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Country Roads of Umbria & Tuscany

Operated by: Insight Vacations

9 Days from $2,655 per person
San Gimignano

Countries Visited


Locations Visited

Rome, Orvieto, Perugia, Assisi, Siena, San Gimignano, Florence, Venice
  1. Day 1 Welcome to Rome.

    Transfers to your centrally located hotel, not far from the Ancient Roman Ruins, depart from Rome's Fiumicino Leonardo da Vinci Airport at 09:30, 12:30 and 15:30. Relax and settle in before meeting your Travel Director at 17:30. Get to know your fellow guests during your Welcome Dinner at a local restaurant.(Dinner with Wine)

    meals Dinner with Wine
    hotel The K Boutique Hotel/Kolbe Hotel Rome.
  2. Day 2 Sistine Chapel, Cooking in Orvieto 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 VIP visit includes fast-tracked entry and behind-the-scenes access to the Bramante Staircase, a part of the Vatican normally closed to visitors. View the imposing Basilica of St. Peter, the largest in the world. Journey north to the Umbrian hilltop town of Orvieto; its cathedral is one of Italy’s most celebrated buildings. You’re welcomed into the kitchens of zesty, Etruscan chef Lorenzo Polegri, who shares with you his virtuoso cooking skills and love of Italian food. Delicious pasta fresca, combined with the local staples of olive oil, cheese, prosciutto and focaccia, make for a memorable Highlight Lunch, all washed down with a chilled glass of Orvieto Classico wine. Continue to Perugia, one of the most beautiful centres of art in Italy. The evening is at leisure to explore and dine as you please.(Breakfast / Lunch with Wine)

    meals Breakfast, Lunch with Wine
    hotel Sangallo Palace Hotel, Perugia.
  3. Day 3 Perugia Sightseeing & Free Time.

    In the morning, 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. Visit an artisanal workshop to meet Marta, beneficiary 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!(Breakfast / Dinner with Wine)

    meals Breakfast, Dinner with Wine
    hotel Sangallo Palace Hotel, Perugia.
  4. 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. Continue through the twisted groves that carpet the side of Mount Subasio. At a family-run olive mill, meet a third generation specialist to follow the evolution of the olive from tree to table. Relish the intense flavours drizzled over crusty bread with a sprinkle of salt – delizioso!(Breakfast)

    meals Breakfast
    hotel Sangallo Palace Hotel, Perugia.
  5. 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. Then, with your Local Expert, there is time to climb up to the black-and-white striped marble cathedral. Travel to your home for the next three nights, a delightful villa near the medieval town of San Gimignano.(Breakfast / Dinner with Wine)

    meals Breakfast, Dinner with Wine
    hotel Villasanpaolo, San Gimignano.
  6. 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 flavours. The rest of the day is at leisure; why not join an Optional Experience to Pisa and Lucca?(Breakfast)

    meals Breakfast
    hotel Villasanpaolo, San Gimignano.
  7. 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 seek bargains in the gold workshops.(Breakfast / Dinner with Wine)

    meals Breakfast
    hotel Villasanpaolo, San Gimignano.
  8. Day 8 Country drive to Ancient Rome.

    Descend from the Apennine Mountains, leaving 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. Toast your travels as you enjoy a delicious Celebration Dinner at a local restaurant.(Breakfast / Dinner with Wine)

    meals Breakfast, Dinner with Wine
    hotel The K Boutique, Rome.
  9. Day 9 Arrivederci Roma.

    Your departure transfer arrives at Rome's Fiumicino Leonardo da Vinci Airport at 07:00 and 09:30.(Breakfast)

    meals Breakfast
Price Includes

Included Insight Services

  • Our highly-skilled Travel Director will ensure your journey is seamless, serving as your expert guide, consummate organiser, and friend overseas.
  • Enjoy the comfort of Insight's luxury, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom.
  • Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
  • We carry your bags for you and promptly deliver them to your hotel door.
  • Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.
  • Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
  • From time to time, your Travel Director will enchant you with an Insight Flourish, which is a local specialty representing the destination.
  • If your arrival and/or departure flights are as per the itinerary start and end dates, then transfers are available at scheduled times. If your flights are outside these times, or you have booked additional nights accommodation with Insight Vacations, you may purchase transfers or make your own way from/to the airport.

Authentic Dining

  • Orvieto: Meet Etruscan Chef Lorenzo Polegri, who shares his virtuoso cooking skills, followed by a memorable Highlight Lunch with wine.
  • Perugia: You are offered a selection of restaurants on your Dine-Around Evening. Choose your own ambience, cuisine and drinks for an intimate culinary experience.
  • Mount Subasio: Follow the evolution of the olive, from tree to table, with a tasting at a family-run olive mill.
  • San Gimignano: Meet world champion gelato maestro, Sergio Dondoli, and sample silky frozen treats in a range of unique flavours.
  • Tuscany: 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.
  • Dining Summary: 8 Breakfasts (B), 1 Lunch with Wine (LW) and 4 Dinners with Wine (DW) all with tea or coffee.

Insight Experiences

  • Vatican City: Gain VIP access into the Vatican Museums and be among the select few to admire the famous Bramante Staircase. Admire the Popes’ treasure-trove and witness the genius of Michelangelo in the Sistine Chapel. Venture inside St. Peter's Basilica and see Michelangelo's Pietà, and the splendid dome.
  • Perugia: Meet Marta, recipient of a TreadRight Foundation grant. Learn how Marta and her weavers are preserving the ancient craft of loom-weaving at their artisanal workshop.

Top Rated Highlights

  • Rome: See the mighty Colosseum and Roman Forum. You will also see other medieval buildings, including Renaissance palaces and Baroque churches, scattered throughout the city.
  • Orvieto: During your orientation of this Umbrian hilltop town with your Travel Director, visit Piazza del Duomo to admire the cathedral.
  • Perugia: Join a Local Expert to navigate the underground labyrinth of little streets, alleys and arches. Promenade the wide Corso Vannucci, resplendent in pale pink stone, past the princely Priors' Palace, cathedral and finely sculptured Great Fountain in the main square.
  • Assisi: See St. Mary of the Angels Church and join your Local Expert to walk through the cobbled streets to St. Clare’s Church and see the cathedral.
  • Assisi: A Local Expert will explain why the Basilica of St. Francis is considered one of the crowning achievements of medieval Europe.
  • Siena: With your Local Expert explore the cobbles streets of Siena. Learn about the Palio horse race while standing in Piazza del Campo. See the 14th century Town Hall and its Mangia Tower.
  • Siena: Led by your Local Expert, wander your way through the medieval streets to visit the black-and-white striped marble cathedral.
  • San Gimignano: Explore the stunning hilltop town with your Travel Director. Navigate the winding streets, hunting out the towers and palaces for which it is so famous.
  • Florence: View the city skyline from the sumptuous terrace of Piazzale Michelangelo. Explore the city and its landmarks with your Local Expert - see the domed cathedral, it's adjacent baptistery with its Gates of Paradise, and the open-air gallery of Piazza della Signoria.
  • Venice: With your Travel Director cruise to St. Mark's Square and see the Doge's Palace, Bridge of Sighs and St. Mark's Basilica.
  • Venice: To the tune of accompanying musicians, you will be serenaded through the atmospheric canals by gondola, past water-lapped doorways and Rococo palaces.

Dates & Prices
Airfare is not included, but can be added to quote upon request
  • Definite Departure
Price Discount Availability Price
Independent Reviews
Trusted Customer
Travel date: Monday, May 20, 2019
Helpful, good explanations, easy process. Traveled with GET two times now.
Chose Country roads to be in the countryside instead of the big cities and Umbria and Tuscany were great areas with interesting small towns. The views were fabulous!
Bernard Moleskie
Travel date: Monday, August 14, 2017
Made all travel and tour arrangements. Process was seamless, great communication and no broken promises.
Well planned sites, facilities, busses, restaurants, tour director and local tour guides.
John Creelman
Travel date: Wednesday, May 31, 2017
The only fault I can mention in regards to GET is the trips description as "leisurely". It belies the actual conditions. There was considerable difficult walking when visiting the hilltop towns especially and to a lesser degree in the long walks getting into and out of the larger cities.
See my earlier comment. **
Trusted Customer
Travel date: Tuesday, April 26, 2016
The Grand European Travel representatives were very efficient and helpful.
Response from Grand European Travel:
Thank you so much for taking the time to write. We're so happy you enjoyed your trip to Italy! Grand European Travel
Wednesday, April 27, 2016
It was very well planned. We had a good variety of activities for the time we had. I took advantage of all the optional activities, which may have made a difference. Our tour guide, GiGi, and driver, Benito, were excellent
Trusted Customer
Travel date: Sunday, November 1, 2015
Our Tour Guide was excellent!! She took very good care of us
My only complaint was that The Country Roads of Umbria and Tuscany was advertised as leisurely and it was anything but. However I was pleased to have covered so much of each region but I was not prepared for the pace.
Trusted Customer
Travel date: Monday, October 19, 2015
Service good.
Response from Grand European Travel:
We're sorry to hear that you felt there was too much included. We will share this information with our planning teams right away. Thank you for your helpful feedback. Grand European Travel
Monday, October 19, 2015
The company tried to include far too much on this tour. Great tour with this exception. Wonderful Tour Guide!
Trusted Customer
Travel date: Saturday, October 3, 2015
Good except in trying to pack too much into the tour. I guess this was a "tasting tour" to give people a quick sense of what they might like to return and visit with more leisure.
Response from Grand European Travel:
There is a lot to see on this particular trip. We do try to include the highlights of what most of our guests are interested in and try to convey that in our brochure and travel documents. We apologize if the daily itinerary was not made clear to you and appreciate you bringing this to our attention. Grand European Travel
Monday, October 5, 2015
The tour covered too much too fast. Four hours for Florence was ridiculous. The hotels were fine. Too much food at special dinners.
Trusted Customer
Travel date: Sunday, September 27, 2015
The registration process was easy with timely reminders of payment. Our fights were well spaced and the coach was comfortable and clean. The hotels were well placed and had good amenities.
The tour was amazing with a good balance of sightseeing and down time. We appreciated the fast track entry into crowded tourist spots such as the Vatican, "the David" and a gondola ride. Belinda Richardson was awesome as our tour director. She went the extra mile to celebrate anniversaries and birthdays (especially mine.) Unforgettable trip.
Trusted Customer
Travel date: Saturday, September 26, 2015
Everything was handled very well. I just wish we had been given a choice between Economy/Prime and Economy seating on our flights. Economy on our Alitalia flight was very uncomfortable and luckily we were able to get upgraded to Economy/Prime on the trip home.
The tour was excellent and our tour guide was wonderful. I was worried that the walking would be too difficult for me and in some cases it was. Our guide was able to arrange cabs for me and another member who was having difficulty. I had called Grand European Travel and had asked them about the walking and they seemed to indicate that it wouldn't be a problem. I think when people have this sort of difficulty, they should be informed as to what they will be encountering.
Trusted Customer
Travel date: Thursday, September 17, 2015
Air transportation and tour arrangements were made without error.
Response from Grand European Travel:
That is one of the benefits in traveling with us. Those little touches and sights you wouldn't see if you were on your own. Thank you for taking the time to share your thoughts and memories. Grand European Travel
Thursday, September 17, 2015
All aspects of the trip exceeded my expectations. The itinerary was spot on and included many things we would never have been able to discover on our own. The accommodations, included food and coach were all outstanding. And our tour director and driver could not have been better.
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