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3 Week Italy Itineraries & Tour Packages

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

Dynamic pricing from $7,513

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

Dynamic pricing from $7,513

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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Family in Venice, Italy
Exploring the Italian Peninsula Tour for Families

21 Day Custom Tour

Dynamic pricing from $7,639

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
Whirlwind 3-Week Tour of Italy

21 Day Custom Tour

Dynamic pricing from $7,513

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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Soul of Sicily Tour: Palermo, Taormina & Syracuse

21 Day Custom Tour

Dynamic pricing from $7,639

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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Romantic Italian Escapade: Intimacy & Seclusion

21 Day Custom Tour

Dynamic pricing from $7,639

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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Benefits of Using Zicasso

Plan Your Trip with
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We Work With the Best Italy Travel Agents for 3 Week Tours

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More About 3 Week Italy Itineraries

Italy Travel Guide
Florence, Italy
Italy Travel Guide

From Roman ruins to the Tuscan countryside, there is something for every traveler in Italy.

Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized vacation.

For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

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Best Time to Visit Italy
Summer Tuscany scenery with red poppy flowers and grain fields surrounding cute Vitaleta chapel and Pienza on the hill in Italy
Best Time to Visit Italy

The best time to visit Italy is in the spring and early summer months, from March through June. During this time, the weather is great for the beaches, sightseeing, wine tasting, food tours, and more. Fall, particularly September and October, are also lovely times, when Italy is quieter and the fall colors are on show.

Your ideal experiences also affect the best time of the year to visit Italy for your vacation. Skiing in the Dolomites is exceptional in December, while enjoying the sun-washed beaches of Sicily is best in May. Rome is brilliant in April, while Florence is stunning in September.

From wine tasting to Roman-ruin exploration and coastal sightseeing, find the best time for your experience. As a family, couple, senior, or adventure traveler, we share ideas to help ...

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How to Plan a Trip to Italy: Frequently Asked Questions
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How to Plan a Trip to Italy: Frequently Asked Questions

As you plan your trip to Italy, consider our tips with the following answers to the most frequently asked questions.

From dreaming of the sunflower fields in Tuscany to searching the ruins of Rome for ancient treasures, you can book a vacation in Italy using our ideas as inspiration. Enjoy the pleasures of La Dolce Vita or alpine panoramas, lounging on golden beaches, or embracing rolling vineyards. It is all about finding the information you need to plan the right trip for you.

Whether you are designing a first-time Italian vacation as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

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Top 15 Things to Do in Italy
The Roman Forum in Rome, Italy
Top 15 Things to Do in Italy

From immersive tours of ancient Rome to the intricacies of artisanal crafts, Italian gastronomy to breathtaking national parks, the top 15 things to do in Italy let travelers unravel the country’s beauty and culture.

You can witness more Unesco World Heritage Sites than in any other country or sample the enticing flavors of celebrated Italian wines. Art, architecture, gastronomy, history, and heritage highlight the depth of Italy’s quintessential allure, with a range of experiences that stretch from the Dolomite Mountains in the north to the shores of Sicily’s Lido Mazzaro in the south.

Discover the top 15 things to do in Italy for a majestic and authentic experience that brings Italian culture and unique experiences to the forefront.

Read More    >
7 Best Places to Visit in Italy
A farmhouse sitting in sunny fields in Tuscany.
7 Best Places to Visit in Italy

Italy practically overflows with must-see destinations, and deciding which to explore can be overwhelming.

The country inspires with ancient cultural riches and unique style, as well as enchanting natural beauty. With endless majesty stemming from the dramatic coastline, beautiful lakes, and rolling hills, it is no wonder we find inspiration throughout the country.

Here are the destinations you must see to discover the essential Italy and savor the simple pleasures offered by Italian life.

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Reviews of Zicasso's Referral Service

4.89 stars based on 4398 reviews.

Southern Italy Vacation Review: Sicily, Pompeii, Lunch &...
"I was very impressed with our guides, they were well above...

Reviewed By Mary D.

Italy Travel Review: Sicily, Ortigia, Taormina, Agrigento,...
"[Our travel agent] was excellent, delivering with no errors."

Reviewed By Thomas F.

Central & Northern Italy Tour Review: Santa Margherita...
"All of the services [our travel planner] booked for us...

Reviewed By Erica S.

Luxury Italy Trip Review: Ortigia, Taormina, Palermo, Mount...
"Alessandra did a wonderful job of finding just the right...

Reviewed By Stephanie C.

Italy Trip Review: Florence, Naples, Catania, Palermo, Syracuse,...
"We absolutely loved working with Eleonora and Elena at...

Reviewed By Stacy L.

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

Reviewed By ANDrew C.