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3 Week Italy Itineraries

Ratings of Zicasso's Service

From the Venetian lagoon and the Eternal City of Rome to the rolling Tuscan hills and the seaside villages of Sicily, your Italian escapade is best done through a customized tour. Discover iconic landmarks, unmatched food and wine, distinct local identities, and much more with a 3-week Italy itinerary from Zicasso. Inquire now to talk to the best local experts.

How Zicasso Works In 3 Simple Steps

  1. 1

    Describe your dream 3 week Italy itinerary.

  2. 2

    We match you with up to 3 top travel specialists. They compete to plan your itinerary.

  3. 3

    Book the trip when you are satisfied.

Ratings of Zicasso's Service

Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

The main square, Piazza Ferrari in Genoa, connects the historic center and the more modern part of the city, Northern Italy.

Northern Italy Three-Week Itinerary: Venice to Genoa

21 Day Custom Tour

From $5,770

Delight in the charming villages, the artistic masterpieces, and the authentic flavors discovered during your custom-tailored tour of Northern Italy. From the reflective waters of Lake Como to the serene footpaths of Cinque Terre, the aristocratic marble palaces of Venice to the maze-like lanes of Genoa’s ancient port, you will experience the luster of Northern Italy’s rich past and dynamic present. Traverse elaborate Renaissance and Baroque palaces, and then experience extraordinary churches decorated with artistry crafted by master painters. Sip Prosecco, dine on savory white truffles and bask in the elegant ambiance of Northern Italy’s famous cities, enchanting towns, and serene countryside.

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Almost cave dwellings combining Roman customs and the vibrancy of modern life, Potenza, Basilicata, Southern Italy

Perfect Three-Week Italy Vacation: Southern Italy & Sicily

21 Day Custom Tour

From $5,770

Relish your introduction to the must-see beaches, the majestic history, and incredible cuisine during your custom-tailored tour of Southern Italy and Sicily. Savor your time in the white sands that lead to clear turquoise waters in Calabria, and then learn about the complexity of flavor in traditional Pugliese olive oil. Explore the enchanting ambiance of cave-dwellings in Basilicata, and then traverse the fuming craters of an active volcano in Sicily. The endless marvels of Southern Italy hold captivating layers that showcase both elegance and rustic charm, ancient Greek aesthetic and preserved Roman customs intertwined with the vibrancy of contemporary life.

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Mother and daughter in Venice, Italy

Exploring the Italian Peninsula Tour for Families

21 Day Custom Tour

From $5,770

Intrigue and excitement will guide you through your customizable Italy family tour that will immerse you in the majesty of the ancient world and marvels of the Renaissance. Traverse the grandeur of Venice on the canals and explore the distinctive ambiance of Rome. Uncover the fascinating flavors of handmade pasta in Bologna, and then learn the art of crafting homemade pizza in Naples. Family comes first in Italy, and your kid-friendly tour will embrace the fun of discovery with custom-tailored scavenger hunts and picturesque views, the thrill of climbing a leaning tower and the magic of bringing rich history and tangible heritage to life.

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Discover Bellagio, a small but very picturesque town on the shores of Lake Como

Trip of a Lifetime: Italy Tour in Three Weeks

21 Day Custom Tour

From $5,770

Your customizable 3-week best of Italy tour captures the beauty, charm, elegance, and glamour of the most popular cities and towns and brings you from Venice to Rome, Bellagio to the Amalfi Coast. Discover the splendor of the Colosseum and the prestige of marble palaces rising out of the Grand Canal, and then Indulge in the complex flavors of treasured Tuscan wine and the ancient preserved life frozen in Pompeii. The dynamic architecture of Florence and fascinating artwork of Pisa will create lasting memories and a love affair with the captivating culture of Italy that will last a lifetime.

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Lipari is the largest of the Aeolian Islands in the Tyrrhenian Sea off the northern coast of Sicily, southern Italy.

Soul of Sicily Tour: Palermo, Taormina & Syracuse

21 Day Custom Tour

From $5,770

Idyllic beaches, enchanting ancient mythology, breathtaking islands, and a welcoming culture will define your custom-tailored tour of Italy that captures the incredible culture and history of Sicily. You will be delighted by the legendary cuisine and the fantastic coastal scenery as you follow dramatic trails to volcanic craters and wander along labyrinthine-cobbled lanes to reach aristocratic piazzas. Alluring Norman architecture and Arab designs will become distinctive features that will connect the island’s distant villages, towns, and cities. You will also discover the natural grandeur, embracing tranquility, and history between Palermo, Taormina, and Aeolian Islands.

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Enjoy the idyllic charm of the Italian countryside, Perugia, Umbria

Romantic Italian Escapade: Intimacy & Seclusion

21 Day Custom Tour

From $5,770

The passion of history and culture will enchant you during your custom-tailored romantic tour of Italy. Your affection for each other and for Italy will grow in the charismatic towns and villages that preserve tradition within elegant, medieval, Renaissance, and Baroque architecture. Beautiful artwork celebrates the virtues of love and private rendezvous. Grand castles and sophisticated palaces will provide a fairytale ambiance while countryside scenery will embody the idyllic charms for which Italy is known. You will indulge in a couple’s visit to a natural thermal spring, bask in the rich flavor of local wine, and enjoy crafting delicious traditional meals as you share a dreamy Italian romance.

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Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
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Reviews of Zicasso's Referral Service

4.89 stars based on 4391 reviews.

Luxury Italy Vacation Review: Sicily, Palermo, Taormina,...
"[Our travel agents'] knowledge of the country as well as...

Reviewed By ANDrew C.

Italy Trip Review: Florence, Lake Garda, Lake Como, 3-Week...
"Cameron put together an outstanding program for our three...

Reviewed By Gene P.

Northern Italy & Sicily Travel Review: Taormina, Bologna,...
"If I was to use 2 words t describe our travel designer,...

Reviewed By Ravi O.

Italy Anniversary Travel Review: Naples, Pompeii, Sorrento,...
"Laura, Veronika and the team at this travel agency were...

Reviewed By Joe L.

Italy Vacation Review: Rome, Pompeii, Positano, Sorrento,...
"[Our travel agent] learned of our basic interests and took...

Reviewed By Bill T.

Luxury Italy Family Trip Review: Venice, Private Tours,...
"Giulio and his team not only met our travel criteria, but...

Reviewed By Natalie S.