Isola Bella in the middle of Lake Maggiore, Italy.
28,000+ Verified Traveler Reviews

Italy Vacation Ideas: 14 Amazing Italy Itinerary Packages

It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation Ideas is here to provide you with the inspiration you need to create a personalized experience tailored to your interests. From wine tasting in Tuscany to trekking in the Dolomites and swimming in the Mediterranean, a grand trip awaits. Explore the endless opportunities with the sample itineraries below.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Positano, Italy

10 Day Trip IdeaFrom $3,600

Italy Family Vacation: Coastline, History, and Food

Sorrento, Pompeii, Positano, Rome, Florence +2 more
Civita di Bagnoregio is one of the most unusual sights in Italy.

12 Day Trip IdeaFrom $4,300

Immersive Italy Vacation: North to South

Milan, Venice, Florence, Bologna, Rome +4 more
Medieval city of Matera in Southern Italy during a sunset

12 Day Trip IdeaFrom $9,400

Exclusive Southern Italy Vacation: Sorrento, Matera, Ostuni

Sorrento, Capri, Herculaneum, Paestum, Matera +7 more
Mountain side village of Castelmezzano in the Potenza Province of Southern Italy

10 Day Trip IdeaFrom $3,600

10 Days Off the Beaten Path Tour of Southern Italy and Sicily

Naples, Sorrento, Palermo (City), Matera, Cosenza +1 more
Aragon Castle on Ischia Island.

9 Day Trip IdeaFrom $6,600

Gems of the Mediterranean Italy Vacation

Capri, Ischia, Ponza, Ventonete, Rome
Couple taking sunset gondola ride on the Grand Canal in Venice, Italy

7 Day Trip IdeaFrom $2,600

Romantic Italy Getaway: Art, Food, Gondolas & More

Florence, Pisa, Lucca, Vernazza, Riomaggiore +3 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  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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Explore the ancient Roman city of Pompeii, near Naples

7 Day Trip IdeaFrom $2,600

A Serene Senior’s Tour of Southern Italy and Sicily

Palermo (City), Taormina, Sorrento, Naples, Matera
Explore the streets of Renaissance Florence, Palazzo Vecchio.

13 Day Trip IdeaFrom $5,900

Highlights of Italy Tour: Venice to Sorrento

Venice,  Florence,  Siena,  Chianti,  Pisa +7 more
Statues of saints on top of St. Peter's Basilica in Rome, Italy

10 Day Trip IdeaFrom $3,600

Best of Italy Tour: Rome, Florence, Tuscany, Venice

Rome, Florence, Sorano, Montalcino, Siena +5 more
Italy Tour for Food Lovers

12 Day Trip IdeaFrom $4,300

Italy Tour for Food Lovers

Venice, Florence, Rome, Tuscany, Sorrento
Frediano castle in Florence, Italy

11 Day Trip IdeaFrom $5,000

Essence of Italy Tour: Cities, Ruins, Canals, History & Beauty

Rome,  Naples,  Pompeii,  Assisi, Deruta +4 more
St. Francis of Assis Basilica in Umbria, Italy

17 Day Trip IdeaFrom $5,600

Perfect Italy Vacation for Senior Travelers

Milan, Bellagio, Santa Maria delle Grazie, Pinacoteca de Brera, Venice +9 more

4.9

Reviews of Zicasso's Italy Vacation Ideas: 14 Amazing Italy Itinerary Packages

Based on 2330 verified traveler reviews.

Italy Family Vacation Review: Sorrento, Naples, Matera, Puglia, Positano, Capri, Pompeii, Wine & Olive Oil Tasting, Pasta Making

We (family of 4 including two teenagers) had a wonderful trip to southern Italy the last two weeks of June:  Sorrento, Naples, Matera, Polignano a Mare (Puglia region).  With Sorrento as our base we saw Positano/Amalfi Coast, Capri and Pompeii.  In Puglia we visited Ostuni, Alberobello and Lecce, went to a wine tasting (with great wine!), and visited two masserias:  one for an olive oil tasting, and another with a pasta-making class.  Our travel agent at at this company helped us to plan a great itinerary.  She was very flexible and helped us keep within our budget, and the logistics she put together were flawless.  I also felt she truly listened to what we wanted - even her first draft itinerary was very close to the mark.  Highly recommended.

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Review: Italy Family Vacation, Rome, Tuscany, Florence, Amalfi Coast, Sorrento, Positano, Pompeii, Pisa, Vatican Papal Mass

Our family of five just got back from the most wonderful vacation in Tuscany and Rome.  Our agent crafted a set of amazing experiences for our family from the private tour guides to Florence, Pisa and Lucca; a private wine tasting lunch at the Capannelle Winery and vineyards in Chianti; tickets to the Papal mass at the Vatican; to a tour beneath the church of San Clemente to see the excavations of a byzantine and then a Roman street neighborhood; a day excursion to the Amalfi coast to visit Positano, Sorrento and Pompeii; and more! Our agent and the guides found excellent restaurants from a simple salumeria where the locals ate to some high end restaurants.  The hotels were right in the center of Florence – on the piazza della Repubblica - and Rome – between the Piazza del Popolo and the Spanish Steps.  Our agent was attentive to our plans and made excellent suggestions.  Everything went extremely smoothly.  All the guides drivers were very friendly, spoke English and were very knowledgeable about art, history and the local culture.  We saw so much every day because everything was so well planned.  Simply the best travel experience ever!

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Luxury Anniversary Vacation Review: Italy, Florence, Venice, Amalfi Coast, Cinque Terre, Tuscany, Verona, Naples, Vatican, Pompeii

I have to begin by saying I've told everyone how pleased I am with Zicasso and the travel agent they recommended.  I also have to say that I was very hesitant to book my trip with a company that I had only communicated with via email.  Turns out I had nothing to worry about.

The initial response I received from my agent was immediate and continued right up until our actual trip while we were in Italy.  I let her know where I wanted to go, what I wanted to see, told her I was interested in a mix of arranged tours and time on our own.  She listened and also made great suggestions.  I honestly can't say enough about how wonderful she was to work with, along with her co-worker.

They arranged for all our hotels, transportation and tours.  Every driver and guide we had was top notch.  They made a point of keeping us in small groups, sometimes only the two of us and the guide.

Our 19 day trip began in Venice where we were met at the airport and driven to a private water taxi.  That driver walked us out of the boat and made sure we knew how to find our hotel. Our departure was just as seamless.  A guide met us in our lobby, walked with us to the water taxi, came into the train station with us and explained the board to us, pointing out our train and track number.  

We continued on to Verona, Cinque Terre, Tuscany, Florence, Naples, the Amalfi Coast and Rome.  Since we weren't in any one place longer than three days it was extremely helpful to have guides, even for just a couple of hours to orient us, which saved us a lot of time.  We had guides for a walking tour in Venice, a morning in Cinque Terre traveling with us between the villages, the Accademia in Florence, Pompeii, an Amalfi Coast drive and the Vatican in Rome.  Every one of the them was passionate and proud and we learned so much.  We had a car in Tuscany and saw many other places on our own, Lucca, Pisa, San Gimignano, Siena, Montalcino, Montepulciano.  We stayed in Sorrento, spent one day on Capri and another full day on a tour to Positano, Amalfi and Ravello, which included a short boat ride along the coast.  Spectacular.  Our only tour in Rome was the Vatican but we saw all the other major sites on our own, taking the metro, bus, taxis and walking, lots of walking.  It was the perfect mix of free time and arranged tours.

And, they also worked with our children who surprised us with a dinner in Venice for our anniversary after a gondola ride!

One great advantage to having your tour guide in the country you're visiting, you're in the same time zone.  We had one mishap with a train and were able to talk to them right away.  Other than that, everything worked liked clockwork.

I would definitely use them again and have told everyone I know what a wonderful job they did for us.

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Italy Travel Review: Naples, Capri, Sorrento, Vieste, Polignano, Monopoli, Lecce, Matera, Historic Sites, Winery, 12-Day Trip

We enjoyed our trip to southern Italy. The hotels in Naples, Capri, Sorrento, Vieste, Polignano, Monopoli, Lecce, and Matera were in great locations, all near or in the historic sites.

We were able to maximize our time in each location and all hotel staff were very helpful. We especially enjoyed our hotel in Matera. However, our tour guide there did not give us the in-depth tour we were expecting.

The drivers assigned to us were very helpful and knowledgeable about the areas we were in. Our driver will be remembered fondly!

Our only concern is that we ordered wine from a Medici winery and haven't been able to contact them.

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Travel Review: Italy Trip, Rome, Sorrento, Florence, Naples, Pompeii, Herculaneum, Ravello, Siena, San Gimignano, Farm & Food Tour

We experienced a fabulous twelve night first trip ever to Europe staying in Rome, Sorrento, and Florence with day visits to Naples, Pompeii and Herculaneum, a drive with stops and photo-ops through the beautiful Amalfi coast villages to Ravello, and a day trip to historic Siena and San Gimignano through the Chianti region of Tuscany. Our travel consultant and her colleague at the company in Rome, proved to be perceptive to our interests, resourceful in finding spot-on solutions within our budget and patient professionals as we explored various itinerary options. Both women spoke and wrote english very well to thoughtfully help us plan our itinerary for three adults with private transportation and guides. Our private guides in Rome; in Pompeii and Herculaneum; in Naples; one a Canadian ex-pat in Florence; and in Siena, informed our discovery of each locale and its many treasures.  We also did two small group tours. First, a farm/food tour near Sorrento with an incredibly informative and entertaining guide, and catacombs at Saint Sebastian with a nameless guide and small group of 9 during our Appian way visit and final full day in Rome. At times we were chaperoned in private vehicles with english speaking drivers knowledgeable of their territories. In Rome, in Naples, in the Bay of Naples Sorrento area, in Tuscany, and in Amalfi. We wouldn't hesitate to recommend this company to help others plan the vacation of a lifetime.

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Review: Italy Family Vacation, Milan, Rome, Florence, Venice, Parma, Modena, San Gimignano, Lake Como, Dolomites Snowmobiling

Thanks for helping me organize my family (of 10 with diverse age from 15 to 63) trip to Italy, from Dec 17 to Dec 31. Whilst different member of my family have different expectation and requirement, I would like to comment you and your team on having planned an excellent trip that not only met each and everyone's interest and expectation but truly exceeded it.

Your planning have brought us to the lovely cities of Parma, Modena, Florence, Orvieto, Civita Di Bagnoregio, Naples, Rome, Venice, Cortina d'Amprezzo and back to our starting point Milan. Throughout the trip, we have a well balance itinerary that covered

- beautiful churches such as the Duomo in Milan, Rome, Florence,

- archeological site like Pompeii, Colosseum, Roman Forum, Pantheon, Pisa, Verona (learning more about romeo and Juliet)

- great local eating places (recommended by the guides you chose)

- lovely country side and unique sight in San Gimignano, Civita Di Bagnoregio, Orvieto, Lake Como,

- great gallery likes Uffizi, Academia

- Interesting activity such as Snow Mobile excursion in Cortina, Learning Cooking 

- Shopping activities

With so much, yet your team immaculate planning never have us rushing from sight to sight, we were both able to enjoy and learn as much as we can of each sight and at times added more activities.

The team of guides you chose, have truly turn stone and history into exciting stories that the provided the group deeper understanding of the sights we visited and saw. Really like to thank each on of them like our guides in Florence, Pisa, San Gimignano, Orvieto and Civita Di Bagnoregio, Naples and Pompeii, Rome, Verona, Venice and Milan.

But most importantly, thank you for getting our driver, he truly ensure our comfort whilst driving steadily through jams on our way to Naple and snow storm on our way to Cortina d Amprezzo and also took very good care of us ensuring we know what to do where we have no guides and leaving us clear instruction when we needed help. He is truly a wonder.

I will definitely tell my friends heading to Italy about this company.... A wonderfully great experience.

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