour
Day tour

In the morning you check out from the hotel in Montepulciano, and your private driver takes you on a sightseeing tour on the way to Florence.

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 city. 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. Upon arrival, you check in to your hotel and have a good rest after a busy though exciting day.

Breakfast is included.

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4-star hotel
4

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.

Welcome to Montepulciano

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.

car
Montepulciano
Florence
1 hr 20 min

Let our experienced driver take care of your trip and enjoy the short ride from Montepulciano to beautiful Florence. Make sure to gaze through the window to admire the scenic Italian landscapes. 

Florence

third destination
3 days in the city
Detailed itinerary
3 nights in a centrally located hotel
Day 8
Florence Sightseeing
City tour
City tour
Museum
Museum

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 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. 

We will 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 Augustinians. 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 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 the evening at your own leisure.

Breakfast is included.

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Day 9
Day Trip to Lucca & Pisa
Day tour
Day tour

Following breakfast, prepare for a beautiful journey outside of Florence. You head for the station to start a train journey which is a great opportunity to enjoy a Tuscany scenic landscape.

In about 1.5 hours you arrive in the town of Lucca, this Italian gem is encircled by an unspoiled Renaissance wall. Here you are met by a local guide and go on a 2-hour sightseeing tour of Lucca's main sights.

Later you take a 30-minute train to Pisa. Upon arrival, you have some free time to explore the highlights of Pisa. You get to see Pisa's Piazza dei Miracoli (Square of Miracles), a UNESCO World Heritage Site, and its world-recognized symbol - the Leaning Tower. This is the world's most famous leaning tower, even though there are at least three dozen leaning towers all over the world.

Following time for your independent sightseeing, you take a return train ride. After a 1-hour ride, you arrive in Florence and have the rest of the evening is free.

Breakfast is included.

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Day 10
Departure
Transfer
Transfer

This is the last day of your amazing Umbria & Tuscany exploration! After breakfast your driver meets you at the hotel lobby and takes you to the airport for your flight back home. We wish you a safe flight and hope to work on your future vacations!

Breakfast is included.

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Hotel De La Ville, Florence
4

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.

Welcome to Florence

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

What's Included

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 Academia 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 Grande Museo del Duomo 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
Dates & Rates

Dates & Rates

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