Country Roads of Umbria & Tuscany - Classic Group
Tour Type: Country Roads
Brochure Type Europe & Britain Premium 2025 v1
Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the Vatican Museums, walk 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. Visit a family-run olive mill, where a third-generation olive maker will share how its olives become the decadent oil you'll taste at the mill. In San Gimignano, eat the best gelato in the world - literally. You'll meet a world champion gelato maestro who will welcome you into his ice cream parlour to indulge in his favorite flavors. 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 2025 v1
Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the Vatican Museums, walk 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. Visit a family-run olive mill, where a third-generation olive maker will share how its olives become the decadent oil you'll taste at the mill. In San Gimignano, eat the best gelato in the world - literally. You'll meet a world champion gelato maestro who will welcome you into his ice cream parlour to indulge in his favorite flavors. 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
- We carry your bags for you and promptly deliver them to your hotel door.
- Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
- From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.
- 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.
- 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, y
- Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
- 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
- Siena Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
- 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.
- Rome Enjoy a Welcome Dinner with your fellow travelers at a uniquely Roman local restaurant.
- Umbria Explore the art of Italian cooking with Chef Lorenzo and take part in a truffle hunting walk followed by a tasty lunch.
- 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.
- Siena Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
- Siena Visit Siena's medieval black and white striped cathedral with your Local Expert.
- Choose between two carefully selected activities
- 1 Lunch with Wine (LW)
- 8 Breakfast (B)
- 4 Dinner with Wine (DW)
- 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
- 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
- Siena Visit Siena's medieval black and white striped cathedral with your Local Expert.
- 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.
- Assisi With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
- "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
- 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 18545643
- 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 for Insight Vacations guests to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica. Gaze in awe at the world's best-preserved Byzantine mosaics, illuminated for this evening's experience, and see the first sculpture by Bernini. End the day getting to know your fellow travelers over Roman specialties during a Welcome Dinner with wine at a local restaurant. Accommodations: NH Roma Centro, Rome. |
| Day 2 | Perugia | Umbria and on to Perugia: 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. View the imposing Basilica of St. Peter, the largest in the world. 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 before being entertained by Chef Lorenzo with a fun 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. Accommodations: Sangallo Palace Hotel, Perugia. |
| Day 3 | Perugia | 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! 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 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. 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 jaunty gelataio doles out his silky, frozen treats 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 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. 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 through the Italian countryside, making your way to Ancient Rome. On arrival, enjoy the afternoon at leisure. Accommodations: Hotel St. Martin, Rome. |
| Day 9 | Rome | Arrivederci Roma: Bid farewell to the glories of Italy. Departure transfers arrive at Rome's Fiumicino Leonardo da Vinci Airport. 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
