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Country Roads of Umbria and Tuscany

9 Day Italy Tour to Rome, San Gimignano & Perugia | Operated by InsightVacations

  • 9 Days

  • 2 Countries

    Italy, Vatican City
  • 9 Cities

    Rome, Vatican, Umbria, Perugia, Assisi, Monte Subasio, Siena, San Gimignano, Florence
  • 13 Meals

    4 Dinner with Wines, 8 Breakfasts, 1 Lunch with Wine
  • Pace: Comfortable

    Mainly 2–3-night stays in each location. Comfortable travel days with numerous stops. Requires 1-3 miles of walking per day that might involve some uneven surfaces, such as cobblestones and stairs.

Trip Itinerary

Day 1: Welcome to Rome

Welcome to Rome. Join your Travel Director at 17:30 to explore the Eternal City, passing the medieval buildings, renaissance palaces and baroque churches scattered throughout the city. Get to know your fellow travelers over a pleasant Welcome Dinner.

Hotel: NH Roma Centro
Included Meals: Dinner with Wine
Top Rated Highlights: Rome Orientation During your orientation with your Travel Director see the medieval buildings, including Renaissance palaces and Baroque churches, scattered throughout the city.
Authentic Dining: Rome Welcome Dinner Welcome Dinner as you dine at your hotel's restaurant, Unique al Palatino.
Notes
Day 2: Umbria and on to Perugia

Explore the Vatican Museums in the morning, where a local historian unveils the gems of the vast Papal art collection. Your special visit includes fast-tracked entry. View the imposing Basilica of St. Peter, the largest in the world. Journey north to the Umbrian village of Baschi. Immerse yourself in the flavors and culture of the region and learn about the secrets of Italian food culture as you join Giovanni and his dog Chris for a truffle hunting session before being entertained by Chef Lorenzo with a fun pasta demonstration and delicious Highlight Lunch accompanied by Orvieto Classico wine. Join a Local Expert in Perugia to navigate the underground labyrinth of little streets, alleys and arches. Walk Corso Vannucci, resplendent in pale-pink stone, passing the princely Priors' Palace, cathedral and finely sculptured Great Fountain in the main square.

Hotel: Sangallo Palace Hotel
Included Meals: Breakfast, Lunch with Wine
Authentic Dining: Umbria Truffle Hunting and Lunch Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by a tasty lunch.
Notes
Day 3: Perugia Sightseeing & Free Time

During a MAKE TRAVEL MATTER® Experience, visit an artisanal workshop to meet Marta, recipient of a TreadRight Foundation grant, and her weavers. See how the fascinating art of loom-weaving textiles has been passed down through the generations and learn how this ancient craft is being preserved. Afterwards, you will be free to enjoy the many delights of Umbria's capital city. For dinner, choose your ideal ambience and palate-pleasing menu from a hand-picked selection of Perugian restaurants for your Dine-Around Evening. Buon appetito!

Hotel: Sangallo Palace Hotel
Included Meals: Breakfast, Dinner with Wine
Make Travel Matter: Meet Artisanal Hand Weavers in Perugia Meet Marta, a recipient of a TreadRight Foundation grant. Learn how she offers employment opportunities for local women and, alongside her weavers, preserves the ancient craft of loom-weaving in an artisan workshop.The workshop is owned by women and actively empowers women and girls through its education and training programs. Marta, and her students help to safeguard the unique patterns while contributing to the protection of Umbria’s cultural heritage.  Laboratorio Guidetta Brozzetti advances UN Sustainable Development Goal 5: Gender Equality and UN Sustainable Development Goal 11: Sustainable Cities & Communities.
Authentic Dining: Perugia Dine-Around Evening You are offered a selection of restaurants on your Dine-Around Evening. Choose your own ambience, cuisine and drinks for an intimate culinary experience.
Notes
Day 4: Assisi, in Search of St. Francis

Journey to Assisi, one of Italy's most beautiful medieval hilltop towns, set high up in the mountains and enclosed by fortress walls. In the valley, see the famous Church of St. Mary of the Angels, much venerated as the place of St. Francis' death, then continue up Mount Subasio to the upper town. Step inside the massive, 13th century Basilica of St. Francis with your Local Expert to learn how Giotto masterfully painted frescoes that inspired a variety of Renaissance artists. 

Hotel: Sangallo Palace Hotel
Included Meals: Breakfast
Top Rated Highlights: Assisi City Tour See St. Mary of the Angels Church and join your Local Expert to walk through the cobbled streets and beautifully preserved medieval laneways of this quaint town.
Top Rated Highlights: Assisi Basilica of St Francis Visit With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
Notes
Day 5: Tuscany to Cortona, Siena and San Gimignano

Follow the shores of Lake Trasimeno to Cortona, one of the oldest hilltop towns in Tuscany. After free time to explore, continue to the narrow cobbled streets of Siena. Standing in the shell-shaped Campo, imagine the frenzied atmosphere of the biannual Palio horse race and see the superb 14th century Town Hall. Explore Siena with Insight Choice. Choose to visit the medieval Cathedral. Alternatively, sample panforte, a traditional Tuscan dessert. Travel to your home for the next three nights, a delightful villa near the medieval town of San Gimignano.

Hotel: Villasanpaolo
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Siena Cathedral Visit Visit Siena's medieval black and white striped cathedral with your Local Expert.
Authentic Dining: Siena Panforte Tasting Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
Notes
Day 6: San Gimignano sightseeing and Free Time

In the morning, your Travel Director will show you San Gimignano's medieval skyscrapers, serpentine streets and hidden squares. The town is also home to world champion gelato maestro Sergio Dondoli. At his artisan ice cream parlour on Piazza della Cisterna, the jaunty gelataio doles out his silky, frozen treats in a range of unique flavors for you to try. The rest of the day is at leisure; why not join an Optional Experience to Pisa and Lucca?

Hotel: Villasanpaolo
Included Meals: Breakfast
Top Rated Highlights: Visit San Gimignano Visit the medieval Manhattan of Italy!
Authentic Dining: San Gimignano Gelato Tasting Ascend serpentine alleyways to the artisan gelato parlour of world champion gelato maestro, Sergio Dondoli for a taste of his finest frozen treats.
Notes
Day 7: Florence and Tuscan Countryside Experience

The morning is devoted to the Renaissance city of Florence. A fascinating walking exploration with a Local Expert takes you to the marble-clad cathedral crowned by Brunelleschi's dome. See the baptistery with its beautiful Gates of Paradise and Giotto's splendid bell tower. Walk on to Piazza della Signoria with its open-air gallery of Renaissance sculptures, followed by free time to shop for top-quality Florentine leather or gold. Toast to your travels during a delicious Farm-to-Table Celebration Dinner at a local restaurant and enjoy tasting flavoursome dishes prepared with locally grown ingredients, sourced from the farm or nearby Tuscan region. Relax as the pairing of home-made pastas with the farm's own traditional Chianti wine rounds off your great Italian adventure.

Hotel: Villasanpaolo
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Florence City Tour Join a Local Expert to view the multi-colored marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square. See the area around Santa Croce Basilica, famous for the quality of its luxury goods.
Authentic Dining: Tuscany Celebration Dinner Nestled in the rolling hills surrounding Sam Gimignano and surrounded by its own vineyards, olive groves, saffron crop and orchards, is the homely Il Vecchio Maneggio. Admire the beautiful views as you enjoy a drink before sitting down to your Celebration Dinner - a delicious Farm-to-Table experience, with all the organic produce sourced from the surrounding farm.
Notes
Day 8: Country drive to Ancient Rome

Leave behind the tower topped town of San Gimignano. Enjoy rolling Tuscan hills as you journey through the Italian countryside, making your way to Ancient Rome. On arrival, enjoy the afternoon at leisure.

Hotel: Hotel St. Martin
Included Meals: Breakfast
Notes
Day 9: Arrivederci Roma

Bid farewell to the glories of Italy. Departure transfers arrive at Rome’s Fiumicino Leonardo da Vinci Airport.

Included Meals: Breakfast
Notes
This itinerary is for reference only. Upon booking with GET, guests will receive tour documents which will list all confirmed hotels and itineraries based upon the guest's departure date.

Price Includes

Dining Summary
  • - 4 Dinner with Wines (DW)
  • - 8 Breakfasts (B)
  • - 1 Lunch with Wine (LW)
Top Rated Highlights
  • During your orientation with your Travel Director see the medieval buildings, including Renaissance palaces and Baroque churches, scattered throughout the city.
  • See St. Mary of the Angels Church and join your Local Expert to walk through the cobbled streets and beautifully preserved medieval laneways of this quaint town.
  • With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
  • Visit Siena's medieval black and white striped cathedral with your Local Expert.
  • Visit the medieval Manhattan of Italy!
  • Join a Local Expert to view the multi-colored marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square. See the area around Santa Croce Basilica, famous for the quality of its luxury goods.
Authentic Dining
  • Welcome Dinner as you dine at your hotel's restaurant, Unique al Palatino.
  • Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by a tasty lunch.
  • You are offered a selection of restaurants on your Dine-Around Evening. Choose your own ambience, cuisine and drinks for an intimate culinary experience.
  • Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
  • Ascend serpentine alleyways to the artisan gelato parlour of world champion gelato maestro, Sergio Dondoli for a taste of his finest frozen treats.
  • Nestled in the rolling hills surrounding Sam Gimignano and surrounded by its own vineyards, olive groves, saffron crop and orchards, is the homely Il Vecchio Maneggio. Admire the beautiful views as you enjoy a drink before sitting down to your Celebration Dinner - a delicious Farm-to-Table experience, with all the organic produce sourced from the surrounding farm.
Make Travel Matter
  • Meet Marta, a recipient of a TreadRight Foundation grant. Learn how she offers employment opportunities for local women and, alongside her weavers, preserves the ancient craft of loom-weaving in an artisan workshop.The workshop is owned by women and actively empowers women and girls through its education and training programs. Marta, and her students help to safeguard the unique patterns while contributing to the protection of Umbria’s cultural heritage.  Laboratorio Guidetta Brozzetti advances UN Sustainable Development Goal 5: Gender Equality and UN Sustainable Development Goal 11: Sustainable Cities & Communities.

Optional Experiences

Optional Experiences are subject to change. Your Travel Director will supply you with a final list of Optional Experiences available on your trip. Optional Experiences cannot be booked online; they can be purchased during your trip through your Travel Director.

Excursion To Spello (Available on Day 3)

Enjoy an afternoon excursion to the breathtaking Umbrian hillside town of Spello, its centro storico still enveloped by Roman walls. With a local expert, we'll ascend through ancient arches and tight cobbled streets, where houses cascade with hanging flower pots and churches seemingly sanctify almost every street corner.

Adult Price: €28 Umbrian Dinner Experience (Available on Day 4)

Umbria is not only a region which is culturally rich and full of beautiful vistas, it is also a region rich in its gastronomic offerings. A journey to explore the edible treasures of the traditional Umbrian kitchen and the superb wines of this region too, all served to you in a beautiful rustic restaurant!

Adult Price: €73 Pisa and Lucca Experience (Available on Day 6)

Enjoy the day visiting two of Italy's most beautiful cities, Pisa and Lucca, with our Local Experts. First, we’re off to Pisa, where you'll have time to explore the famous Square of Miracles, dominated by the leaning tower. We'll continue to the quaint and picturesque town of Lucca where you’ll take a leisurely tour of the medieval center to admire the beauty of this Tuscan gem. Then, enjoy free time to do your own exploring.

Adult Price: €64 Dinner in the Tuscan Hills (Available on Day 6)

A fabulous dinner of Tuscan specialties awaits you. We drive into the hills surrounding Florence for a delicious typical Florentine meal complete with Chianti wine, music and lots of fun! An evening to remember. Viva Italia!

Adult Price: €74 Bagno Vignoni & Pienza (Available on Day 8)

We travel through the beautiful Italian countryside to explore the medieval spa town of Bagno Vignoni, renowned for its mineral rich thermal baths, before our journey continues on to the 'model' renaissance town of Pienza most famous for its delicious pecorino cheese!

Adult Price: €34 Roman Dinner Party (Available on Day 8)

Enjoy an evening of delicious Roman cuisine with drinks and a great Italian ambiance.

Adult Price: €71