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Italy Tours & Vacations in September

Embrace the plentiful charms of Italy as you explore legendary cities, tranquil countrysides, and indulge in tantalizing cuisine. September is one of the best times to visit Italy because of pleasant weather, smaller crowds, and local experiences. When you design your September tour with Zicasso your trip will be created alongside the best Italian experts.

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Let these itineraries inspire your personalized travel experience

Cathedral of Palermo in Italy

14 Day Trip IdeaFrom $6,300

Two-Week Highlights of Southern Italy Tour

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more
Discover the endless charm of the Tuscan countryside near Florence in Italy

8 Day Trip IdeaFrom $7,800

Enticing Flavors of Italy Tour: Private Cooking Courses, Wine & Olive Oil Tasting

Rome, Trevi, Tuscany, Florence, Umbria
City view and Arco della Pace at Piazza Sempione, Milan, Italy

8 Day Trip IdeaFrom $3,600

The Great Escape to Tuscany Tour

Florence, Lucca, Apuan Alps. Greve, Mutigliano, Bagni di Pisa +1 more
Skyline of Florence, Italy

15 Day Trip IdeaFrom $6,800

Best of Italy and Sicily Tour

Rome, Pisa, Florence, Venice, Assisi +6 more
The Faraglioni rock formations of Capri, Italy

8 Day Trip IdeaFrom $3,600

Romantic Escape to Italy: Amalfi Coast, Rome, and Venice Tour

Ravello, Rome, Vatican City, Venice, Amalfi Coast
Manarola on the cliffs of the Cinque Terre in Italy

15 Day Trip IdeaFrom $14,200

Private Northern Italy Vacation Package

Milan, Verenna, Bellagio, Verona, the Dolomites +7 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 Italy Tours & Vacations in September

Based on 1068 verified traveler reviews.

Italy Trip Review: Sorrento, Positano, Amalfi, Ravello, Pompeii, Herculaneum, Naples, 5 Days

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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Italy Tour Review: Venice, Florence, San Gimignano, Siena, Rome, Vatican, Amalfi Coast, Capri, Sorrento, Positano, Doge's Palace, Colosseum, Palatine Hill, Boat Ride, 12 Days

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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Italy Trip Review: Venice, Amalfi, Capri, Sorrento, Pompeii, Rome, Colosseum, Roman Forum, 12 Days

Italy was fantastic! We visited Venice, Amalfi, Capri, Sorrento, Pompeii, and Rome.

Zicasso’s travel specialist was knowledgeable and patient with me when planning the trip. She was amazing at taking in the information I shared about my family and creating an itinerary that worked well for our family of five (our three children, ages 20, 20, and 22), including food-allergy limitations.

The chosen tours and tour guides were incredible, knowledgeable, engaging, attentive, thoughtful, and a pleasure with which to spend the day or half-day.

When we were in Italy, our travel specialists quickly responded to inquiries and to new requests for transportation needs resulting from unanticipated and good “extra” opportunities.

I highly recommend the travel company and our travel specialists.

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Italy Trip Review: Naples, Capri, Pompeii, Amalfi Coast, Ischia, Cooking Class, Boat Tour, 12-Day Tour

On the whole, we enjoyed our trip. However, we want to make note of a few things that could have been done better. When we landed in Naples, our driver was waiting for us. But instead of bringing the car to where we were, the 4 senior adults had to walk with luggage in the heat to get to his car. On our first full day in Naples, we were picked up for our cooking class. The driver did not speak any English, and when we arrived at the address, he expected us to get out of the car. We did not know where to go, and he was not able to assist us. Lucky for us, we met a nice lady who spoke English and was able to help us. The cooking class was wonderful. One of the highlights of the trip. The Capri boat tour was enjoyable. The tour of Pompeii was fascinating. The day we were taken to the Amalfi Coast was a holiday, and we mostly sat in traffic. Not anyone's fault but not very pleasant. On June 3 we were picked up very early to go to the port for the Hydrofoil to Ischia. At the port, we had to wait around for almost 2 hours. We were not sure why we were picked up so early. On June 6 we checked into our hotel in Naples, looking forward to our Jewish Heritage tour the following day. Our tour guide was lovely - 4 stars for her - but we learned there is no Jewish heritage in Naples, so that was quite disappointing. It would have been nice to establish realistic expectations.

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Italy Tour Review: Amalfi Coast, Ravello, Positano, Florence, Rome, Siena, Winery Visit, 11 Nights

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!

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Italy Vacation Review: Sorrento, Rome, Capri, Amalfi Coast, Positano, Ravello, Schiazzano, Pompeii, Vatican, Colosseum, Forum, Boat Ride, Limoncello Tasting, Pizza Making, 1 Week

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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