Assisi, Umbria, Italy
Tuscany Region, Italy
Pisa, Italy
Siena, Italy
Florence, Italy

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Overview

Dive into the impeccable beauty of Italy's two iconic regions. Together with a petite group and professional guides, explore the top attractions, enjoy fun activities, including tastings and cooking classes, as well as stays at fine central properties.
 

Tour type:
Small group tour
Tour rating:
4.89 / 5, Based on
  • BEST HOTELS
  • 4-star centrally-located hotels:
    8 nights
    Standard rooms
  • BEST CONNECTIONS
  • Private airport transfers
    Drivers for day trips &
    connections between cities
  • BEST SIGHTSEEING
  • 1 guided walking city tour
    5 day trips outside the cities
    Cheese farm & winery tour in Pienza
  • MEALS
  • 8 breakfasts
    Cheese & wine tastings
    Cooking class with lunch in Montalcino

Day-by-Day

Day 1
Arrival to Rome

Welcome to Rome - one of the most charming cities and capital of Italy. Upon arrival, you are met by your private driver at the airport, who transfers you to the hotel.

The rest of the day is free so you can start exploring the magnificent city center on your own, dine in one of the local restaurants or take a good rest in your comfortable room.

Not included.

Day 2
Day at Leisure in Rome & Transfer to Assisi

In the morning, following breakfast and check-out, you have some time at leisure to explore magnificent Rome on your own. We suggest you visit the major sights of the city, including the Trevi Fountain, the Pantheon, the Colosseum, the Spanish Steps, among others, or join one of our carefully planned optional tours.

In the afternoon, you meet your driver 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.

Breakfast is included.

Day 3
Assisi City Tour & Trip to Gubbio

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.

Day 4
Exploring the Umbria Countryside

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 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.

Day 5
Touring Perugia & Cortona

After breakfast, you check out, meet your 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 Castiglione d'Orcia, a beautiful small town in Tuscany. Upon arrival, you check in to your hotel and have a good rest.

Breakfast is included.

Day 6
Tour to Cheese Farm and Winery in Pienza & Montepulciano Sightseeing

In the morning after breakfast, you have another amazing experience as today you visit a Pecorino cheese farm.

Your driver and guide take 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 in 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 in Castiglione d'Orcia.

  • 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.

Day 7
Cooking Class in Montalcino

Today following breakfast your driver and guide pick you up from the hotel and drive 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 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 in Castiglione d'Orcia and have the evening on your own.

Breakfast, lunch, and wine tasting included.

Day 8
Siena & San Gimignano Sightseeing

In the morning you check out from the hotel in Montepulciano, and your 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.

Day 9
Departure from Florence

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!

  • Optional extension: We recommend extending your stay in Florence to explore the city's best sights during guided tours and go on a day trip to see Pisa and its Leaning Tower as well as the nearby historic town of Lucca.

Breakfast is included.


Included

8 nights at centrally-located 4-star hotels

  • Hand picked hotels
  • Best value rooms
  • Restaurant
8 nights at centrally-located 4-star hotels

Always included:

  • Best location for sightseeing
  • Breakfasts
  • All taxes and fees

What's included
  • Accommodation at remarkable 4-star centrally located hotels in Rome, Assisi, Castiglione d'Orcia, and Florence;
  • Delicious breakfasts at your hotels;
  • Airport transfers and all transportation according to the itinerary with private drivers;
  • Sightseeing tours with private professional English-speaking guides according to the itinerary;
  • Entrances to the 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;
  • Emergency line support 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.

Tour highlights
  • Intimate group size of up to only 14 travelers
  • Professional local guides
  • 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
  • Exploring the 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
Aug 31
Sep - 8, 2019
Sep 14
Sep - 22, 2019
Oct 19
Oct - 27, 2019
Oct 26
Nov - 3, 2019
Friends trip: 4+ travelers (price per person)
$3,398
deposit
$680
$3,398
deposit
$680
$3,398
deposit
$680
$3,398
deposit
$680
Two travelers: double occupancy (price per person)
$3,598
deposit
$720
$3,598
deposit
$720
$3,598
deposit
$720
$3,598
deposit
$720
Single traveler
$5,098
deposit
$1,020
$5,098
deposit
$1,020
$5,098
deposit
$1,020
$5,098
deposit
$1,020
Dates
Aug 31
Sep - 8, 2019
Sep 14
Sep - 22, 2019
Oct 19
Oct - 27, 2019
Oct 26
Nov - 3, 2019
Friends trip: 4+ travelers (price per person)
$3,398
deposit
$680
$3,398
deposit
$680
$3,398
deposit
$680
$3,398
deposit
$680
Two travelers: double occupancy (price per person)
$3,598
deposit
$720
$3,598
deposit
$720
$3,598
deposit
$720
$3,598
deposit
$720
Single traveler
$5,098
deposit
$1,020
$5,098
deposit
$1,020
$5,098
deposit
$1,020
$5,098
deposit
$1,020

Map


Reviews

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I think that no place on Earth can be more interesting to tour than Italy

A million times thank you! Italy is an incredibly beautiful country. I think that no place on Earth can be more interesting to tour than Italy. Venice is the living definition of romance, so stunning with gandolas and canals. The truly Italian feeling and numerous tourist attractions were impressive. Anywhere you turn ...

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Superb tour to Italy! You really deserve a round of applause

I wasn't sure what to expect from our trip to Italy but my mom and I were very surprised with how smoothly everything went. Only a few minor hiccups that were too minor to even mention. We enjoyed the guided tours because all the views were really great and the buildings so old. The sites were a bit crowded but still ...

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Reviews

Sylvia & Ethan Gale

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October 16, 2016

I think that no place on Earth can be more interesting to tour than Italy

A million times thank you! Italy is an incredibly beautiful country. I think that no place on Earth can be more interesting ...

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Regina Mayer

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October 16, 2016

Superb tour to Italy! You really deserve a round of applause

I wasn't sure what to expect from our trip to Italy but my mom and I were very surprised with how smoothly everything went. ...

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Pat Ottman

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October 16, 2016

Attention to detail was outstanding - Essence of Northern Italy, April 2017

Everything was perfect. Would certainly use Firebird Tours again and have recommended to friends and family. Attention to ...

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