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Our 20 Best Italy Itineraries & Vacation Packages

Ratings of Zicasso's Service
<p>The cradle of European civilization, Italy is a region that has conquered imaginations since the Ancient Roman Empire and one that has prospered under the Roman Catholic Church. Birthplace of the Renaissance, home to the highest number of UNESCO World Heritage Sites in the world, and a haven for food lovers who treasure the freshest seasonal produce coupled with a fine wine, it comes as no surprise that Italy has many travelers returning for a second and even a third visit.</p>

The cradle of European civilization, Italy is a region that has conquered imaginations...

The cradle of European civilization, Italy is a region that has conquered imaginations since the Ancient Roman Empire and one that has prospered under the Roman Catholic Church. Birthplace of the Renaissance, home to the highest number of UNESCO World Heritage Sites in the world, and a haven for food lovers who treasure the freshest seasonal produce coupled with a fine wine, it comes as no surprise that Italy has many travelers returning for a second and even a third visit.

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    Trips curated by the world’s top destination experts

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Walk through the historic city of Bologna to see one of the oldest universities in Europe

First-Time Traveler’s Tour of Italy: Venice, Florence, Rome

Places Visited: Rome, Bologna +3 more
Places Visited: Rome, Bologna, Siena, Florence, Venice 

10 Day Custom Tour

From $3,575

The coast of Sorrento in Italy

Italian Adventure to Rome, Amalfi Coast and Sicily

Places Visited: Rome, Sorrento +7 more
Places Visited: Rome, Sorrento, Capri, Amalfi, Positano +4 more

12 Day Custom Tour

From $9,199

Colosseum in Rome, Italy

Joys of Rome and Southern Italy Itinerary for Seniors

Places Visited: Rome, Pompeii +5 more
Places Visited: Rome, Pompeii, Naples, Amalfi, Capri +2 more

8 Day Custom Tour

From $2,595

Inlet and beaches in the Maddalena archipelago in Sardinia, Italy

Fully Immersive Tour of Italy: Highlights and Hidden Gems

Places Visited: Venice, Bologna +5 more
Places Visited: Venice, Bologna, Cinque Terre, Siena, Sorrento +2 more

21 Day Custom Tour

From $16,375

Gondola ride on the Grand Canal in Venice, Italy

Splendors of Italy 17-Day Tour

Places Visited: Venice, Lake Como +4 more
Places Visited: Venice, Lake Como, Milan, Portovenere, Florence +1 more

17 Day Custom Tour

From $5,979

Terraced vineyards above Manarola in the Cinque Terre, Italy

Exploring Cinque Terre Itinerary: From Levanto to Santa Margherita

Places Visited: Levanto, Val di Vara +2 more
Places Visited: Levanto, Val di Vara, Santa Margherita, Cinque Terre 

8 Day Custom Tour

From $2,859

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Medival Castello di Roccascalegna on a hill surrounded by fields and vineyards in Roccascalegna, Province of Chieti, Abruzzo

7-Day Italian Culinary, Wine, and Gelato Making Tour

Places Visited: Vasto, San Giovanni in Venere +1 more
Places Visited: Vasto, San Giovanni in Venere, Roccascalegna 

7 Day Custom Tour

From $2,501

Vineyards in Montepulciano, Italy

Wine Connoisseur's Dream Tour of Tuscany

Places Visited: Florence, Siena +6 more
Places Visited: Florence, Siena, Montalcino, Montepulciano, Pitigliano +3 more

8 Day Custom Tour

From $2,859

Ancient town of Matera in Italy

Italy for Second Timers: Puglia and Amalfi Coast Itinerary

Places Visited: Bari, Savelletri di Fasano +8 more
Places Visited: Bari, Savelletri di Fasano, Ravello, Amalfi, Positano +5 more

8 Day Custom Tour

From $2,859

Municipal Library of Bologna in Italy

Luxury Tour of Italy's Finest: Lake Como, Venice, Florence, Rome Itinerary

Places Visited: Lake Como, Venice +5 more
Places Visited: Lake Como, Venice, Florence, Siena, San Gimignano +2 more

12 Day Custom Tour

From $9,355

Enjoy unique customs in the historic center of Rovinj, Croatia

Jewels of the Adriatic Sea: Croatia and Italy Tour

Places Visited: Venice, Rovinj 
Places Visited: Venice, Rovinj 

8 Day Custom Tour

From $2,467

Young girl enjoying a gelato in Rome, Italy

Kid-Friendly Family Tour of Italy's Highlights

Places Visited: Rome, Florence +9 more
Places Visited: Rome, Florence, Pisa, orvieto, Lucca +6 more

10 Day Custom Tour

From $3,575

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Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

We Work With the Best Travel Agents for Italy Itineraries

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More About Italy Itineraries & Vacations

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 tour.

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.

Read More    >
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 trip. 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 you ...

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How to Plan a Trip to Italy: Frequently Asked Questions
Skyline highlighting the architecture of Rome, Italy
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 trip 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 tour as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

Read More    >
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.

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

From ancient ruins in the capital city of Rome to glistening canals in Venice, you can explore the best places to visit in Italy for inspiring travel ideas.

Italy enchants with ancient cultural riches and unique style, as well as enchanting natural beauty, from the colorful seaside Amalfi Coast towns to the golden hills of Tuscany. With endless majesty stemming from the dramatic coastline, beautiful lakes, and rolling landscapes, you can immerse yourself in the storied beauty as you explore the top places to visit.

Discover essential experiences and savor the pleasures of Italian life on a trip to the best places to go in Italy.

Read More    >

Reviews of Zicasso's Referral Service

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Italy Tour Review: Rome, Florence, Tuscany, Cinque Terre,...
"In general, the trip was fantastic! I worked with a Zicasso...

Reviewed By Thomas B.

Italy Tour Review: Venice, Rome, Florence, Pisa, Cinque...
"In a word, Zicasso's travel agent was extraordinary. She...

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Italy Vacation Review: Mask Workshop, Pasta-Making Class,...
"Our Zicasso agent’s planning and communication made our...

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Italy Luxury Vacation Review: Milano, Lake Maggiore, Lake...
"We were guided privately every day through different experiences...

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Italy Travel Review: Venice, Florence, Pisa, Sorrento, Positano,...
"The Zicasso trip planner did an exceptional job of planning...

Reviewed By Laura L.

Italy Vacation Review: Florence, Bologna, San Gimignano,...
"This is the second Italian adventure our Zicasso travel...

Reviewed By TRACEY U.