14 Day Italy Itineraries & Vacation Packages

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.

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!

Overall, the trip was perfect! The hotels were really nice and the itinerary was great.

A few things I would have changed. First, the Amalfi tour day. There was not enough time in Ravello or Positano. We needed more time to relax and shop.

The class of train could have been nicer for the Florence-to-Rome portion of the trip.

We've been to many wineries throughout Europe and the one we went to on our way to Siena was okay, but we have been to much nicer wineries, with better wine and food tastings. It was not a great wine tour experience.

Everything else was wonderful and we really enjoyed the trip with our sons!!!

Thank you!

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!

Our trip to the Amalfi Coast, arranged by Zicasso's travel specialist, could not have been more perfect! All our travel ran so smoothly. It was so nice not to worry about arranging pick-up and transportation. We were even met right as we got off the plane in Rome! All the drivers and guides were excellent, sharing helpful tips that ensured we used our time wisely to see the most interesting sites.

The hotels were all wonderful, with perfect locations, beautiful and spacious rooms, and breathtaking views. Our food journey was inspiring, with lots of fish, buffalo mozzarella cheese, pasta, and even a wonderful cooking class at an organic farm for my birthday! A team member made sure all our restaurant reservations were secured and even tipped us off to a transit strike in Italy so we could arrive early at the airport.

The travel specialist's suggestion that we visit a winery on Mount Vesuvius and visit Pompeii was excellent, so fascinating! The travel specialist and her team also arranged boat rides for us in Capri and in Sorrento to Ischia, which were extra-special. Our Sorrento boat captain even brought a delicious chocolate cake to celebrate my birthday!

Thank you so much for arranging such a special birthday trip and for making our travel so effortless, a truly relaxing retreat!

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.