Country Roads of Tuscany & Central Italy
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.
- 10 May 2026 – 18 May 2026
from $4,072.50 pp twin share * - 24 May 2026 – 01 Jun 2026
from $5,062.50 pp twin share * - 21 Jun 2026 – 29 Jun 2026
from $4,925 pp twin share * - 30 Aug 2026 – 07 Sep 2026
from $4,252.50 pp twin share * - 13 Sep 2026 – 21 Sep 2026
from $5,795 pp twin share * - 27 Sep 2026 – 05 Oct 2026
from $5,795 pp twin share * - 28 Mar 2027 – 05 Apr 2027
from $4,825 pp twin share * - 25 Apr 2027 – 03 May 2027
from $5,295 pp twin share * - 23 May 2027 – 31 May 2027
from $5,295 pp twin share * - 20 Jun 2027 – 28 Jun 2027
from $4,925 pp twin share * - 04 Jul 2027 – 12 Jul 2027
from $4,825 pp twin share * - 01 Aug 2027 – 09 Aug 2027
from $4,750 pp twin share * - 29 Aug 2027 – 06 Sep 2027
from $4,825 pp twin share * - 12 Sep 2027 – 20 Sep 2027
from $5,825 pp twin share * - 26 Sep 2027 – 04 Oct 2027
from $5,295 pp twin share *
* Prices and category availability are subject to change without notice.
Itinerary
- Day 1 – Welcome to the Eternal City of Rome:
Welcome to Rome, a glorious city filled with classical antiquities, medieval buildings, Renaissance palaces and Baroque churches. Settle in before joining your Travel Director and get to know your fellow travellers over Roman specialities during dinner at a local restaurant. - Day 2 – Umbria and on to 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. - Day 3 – Perugia Sightseeing & Free Time Relaxed Start:
This morning, during a MAKE TRAVEL MATTER® Experience, visit an artisanal workshop to meet Marta—recipient of a TreadRight Foundation grant—and her team of weavers. Discover how the fascinating art of loom weaving has been passed down through generations and learn how this ancient craft is being preserved today. Later, enjoy free time to explore the many delights of Umbria’s capital city or join an Optional Experience to Cortona. In the evening, take your pick from a hand-picked selection of Perugian restaurants for a Dine Around experience—choosing the ambience and menu that suit you best. Buon appetito! - 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. - Day 5 – Tuscany to Siena and 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 nestled in the Tuscan countryside. - Day 6 – Tuscany and Free Time Relaxed Start:
Enjoy your day at leisure, taking in your Tuscan surroundings. Relax at your hotel or you could opt to join an Optional Experience to Lucca. - 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 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. - Day 8 – Country drive to Ancient Rome:
Enjoy the rolling Tuscan hills as you journey south through the Italian countryside. This morning, visit the medieval spa town of Bagno Vignoni, renowned for its mineral-rich thermal baths, then continue to the ‘model’ Renaissance town of Pienza, famous for its delicious pecorino cheese, before making your way to Rome. - Day 9 – Arrivederci Roma:
Bid farewell to the glories of Italy.
Highlights
- Explore the charming cobblestone streets and shell-shaped Piazza del Campo in Siena.
- Learn the art of truffle-hunting and pasta making from local experts.
- Savor the world’s best gelato in San Gimignano.
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.
Inclusions
- Choose between two carefully selected activities.
- Siena: Visit the cathedral with your Local Expert.
- Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
- Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert’s fascinating commentary.
- 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.
FAQs
- Bettoja Mediterraneo, Rome
- Cappuccina Country Resort & Spa, San Gimignano
- NH Roma Centro, Rome
- Sangallo Palace, Perugia
How long is this journey?
This itinerary runs for 9 days and 8 nights.
When can I travel?
Departures are currently scheduled between 10 May 2026 and 04 Oct 2027, subject to live availability.
Are there different departure options?
Yes, multiple departures may be available depending on your preferred travel period.
Are discounts available?
Seasonal or loyalty discounts may be available on selected departures at the time of enquiry.
What is generally included?
Inclusions typically cover guided touring and selected experiences, with exact details listed in the itinerary.
Provided by: Insight VacationsFine Print
Terms and conditions apply. Click here for more details.