
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.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $6,300
Two-Week Highlights of Southern Italy Tour

8 Day Trip IdeaFrom $7,800
Enticing Flavors of Italy Tour: Private Cooking Courses, Wine & Olive Oil Tasting

8 Day Trip IdeaFrom $3,600
The Great Escape to Tuscany Tour

15 Day Trip IdeaFrom $6,800
Best of Italy and Sicily Tour

8 Day Trip IdeaFrom $3,600
Romantic Escape to Italy: Amalfi Coast, Rome, and Venice Tour

15 Day Trip IdeaFrom $14,200
Private Northern Italy Vacation Package
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.
More Italy Tours by Travel Style
Reviews of Zicasso's Italy Tours & Vacations in September
Based on 712 verified traveler reviews.
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We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.
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Zicasso's tour company did a wonderful job of planning our dream honeymoon! Our travel agent took into consideration our wants and wishes, and created half- and full-day activities for us throughout the trip. We were able to visit four locations (Rome, Sorrento, Florence, and Venice) while in Italy. The trip was a perfect mix of relaxation and exploration. The tour company took away the stress of traveling and allowed us to enjoy the days without worries.
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We had the good fortune to be introduced to Zicasso's travel consultant in 2024. She planned for us a perfect trip through Amalfi and Sicily. We were so impressed with her professionalism, attention to detail, and communication that we did not hesitate to seek her out for Naples and Apulia in June 2025. Her guides (who were always special) and drivers are dedicated to her.
Last year, I recall saying you should stay away from Google, tell her your vision, and let her do the rest. She will present every option. We did want to fine-tune a few small preferences this time, but overall, I would give the same advice. We find her to be exceptional and have told her so.
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Zicasso’s tour operator planned the most amazing trip to Italy for us! My requirements were culture, romance, and relaxation. She delivered on every aspect. Although we missed our tour of the Vatican due to the Pope's funeral, my husband and I actually attended his funeral!! Our hotel, though planned many months before, was next to the basilica where Pope Francis was laid to rest. Talk about being a part of history!
We stayed in a beautiful converted villa to boutique hotel in Florence; got whisked away through the Tuscan countryside in a vintage Fiat 500; took cooking classes; sipped lovely wine, accompanied by excellent lunches on our winery tours; soaked in Italy's rich culture and museum scene; and even ticked the relaxation box by spending time by the pool, in the spa, and resting on our large deck overlooking the Amalfi coastline.
Every tour guide was extremely knowledgeable and personable, and it was evident they loved their jobs. Between memories of the boat ride along the Amalfi Coast, tips from the cooking classes I have already started using at home, and the cases of wine we are eagerly awaiting delivery of, my husband and I will forever hold Italy in our hearts and la dolce vita it provided us.
Talk with our tour operator; you will be glad you did!
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We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.
I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.
Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.
As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.
I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.
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