Country Roads of Umbria & Tuscany - Classic Group
Dates & Prices
Start Date | End Date | Offers | Brochure Land Price | Quote |
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Sunday, Mar 30, 2025 | Monday, Apr 07, 2025 | Get Lower Price | Get Quote | |
Sunday, Apr 27, 2025 | Monday, May 05, 2025 | Get Lower Price | Get Quote | |
Sunday, May 25, 2025 | Monday, Jun 02, 2025 | Get Lower Price | Get Quote | |
Sunday, Jun 22, 2025 | Monday, Jun 30, 2025 | Get Lower Price | Get Quote | |
Sunday, Jul 06, 2025 | Monday, Jul 14, 2025 | Get Lower Price | Get Quote | |
Sunday, Aug 03, 2025 | Monday, Aug 11, 2025 | Get Lower Price | Get Quote | |
Sunday, Sep 14, 2025 | Monday, Sep 22, 2025 | Get Lower Price | Get Quote | |
Sunday, Sep 28, 2025 | Monday, Oct 06, 2025 | Get Lower Price | Get Quote |
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Promotion Details
Offer does not apply to all vacations, contact your travel consultant for applicable vacations. There is a no-smoking policy in all shared rooms. Does not apply to additional accommodation, stopovers, airfare or flight supplements, Independent City Breaks, Israel, Jordan, Eastern Mediterranean trips with included cruises or cruise extensions. Exceptions apply.
Tour Itinerary
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.
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Day 1
Welcome to the Eternal City of RomeWelcome 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.Accommodation: NH Roma Centro, Rome
Meals: Dinner -
Day 2
Umbria and on to PerugiaSee 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.Accommodation: Sangallo Palace Hotel, Perugia
Meals: Breakfast Lunch -
Day 3
Perugia Sightseeing & Free Time Relaxed StartThis 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!Accommodation: Sangallo Palace Hotel, Perugia
Meals: Breakfast Dinner -
Day 4
Assisi, in Search of St. Francis Relaxed StartJourney 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.Accommodation: Sangallo Palace Hotel, Perugia
Meals: Breakfast -
Day 5
Tuscany to Siena and San GimignanoFollow 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.Accommodation: Villasanpaolo, San Gimignano
Meals: Breakfast Dinner -
Day 6
San Gimignano sightseeing and Free Time Relaxed StartIn 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?Accommodation: Villasanpaolo, San Gimignano
Meals: Breakfast -
Day 7
Florence and Tuscan Countryside Experience Relaxed StartThe 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.Accommodation: Villasanpaolo, San Gimignano
Meals: Breakfast Dinner -
Day 8
Country drive to Ancient RomeLeave 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.Accommodation: Hotel St. Martin, Rome
Meals: Breakfast -
Day 9
Arrivederci RomaBid farewell to the glories of Italy.
Meals: Breakfast
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Dining Summary
- 1 Dinner (D)
- 8 Breakfast (B)
- 1 Lunch with Wine (LW)
- 3 Dinner with Wine (DW)
Choice Highlights
- Choose between two carefully selected activities
- Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
- Siena: Visit the Cathedral with your Local Expert.
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.
- 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.
Authentic Dining
- 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.
- 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.
Insight Choice
- Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.
- Siena: Visit the Cathedral with your Local Expert.
Insight Experiences
- 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’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
Make Travel Matter
- 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.
Top Rated Highlights
- 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 medieval Manhattan of Italy.
- 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 quality of its luxury goods.
Travel Director
- "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."
Well-being
- 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.
- Hand sanitizer is freely available on board for you to use throughout the day.
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Question: How many suitcases can I take with me on my trip?
Question: Is Airfare Included in the Price?
The tour guide was super, always trying to bring comfort when possible. The hotels were very good except for the last night in Rome at the NH Centro. Staying at the same hotel for 3 days in Umbria and again in Tuscany was a joy especially with the overcrowded cities of Siena and Florence.
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I loved this tour and loved seeing all of the towns that we visited in Tuscany and Umbria. The tour director was fantastic. This is the second Insight tour that I've taken in which he was the tour director. The optional tours/meals were excellent. One optional meal was the best on the whole trip. This tour had only 28 people which was so much nicer than the usual Insight 40.