Country Roads of Italy - Classic Group - Insight Tour
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Insight Guided Tour

Country Roads of Italy - Classic Group

16 Days 5 Departures
From $5,478 per person

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 through the living history of Rome’s vibrant streets before journeying back in time to the ancient pathways of Pompeii. Sail to the rock Isle of Capri, where you can climb nearly 2,000 feet 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 to Burano, an idyllic, colorful island in the Venetian Lagoon where you’ll toast to a fantastic trip and indulge in local specialties.

Tour Summary

Duration16 Days / 15 Nights
OperatorInsight
Departures5 in 2026
Starting From$5,478 pp

Tour Route

Map of your 16-day journey

Country Roads of Italy - Classic Group route map

Day-by-Day Itinerary

16 days through your journey

Day 1

Welcome to the Eternal City of Rome

Welcome to Rome, a glorious city filled with classical antiquities, medieval buildings, Renaissance palaces and Baroque churches. Settle in before joining your Travel Director and get to know your fellow travelers over Roman specialties during dinner at a local restaurant.
Day 2

Rome with a Local

Today is devoted to The Eternal City. Join a Local Expert to discover the modern-day city and how people lived in Ancient Rome. See St. Peter's Basilica in the Vatican City. Then cross the Tiber river to see the Circus Maximus and learn about the history, the construction and the legends of the iconic Colosseum on a guided visit. Imagine the roar of the spectators as you enter the arena and stroll around picturing the gladiators and their adoring fans.
Day 3

Castel Gandolfo

Venture to Castel Gandolfo to explore the artistic treasures of the Villa Barberini Gardens. Ride an electric train along winding pathways and marvel at the intricately designed mosaic flower beds and fountains. After visiting the former papal gardens, continue south—drinking in sweeping views of the Bay of Naples—where the sparkling turquoise waters of the Tyrrhenian Sea meet dramatic cliffs and fishing villages that shimmer along the coastline.
Day 4

Capri, the Isle of Dreams

Discover the enchanting Isle of Capri, a jewel of the Bay of Naples rising dramatically from the Mediterranean’s shimmering blue waters. For more than 2,000 years, the island has drawn visitors to its shores, from Roman emperors such as Tiberius Caesar to celebrated figures captivated by its natural beauty and cosmopolitan charm. Stroll through Capri’s narrow alleyways and lively piazzas with a Local Expert. As you explore, take in panoramic views over the water and the distinctive atmosphere that has made Capri one of Italy’s most enduringly alluring destinations. You may also choose to join an Optional Experience cruising across the Tyrrhenian Sea to Positano, with time ashore before returning to your hotel.
Day 5

Pompeii and Todi

Journey to the ancient Roman city of Pompeii and explore this extraordinary site with your Local Expert. Travel into the heart of Italy to enjoy free time in Todi, located on a hilltop pedestal overlooking a vineyard-covered plain. Savor the distinctly medieval ambiance during your orientation and admire the Piazza del Popolo where locals take their evening 'passeggiata'. Take in the flavors of the region and enjoy dinner at a local restaurant with a glass of Orvieto Classico wine - a magical culinary experience!
Day 6

Todi

Immerse yourself in the enchanting medieval town of Todi, where you can wander through picturesque streets, marvel at historic architecture, and enjoy stunning views of the surrounding Umbrian countryside.
Day 7

Assisi and on to Perugia

In Assisi, see St. Clare’s Church and the Roman Temple of Minerva. 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.
Day 8

Perugia, the Jewel of Umbria

Time to explore more about this gem of a town. 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. With the rest of your day at leisure, 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 center 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

Renaissance Florence and Tuscany

Journey past Lake Trasimeno to Renaissance Florence. On arrival, walk with a Local Expert to see the marble-clad cathedral, bell tower and the Gates of Paradise on the baptistery. Afterwards, witness the intricate craftsmanship behind Florence’s famed leatherwork and gold during an artisan demonstration before enjoying 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. Then journey through the rolling, cypress-clad hills and vineyards of Tuscany, where you’ll enjoy a delicious exploration of Tuscany's red wines, discovering their robust flavors and absorbing history before arriving at your elegant hotel.
Day 10

Siena and San Gimignano

This morning, explore Siena with Insight Choice. Choose to visit the medieval Basilica of St. Domenico or alternatively, sample panforte, a traditional Tuscan dessert. Continue to the hilltop town of San Gimignano strikingly visible from every angle, its towers dominate the skyline and give it the nickname the Medieval Manhattan of Tuscany. Enjoy tasting the award-winning frozen delights of master gelato maker, Sergio Dondoli, whose great inventions include innovative and mouth-watering flavor combinations. Journey through the rolling, cypress-clad hills and vineyards of Tuscany as you return to your hotel.
Day 11

On to Lucca

Travel to Lucca to view the churches, squares and palaces, perfectly preserved within encircling medieval ramparts. Enjoy a sampling of a local specialty – freshly baked Tuscan bread. Later, you could take the opportunity to explore Pisa.
Day 12

Exploring the Cinque Terre

Get ready to explore the Cinque Terre, or Five Villages, which for years were accessible only on 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). You’ll have plenty of time to explore the medieval quarter and the popular sandy beach before returning to your hotel in Lucca.
Day 13

On to Parma

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

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

Join a MAKE TRAVEL MATTER® Experience during a visit to a traditional glassblowing workshop, 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. In the evening, cruise the islands of the Venetian Lagoon to arrive at Burano, famous for its candy colored houses. Sit down to a sumptuous dinner with wine, sampling the local specialties.
Day 16

Arrivederci Venice

Your departure transfer arrives at Venice Marco Polo airport.

Departure Dates & Pricing

5 departures available

Departure DateEnd DateStatusPrice Per Person
Aug 28, 2026 Sep 12, 2026 Available $5,478per person Get Quote
Sep 4, 2026 Sep 19, 2026 Available $6,156per person Get Quote
Sep 11, 2026 Sep 26, 2026 Available $6,156per person Get Quote
Sep 18, 2026 Oct 3, 2026 Available $6,332per person Get Quote
Oct 2, 2026 Oct 17, 2026 Available $6,244per person Get Quote

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