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Italy Tours & Vacations in September

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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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    Describe your dream tour.

  2. 2

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

  3. 3

    Book the trip when you are satisfied.

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Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Skyline and Bay in Naples, Italy.
Two-Week Highlights of Southern Italy Tour

14 Day Custom Tour

Dynamic pricing from $5,007

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

Your 8-day custom-tailored Italy tour of private cooking courses, wine, and olive oil tasting lets you explore illustrious flavors along your journey. The enticing aroma of fresh pasta emerges from a small restaurant in an antique building. Michelangelo’s David stares down at you from a stunning perch etched in brilliant marble and the Colosseum lights up the night with powerful arches. Wander a medieval town with a chef as your guide. finding tradition, culture, and heritage along the way. 

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City view and Arco della Pace at Piazza Sempione, Milan, Italy
The Great Escape to Tuscany Tour

8 Day Custom Tour

Dynamic pricing from $2,859

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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Skyline of Florence, Italy
Best of Italy and Sicily Tour

15 Day Custom Tour

Dynamic pricing from $5,365

Culture perpetually surrounds you, and the depths of history arise anew on your custom tailored  15-day 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 a breathtaking Italy vacation.

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The Faraglioni rock formations of Capri, Italy
Romantic Escape to Italy: Amalfi Coast, Rome, and Venice Tour

8 Day Custom Tour

Dynamic pricing from $2,859

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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Enjoy luxury living on the steep yet magnificent cliffs of the Cinque Terre, Italy
Private Northern Italy Vacation Package

15 Day Custom Tour

Dynamic pricing from $11,305

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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We Work With The Best Italy Travel Agents for September Tours

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More About Italy Vacations in September

Italy Travel Guide
Florence, Italy
Italy Travel Guide

From Roman ruins to the Tuscan countryside, there is something for every traveler in Italy.

Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized vacation.

For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

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Best Time to Visit Italy
Summer Tuscany scenery with red poppy flowers and grain fields surrounding cute Vitaleta chapel and Pienza on the hill in Italy
Best Time to Visit Italy

The best time to visit Italy is in the spring and early summer months, from March through June. During this time, the weather is great for the beaches, sightseeing, wine tasting, food tours, and more. Fall, particularly September and October, are also lovely times, when Italy is quieter and the fall colors are on show.

Your ideal experiences also affect the best time of the year to visit Italy for your vacation. Skiing in the Dolomites is exceptional in December, while enjoying the sun-washed beaches of Sicily is best in May. Rome is brilliant in April, while Florence is stunning in September.

From wine tasting to Roman-ruin exploration and coastal sightseeing, find the best time for your experience. As a family, couple, senior, or adventure traveler, we share ideas to help ...

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How to Plan a Trip to Italy: Frequently Asked Questions
Skyline highlighting the architecture of Rome, Italy
How to Plan a Trip to Italy: Frequently Asked Questions

As you plan your trip to Italy, consider our tips with the following answers to the most frequently asked questions.

From dreaming of the sunflower fields in Tuscany to searching the ruins of Rome for ancient treasures, you can book a vacation in Italy using our ideas as inspiration. Enjoy the pleasures of La Dolce Vita or alpine panoramas, lounging on golden beaches, or embracing rolling vineyards. It is all about finding the information you need to plan the right trip for you.

Whether you are designing a first-time Italian vacation as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

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7 Best Places to Visit in Italy
A farmhouse sitting in sunny fields in Tuscany.
7 Best Places to Visit in Italy

Italy practically overflows with must-see destinations, and deciding which to explore can be overwhelming.

The country inspires with ancient cultural riches and unique style, as well as enchanting natural beauty. With endless majesty stemming from the dramatic coastline, beautiful lakes, and rolling hills, it is no wonder we find inspiration throughout the country.

Here are the destinations you must see to discover the essential Italy and savor the simple pleasures offered by Italian life.

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Top 15 Things to Do in Italy
The Roman Forum in Rome, Italy
Top 15 Things to Do in Italy

From immersive tours of ancient Rome to the intricacies of artisanal crafts, Italian gastronomy to breathtaking national parks, the top 15 things to do in Italy let travelers unravel the country’s beauty and culture.

You can witness more Unesco World Heritage Sites than in any other country or sample the enticing flavors of celebrated Italian wines. Art, architecture, gastronomy, history, and heritage highlight the depth of Italy’s quintessential allure, with a range of experiences that stretch from the Dolomite Mountains in the north to the shores of Sicily’s Lido Mazzaro in the south.

Discover the top 15 things to do in Italy for a majestic and authentic experience that brings Italian culture and unique experiences to the forefront.

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18 Best Places to Travel in September
Taj Mahal, India
18 Best Places to Travel in September

September is a magnificent time of year to discover the world’s beauty and these 18 destinations demonstrate the diverse and exciting adventures you can experience for the perfect trip, depending on your travel preferences.

From welcoming Mediterranean culture to wildlife adventures across the African plains, the rugged Scandinavian expanse to legendary volcanic islands, September balances the distinctive climates and shifting seasons across the Southern and Northern hemispheres.

Whether looking for waterfalls or elephants, ancient ruins or alpine majesty, the following suggestions offer some of the best destinations you can visit, with trips personalized to your preferences.

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Reviews of Zicasso's Referral Service

4.89 stars based on 4395 reviews.

Italy Vacation Review: Venice, Florence, Rome, Tuscany,...
"Michela planned a fantastic adventure for our family."

Reviewed By Alvin Y.

Italy Travel Review: Venice, Florence, Rome, Tuscany, Vatican,...
"Darya planned an amazing trip for us in Venice, Florence,...

Reviewed By Elissa T.

Italy Trip Review: Florence, Venice, Rome, Vatican, Cooking...
"The trip to Italy was excellent and Doug at this travel...

Reviewed By Bradley C.

Central & Northern Italy Tour Review: Santa Margherita...
"All of the services [our travel planner] booked for us...

Reviewed By Erica S.

Italy Anniversary Trip Review: Sorrento, Capri, Rome, Tuscany,...
"The vacation went very smoothly and was full of pleasant...

Reviewed By kathleen v.

Italy Trip Review: Tuscan Countryside, Private Wine Tasting,...
"Our 12-day trip to Italy was amazing, in no small part...

Reviewed By Jill M.