Country Roads of Italy - Insight Guided Vacations

Between the major cities, you'll find little-known gems like Orvieto, Assisi and Perugia, Tuscan hill towns, gastronomic icons, a formidable abbey and Italy's finest stretch of coastline.

Vacation type: Country Roads

Insight Experiences

  • Rome: Explore with a Local Expert
  • Perugia: Meet Marta, recipient of a TreadRight Foundation grant. Learn how Marta and her weavers are preserving the ancient craft of loom-weaving at their artisanal workshop.
  • Vatican City: Visit the Vatican Museums, Sistine Chapel, Bramante Staircase and St. Peter's Basilica with a Local Expert
  • Venice: Experience a glassblowing and gondola crafting workshop.

Top Rated Highlights

  • CRUISE by hydrofoil to the Isle of Capri.
  • RIDE in an open-air taxi, Travel by train and boat to explore Cinque Terre, Ride a gondola through the canals of Venice while being serenaded.
  • VISIT Papal Gardens and Castel Gandolfo, Positano, Basilica of St. Francis in Assisi, Siena Cathedral, San Gimignano.
  • CITY TOURS of Pompeii, Isle of Capri, Assisi, Perugia, Siena, Florence and Cinque Terre with Local Experts.

Authentic Dining

  • Orvieto: Explore the art of Italian cooking with Chef Lorenzo and master the art of making fresh pasta by hand.
  • Radda in Chainti: Learn what to look for in a quality vino rosso, and what foods to pair it with when ordering Florentine cuisine.
  • San Gimignano: Enjoy a tasting with award-winning, master gelato maker.
  • Lucca: At a traditional steam bakery, sample Lucca's famous anise bread, buccellato.
  • Modena: Visit a producer of authentic balsamic vinegar to learn about its production, history and distinctive taste.
  • Parma: Witness the cheese-making and ageing process of Parmigiano-Reggiano.
  • Venice: Enjoy a delicious Celebration Dinner with wine and new-found friends on the Venetian island of Burano.


Rome, Lazio, Italy, Sorrento, Campania, Italy, Perugia, Umbria, Italy, Radda in Chianti, Siena, Italy, Lucca, Lucca, IT, Parma, Northern Italy, IT, Venice, Veneto, Italy, Italy

17  Days | 15  nights
Call to book: 1-866-529-2079
Travelling as a group of 10 or more?  Request a group quote.


  • Flight to Rome; return from Venice (if flight and tour package option is chosen)
  • 15 nights of accommodation
  • 20 meals including 15 Buffet Breakfasts (BB) and 5 Dinners with Wine (DW), all with tea or coffee
  • Transportation by luxury air-conditioned coach
  • Porterage (1 piece of luggage per passenger)
  • $50 CAD credit voucher for an Optional Experience (described in the itinerary below; 1 voucher per person)
  • All hotel tips, charges and local taxes
  • English-speaking travel director
  • Audio headsets for flexible sightseeing
  • Earn and redeem Aeroplan® Miles

Insight Services

  • Our highly skilled Travel Director will ensure your journey is seamless, serving as your expert guide, consummate organizer, and friend overseas.
  • Enjoy the comfort of Insight's luxury, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom.
  • Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
  • We carry your bags for you and promptly deliver them to your hotel door.
  • 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.
  • Stay connected with friends and family with our complimentary coach and hotel WiFi (where available).
  • From time to time, your Travel Director will enchant you with an Insight Flourish, which is a local specialty representing the destination.
  • 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 Air Canada Vacations, you may purchase transfers or make your own way from/to the airport.


Day 1

Depart Canada

Fly to Rome.

Country Roads of Italy - Insight Guided Vacations

Day 2

Welcome to Rome

Rome is not only the modern capital of Italy, but also a spectacular encyclopedia of living history. You will be met on arrival at Rome’s Fiumicino Leonardo da Vinci Airport. At 09:30, 12:30 & 15:30, transfers depart for your hotel. At 17:30, join your Travel Director and fellow travellers for a Welcome Dinner with the opportunity to get to know each other over a pleasant evening.

Meal(s): Dinner with wine
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 3



In the morning, you will be joined by a Local Expert who guides you through the art collection of the Vatican Museums, culminating beneath Michelangelo’s famous ceiling in the Sistine Chapel. Your VIP visit includes fast-tracked entry and a behind-the-scenes look at the Bramante Staircase, part of the Vatican closed to the general public. Your venture continues inside St. Peter's Basilica to see Michelangelo's Pietà, and the splendid dome.There’s free time to do as the Romans do. Perhaps join a tour inside the Colosseum? Rome is about art, antiquity, piazzas and pizzazz, and our included walking exploration has it in abundance. 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.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 4

Rome - Pompeii - Sorrento


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.  Continue on to Sorrento.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 5

Sorrento - Capri - Sorrento


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 and 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.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 6

Sorrento - Amalfi Coast - Sorrento


Travel along Italy's finest coastline, the Amalfi Coast. Stop to admire a view of the terraced houses of the artist's paradise of Positano, clinging to the cliff face, before boarding minibuses to the heart of the town. Take time to be tempted by the local boutiques.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 7

Sorrento - Orvieto

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, learn about the ingredients and Italian food culture when you join Chef Lorenzo for a fascinating cooking demonstration, followed by a Highlight Dinner and a glass of the Orvieto Classico wine - a magical culinary experience!

Meal(s): Buffet breakfast, Dinner with wine
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 8

Assisi - Perugia


Cross the River Tiber to arrive at St. Mary of the Angels Church in Assisi. Under the dome is a small medieval chapel and the spot where St. Francis died. Continue to visit the huge Basilica of St. Francis. With a Local Expert, walk down the Via San Francesco to St. Clare's Church and see the cathedral. 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. Visit an artisanal workshop to meet Marta, recipient of a TreadRight Foundation grant. Learn how Marta and her weavers are preserving the ancient craft of loom-weaving.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 9


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.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 10

Perugia - Siena - Radda in Chianti

Drive past Lake Trasimeno to Siena. On arrival, walk with a Local Expert through narrow cobbled streets to the Piazza del Campo, where the bi-annual Palio horse race takes place. See the superb 14th-century Town Hall with its slim Mangia Tower, then climb up to the hill-top cathedral decorated with stripes of black and white marble. Travel through the cypress-clad hills and vineyards of Tuscany to your elegant hotel. On arrival, enjoy a delicious exploration of Tuscany's red wines, discovering their robust flavours and absorbing history.

Meal(s): Buffet breakfast, Dinner with wine
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 11

Radda in Chianti - San Gimignano - Radda in Chianti

Visit the hilltop town of San Gimignano. Enjoy a tasting with award-winning, master ice cream maker, Sergio Dondoli, whose great inventions include innovative and mouth-watering flavour combinations. After enjoying time to explore at your leisure, return to the tranquil surroundings of your hotel.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 12

Radda in Chianti - Florence - Lucca

Journey to Renaissance Florence, where 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. Continue to Lucca, to view its churches, squares and palaces that are 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.

Meal(s): Buffet breakfast, Dinner with wine
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 13

Lucca - Cinque Terre - Lucca

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.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 14

Lucca - Modena - Parma

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 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 the Signora shares with you her passions for Italian food, especially excellent quality Parmesan cheese. Taste samples of the organic cheese and other delicious local delicacies, accompanied with a glass of wine.


Meal(s): Buffet breakfast, Afternoon tasting
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 15

Parma - Venice

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 by gondola, past water-lapped doorways and Rococo palaces.

Meal(s): Buffet breakfast
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 16


Wake up ready to embrace this romantic city. Witness the art of glassblowing on a visit to a traditional arts centre on Giudecca Island and witness the glassblowing skills of local craftsmen. Then only minutes away by private boat is St. Mark's Square, where the city's former wealth and power is evidenced by the riches of St. Mark's Basilica. Admire also the Doge's Palace and its adjoining Bridge of Sighs. The rest of the day is yours to spend at leisure. 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.

Meal(s): Buffet breakfast, Dinner with wine
(1 night)
Country Roads of Italy - Insight Guided Vacations

Day 17

Venice - Return to Canada

Alas, you must bid farewell to this enchanting city. Your departure transfer arrives at Venice airport at 8:00 a.m. or 9:30 a.m.

Meal(s): Buffet breakfast
Country Roads of Italy - Insight Guided Vacations



The hotels listed below are presented as examples for your reference only. Where “or similar” is indicated, guests will stay at a hotel of the same star rating. The hotel accommodations will be communicated to the consumer or travel agent prior to departure.

Rome, Lazio, Italy
Veneto Palace Hotel(or similar)
Sorrento, Campania, Italy
Majestic Palace Hotel(or similar)
Orvieto, Terni, Italy
Aquila Bianca Hotel(or similar)
Perugia, Umbria, Italy
Sangallo Palace Hotel(or similar)
Radda in Chianti, Siena, Italy
CDH Hotel Radda(or similar)
Lucca, Lucca, IT
Hotel Villa La Principessa(or similar)
Parma, Northern Italy, IT
Du Parc Parma(or similar)
Venice, Veneto, Italy
Hilton Molino Stucky(or similar)

Room Specifications

Unless otherwise indicated, guests will stay in a standard room at all hotels during the trip.
Room occupancy: 2 adults travelling together.
Single or Triple occupancy option: Travellers who prefer to stay in a single occupancy or a triple occupancy room can call us book: 1-866-529-2079. Subject to availability.



2020 Dates:
April 24
May 8 & 22
June 12
July 3 & 31*
August 21* & 28
September 4, 11 & 25
October 2* & 9*

*Non-definite departure dates

Travel to Europe often requires an overnight flight. Please arrange your departure flight to arrive on or before the Tour Start Date.


For an additional $222 CAD per person, travellers can pre-pay gratuities for the Travel Director and Driver. Call us at 1 866 529-2079 to add this option to your reservation.


Most Insight Guided Vacations already include a host of bonus highlights and comprehensive sightseeing. There may also be an exciting array of Optional Experiences ($) which will turn an already amazing experience into the trip of a lifetime! These are entirely optional and can be booked through your Travel Director/Local Representative at the commencement of your trip. Please note, many Optional Experiences are operated by independent third party suppliers, not Insight Vacations. The Optional Experiences and pricing listed here are a guideline only and subject to change.

Roman Dinner Party

Enjoy an evening of delicious Roman cuisine with drinks and a great Italian ambience.

Adult Price: EUR 62

Code: ROM0002

Guided Visit to the Colosseum

With our Local Expert, we'll explore the glorious history of the Roman Empire. Admire the Arch of Constantine and tread in the footsteps of Gladiators and Roman Soldiers. Enjoy priority reserved entrance ahead of the crowds and once inside the mighty Colosseum hear tales of deadly gladiatorial combat and the mighty Roman Empire.

Please note: This optional is subject to availability and involves reservations and entrance prepayments. If you decide to cancel this Optional Experience, a 50% cancellation fee will be incurred.

Adult Price: EUR 50

Code: ROM0003

Sorrento Evening

A chance to enjoy a delicious dinner of local specialities. We arrive at one of the area's unique local restaurants for an incredible dining experience featuring some of the famous dishes of this region!

Adult Price: EUR 61

Code: SOR0002

Delights of the Bay of Naples

Among the lemon and olive groves of Sorrento is a small farm owned by the third generation of the Marciano family. Meet Rosa and Maria and see how fresh mozzarella is made by hand. Walk through lemon groves, past the old olive mill before indulging your taste buds in a delicious meal of Italian specialities all fresh from the farm. Finish with a taste of the famous limoncello.

Adult Price: EUR 49

Code: SOR0005

Island Tour of Capri

Experience the spectacular cliffs and famous turquoise waters of Capri during a relaxing cruise to the most beautiful part of the island, the southern side. View the beautiful grottoes and unique coastline before ascending to Capri town. This Optional Experience is weather dependent and may be replaced by a minibus tour of the island with a visit to Anacapri and the Villa San Michele.

Adult Price: EUR 42

Code: SOR0001

The Amalfi Experience

Extend your day to complete the entire "World Heritage Coastline" and visit gorgeous Amalfi after which the coast is named. This is an unforgettable experience, we stop to capture the stunning panoramas, impossible sights and enjoy local refreshments en route before plenty of free time to explore the colourful village of Amalfi. A thrilling excursion not to be missed!

Adult Price: EUR 47

Code: SOR0003

Cortona Under the Tuscan Sun

Visit beautiful Cortona, one of the oldest hill towns in Tuscany and setting for Frances Mayes' Under the Tuscan Sun. A scenic panoramic drive takes you to a recently unearthed Etruscan Temple and to see Ms. Mayes' actual creative hideaway, "Casa Bramasole." This is followed by a guided walk through the historic centre to soak up the history and enjoy stupendous views to Lake Trasimeno and the Val di Chiana.

Adult Price: EUR 33

Code: PER0002

Umbrian Dinner Experience

Umbria is not only a region which is culturally rich and full of beautiful vistas, it is also a region rich in its gastronomic offerings as well! A journey to explore the edible treasures of the traditional Umbrian kitchen and the superb wines of this region too, all served to you in a beautiful rustic restaurant!

Adult Price: EUR 62

Code: PER0003

A Taste of Tuscany

A delightful and bucolic experience, designed to bring you in touch with the enchanting Tuscan countryside, food and wine. Settle in for an authentic Tuscan feast in a traditional setting.

Adult Price: EUR 60

Code: LUC0007

Local Tuscan Dinner

The secret to dining well in Tuscany is knowing where to go, picking the small towns and restaurants where locals dine. Exploiting our countryside location, this evening we'll dine locally, keeping away from the big-city crowds. We'll enjoy classic Tuscan specialties, the favourites of the Sienese province, using the fresh territorial produce that makes this region so well known.

Adult Price: EUR 65

Code: RAD0001

Prices listed in the itinerary are valid as of August 15, 2019 and are subject to change without notice.


On arrival at Rome airport, transfers leave for your hotel at 9:30 a.m., 12:30 p.m. and 3:30 p.m. Guests arriving later should make their own way to the hotel. Return transfers on the last travel day will arrive at Venice airport at 8:00 a.m. or 9:30 a.m.

Pricing display

Prices take into account taxes and are rounded to the nearest full dollar. Full details on taxes and fees are on the booking page.