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Our 20 Best Italy Itineraries & Vacation Packages

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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

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

10 Day Trip IdeaFrom $4,500

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

Rome, Bologna, Siena, Florence, Venice 
The coast of Sorrento in Italy

12 Day Trip IdeaFrom $11,600

Italian Adventure to Rome, Amalfi Coast and Sicily

Rome, Sorrento, Capri, Amalfi, Positano +4 more
Colosseum in Rome, Italy

8 Day Trip IdeaFrom $3,300

Joys of Rome and Southern Italy Itinerary for Seniors

Rome, Pompeii, Naples, Amalfi, Capri +2 more
Riomaggiore, Cinque Terre, Italy.

21 Day Trip IdeaFrom $20,500

Fully Immersive Tour of Italy: Highlights and Hidden Gems

Venice, Bologna, Cinque Terre, Siena, Sorrento +2 more
Lake Como, Italy

17 Day Trip IdeaFrom $7,500

Splendors of Italy 17-Day Tour

Venice, Lake Como, Milan, Portovenere, Florence +1 more
Terraced vineyards above Manarola in the Cinque Terre, Italy

8 Day Trip IdeaFrom $3,600

Exploring Cinque Terre Itinerary: From Levanto to Santa Margherita

Levanto, Val di Vara, Santa Margherita, Cinque Terre 

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  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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

7 Day Trip IdeaFrom $3,200

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

Vasto, San Giovanni in Venere, Roccascalegna 
Vineyards in Montepulciano, Italy

8 Day Trip IdeaFrom $3,600

Wine Connoisseur's Dream Tour of Tuscany

Florence, Siena, Montalcino, Montepulciano, Pitigliano +3 more
Ancient town of Matera in Italy

8 Day Trip IdeaFrom $3,600

Italy for Second Timers: Puglia and Amalfi Coast Itinerary

Bari, Savelletri di Fasano, Ravello, Amalfi, Positano +5 more
Municipal Library of Bologna in Italy

12 Day Trip IdeaFrom $11,700

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

Lake Como, Venice, Florence, Siena, San Gimignano +2 more
Enjoy unique customs in the historic center of Rovinj, Croatia

8 Day Trip IdeaFrom $3,100

Jewels of the Adriatic Sea: Croatia and Italy Tour

Venice, Rovinj 
Boys enjoying a delicious Italian pizza.

10 Day Trip IdeaFrom $4,500

Kid-Friendly Family Tour of Italy's Highlights

Rome, Florence, Pisa, orvieto, Lucca +6 more

4.9

Reviews of Zicasso's Our 20 Best Italy Itineraries & Vacation Packages

Based on 6169 verified traveler reviews.

Ken M.
Italy Vacation Review: Florence, Private Tour, 10 Nights

Working with Zicasso’s tour operator and the travel specialist was outstanding. The travel specialist not only listened to what we needed, but delivered. Thanks for everything.

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Linda H.
Italy Tour Review: Vatican City, Cooking Class, 9-Day Trip

We were very pleased with the reservation experience. Zicasso’s trip coordinator was helpful many times and was able to guide us through our first visit abroad.

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Olivia K.
Italy, France Trip Review: 2 Weeks

Zicasso’s tour operator created a wonderful trip for us to Italy and France! All of the transportation and tours arranged were professional, timely, and made us feel comfortable traveling in foreign countries.

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Todd L.
Italy Travel Review: Cooking Class, 1 Week

Zicasso's travel specialist was perfect. She did everything, from tracking down lost sunglasses to making sure all our rides were available and on time. Our trip was very eventful.

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James B.
Italy Tour Review: Vatican Museum, Cooking Class, 2 Weeks

Zicasso's tour company did a wonderful job meeting our requirements. The individual guides were amazing. They were all subject-matter experts, who spoke English with an accent, but were very understandable. They were all full of additional tips and recommendations, including where to eat and tourist traps to avoid when shopping for souvenirs.

The cars were always clean and the drivers were very professional. The specialized tours were amazing, especially the pasta-making/cooking class. It was above and beyond our expectations.

There was just one minor hiccup, which the tour operator rectified immediately and above our expectation.

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Robin M.
Italy Trip Review: Rome, Florence, Tuscany, Food Tour, Wine Tasting, Art, 9 Nights

It was the trip of a lifetime! Zicasso’s travel agency planned the perfect vacation for us. Our travel specialist listened to what we wanted and delivered. It was perfect!

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