Italy Vacations in September

Ratings of Zicasso's Service

How Zicasso WorksCustom Italy Tours

  1. Describe your dream tour.

  2. We match you with up to 3 top travel specialists. They compete to plan your trip.

  3. Book the trip when you are satisfied.

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.

Sample Itineraries

Get inspired with our sample trips below. You can have any trip tailor made for your private travel. Any number of days.
Any departure date. Any experience you want.

Two-Week Highlights of Southern Italy Tour

Two-Week Highlights of Southern Italy Tour

14 Day Custom Tour

From $3,845

Southern Italy offers a genuine contrast to the icy elegance of the North as this is a land that has no time for the inauthentic. This luxurious, 14-day tour of the Bay of Naples, the Amalfi Coast, and Sicily’s capital is handcrafted to reveal what is unique about the South while offering all the sights, sounds, and flavors that have made Italy one of the most sought after destinations in Europe. From the heights of Mount Vesuvius to the depths of the Grotta Azzurra, this adventure will ensure that there is nothing to distract you from the rich heritage and cultural legacy that are waiting for you.  

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

Enticing Flavors of Italy Tour: Private Cooking Courses,...

8 Day Custom Tour

From $4,795

Your custom tailored Italy tour of private cooking courses, wine, and olive oil tasting takes you through the sites and flavors of Italy, exploring illustrious dishes every step of the way. The enticing aroma of fresh pasta emanates from a small restaurant in an antique building. Wander a medieval town with a chef as your guide, stepping into historic cheese and butcher shops to find the perfect ingredients to use for cooking. Michelangelo’s David stares down at you from a stunning perch etched in brilliant marble and eternalized in a gallant pose. The Colosseum lights up the night with powerful arches standing as a reminder of Rome’s continuous history.

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The Great Escape to Tuscany Tour

The Great Escape to Tuscany Tour

8 Day Custom Tour

From $2,195

This is a land of gentle rises and fecund meadows, where grapes grow fat in the summer sun and Italian nobles retire to enjoy the countryside. It’s a place of fine art and delectable food, cosmopolitan cities and entrancing towns, timeless history and endless culture. It’s a region of untrammeled natural beauty and unbounded imagination, the home to some of the great minds and great landscapes in the world. This is Tuscany, and there’s nowhere else quite like it.

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Best of Italy and Sicily Tour

Best of Italy and Sicily Tour

15 Day Custom Tour

From $4,120

Culture perpetually surrounds you, and the depths of history arise anew on your custom tailored Italy and Sicily tour. Gondolas float down the maze-like network of canals in Venice. The eclectic, historic cultures that once called Palermo home remain strong in the traditions of the marketplace. The summits of Mount Etna and Mount Vesuvius loom over cities both ancient and contemporary. Roman ruins and Doric temples, opulent beaches and Renaissance artwork combine for breathtaking vacation, showing you the unparalleled wonders of Italy expanding from north to south.

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

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

8 Day Custom Tour

From $2,195

Escape to your dream destination with the love of your life during your personalized Italy tour steeped in romance. Dramatic cliffs, sun-drenched beaches, hidden gardens, ancient ruins, and lavish palaces shape the enchanting ambiance of the Amalfi Coast, Rome, and Venice. Let the love of Romeo and Juliet inspire you in Verona, savor the sight of the ancient ruins of Rome at sunrise and gaze into each other’s eyes during a candlelit dinner after a private gondola ride. Whether enjoying azure waters or magnificent gardens, romance abounds on your romantic Italy tour. 

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Private Northern Italy Vacation Package

Private Northern Italy Vacation Package

15 Day Custom Tour

From $8,695

This is the Italy of Michelangelo and the Medici, the Italy of Dante and the Dolomites. It’s the Italy of hearty food and rich wines, unmatched art and incomparable style, the height of culture and the pinnacle of natural splendor. It’s the Italy of opulent duomos and luxurious villas, the canals of Venice and the cliffs of Cinque Terre. This private Northern Italy vacation package will show you areas unlike anywhere else on Earth.

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Reviews of Zicasso's Referral Service

4.88 stars based on 4471 reviews. See all our reviews.

Couple's European Vacation Review: England, France, Italy,...
"Our Itinerary included a myriad of daily activities that

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Reviewed By Bruce R.

Luxury Italy Travel Review: Sicily, Siracuse, Greek Temples...
"Getting things done, arranging the best, and satisfying

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Reviewed By Gerald H.

Italy Travel Review: Venice, Florence, Tuscany, Cinque Terre,...
"Our tour guides in each city were extremely knowledgeable,

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Reviewed By Ashley P.

Travel Review: Italy Vacation, Florence, Rome, Palermo,...
"Every detail was seen too."

Reviewed By Trudi W.

Italy Vacation Review: Sicily, Amalfi Coast Path of Gods...
"Our travel agent was fun to work with..."

Reviewed By Nancy W.

Italy Family Vacation Review, Trastevere Rome, Naples, Pompeii,...
"Our travel designer coordinated a tour guide with about

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Reviewed By Tim C.