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.
Country Roads of Tuscany & Central Italy - Classic Group
Deal number: 21500377
INSIGHT VACATIONS
This deal expires 19 Aug 2025
From 29/03/2026 to 05/10/2026
Rome
9-day tour
Price from
$5,075*
per person
Deal number: 21500377
Highlights
4 Dinner (D)8 Breakfast (B)1 Lunch (L)Choose between two carefully selected activitiesSiena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.Siena: Visit the cathedral with your Local Expert.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.We carry your bags for you and promptly deliver them to your hotel door.From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).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.Rome: Savour dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavours.Umbria: Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by 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.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.Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.Siena: Visit the cathedral with your Local Expert.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.Rome: Visit the Colosseum, still echoing with the thronging crowds and ghostly cries of gladiatorial combat.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.San Gimignano: Visit the Tuscan town of San Gimignano, often called 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."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."Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.
4 Dinner (D)8 Breakfast (B)1 Lunch (L)Choose between two carefully selected activitiesSiena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.Siena: Visit the cathedral with your Local Expert.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.We carry your bags for you and promptly deliver them to your hotel door.From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).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.Rome: Savour dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavours.Umbria: Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by 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.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.Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.Siena: Visit the cathedral with your Local Expert.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.Rome: Visit the Colosseum, still echoing with the thronging crowds and ghostly cries of gladiatorial combat.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.San Gimignano: Visit the Tuscan town of San Gimignano, often called 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."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."Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.
Day 1
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
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
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
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
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.
Day 6
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.
Day 7
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
Leave behind the tower-topped town of San Gimignano and 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
Bid farewell to the glories of Italy.
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
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
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
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
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.
Day 6
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.
Day 7
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
Leave behind the tower-topped town of San Gimignano and 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
Bid farewell to the glories of Italy.
Enquire to book this trip
Deal number: 21500377
Country Roads of Tuscany & Central Italy - Classic Group
INSIGHT VACATIONS
From 29/03/2026 to 05/10/2026
Rome
9-day tour
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*Travel restrictions & conditions apply. Review any specific conditions stated and our general terms at Terms and Conditions. Prices & taxes are correct as at the date of publication & are subject to availability and change without notice. Prices quoted are on sale until the dates specified unless otherwise stated or sold out prior. Prices are per person.
