Country Roads of Italy - Small Group

Country Roads of Italy - Small Group

16 Days



Country Roads of Italy - Small Group

16 Days Starting in Rome and ending in Venice

Visiting: Rome, Vatican, Castel Gandolfo, Sorrento, Capri, Positano, Orvieto, Pompeii, Assisi, Perugia, Florence, Radda in Chianti, San Gimignano, Siena, Lucca, Cinque Terre, Parma, Modena, Venice, Vatican City

Tour operator:

Insight Vacations

Tour code:


Guide Type:

Fully Guided

$6804 (USD) Operator discount: -$264 The Big ADVENTURE Sale: -$192

This tour is no longer available, please see similar tours below or send an enquiry

Tour Overview

Journey across the Italian peninsula in this 16-day guided tour that stretches from the sapphire waters of the Amalfi Coast to the calming canals of Venice. Step outside Rome to Vatican City, where you’ll be treated to a behind-the-scenes viewing of the winding Bramante Staircase. Before reaching Sorrento, stop at Castel Gandolfo to ride an electric train past its papal gardens, marveling at the mosaic flower beds. Sail to the rock isle of Capri, where you can climb nearly 2,000 feet by an open-top taxi for unrivaled views of the Tyrrhenian Sea. In Perugia, learn the art of loom-weaving from a Local Expert. And in Venice, cruise along the canals and to Burano, an idyllic, colorful island in the Venetian Lagoon where you’ll toast to a fantastic trip and indulge in local specialties.


  • Choose between two carefully selected activities

  • Siena: Visit Siena's medieval black and white striped cathedral with your Local Expert.

  • Siena: Enjoy a tasting of Panforte, a traditional Tuscan dessert containing fruits and nuts.

  • Rome: Enjoy a Welcome Dinner with your fellow travellers at a uniquely Roman local restaurant.

  • Orvieto: Handmade pasta, genuine Umbrian specialties and rich flavours make for a special Highlight Dinner at La Buca di Baco di Ely.

  • Radda in Chianti: Learn what to look for in a quality vino rosso, and what foods to pair it with when ordering Florentine cuisine.

  • 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.

  • Lucca: Visit a traditional steam bakery and sample Buccellato, the sweet raisin bread typical of the region.

  • Modena: Visit a producer of authentic balsamic vinegar to learn about its production, history and distinctive taste.

  • Parma: At Ciaolatte Parmesan you will meet, Signor Paolo, a local passionate about Italian food and quality cheese. Witness the cheese-making and ageing process of Parmigiano-Reggiano.

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Day 1: Welcome To The Eternal City Of Rome
Location: Rome
Accommodation: room 007 Select, Rome.
Meals Included: Dinner with Wine

Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Transfers depart from Rome's Fiumicino Leonardo da Vinci Airport for your hotel at 09:30, 12:30 and 15:30. Relax and settle in before joining your Travel Director at 17:30, and get to know your fellow travellers over a delicious Welcome Dinner with wine at a local restaurant.

Day 2: Vatican And Rome With A Local
Location: Rome, Vatican
Accommodation: room 007 Select, Rome.
Meals Included: Breakfast

Today is devoted to The Eternal City. Join a Local Expert for an in-depth visit to the Vatican Museums, full of priceless art treasures collected by the Popes. Insight has arranged special priority entry to gain behind-the-scenes access to the Bramante Staircase, a marvel of renaissance architecture, normally off-limits to visitors. Visit the Sistine Chapel, where the Popes are elected, to admire Michelangelo’s famous ceiling. Continue to St. Peter’s Basilica, to wonder at another of his works, the emotive ‘Pietà,’ and stand beneath the dome completed after his death. Cross the Tiber river to enjoy views of ancient Rome. See the incredible Circus Maximus and the legendary Colosseum. There’s free time to do as the Romans do, or perhaps join a walking tour and toss a coin into the spectacular Trevi Fountain, see the Pantheon, the best preserved monument from the Roman period, and enjoy free time in Piazza Navona.

Day 3: Castel Gandolfo
Location: Rome, Castel Gandolfo, Sorrento
Accommodation: Majestic Palace Hotel, Sorrento.
Meals Included: Breakfast

Venture to Castel Gandolfo to explore the artistic treasure of the Villa Barberini Gardens. Ride an electric train along the pathways to marvel at the intricately designed mosaic flower beds and fountains. After our visit to the former papal gardens our journey continues on south past Naples to the resort town of Sorrento.

Day 4: Capri, The Isle Of Dreams
Location: Sorrento, Capri
Accommodation: Majestic Palace Hotel, Sorrento.
Meals Included: Breakfast

Meet your Local Expert and cross the Bay of Naples to reach the beautiful Isle of Capri, a rock rising sheer from the Mediterranean! For 2,000 years, Capri has beckoned visitors from Tiberius Caesar to Gracie Fields. Arriving at the Marina Grande by boat, ascend to Capri town by one of the island's iconic open-top taxis. Explore the narrow alleyways, browse in exclusive boutiques and wonder at the views over the Tyrrhenian Sea. Descend to the port by funicular railway and return to Sorrento, where you are at leisure for the rest of the day.

Day 5: The Picturesque Amalfi Coast
Location: Sorrento, Positano, Orvieto
Accommodation: Aquila Bianca Hotel, Orvieto.
Meals Included: Breakfast

Travel along Italy’s finest coastline, the Amalfi Coast. Board minibuses and stop to admire a view of the terraced houses of the artist's paradise of Positano, clinging to the cliff face. Take time to be tempted by the local boutiques before continuing to Orvieto.

Day 6: Pompeii And Orvieto
Location: Sorrento, Pompeii, Orvieto
Accommodation: Hotel Bramante Todi
Meals Included: Breakfast, Dinner with Wine

Journey to the ancient Roman city of Pompeii and explore with your Local Expert. Travel into the heart of Italy to enjoy free time in Orvieto, located on a rock pedestal overlooking a vineyard-covered plain. Savour the distinctly medieval ambiance during your orientation and admire the richly decorated facade of the cathedral in Piazza del Duomo. Take in the flavours of the region and enjoy a Highlight Dinner at a local restaurant with a glass of Orvieto Classico wine - a magical culinary experience!

Day 7: Assisi And On To Perugia Relaxed Start
Location: Orvieto, Assisi, Perugia
Accommodation: Sangallo Palace Hotel, Perugia.
Meals Included: Breakfast

Cross the River Tiber to see the church of St. Mary of the Angels. Under the dome is a small medieval chapel and the spot where St. Francis died. In Assisi see St. Clare’s Church and the cathedral. Continue to walk down the Via San Francesco and visit the huge Basilica of St. Francis with a Local Expert. Journey to beautiful Perugia - the jewel of Umbria. Your guided walking exploration begins in the main street of Perugia's Old Town. See the Collegio del Cambio, the splendid Priors' Palace, the Cathedral and the finely sculptured Great Fountain in the magnificent main square. Join a MAKE TRAVEL MATTER® Experience as you visit an artisanal workshop and meet Marta, a recipient of a TreadRight Foundation grant. Learn how Marta and her weavers are preserving the ancient craft of loom-weaving.

Day 8: Perugia, The Jewel Of Umbria Relaxed Start
Location: Perugia
Accommodation: Sangallo Palace Hotel, Perugia.
Meals Included: Breakfast

The entire day is at leisure for you to explore this gem of a town on your own. Perhaps visit Cortona, one of the oldest hill towns in Tuscany. On this Optional Experience, journey to a recently unearthed Etruscan Temple before a guided exploration through the town's historic centre with views of Lake Trasimeno and the Val di Chiana. In the evening there is the option to discover the edible treasures of a traditional Umbrian kitchen, accompanied with wines of the region.

Day 9: Florence And Radda In Chianti Relaxed Start
Location: Perugia, Florence, Radda in Chianti
Accommodation: CDH Hotel Radda, Tuscany.
Meals Included: Breakfast, Dinner with Wine

Journey past Lake Trasimeno to Renaissance Florence. On arrival you will walk with a Local Expert to see the marble-clad cathedral, bell tower and Gates of Paradise on the baptistery. Enjoy time at leisure to explore Piazza della Signoria, still the political heart of Florence and an open-air gallery of Renaissance masterpieces. Spend time gazing at the fountains and sculptures along the front of the Palazzo Vecchio. Wander the area around Santa Croce Basilica, famous for the quality of its luxury goods of gold and leather. Later, travel through the cypress-clad hills and vineyards of Tuscany to your elegant hotel.

Day 10: San Gimignano And Siena
Location: Radda in Chianti, San Gimignano, Siena, Radda in Chianti
Accommodation: CDH Hotel Radda, Tuscany.
Meals Included: Breakfast

This morning visit the hilltop town of San Gimignano. Enjoy a tasting with award-winning, master gelato maker, Sergio Dondoli whose great inventions include innovative and mouth-watering flavour combinations. Continue to Siena and explore with Insight Choice. Choose to visit the medieval Cathedral or alternatively, sample panforte, a traditional Tuscan dessert. This afternoon enjoy a delicious exploration of Tuscany's red wines, discovering their robust flavours and absorbing history.

Day 11: On To Lucca Relaxed Start
Location: Radda in Chianti, Lucca
Accommodation: Hotel Villa La Principessa, Lucca.
Meals Included: Breakfast, Dinner with Wine

Travel to Lucca to view the churches, squares and palaces, perfectly preserved within encircling medieval ramparts. Pause a while and taste the lavish loaves of buccellato, Lucca's sweet raisin anise bread, said to be a favourite of the ancient Roman army. Later, perhaps explore Pisa?

Day 12: Exploring The Cinque Terre
Location: Lucca, Cinque Terre, Lucca
Accommodation: Hotel Villa La Principessa, Lucca.
Meals Included: Breakfast

Get ready to explore the Cinque Terre, or five villages, which for years were only accessible by foot. This UNESCO World Heritage site is one of Italy's most beautiful landscapes. Join a Local Expert in one of the picturesque fishing villages, before cruising along the rugged coastline (weather permitting). There is plenty of time to explore the old medieval quarter and popular sandy beach before returning to your hotel in Lucca.

Day 13: On To Parma
Location: Lucca, Parma
Accommodation: Starhotels Du Parc, Parma.
Meals Included: Breakfast

Journey to the beautiful university town of Parma, world-famous for its local ham and cheese. Meet one of the locals, Paolo. Learn about the process of making Parmigiano-Reggiano as Signor Paolo shares with you his passions for Italian food, especially excellent quality Parmesan cheese. Taste samples of the famous Parmigiano-Reggiano, accompanied by a glass of wine.

Day 14: Modena And On To Venice
Location: Parma, Modena, Venice
Accommodation: Hilton Molino Stucky, Venice
Meals Included: Breakfast

Visit one of Modena's top producers of authentic, traditional, artisan balsamic vinegar and take a master class to understand what makes this vinegar as expensive as top-rated wines. Continue on through the Soave vineyards past Padua to Venice, Queen of the Adriatic. To the tune of accompanying musicians, you will be serenaded through the atmospheric canals as you glide by gondola, past water-lapped doorways and rococo palaces.

Day 15: The Magic Of La Serenissima
Location: Venice
Accommodation: Hilton Molino Stucky, Venice
Meals Included: Breakfast, Dinner with Wine

Join a MAKE TRAVEL MATTER® Experience during a visit to a traditional arts centre, where you can see how beautiful handcrafted glass is made by expert glassblowers, safeguarding traditional skills. Visit St. Mark’s Square where the city’s former wealth and power is evidenced by the riches of St. Mark’s Basilica and admire the Doge's Palace with its adjoining Bridge of Sighs. The waterways of Venice are renowned for gondolas that drift by. In the evening, cruise the islands of the Venetian Lagoon to arrive at Burano, famous for its candy coloured houses. Sit down to a sumptuous Celebration Dinner with wine, sampling the local specialities.

Day 16: Arrivederci Venice
Location: Venice
Meals Included: Breakfast

Alas, you must bid farewell to this enchanting city. Your departure transfer arrives at Venice Marco Polo Airport at 08:00 and 09:30.

Check out our Q&As

  • Can I join the tour once it has departed?

    We regret that no refunds can be made for absences from a tour, including experiences such as missed meals or sightseeing.

  • How long has the tour company been trading?

    Since 1978.

  • What Ethical Travel credentials does the tour company have?

    Insight Vacations is a founding member of the TreadRight Foundation, a joint initiative created by the brands within The Travel Corporation (TTC) almost 15 years ago to ensure our impact through tourism is positive. Our ethos to #MakeTravelMatter guides our decision-making at every level of our business.

  • Will the accommodation included meet local health and safety regulations?


  • Do you operate a “single share” option and how does it work?

    You have two options as a solo traveller. Either choose to be matched with a same sex partner for a room share - at no extra cost. Or choose a room of your own with a reduced or even free private room upgrade on select tours.

  • What policies are in place for Covid-19?

    Please contact us for latest COVID-19 policies

Reviews of this Operator

Peggy Lindenborn  

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Country Roads of Southern Italy and Sicily is a delightful trip and our travel guides and driver, Enzo, Chris and Greg were amazing and made the trip very memorable. We saw so many places and had great experiences along the way! Thanks to them for such a wonderful vacation.!

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Trusted Customer  

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Great itinerary, good pace, tour director was friendly and very knowledgeable and organised. Bus was very spacious and driver was great. Yes would recommend insight to friends and families

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Jacqueline Thornberry  

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The number is our group was small which meant we got to know each other. Our tour guide, Laura Spiers, was excellent as was our driver. The food was good, and of course everything we saw in Iceland was beautiful and educational.

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Kathryn Ronca  

Enchanting Canyonlands


The trip was fantastic. Everything was well planned and exceeded my expectations. All insight personal were courteous helpful and professional Ann Manual and Kevin were a topnotch team There was attention to every detail and at all times felt safe and always a personal touch to the trip. The motor coach was clean and roomy and there was multiple wipe downs during the day All hotels were top notch and all staff at the hotels and restaurants were helpful and courteous I would recommend this trip as it gave you a fantastic view of the natural wonders of the the West.

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Patrick Ong  

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This trip is absolutely amazing! Worth every Penny! Our Tour guide did not Disappoint.

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Dates & Availability

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Friday - Saturday

Apr 19, 2024 - May 04, 2024
$7314 $6856 (USD)

Operator discount: -$264 (USD)

The Big ADVENTURE Sale: -$194 (USD)

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Friday - Saturday

May 24, 2024 - Jun 08, 2024
$7554 $7090 (USD)

Operator discount: -$264 (USD)

The Big ADVENTURE Sale: -$200 (USD)

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Friday - Saturday

Aug 16, 2024 - Aug 31, 2024
$7260 $6804 (USD)

Operator discount: -$264 (USD)

The Big ADVENTURE Sale: -$192 (USD)

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Friday - Saturday

Apr 18, 2025 - May 03, 2025
$7495 $7075 (USD)

Operator discount: -$220 (USD)

The Big ADVENTURE Sale: -$200 (USD)

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Friday - Saturday

May 23, 2025 - Jun 07, 2025
$7725 $7299 (USD)

Operator discount: -$220 (USD)

The Big ADVENTURE Sale: -$206 (USD)

Instant Booking Available

Friday - Saturday

Jun 27, 2025 - Jul 12, 2025
$7595 $7172 (USD)

Operator discount: -$220 (USD)

The Big ADVENTURE Sale: -$203 (USD)

Instant Booking Available

Friday - Saturday

Aug 15, 2025 - Aug 30, 2025
$7450 $7031 (USD)

Operator discount: -$220 (USD)

The Big ADVENTURE Sale: -$199 (USD)

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  • Low Deposit

    Insight Vacations requires a minimum deposit of 350 USD per person or the full booking value, whichever is less, with the final balance not due until 90 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of insight vacations charges.

    Up to 91 days before tour starts: Forfeit 100% of deposit.

    At 90 days before tour starts: Forfeit 50% of booking price.

    At 29 days before tour starts: Forfeit 80% of booking price.

    At 1 days before tour starts: Forfeit 100% of booking price.

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