
Italy Trip Planner
Whether you are searching for the most delicious fare, the finest art, or the grandest cities, Italy is full of experiences that will revitalize your senses. Zicasso’s Italian Trip Planner possesses a wide variety of authentic, Italian experiences, and our custom itineraries cultivate the opportunity for travelers of all ages and interests to find an Italian experience that is best suited for them. Inspiration starts here.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $6,200
Iconic Italy: Fast-Paced Exploration from Venice to Sicily

12 Day Trip IdeaFrom $11,700
Best of Italy Vacation in 12 Days

8 Day Trip IdeaFrom $3,600
Soulful Italy: Umbria, The Marches, and Abruzzo Tour

12 Day Trip IdeaFrom $11,600
Italian Adventure to Rome, Amalfi Coast and Sicily

12 Day Trip IdeaFrom $5,400
Honeymoon Highlights: Rome, Florence, Venice Tour
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
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.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.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.

12 Day Trip IdeaFrom $5,400
Family Trip to Italy: Nature, Ancient Temples, and Cuisine

7 Day Trip IdeaFrom $3,200
One Week in the Tuscan Countryside Tour

21 Day Trip IdeaFrom $20,500
Fully Immersive Tour of Italy: Highlights and Hidden Gems

8 Day Trip IdeaFrom $3,300
Joys of Rome and Southern Italy Itinerary for Seniors

10 Day Trip IdeaFrom $4,500
Flavors of the Vine & Countryside: Exploring Italy’s Slow Food Movement Tour
More Trip Planners Near Italy
Reviews of Zicasso's Italy Trip Planner
Based on 1126 verified traveler reviews.
We had an incredible time in Italy! Thank you to Zicasso’s travel company! You thoughtfully planned our time in Sorrento and Rome to ensure we had the best experiences, while allowing for some free time to explore.
Our day-trip boat ride around Capri was beyond perfect. The boat captain and guide were very professional and truly charming. He gave us options on how to take in the sights and provided great commentary about the history and culture of the island. We selected to go to Marina Piccola for lunch, which was a great experience. The view from the restaurant was enchanting and the food was delicious. The grottos, Faraglioni rocks, and swimming in the Mediterranean were experiences of a lifetime.
We spent a day driving along the Amalfi Coast. We had a great driver on the mountainous winding roads. We visited charming Positano and beautiful Ravello. Our driver had great advice about where to visit and what to see. We enjoyed an amazing lunch, with a beautiful view, in Ravello.
On day three we enjoyed free time on the beach in the morning. Then we headed out for our limoncello experience! And it was a wonderful experience. The people we met in Schiazzano were very special. We loved the goal of the family businesses to keep and honor their traditions. Our pickup was prompt and we were served a drink at their general store. It is very touching that they began the tour in their church and shared the pride in their community. Then we were off up the hill, along narrow streets to the lemon groves. We learned about farming lemons from two enthusiastic young farmers, we smelled the lemon zest, and they served us fresh lemonade. Then we all got an exciting tuk-tuk ride up and down the very narrow streets to the hilltop farm, where we tasted olive oils, had a cheese-making demonstration, and tasted all the phases of cheese. Then we tasted the limoncello! We really enjoyed the spectacular view. Last, but certainly not least, we enjoyed making our own pizza using tomato sauce that was prepared by grandma that morning using freshly picked tomatoes. We tossed our pizza dough and used fresh mozzarella. The wood-fired oven cooked the pizzas perfectly. We enjoyed eating every bite. When we were planning our trip, I asked for limoncello tasting, but this experience was so much more!
We also had a wonderful time in Pompeii and at the Vatican, Colosseum, and Forum in Rome. All the history is so fascinating. There were many tourists in Pompeii and Rome, and all of our guides were terrific, energetic, and skilled at navigating the crowds.
All of the private transfers, train travel, and hotels were perfect. Thank you for your help and expertise with planning this once-in-a-lifetime trip!
We hope to travel to Italy in the future and would love to work with this travel company again to help us plan that next trip.
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Zicasso’s travel company helped us plan and execute a vacation to the Amalfi Coast. The travel specialists suggested sites and arranged hotels, ground transport, and guides. It was all accomplished flawlessly; we had a perfectly paced itinerary.
Not only were the drivers well experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local colorhighly experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local color and conversation, and, above all, they conversation, and, above all, showed their love for the country and region.
We had several guides who were spot-on, including an archaeology graduate for Pompeii and Herculaneum, and an incredible historian on a walking tour of Naples.
The hotels were wonderful, with experience and professionalism throughout.
The drive along the coast to Amalfi and Ravello was spectacular!
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We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.
The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.
The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.
One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.
Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.
While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!
Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.
Every experience felt personal, meaningful, and special.
This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!
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When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.
Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.
Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.
A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.
Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.
When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.
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This was possibly the best trip of my life!
Once I arrived in Venice and put myself in the hands of Zicasso’s tour company, I was supremely well taken care of.
I left my passport on the plane, so I was held up in the airport for probably two hours. This was the first time I used the emergency number (or the chat app). The communication was answered immediately and we were able to let my first guide know I was being held up. I thought the first person who helped me was just someone to get me to the hotel, but she was also a guide in the sense that she described many of the things we saw on the way to the hotel. A very pleasant and gracious guide who made sure also that I was prepared for where to be the next day. It was a very great first experience of the tour company’s service.
Throughout this adventure, the guides were outstanding, the hotels were located practically on top of the interesting sites (especially in Rome) and very pleasant to be in.
Also, I continued to use the emergency number or the chat app multiple times. They were very responsive, very pleasant, and perfectly helpful each time. I don't know if I was high-maintenance compared to other clients the tour company has had, but though I felt like it in my mind, I was treated completely graciously each time.
I loved every destination and I loved having a structured tour, combined with a good portion of free time to explore on my own. Perfect.
I was very well guided on each travel day, being met by drivers to drop me off and to pick me up, and the train travel was very fun.
I think there was only one guide who I thought was just going through the motions, but all the other guides were the height of professionalism. I loved being met by our guides at Doge's Palace, which was absolutely outstanding. Walking around old Florence was great fun! The drive out to San Gimignano and Siena was well-planned and well-guided! In Rome, the guide who took us to the Colosseum and Palatine Hill was outstanding, and it was a great outing. (I had also already pretty much visited all the sights since my hotel was practically in the middle of it all.)
The trip to the Vatican was a whole other story. Unfortunately, I forget that guide's name. This guide was also excellent—entertaining, informative, approachable, and professional. The trip to the Amalfi Coast was a long train ride, followed by a very long car ride, but it was worth it. What a beautiful setting! My trip to Capri was absolutely fulfilling and I was a little sad to say goodbye to the guide—we connected with him so well. The next day was our boat tour from Sorrento to Amalfi and Positano. I absolutely enjoyed being guided by our guides! On the way back after that beautiful excursion, we were just cruising along the water, 1970s music playing, wind rushing by and I had a peak moment of happiness. Truly.
This trip was as if the tour company had read my mind and provided even more than I had imagined. I come away deeply grateful.
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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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