The Roman Forum in Rome, Italy
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Italy Tours & Vacations for First Timers

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Embrace the treasures of Italy to discover the culture and explore iconic monuments on the perfect itinerary for a first-time visitor. Explore medieval hilltop towns or lounge on celebrated Mediterranean beaches, visit the Vatican Museum after hours or learn how to steer a gondola in Venice. Use our sample itineraries to find and enjoy the experiences that matter to you before speaking with a travel specialist to plan your perfect trip.

How Zicasso Works In 3 Simple Steps

  1. 1

    Describe your dream Italy vacation.

  2. 2

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

  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.

Umbrian Hills in the Midday Sun, Italy
Italy Family Vacation for First Timers

9 Day Custom Tour

Dynamic pricing from $3,217

Immerse yourself in Italy with unique and interactive experiences at every turn. Travel through Italy’s heartland with stops in bustling, metropolitan cities and countryside estates before walking the cobblestone avenues of ancient gladiators, sailing down gentle waterways, and basking in the Tuscan sunshine. The architectural and artistic masterpieces, colorful frescoes, and gorgeous mosaics will give you something to take your breath away before you master the art of Italian cuisine and learn the techniques behind the perfect pizza, creamy gelato, and chocolate delights. Cathedrals, castles, museums, and monuments are waiting to be explored, and expert guidance in addition to customized experiences at each location make this luxurious, 9-day adventure through Italy the perfect family break.

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Gorgeous view of the Calabria, Italy coastline
Best of Southern Italy & Sicily Tour

14 Day Custom Tour

Dynamic pricing from $5,007

Capture the essence of history, culture, and cuisine during your customizable, 14-day highlights tour of Southern Italy and Sicily. Indulge in the alluring splendor of heritage featured in colorful towns around the Amalfi Coast and within the elegantly-preserved architecture of Palermo. From walking the excavated streets of Pompeii to strolling beneath luxurious, Baroque adornments in Lecce, your Southern Italy and Sicily tour embraces grandeur and immerses you in unrivaled beauty.

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Capri Island in the Bay of Naples, Italy
Amazing Italy Tour to Amalfi Coast, Capri, Positano and Rome

10 Day Custom Tour

Dynamic pricing from $3,695

Embark on this 10-day luxury tour of the Amalfi Coast, Capri, Positano, and Rome that combines modern comforts with historic Italian delights. A picturesque canvas of seaside towns inhabited with warm indigenous hospitality and vibrant beach culture, the Amalfi is Italy’s meridian of relaxation and beauty. Sip champagne and dine on seafood at one of the many gourmet restaurants along the crystal blue seashore and find yourself enjoying gelato at “The Terrace of Infinity” in Ravello, perched upon the jagged cliffs that overlook the Mediterranean. Travel back through ancient civilization and visit the marvels that define Rome, Capri, and the Amalfi Coast.

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Boat sailing on Tiber River with Saint Peter's Basilica in Rome, Italy

Embrace the wonderment of Rome, Florence and Venice as you enjoy the highlights of these iconic cities on this 10-day itinerary. From lavish gardens to the impressive museums, romantic cafes to private corridors, you have the key to the picturesque treasures of Italy.

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The Colosseum, the most recognizable symbol of Rome and the largest amphitheater of antiquity
Best of Italy for First Timers

7 Day Custom Tour

Dynamic pricing from $2,501

Soak up the essence of Italy during this once-in-a-lifetime trip. Discover hidden gems around every corner of Italy’s charming cities, stroll along cobblestone streets while taking in the smell of roasting espresso beans and freshly wood-fired pizza, and hear the sounds of church bells as they ring across the piazza. In Italy, you will explore ancient sites, bask in world-renowned artistic masterpieces, and taste local delicacies such as artisan olive oil and regional wines from the many vineyards that dot the rolling hills. Experience three very different and unique regions in Italy on this luxurious, 7-day excursion that will leave you with vivid and lasting memories.

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Fishing Village in Cinque Terre in Riomaggiore, Italy.
Culture and Coastal Treasures of Northern Italy

10 Day Custom Tour

Dynamic pricing from $3,575

Northwest Italy is yours to explore on this tailored tour that leads from the rich city of Turin to the spectacular coastline of the Cinque Terre and the magic metropolis of Milan. Every step of the way, you will treat yourself to the tantalizing flavors of Italian cuisine and witness the breathtaking unspoiled backdrops of Italy’s countryside while learning more about the local culture and heritage.

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Benefits of Using Zicasso

Plan Your Trip with
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We Work With the Best Italy Travel Agents for First Timer Tours

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More About Italy Tours for First Timers

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.

Read More    >
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 ...

Read More    >
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.

Read More    >
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.

Read More    >
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.

Read More    >

Reviews of Zicasso's Referral Service

4.89 stars based on 4397 reviews.

Italy Family Trip Review: Rome, The Vatican, Pompeii, Florence,...
"Carmen is absolutely a master at designing a trip which...

Reviewed By Michael F.

Travel Review: Italy Honeymoon Vacation, Rome, Sorrento,...
"The trip itself was amazing and incredibly smooth"

Reviewed By Jack C.

Italy Tour Review: Venice, Sienna, San Gimignano, Rome,...
"We were provided first-class treatment every day, our transfers,...

Reviewed By Tori S.

Italy Travel Agent Review: Tuscany, Amalfi Coast, Rome,...
"Alessandra was very nice and easy to work with"

Reviewed By Neha P.

Italy Family Vacation Review: Amalfi Coast, Sorrento, Capri,...
"Alessandro was extremely responsive and that was much appreciated."

Reviewed By Denise B.

Italy Family Trip Review: Rome, Sorrento, Capri, Pompeii,...
"Marcella went above and beyond to answer my many questions...

Reviewed By Francesca P.