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Our 20 Best Italy Itineraries & Vacation Packages

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<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 $4,500

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 $11,600

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 $3,300

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 $20,500

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 $7,500

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 $3,600

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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 $3,200

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 $3,600

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 $3,600

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 $11,700

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 $3,100

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 $4,500

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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

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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.

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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

From spring's awakening in Roman gardens to winter's snow-dusted alpine peaks, each season reveals different facets of Italy's magnificent character.

The essence of timing in Italy lies in understanding when morning mist lifts from Tuscan vineyards, when truffle season perfumes Umbrian forests, and when Venice's canals shimmer with golden light instead of tourist crowds. True luxury travel transcends weather predictions, embracing instead the pace of Italian life, with its harvest festivals, Easter processions, carnival celebrations, and quiet moments when locals reclaim their beloved piazzas.

Our destination specialists understand these subtle seasonal nuances, crafting journeys that align with Italy's natural and cultural routines for experiences that feel authentically It...

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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.

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

The allure of Italy lies in its iconic landmarks and the sensory experiences you can uncover when exploring the top things to do in Italy, all woven through sunlit piazzas, vineyard-clad hills, and whispered histories.

Italy reveals itself through curated moments, whether private viewings of Renaissance masterpieces, truffle hunts in misty forests, or gondola rides through Venice’s moonlit canals. We distill Italy’s essence into transformative experiences to immerse you in la dolce vita, while honoring the nation’s profound cultural legacy.

Extraordinary travel begins with a human touch, and our destination specialists design every journey with care, insight, and personal attention. As you consider a visit to Italy, use the following information to guide yo...

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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

The essence of the best places to visit in Italy lies not in crowded piazzas, but in secrets whispered by the marble of a Medici palace, the citrus-kissed breeze off Capri’s cliffs, the way golden hour gilds Venice’s canals.

From ruins in Rome to Venetian waterways, Tuscan wine estates to famous landmarks in Florence, the top places to go in Italy will give you a remarkable vision of the country.

Extraordinary travel begins with a human touch, and our destination specialists design every journey with care, insight, and personal attention. As you consider a visit to Italy, use the following information as a guide before connecting with our travel experts to help you plan your trip.

Read More    >

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