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

14 Day Custom Tour
Dynamic pricing from $5,007
Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.

14 Day Custom Tour
Dynamic pricing from $4,923
Classic beauty and indelible charm will radiate from ancient ruins, Renaissance artwork, and captivating coastlines during your custom-tailored 2-week tour of Italy. The iconic wonder of Italy will seduce you with panoramas of the rugged Amalfi Coast and the glamour of St. Mark’s interior shimmering with gilded mosaics. The Colosseum reflects remarkable achievement of ancient engineering and the Uffizi Gallery displays the triumphs of spirited expression. Wander along the cherished shores of Lake Como and travel into the past while strolling down the streets of Pompeii. Embrace Italy as an embodiment of culture with classic style and timeless charisma.

14 Day Custom Tour
Dynamic pricing from $5,007
Your 14-day Italy honeymoon is remarkable, filled with fine food and fun times, dictated by nothing but the slow circuit of the sun across a cloudless blue sky. It is notable for its uniqueness, taking you to the wonder of Rome and the marvels of Tuscany, the beauty of Florence and the luxuries of the Amalfi Coast for an experience that can only be done in inimitable Italy.

14 Day Custom Tour
Dynamic pricing from $4,545
Open your eyes to the expansive plains of Umbria and vast olive groves of Puglia, the seaside ambiance of Calabria and the flavors of Emilia-Romagna during your personalized Italy tour that will immerse you in the marvels of discovery. Savor the authentic beauty of medieval towns and Baroque cities preserved in time and steeped in tradition. Greek theaters decorate the landscape of Sicily and caves pockmark the soft tufa limestone of Basilicata. Travel from the Adriatic’s turquoise waters to the Tyrrhenian’s azure hues and the Ionian’s sapphire glow uncovering whitewashed homes, pastel-colored cathedrals, and an endless inviting ambiance.

14 Day Custom Tour
Dynamic pricing from $5,007
Bask in the authentic charm and the simple wonder of Italy during your custom-tailored tour taking you from Rome to Capri, Lake Maggiore to Assisi. Travel across breathtaking horizons to uncover hidden sagas while gaining cultural insight into more than 3,000 years of history. Engage with the stories of the Medici family and witness the fruits of Michelangelo’s celebrated hands. Wander through lavish galleries showing the wealth of the former aristocracy and sample the treasured flavors of the remarkable wines. Engage with the extraordinary local specialties, travel the historical castles, and bask in the majestic landscapes discovered from the Amalfi Coast to Italian Alps.

14 Day Custom Tour
Dynamic pricing from $5,007
The sensations of Italy come from traditions ingrained within the soil of the countryside and rising up through the towns and villages. On this 14-day tour through the north and south of the country you will find the most beautiful scenery displayed in Italy’s natural majesty. Climb through medieval villages and find the hidden waterfalls of Umbria, revel in the Tuscan hills and visit the marvelous art of the Renaissance. From natural magnificence to humanity’s endless striving for beatific perfection, you will find, wander, and wonder through it all.
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More About 14 Day Italy Itineraries
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.
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 ...
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.
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.
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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