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Country Roads of Umbria & Tuscany – Classic Group

9 Days

  • Tour Description
  • Itinerary
  • Dates & prices
  • Enquire Now
  • Travel Insurance by Allianz

Tour Description

Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the narrow cobblestone streets of Siena to the shell-shaped Piazza del Campo and see the Torre del Mangia, the second-tallest tower in Italy. Discover the art of truffle-hunting and learn how to make pasta from a professional before delighting in a local lunch. In San Gimignano, eat the best gelato in the world - literally. Indulge in your favourite flavours or try something unexpected. Alongside a Local Expert, marvel at the cathedral at the centre of Florence: Basilica di Santa Maria del Fiore, nicknamed 'the Duomo' for its awe-inspiring crown made by a master goldsmith.

Priced From:

$ 5165pp *

From: 2026-03-29

To: 2026-10-11

Start Location: Rome, Italy

End Location: Rome, Italy

Trip Type: Country Roads

Tour Advisors

Tiffany McCrea-Lennon

Managing Director

Russell Mein

Travel Specialist

Caitlin Lennon

Travel Coordinator

Michelle Baldwin

Travel Specialist

Gaylyn Murdoch

Administration Manager

Holly Skene

Travel Co-ordinator

Kim Thomas

Broker

Itinerary

Welcome to the Eternal City of Rome
Day 1
Duration: 1
Accommodation: NH Roma Centro, Rome
Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in before joining your Travel Director for a private visit to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica. End the day getting to know your fellow travellers over Roman specialties during dinner at a local restaurant.
Umbria and on to Perugia
Day 2
Duration: 1
Accommodation: Sangallo Palace Hotel, Perugia
See the imposing Basilica of St. Peter in the Vatican City before crossing the Tiber into Ancient Rome and imagining the gladiatorial combats and sounds of roaring spectators as you visit the mighty Colosseum with your Local Expert. 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. Afterwards, be entertained by Chef Lorenzo with a fun pasta demonstration and enjoy a delicious lunch accompanied by Orvieto Classico wine. Join a Local Expert in Perugia to navigate the underground labyrinth of little streets, alleys, and arches. Walk along Corso Vannucci, resplendent in pale-pink stone, passing the princely Priors' Palace, the cathedral, and the finely sculptured Great Fountain in the main square.
Perugia Sightseeing & Free Time Relaxed Start
Day 3
Duration: 1
Accommodation: Sangallo Palace Hotel, Perugia
This morning, 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. Then enjoy free time to explore the many delights of Umbria's capital city or join an optional experience to Cortona. 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!
Assisi, in Search of St. Francis Relaxed Start
Day 4
Duration: 1
Accommodation: Sangallo Palace Hotel, Perugia
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.
Tuscany to Siena and San Gimignano
Day 5
Duration: 1
Accommodation: Villasanpaolo, San Gimignano
Follow the shores of Lake Trasimeno and 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 Town Hall. Explore Siena with Insight Choice. Choose to visit the medieval Cathedral, or, alternatively, sample panforte, a traditional Tuscan dessert. Travel to the medieval town of San Gimignano where your Travel Director will show you the 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 silky smooth, frozen treats are beautifully displayed in a range of unique flavours for you to try. Your home for the next three nights is a delightful villa near this jewel of medieval architecture.
San Gimignano and Free Time Relaxed Start
Day 6
Duration: 1
Accommodation: Villasanpaolo, San Gimignano
Enjoy your day at leisure, taking in your Tuscan surroundings. Relax at your hotel or you could opt to join an Optional Experience to Pisa and Lucca.
Florence and Tuscan Countryside Experience
Day 7
Duration: 1
Accommodation: Villasanpaolo, San Gimignano
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 dinner at a local restaurant and enjoy tasting flavoursome dishes prepared with locally grown ingredients, home-made pastas, traditional Chianti wine, all sourced from the farm in the Tuscan region.
Country drive to Ancient Rome
Day 8
Duration: 1
Accommodation: Hotel St. Martin, Rome
Leave behind the tower topped town of San Gimignano. Enjoy rolling Tuscan hills as you journey south through the Italian countryside. This morning, delight in the medieval spa town of Bagno Vignoni, renowned for its mineral rich thermal baths and continue to the 'model' renaissance town of Pienza, famous for its delicious pecorino cheese, before making your way to Rome.
Arrivederci Roma
Day 9
Duration: 1
Bid farewell to the glories of Italy.

Dates & prices

Start Date: 2026-03-29
End Date: 2026-04-06
twin
Child Price: 4880
Adult Price: 5450
twinShare
Child Price:
Adult Price: 5450
triple
Child Price: 4650
Adult Price: 5220
single
Child Price:
Adult Price: 7070
Start Date: 2026-04-26
End Date: 2026-05-04
twin
Child Price: 4955
Adult Price: 5525
twinShare
Child Price:
Adult Price: 5525
triple
Child Price: 4725
Adult Price: 5295
single
Child Price:
Adult Price: 7195
Start Date: 2026-05-24
End Date: 2026-06-01
twin
Child Price: 5005
Adult Price: 5575
twinShare
Child Price:
Adult Price: 5575
triple
Child Price: 4775
Adult Price: 5345
single
Child Price:
Adult Price: 7295
Start Date: 2026-06-21
End Date: 2026-06-29
twin
Child Price: 5005
Adult Price: 5575
twinShare
Child Price:
Adult Price: 5575
triple
Child Price: 4775
Adult Price: 5345
single
Child Price:
Adult Price: 7295
Start Date: 2026-07-05
End Date: 2026-07-13
twin
Child Price: 4880
Adult Price: 5450
twinShare
Child Price:
Adult Price: 5450
triple
Child Price: 4650
Adult Price: 5220
single
Child Price:
Adult Price: 7070
Start Date: 2026-08-02
End Date: 2026-08-10
twin
Child Price: 4825
Adult Price: 5395
twinShare
Child Price:
Adult Price: 5395
triple
Child Price: 4595
Adult Price: 5165
single
Child Price:
Adult Price: 6955
Start Date: 2026-08-30
End Date: 2026-09-07
twin
Child Price: 4925
Adult Price: 5495
twinShare
Child Price:
Adult Price: 5495
triple
Child Price: 4695
Adult Price: 5265
single
Child Price:
Adult Price: 7115
Start Date: 2026-09-13
End Date: 2026-09-21
twin
Child Price: 5025
Adult Price: 5595
twinShare
Child Price:
Adult Price: 5595
triple
Child Price: 4795
Adult Price: 5365
single
Child Price:
Adult Price: 7315
Start Date: 2026-09-27
End Date: 2026-10-05
twin
Child Price: 5025
Adult Price: 5595
twinShare
Child Price:
Adult Price: 5595
triple
Child Price: 4795
Adult Price: 5365
single
Child Price:
Adult Price: 7315
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