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3 Week Italy Itineraries & Tour Packages

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.

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Let these itineraries inspire your personalized travel experience

The main square, Piazza Ferrari in Genoa, connects the historic center and the more modern part of the city, Northern Italy.

21 Day Trip IdeaFrom $9,500

Northern Italy Three-Week Itinerary: Venice to Genoa

Venice, Padua, Verona, Lake Garda, Milan +17 more
Matera, Italy

21 Day Trip IdeaFrom $9,500

Perfect Three-Week Italy Vacation: Southern Italy & Sicily

Bari, Lecce, Alberobello, Taranto, Otranto +16 more
Family in Venice, Italy

21 Day Trip IdeaFrom $9,600

Exploring the Italian Peninsula Tour for Families

Venice, Murano, Burano, Torcello, Padua +23 more
Discover Bellagio, a small but very picturesque town on the shores of Lake Como

21 Day Trip IdeaFrom $7,600

Whirlwind 3-Week Tour of Italy

Venice, Murano, Burano, Torcello, Milan +26 more

21 Day Trip IdeaFrom $9,600

Soul of Sicily Tour: Palermo, Taormina & Syracuse

Palermo, Salina, Lipari, Taormina, Syracuse +9 more

21 Day Trip IdeaFrom $9,600

Romantic Italian Escapade: Intimacy & Seclusion

Rome, Perugia, Florence, Bologna, orvieto +18 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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4.9

Reviews of Zicasso's 3 Week Italy Itineraries & Tour Packages

Based on 2883 verified traveler reviews.

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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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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Travel Review: Anniversary Trip to Italy, Rome, Florence, Pisa, San Gimignano, Positano, Truffle Hunt, Cooking Class, Food Tour

Locations Visited: Venice, Verona, Florence, San Gimignano, Siena, Pienze, Rome, Pompeii, Positano

My husband and I planned this trip for our 10-year anniversary. I’m a person with high expectation and this travel agency exceeded all my expectations. The entire trip was dream.

We opted for personalized tours and transport for 95% of our trip. All of our drivers were wonderful. They arrived on time and made sure we made it to all of our destinations without issue. They had the contact information for the tour guides we were meeting. Upon arrival to our first hotel, a local cell phone and gift were given to us. Having the iPhone during our trip made any needed communication with our agent and his team a breeze. In addition, we used the phone apps for navigation throughout the cities we visited. We made a last-minute request for an additional private transport, and our agent was able to make it happen. We greatly appreciated their customer service.

We participated in a several unique experiences while in Italy. We went truffle hunting in Pienza, which was amazing. After, we were served a meal that highlighted truffles and the cheeses made locally. In addition, we did a cooking day in Rome. This was a private cooking class where we made pasta, several sauces, and appetizers. The one disappointment is that we never received the recipes from the chef (we were told by the chef that they would be emailed to us). However, this is a knock on the chef and not our travel agent. Once the class was done, we were served a meal in a private garden area. Lastly, we did a food walking tour in Rome. This was an amazing way to find local cuisine that we wouldn’t have known about otherwise. A wonderful experience.

All of our tour guides were excellent. They were knowledgeable, friendly, and familiar with the cities. We had one guide that really went into the details and reasons for expressions in the art. We didn’t care for that, but we didn’t specify that ahead of time or to the guide. It was wonderful seeing her excitement and passion for all of the amazing working works of art and sculpture that we saw.

Overall, I would highly recommend this travel agent and his team if you are traveling to Italy!! You will not be disappointed. We gave him our wish list of activities, accommodation preferences, etc. ahead of time and he made sure we got them all! Thank you for such a wonderful and memorable trip. If we are able to return to Italy, you will be hearing from us.

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Italy Tour Review: Bologna, Parma, Modena, Balsamic Vinegar Factory, Wine Tasting, Cuisine, Cooking Class, 2 Weeks
"We set out to experience culture and food, and Zicasso’s travel agency did not disappoint."

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Travel Review: Family Trip to Italy, Verona, Rome, Venice, Naples, Positano, Bologna, Florence, Assisi, Siena, Pisa, Gelato-Making

My family of 6  (Michigan, USA) made a once in a lifetime trip to Italy in June 2018.

We worked with this travel agent as recommended by Zicasso, for 9 months starting in August 2017 in order to customize a trip for us to privately see the all the places we wished to see in June 2018. Our travel agent was very responsive and accommodating in working within a budget and the planning process. He provided alternatives to choose from when suggesting accommodation’s and activities. We ended up with 2 fabulous weeks touring the entire country, stopping for private tours (yes…just the 6 of us) in the following cities.

Pompeii - Amalfi Coast - Island of Capri - Naples - Rome - Assisi - Cascia - Florence - Siena - Pisa - Bologna - Verona - Venice

We were greeted at the airports and personally escorted throughout the arrival and departure process which was invaluable when you do not speak/read or comprehend Italian. Our agent set up private transportation with English speaking drivers, within and in between each city, for our family which made our experience with the local culture and communities that much more rich. The travel guides in each city were very well selected and highly educated. They took their time giving us fun facts as well as historical information about their city and its traditions. They were also accommodating with all of our requests for bathroom or food breaks, recommendations to local restaurants and additional activities. Our overnight hotel accommodations were extremely luxurious and we felt very lucky to be treated so special. Each hotel offered complimentary breakfast so we were able to start each day with excitement and full stomachs.

We would highly recommend this travel agent to schedule anyone’s tour in the beautiful county of Italy.

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Italy Trip Review: Milan, Verona, Venice, Lake Como, Lake Maggiore, Lake Garda, Dolomites, Hiking
Rose and the travel company's team created the perfect custom tour of northern Italy for us! It was a combination of visiting some of the major cities like Milan, Verona, and Venice, along with time in the lake country (Lake Como, Lake Maggiore, and Lake Garda), and four days of hiking in the Dolomites! This was the only company that was able to create an itinerary and travel plan that worked for us. It was an active trip, but with plenty of time to relax and explore on our own. Thank you for the tremendous attention to detail and making this trip such a memorable experience!

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