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Italy Tours & Vacations in September

Ratings of Zicasso's Service
<p>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.</p>

Embrace the plentiful charms of Italy as you explore legendary cities, tranquil...

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.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
Cathedral of Palermo in Italy

Two-Week Highlights of Southern Italy Tour

Places Visited: Naples, Pompeii +6 more
Places Visited: Naples, Pompeii, Sorrento, Amalfi, Positano +3 more

14 Day Custom Tour

From $6,300

Discover the endless charm of the Tuscan countryside near Florence in Italy

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

Places Visited: Rome, Trevi +3 more
Places Visited: Rome, Trevi, Tuscany, Florence, Umbria 

8 Day Custom Tour

From $7,800

City view and Arco della Pace at Piazza Sempione, Milan, Italy

The Great Escape to Tuscany Tour

Places Visited: Florence, Lucca +4 more
Places Visited: Florence, Lucca, Apuan Alps. Greve, Mutigliano, Bagni di Pisa +1 more

8 Day Custom Tour

From $3,600

Skyline of Florence, Italy

Best of Italy and Sicily Tour

Places Visited: Rome, Pisa +9 more
Places Visited: Rome, Pisa, Florence, Venice, Assisi +6 more

15 Day Custom Tour

From $6,800

The Faraglioni rock formations of Capri, Italy

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

Places Visited: Ravello, Rome +3 more
Places Visited: Ravello, Rome, Vatican City, Venice, Amalfi Coast 

8 Day Custom Tour

From $3,600

Manarola on the cliffs of the Cinque Terre in Italy

Private Northern Italy Vacation Package

Places Visited: Milan, Verenna +10 more
Places Visited: Milan, Verenna, Bellagio, Verona, the Dolomites +7 more

15 Day Custom Tour

From $14,200

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

We Work With the Best Italy Travel Agents for September Tours

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Reviews of Zicasso's Referral Service

4.9 stars based on 5841 reviews.

Italy Vacation Review: Venice, Florence, Rome, Tuscany,...

"Michela planned a fantastic adventure for our family."

Reviewed By Alvin Y.

Travel Review: Italy Tour, Florence, Venice, Tuscany, Rome,...

"I highly recommend this company..."

Reviewed By Diane F.

Italy Family Vacation Review: Venice, Verona, Florence,...

Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.

Reviewed By Carmina M.

Travel Review: Italy Tour, Rome, Milan, Venice, Florence,...

"Everything was effortless and we had zero stress."

Reviewed By Dave H.

Italy Luxury Tour Review: Amalfi Coast, Tuscany, Florence,...

"The Zicasso travel company did a wonderful job planning our trip. They were a pleasure to communicate with."

Reviewed By Alyson H.

Italy Vacation Review: Venice, Florence, Tuscan Hills, Pompeii,...

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.

Reviewed By Kristen B.