Best of Italy - Classic Group - Insight Tour
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Insight Guided Tour

Best of Italy - Classic Group

11 Days 74 Departures
From $3,506 per person

Tour Overview

Explore the best of Italy on this 11-day guided tour. In Rome, marvel at the treasures around every corner and learn about its three thousand years of history. As your travels continue along the Bay of Naples, stop on the slopes of Mount Vesuvius for lunch at a local farm still growing traditional produce unique to the region. In Florence, learn the secrets of leather making from a local leatherworker. Fall in love with Venice as you see churches and palaces from a private boat, and cruise its canals on a romantic gondola ride. Sail to Capri, where craggy mountains cascade into the Tyrrhenian Sea; a Local Expert will help you navigate its narrow alleys. Before you say arriverderci to Italy, enjoy one last experience: a private performance of popular songs and arias from some of Italy’s best loved operas during dinner.

Tour Summary

Duration11 Days / 10 Nights
OperatorInsight
Departures74 in 2026–2028
Starting From$3,506 pp

Tour Route

Map of your 11-day journey

Best of Italy - Classic Group route map

Day-by-Day Itinerary

11 days through your journey

Day 1

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 and get to know your fellow travelers over Roman specialties during dinner at a local restaurant.
Day 2

Vatican City and Rome with a Local

The day 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. Visit the Sistine Chapel, where Popes are elected, to admire Michelangelo’s famous ceiling, and see the beautiful exterior of St. Peter's Basilica. Cross the Tiber River to enjoy ancient Rome. See the incredible Circus Maximus. Admire the beautifully preserved Arch of Constantine and discover the history, the construction and the legends of the iconic Colosseum on a guided visit. As you stroll with your Local Expert, imagine the gladiatorial battles and roaring spectators around the arena. Later, perhaps continue your exploration of Rome to see the Pantheon and the stunning piazzas and fountains of Rome.
Day 3

The Chianti Hills to Florence

Continue this guided tour of Italy with a drive to the picturesque Chianti Hills and the historic city of Florence. Travel north from Rome, passing through the rolling landscapes of Lazio and into the heart of Tuscany. Later this evening, indulge in a delicious meal at a local restaurant, savoring the authentic flavors of Florentine cuisine.
Day 4

Florence, Birthplace of the Renaissance

Explore Florence with Insight Choice. Choose to visit the Accademia Museum and see Michelangelo’s David. After, continue on foot to admire the multicoloured marble cathedral, bell tower and baptistery, where Ghiberti’s Gates of Paradise have been recreated in all their glory. Continue into the Piazza della Signoria, still the political heart of Florence and an open-air gallery of Renaissance masterpieces. Spend time gazing at statues such as Neptune and Hercules and Cacus along the front of the Palazzo Vecchio. Alternatively, take a stroll with your Travel Director to enjoy a typical Italian treat in a local cafe. This city is renowned for its intricate crafts, so later in the day, enjoy a demonstration of traditional leatherwork and goldsmithing.
Day 5

Pisa to Venice, the Queen of the Adriatic

Journey to the coastal town of Pisa and see the famous Leaning Tower in the Square of Miracles, as well as the baptistery and colonnaded bell tower behind the cathedral. Relax and enjoy the scenery as you cross the spectacular Apennine Mountains, passing through the Emilia-Romagna region, one of Europe's most intensely farmed and fertile plains. Continue through the marshes of the Venetian Lagoon before crossing the causeway into the enchanting floating city of Venice. As evening falls, day-trippers leave the city to return to the mainland, allowing you to appreciate the peace and tranquility of Venice from your centrally located hotel. Tonight, indulge in a delicious dinner at a local restaurant, savoring the unique flavors of Venetian cuisine.
Day 6

Venice and the Magic of La Serenissima

Cruise by private boat on a journey of discovery past churches and palaces reflecting the rich architectural history of Venice from the 13th to the 18th centuries. Marvel at the intricate facades and learn about the stories behind these historical buildings. Arrive close to St. Mark's Square and stroll along the waterfront, passing the iconic Bridge of Sighs and the majestic Doge's Palace. It was from here that the infamous Casanova made his daring escape. Turn the corner into St. Mark's Square and be captivated by the grandeur of the basilica. Afterwards, board a traditional gondola for a serenade along the romantic canals. Join a MAKE TRAVEL MATTER® Experience and witness the artistry of expert glassblowers as they create beautiful, handcrafted glass pieces, preserving centuries-old techniques and traditions.
Day 7

Assisi

Continue your 11 days in Italy with a journey to the peaceful town of Assisi, nestled on the slopes of Mount Subasio and renowned for its medieval churches, vibrant frescoes and sun-dappled courtyards. In the valley, see the Church of St. Mary of the Angels, revered as the place of St. Francis’ passing. Then ascend to the upper town to meet your Local Expert. Step inside the monumental Basilica of St. Francis, a 13th-century marvel whose frescoes by Giotto marked a turning point in European art. Enjoy free time to soak up the serenity of Assisi. You might choose to stroll along Via San Francesco, lined with quaint stone buildings offering artisan foods, devotional keepsakes and locally crafted wares.
Day 8

Sorrento on the coast

Travel south, passing Cassino, the site of a fierce and pivotal battle during World War II. Continue your journey along the spectacular clifftop road, offering breathtaking views, to reach the resort of the Sorrento coast. This charming area overlooks the Bay of Naples and provides stunning vistas of Mount Vesuvius. After checking in to your hotel, spend the rest of the day at your leisure, exploring the beautiful surroundings or relaxing in the comfort of your accommodations.
Day 9

Capri, the Isle of Dreams

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 Emperor Tiberius to Gracie Fields. Arriving at the Marina Grande by boat, ascend to Capri town. A Local Expert joins you for an exploration of the narrow alleyways. Descend to the port by funicular railway and return to Sorrento, where you are at leisure for the rest of the day. Perhaps head to Positano for an exploration of the colorful Amalfi Coast?
Day 10

Pompeii and Rome

Continue to Pompeii, the opulent Roman town that was preserved by layers of ash from the disastrous eruption of Mount Vesuvius in A.D. 79. A walk with your Local Expert through the cobbled streets and extensive excavations reveals the daily life of ancient Roman civilization. Visit the Forum and peer into shops and patrician villas, decorated with colorful wall paintings. Join a MAKE TRAVEL MATTER® Experience in Vesuvius National Park and visit Casa Barone. This small family-run farm on the slopes of the volcano is one of the world’s only producers of Piennolo tomatoes, an endangered fruit that only thrives in the fertile volcanic soil. Each harvest is sustainably farmed and cared for by the extended Barone family, who all work here. Be sure to savor the unique flavors of this rare tomato during a truly unique Farm-to-Table lunch. Your journey continues to Rome. In the evening, enjoy an elegant dinner with local wine at a Roman restaurant. As you dine, enjoy a private performance of popular songs and arias from some of Italy's best-loved operas.
Day 11

Arrivederci Roma

Bid farewell to the glories of Italy, savoring the memories of its enchanting cities, historic landmarks and stunning landscapes. Italy's unique allure will linger in your heart long after you leave.

Departure Dates & Pricing

74 departures available

Departure DateEnd DateStatusPrice Per Person
Jun 27, 2026 Jul 7, 2026 Available $5,355per person Get Quote
Jul 2, 2026 Jul 12, 2026 Available $4,761per person Get Quote
Jul 11, 2026 Jul 21, 2026 Available $5,050per person Get Quote
Jul 16, 2026 Jul 26, 2026 Available $4,185per person Get Quote
Jul 25, 2026 Aug 4, 2026 Available $5,195per person Get Quote
Aug 6, 2026 Aug 16, 2026 Available $4,905per person Get Quote
Aug 13, 2026 Aug 23, 2026 Available $5,495per person Get Quote
Aug 22, 2026 Sep 1, 2026 Available $4,905per person Get Quote
Aug 27, 2026 Sep 6, 2026 Available $5,650per person Get Quote
Aug 29, 2026 Sep 8, 2026 Available $5,108per person Get Quote
Sep 5, 2026 Sep 15, 2026 Available $6,425per person Get Quote
Sep 17, 2026 Sep 27, 2026 Available $6,425per person Get Quote
Sep 26, 2026 Oct 6, 2026 Available $6,295per person Get Quote
Oct 3, 2026 Oct 13, 2026 Available $6,295per person Get Quote
Oct 10, 2026 Oct 20, 2026 Available $5,995per person Get Quote
Oct 22, 2026 Nov 1, 2026 Available $6,295per person Get Quote
Oct 29, 2026 Nov 8, 2026 Available $4,973per person Get Quote
Nov 5, 2026 Nov 15, 2026 Available $4,695per person Get Quote
Nov 26, 2026 Dec 6, 2026 Available $3,506per person Get Quote
Dec 19, 2026 Dec 29, 2026 Available $3,893per person Get Quote
Dec 26, 2026 Jan 5, 2027 Available $4,550per person Get Quote
Feb 25, 2027 Mar 7, 2027 Available $3,895per person Get Quote
Mar 4, 2027 Mar 14, 2027 Available $3,950per person Get Quote
Mar 18, 2027 Mar 28, 2027 Available $4,050per person Get Quote
Mar 25, 2027 Apr 4, 2027 Available $3,866per person Get Quote
Apr 8, 2027 Apr 18, 2027 Available $4,703per person Get Quote
Apr 15, 2027 Apr 25, 2027 Available $4,703per person Get Quote
Apr 29, 2027 May 9, 2027 Available $5,450per person Get Quote
May 1, 2027 May 11, 2027 Available $4,946per person Get Quote
May 8, 2027 May 18, 2027 Available $4,946per person Get Quote
May 13, 2027 May 23, 2027 Available $4,946per person Get Quote
May 15, 2027 May 25, 2027 Available $4,946per person Get Quote
May 22, 2027 Jun 1, 2027 Available $4,946per person Get Quote
May 27, 2027 Jun 6, 2027 Available $4,946per person Get Quote
May 29, 2027 Jun 8, 2027 Available $5,550per person Get Quote
Jun 5, 2027 Jun 15, 2027 Available $4,995per person Get Quote
Jun 10, 2027 Jun 20, 2027 Available $5,950per person Get Quote
Jun 12, 2027 Jun 22, 2027 Available $4,995per person Get Quote
Jun 17, 2027 Jun 27, 2027 Available $5,950per person Get Quote
Jun 19, 2027 Jun 29, 2027 Available $4,995per person Get Quote
Jun 26, 2027 Jul 6, 2027 Available $4,995per person Get Quote
Jul 1, 2027 Jul 11, 2027 Available $4,703per person Get Quote
Jul 10, 2027 Jul 20, 2027 Available $4,703per person Get Quote
Jul 15, 2027 Jul 25, 2027 Available $5,225per person Get Quote
Jul 22, 2027 Aug 1, 2027 Available $5,225per person Get Quote
Jul 24, 2027 Aug 3, 2027 Available $4,676per person Get Quote
Aug 5, 2027 Aug 15, 2027 Available $4,676per person Get Quote
Aug 12, 2027 Aug 22, 2027 Available $4,676per person Get Quote
Aug 21, 2027 Aug 31, 2027 Available $4,676per person Get Quote
Aug 28, 2027 Sep 7, 2027 Available $5,475per person Get Quote
Sep 2, 2027 Sep 12, 2027 Available $5,550per person Get Quote
Sep 4, 2027 Sep 14, 2027 Available $4,995per person Get Quote
Sep 11, 2027 Sep 21, 2027 Available $4,995per person Get Quote
Sep 16, 2027 Sep 26, 2027 Available $4,995per person Get Quote
Sep 18, 2027 Sep 28, 2027 Available $4,995per person Get Quote
Sep 25, 2027 Oct 5, 2027 Available $5,550per person Get Quote
Oct 2, 2027 Oct 12, 2027 Available $4,995per person Get Quote
Oct 9, 2027 Oct 19, 2027 Available $4,995per person Get Quote
Oct 14, 2027 Oct 24, 2027 Available $4,995per person Get Quote
Oct 28, 2027 Nov 7, 2027 Available $4,815per person Get Quote
Nov 4, 2027 Nov 14, 2027 Available $4,075per person Get Quote
Nov 11, 2027 Nov 21, 2027 Available $4,075per person Get Quote
Nov 18, 2027 Nov 28, 2027 Available $4,075per person Get Quote
Nov 25, 2027 Dec 5, 2027 Available $4,075per person Get Quote
Dec 18, 2027 Dec 28, 2027 Available $4,525per person Get Quote
Dec 23, 2027 Jan 2, 2028 Available $4,750per person Get Quote
Feb 24, 2028 Mar 5, 2028 Available $4,075per person Get Quote
Mar 2, 2028 Mar 12, 2028 Available $4,125per person Get Quote
Mar 9, 2028 Mar 19, 2028 Available $4,125per person Get Quote
Mar 11, 2028 Mar 21, 2028 Available $4,125per person Get Quote
Mar 16, 2028 Mar 26, 2028 Available $4,225per person Get Quote
Mar 23, 2028 Apr 2, 2028 Available $4,495per person Get Quote
Mar 25, 2028 Apr 4, 2028 Available $4,495per person Get Quote
Mar 30, 2028 Apr 9, 2028 Available $4,495per person Get Quote

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