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Country Roads of Umbria and Tuscany

Operated by: Insight Vacations

9 Days from $2,196 per person
APR - OCT 2023
Tours of San Gimignano in Siena, Tuscany, Italy

Countries Visited

Italy, Vatican City ...more Italy, Vatican City

Locations Visited

Rome, Vatican, Umbria, Perugia, Assisi, Monte Subasio, Siena, San Gimignano, Florence ...more Rome, Vatican, Umbria, Perugia, Assisi, Monte Subasio, Siena, San Gimignano, Florence
  1. Day 1 Welcome to Rome

    Transfers to your hotel depart from Rome's Fiumicino Leonardo da Vinci Airport at 09:30, 12:30 and 15:30. Join your Travel Director at 17:30 to explore the Eternal City, passing the renaissance palaces and baroque churches scattered throughout the city. Get to know your fellow travellers over a Welcome Dinner at a local restaurant.

    meals Dinner with Wine
    hotel Hotel St. Martin, Rome.
  2. Day 2 Umbria and on to Perguia

    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 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 village of Baschi. Immerse yourself in the flavours 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. Then join Chef Lorenzo for an entertaining 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.

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

    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!

    meals Breakfast, Dinner with Wine
    hotel Sangallo Palace Hotel, Perugia.
  4. Day 4 Assisi, in Search of St. Francis Relaxed Start

    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.

    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. 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.

    meals Breakfast, Dinner with Wine
    hotel Villasanpaolo, San Gimignano.
  6. Day 6 San Gimignano sightseeing and Free Time Relaxed Start

    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 for you to try. The rest of the day is at leisure; why not join an Optional Experience to Pisa and Lucca?

    meals Breakfast
    hotel Villasanpaolo, San Gimignano.
  7. Day 7 Florence and Tuscan Countryside Experience Relaxed Start

    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.

    meals Breakfast, Dinner with Wine
    hotel Villasanpaolo, San Gimignano.
  8. 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.

    meals Breakfast
    hotel NH Roma Centro, Rome.
  9. Day 9 Arrivederci Roma

    Bid farewell to the glories of Italy. Departure transfers arrive at Rome’s Fiumicino Leonardo da Vinci Airport at 07:00 and 09:30.

    meals Breakfast
Map
Price Includes

Dining Summary

  • 4 Dinner with Wine (DW)
  • 8 Breakfast (B)
  • 1 Lunch with Wine (LW)

Choice Highlights

  • Choose between two carefully selected activities
  • Siena: Visit Siena's medieval black and white striped cathedral with your Local Expert.
  • Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.

Authentic Dining

  • Rome: Welcome Dinner as you dine at your hotel's restaurant, Unique al Palatino.
  • Umbria: Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by a tasty lunch.
  • 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.
  • Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
  • San Gimignano: Ascend serpentine alleyways to the artisan gelato parlour of world champion gelato maestro, Sergio Dondoli for a taste of his finest frozen treats.
  • 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.

Insight Experiences

  • Vatican: Gain priority access into the Vatican Museums and admire the famous Bramante Staircase. Witness the genius of Michelangelo in the Sistine Chapel and view the splendid dome of St. Peter's Basilica.

Make Travel Matter

  • 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.

Top Rated Highlights

  • Rome: During your orientation with you Travel Director see the medieval buildings, including Renaissance palaces and Baroque churches, scattered throughout the city.
  • Assisi: 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.
  • Assisi: With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
  • Siena: Visit Siena's medieval black and white striped cathedral with your Local Expert.
  • San Gimignano: Visit the medieval Manhattan of Italy!
  • Florence: Join a Local Expert to view the multi-coloured 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.

Travel Director

  • : "One thing I really love about showing guests about Italy is how art and beauty can be found around every corner of some of Italy's cities, which are real open air museums."
  • : "One fun fact people don't usually know before they come to Italy is that the Italian alphabet only has 22 letters."
  • : "I really love about showing guests the huge variety that Italy has to offer, from quaint countryside villages to cities full of stupendous art and architecture."

Dates & Prices

Prices shown are per person based on two people sharing a twin room. To request a personalized travel quote, click "Request Quote" and a Travel Specialist will send your custom quote including airfare if requested.

Online Booking Process

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June 2023
AARP Members Save up to $100
Jun 25 Sun
Jul 3 Mon
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Guaranteed Departure This departure is guaranteed
DOUBLE OCCUPANCY PRICE/PERSON
$2,495 $2,196 Save $299
GETAWAY DEALS
September 2023
AARP Members Save up to $100
Sep 3 Sun
Sep 11 Mon
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Guaranteed Departure This departure is guaranteed
DOUBLE OCCUPANCY PRICE/PERSON
$2,850 $2,565 Save $285
FALL TRAVEL SALE
October 2023
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Oct 1 Sun
Oct 9 Mon
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Guaranteed Departure This departure is guaranteed
DOUBLE OCCUPANCY PRICE/PERSON
$2,825
Optional Add-Ons

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.

Perugia

Available on Day 3

Excursion To Spello

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: € 25

Available on Day 4

Umbrian Dinner Experience

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 as well! 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: € 62

Florence

Available on Day 6

Dinner in the Tuscan Hills

A fabulous dinner of Tuscan specialities 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: € 65

San Gimignano

Available on Day 6

Pisa and Lucca Experience

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 centre to admire the beauty of this Tuscan gem. Then, enjoy free time to do your own exploring.
Adult Price: € 59

Chianciano Terme

Available on Day 8

Bagno Vignoni & Pienza

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: € 31

Rome

Available on Day 8

Roman Dinner Party

Enjoy an evening of delicious Roman cuisine with drinks and a great Italian ambiance.
Adult Price: € 62

Reviews
Service
Vacation
Independent Reviews
Trusted Customer
Monday, May 20, 2019
Service
Helpful, good explanations, easy process. Traveled with GET two times now.
Vacation
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
Monday, August 14, 2017
Service
Made all travel and tour arrangements. Process was seamless, great communication and no broken promises.
Vacation
Well planned sites, facilities, busses, restaurants, tour director and local tour guides.
John Creelman
Wednesday, May 31, 2017
Service
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.
Vacation
See my earlier comment. **
Trusted Customer
Tuesday, April 26, 2016
Service
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
Vacation
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
Sunday, November 1, 2015
Service
Our Tour Guide was excellent!! She took very good care of us
Vacation
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
Monday, October 19, 2015
Service
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
Vacation
The company tried to include far too much on this tour. Great tour with this exception. Wonderful Tour Guide!
Trusted Customer
Saturday, October 3, 2015
Service
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
Vacation
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
Sunday, September 27, 2015
Service
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.
Vacation
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
Saturday, September 26, 2015
Service
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.
Vacation
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
Thursday, September 17, 2015
Service
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
Vacation
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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