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 1691 verified traveler reviews.

Italy Tour Review: Amalfi Coast, Sorrento, Positano, Path of the Gods, Cooking Class, Hike, 1 Week

The travel company did a fantastic job planning our Italian vacation to the Amalfi and Sorrento coasts. The hotel in Positano was breathtaking. The excursions that Zicasso's travel designer recommended were fantastic. The cooking class in the hills overlooking the coast was amazing. Our travel plans changed due to airline difficulties and she was incredibly helpful in making adjustments on the fly to ensure our trip went as smoothly as possible.

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Italy Travel Review: Taormina, Syracuse, Catania, Militello, Ragusa, Aci Castello, Modica, Mount Etna, Private Tour, Cooking Class, Boat Ride, 9 Nights

This was a superb trip that allowed us to combine personal visits to Taormina and Syracuse with a pre-planned group meeting in Catania. Planning and communication were excellent, supported by an app that let us easily view our itinerary, complete with phone numbers for the drivers, hotels, and the tour operator contacts.

The hotels were perfect! They were wonderfully located, with impeccable service in Taormina and Syracuse. Our excursions were private and diverse, and allowed us to combine culture, foodie interests, and free time. The guides were top-notch, knowledgeable, and flexible.

We especially loved seeing the smaller towns of Sicily; Militello, Ragusa, Aci Castello, and Modica. We even arrived in one small town during their annual festival.

We had a dedicated driver for our trip who was, himself, a treasure; always on time, always ready to adjust to changes, and a delightful personality.

This was such a good experience that we have selected Zicasso's tour operator to book another Italy trip next year.

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Italy Tour Review: Private Guides, Rome, Colosseum, Vatican City, Positano, Capri, Tuscany, Venice, Medieval Towns, Winery Tour, Cooking Class, Boat Ride, 2-Week Trip

Our Zicasso travel agent and her team created the most incredible experience for us. She tailored our trip to match exactly what we asked for. Every personal guide was exceptionally kind and knowledgeable. Every transport pick-up was seamless; our driver was waiting for us with our name on a plaque, so we had absolutely zero stress.

We enjoyed Rome, with personal guides to the Colosseum and Vatican City. We then went to Positano and got to experience a private boat ride to the Island of Capri, and the next day, we had a private cooking lesson with our chef, with door-to-door service.

Next was Tuscany, where we had the most amazing day touring medieval towns and wineries with our exceptional guide. And, finally, we ended in Venice, with no plans... we just got lost wandering the beautiful streets, enjoying the food, drinks, and shopping.

I highly recommend using Zicasso and our travel agent's team. We had an absolutely life-changing vacation and will use her again!

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Italy Trip Review: Amalfi Coast, Herculaneum, Vatican, Capri, Pompeii, Naples, Sorrento, Pantheon, Boat Ride, Street Food Tour, History, Culture, Local Cuisine, 10 Days

We had a fantastic time and Zicasso's tour operator did an excellent job organizing every detail of our trip. Drivers and guides were always punctual, and the itinerary was perfectly balanced—full days, without ever feeling rushed.

Some real highlights for us were Herculaneum, the Pantheon, the Vatican, and our unforgettable Capri boat tour. Our guide brought Pompeii's history to life in a way that made it feel like stepping back in time and the Naples street food tour was delicious and nostalgic—her pizza fritta instantly took me back to the calzones I grew up with in Niles, Ohio. Our driver was with us for several days and made every transfer feel effortless.

There was a small hiccup at the very end with a trip planner, but it was minor compared to the overall quality of the trip. The organization, communication, and attention to detail throughout made this a truly memorable experience and we wouldn’t hesitate to book with this tour agency again. We had a fantastic time and the tour company did an excellent job organizing every detail of our trip.

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Italy Travel Review: Rome, Ravello, Amalfi Coast, Positano, Sorrento, Naples, Pompeii, Capri, Mount Vesuvius, Cooking Class, Local Cuisine, 20 Days

My husband and I were thrilled with our recent trip to Italy that Zicasso’s travel designer put together. We began by attending a family friend’s wedding, held in Ravello, on the Amalfi Coast. Due to my husband’s mobility issues, we were met by a driver and headed to the Amalfi Coast. The driver was first class and the trip was very comfortable.

After the wedding festivities, we were able to have the most wonderful experiences visiting the towns of Amalfi and Positano, and our base for one week was in beautiful Sorrento. We attended a cooking class and enjoyed eating what we prepared. We had in-depth learning opportunities in Naples and Sorrento. Every guide we had spoke excellent English and was so knowledgeable. We especially enjoyed Pompeii! A super-fun day was had on the small group tour of Capri. The crew was fantastic and very accommodating in consideration of my husband’s mobility issues.

From beginning to end everything went well. The use of a messaging app was great for making sure everyone was on the same page.

The only thing that was a disappointment was the pizza in Naples. It wasn’t the best.

The hotel in Sorrento was phenomenal - it couldn’t have been better. The view of Mt. Vesuvius from our balcony helped create memories we will have forever. The hotel in Rome was also very nice. It was right in the middle of the main attractions.

We are very happy with our experience with this travel company and would not hesitate to recommend it!

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Italy Vacation Review: Venice, Florence, Tuscan Hills, Pompeii, Rome, Amalfi Coast, Sorrento, Capri, Cooking Class, Lemon Farm, Wine Tasting, Olive Oil Tasting, 2 Weeks

We had the pleasure of working with Zicasso’s travel agents to create the perfect Italian adventure. I had quite a few specific requests, from travel logistics to hotel preferences, and they were incredibly patient and collaborative, offering multiple variations of the itinerary until it matched exactly what we envisioned.

Our journey began in Venice, where we were seamlessly picked up by a private driver, transferred to a water taxi, and dropped directly at our hotel. After a wonderful stay, we were taken by private driver to the train station for our ride from Venice to Florence, our one and only train trip, as we opted (based on their smart recommendation) for private transportation for the rest of our travels to avoid potential delays and enjoy added convenience.

From Florence, we were driven into the Tuscan hills, where we experienced magical wine tastings, vineyard tours, olive oil tastings, and unforgettable meals with wine pairings. 

Next, our private driver brought us to Pompeii, where we enjoyed a fascinating tour with our private guide, and then continued on to Rome. In Rome, we loved the private golf cart tour of the city’s major landmarks, as well as a delightful cooking class that was arranged for us; it was a real highlight!

Finally, we traveled by private driver to Sorrento. From there, we had a breathtaking driving tour of the Amalfi Coast, a lemon farm tour, and an amazing day trip to Capri. Every detail was thoughtfully planned and executed.

Summary:

Planning and Itinerary Creation: Zicasso’s consultants made the entire process easy and stress-free. They worked closely with us to perfect the itinerary and were always receptive to changes and feedback.

Hotels: My sister and I requested adjoining rooms and were provided with beautiful family suites throughout the trip. Each hotel was ideally located, comfortable, and well-appointed, with all the amenities we needed.

Transportation: Every transfer was smooth and punctual. The private drivers were professional, friendly, and knowledgeable. (A special shoutout to our driver in Florence/Tuscany – he was the best!)

Communication: Throughout our trip, the travel company’s team was always accessible. Whether we needed to make adjustments or had a question, they handled everything promptly, allowing us to relax and fully enjoy our vacation.

We spent just over two unforgettable weeks in Italy and it was absolutely perfect, all thanks to the hard work, attention to detail, and excellent communication from Zicasso’s travel company! I highly recommend them and would not hesitate to use them again for future adventures.

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