Country Roads of Umbria & Tuscany - Classic Group
Tour Type: Country Roads
Brochure Type Europe & Britain Premium 2026 v1
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 favorite flavors or try something unexpected. Alongside a Local Expert, marvel at the cathedral at the center of Florence: Basilica di Santa Maria del Fiore, nicknamed 'the Duomo' for its awe-inspiring crown made by a master goldsmith.
Additional Included Highlights
Brochure Type Europe & Britain Premium 2026 v1
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 favorite flavors or try something unexpected. Alongside a Local Expert, marvel at the cathedral at the center of Florence: Basilica di Santa Maria del Fiore, nicknamed 'the Duomo' for its awe-inspiring crown made by a master goldsmith.
Additional Included Highlights
- 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.
- 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
- Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
- From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.
- 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.
- 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 Ce
- 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.
- Rome Savor dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavors.
- Umbria Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by lunch.
- 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.
- 8 Breakfast (B)
- 1 Lunch with Wine (LW)
- 1 Dinner (D)
- 3 Dinner with Wine (DW)
- Siena Visit the Cathedral with your Local Expert.
- Siena Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
- Rome Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica's simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior
- 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
- 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 medieval Manhattan of Italy.
- 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.
- Florence Join a Local Expert to view the multi-colored 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
- "One fun fact people don't usually know before they come to Italy is that the Italian alphabet only has 22 letters."
- "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."
- "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 d
- Hand sanitizer is freely available on board for you to use throughout the day.
Call 410-638-5822 for more information or to book today! Mention code 18907395
- Tour Operator
- Insight Vacations
- Duration
- 9 Days
- Escorted
- Escorted - Yes
| Day | Destination | Description |
| Day 1 | Rome | Welcome to the Eternal City of 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 travelers over Roman specialties during dinner at a local restaurant. Accommodations: NH Roma Centro, Rome |
| Day 2 | Perugia | 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 flavors 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. Accommodations: Sangallo Palace Hotel, Perugia |
| Day 3 | Perugia | Perugia Sightseeing & Free Time Relaxed Start: This morning enjoy free time to explore the many delights of Umbria's capital city or join an optional experience to Cortona. Later, 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. 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! Accommodations: Sangallo Palace Hotel, Perugia |
| Day 4 | Monte Subasio | 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. Accommodations: Sangallo Palace Hotel, Perugia |
| Day 5 | San Gimignano | 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 your home for the next three nights, a delightful villa near the medieval town of San Gimignano. Accommodations: Villasanpaolo, San Gimignano |
| Day 6 | San Gimignano | 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 silky smooth, frozen treats are beautifully displayed in a range of unique flavors for you to try. The rest of the day is at leisure; why not join an Optional Experience to Pisa and Lucca? Accommodations: Villasanpaolo, San Gimignano |
| Day 7 | Florence | 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 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. Accommodations: Villasanpaolo, San Gimignano |
| Day 8 | Rome | Country drive to Ancient 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 Ancient Rome. Accommodations: Hotel St. Martin, Rome |
| Day 9 | Rome | Arrivederci Roma: Bid farewell to the glories of Italy. Accommodations: |
- Dates/Pricing
- Disclaimer
- Twin prices are per person.
- These prices are correct at the time of the website going live, however are subject to confirmation at the time of booking.
- All tour information is correct at time of tours going live, however is subject to change, please confirm all details at time of booking.
- For full terms and conditions, please refer to our Conditions page.
- Hotel Class Key: D: Deluxe SF: Superior First Class F: First Class
