Isola Bella in the middle of Lake Maggiore, Italy.
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Italy Vacation Ideas: 14 Amazing Italy Itinerary Packages

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<p>It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation Ideas is here to provide you with the inspiration you need to create a personalized experience tailored to your interests. From wine tasting in Tuscany to trekking in the Dolomites and swimming in the Mediterranean, a grand trip awaits. Explore the endless opportunities with the sample itineraries below.</p>

It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation...

It is hard to know where to start when planning a vacation. Zicasso’s Italy Vacation Ideas is here to provide you with the inspiration you need to create a personalized experience tailored to your interests. From wine tasting in Tuscany to trekking in the Dolomites and swimming in the Mediterranean, a grand trip awaits. Explore the endless opportunities with the sample itineraries below.

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    Book the trip when you are satisfied.

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Positano, Italy
Italy Family Vacation: Coastline, History, and Food

10 Day Custom Tour

Dynamic pricing from $3,575

Experience history and culture as it comes to life during your custom-tailored family tour through Italy that highlights the monuments, landmarks, and customs from the Amalfi Coast to Bologna, Rome, and Florence. Your immersive experience captures the splendor of Renaissance art and the brawn of ancient gladiators, offering a unique perspective of the past. Make delicious pizza as a family, scour for treasures in celebrated museums, and participate as classic cities become interactive galleries that display ancient ruins and magnificent architecture. Whether sampling delicious cheese or wandering through a hidden corridor, your family-friendly tour through Italy will reveal tradition and unforgettable adventure.

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Civita di Bagnoregio is one of the most unusual sights in Italy.
Immersive Italy Vacation: North to South

12 Day Custom Tour

Dynamic pricing from $4,291

Interweave luxury and culture, authenticity, and heritage during your custom-tailored Italy tour brimming with exclusive experiences. Wander the galleries of the Vatican with a guide before the doors open to the public, enjoy a simple pastry after witnessing the intricacies of Michelangelo’s David, explore the vast halls of the Uffizi Gallery after-hours and immerse yourself into the secrets of the Venetian Republic uncovering hidden histories akin to legend. Whether indulging in fashionable company in Milan or relaxing with a glass of delicious wine in Montalcino, your Italy vacation brings the best of La Dolce Vita’s many opulent pleasures.

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Medieval city of Matera in Southern Italy during a sunset
Exclusive Southern Italy Vacation: Sorrento, Matera, Ostuni

12 Day Custom Tour

Dynamic pricing from $9,355

Embrace the soul of Italy found in history, culture, and cuisine on your custom-tailored Italy that will take you away from the beaten path to explore rugged coastlines, pristine beaches, historical towns, and archeological treasures. Stretch your legs along the Amalfi Coast and expand your understanding of ancient heritage found along the peninsula dating back to the Greeks. Uncover brilliant Baroque architecture and charming fairytale homes, the splendor of Capri and the charm of contemporary caves. The distinctive spirit of Southern Italy takes you from the Tyrrhenian Sea to the Adriatic on an immersive scenic tour of villages, customs, and scenery.

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Mountain side village of Castelmezzano in the Potenza Province of Southern Italy
10 Days Off the Beaten Path Tour of Southern Italy and Sicily

10 Day Custom Tour

Dynamic pricing from $3,575

Experience scenic hikes, exhilarating ziplines, intriguing caves with this immersive 10-day vacation to southern Italy and Sicily. Unique experiences and private day trips are included in this amazing and unforgettable vacation. Zipline in Castelmezzano, climb Mt. Vesuvius to enjoy incredible views of Naples, and venture to the Blue Grotto.

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Aragon Castle on Ischia Island.
Gems of the Mediterranean Italy Vacation

9 Day Custom Tour

Dynamic pricing from $5,260

The Amalfi Coast awaits your exploration on this handcrafted and luxurious 9-day tour to Italy’s beloved Capri, Ischia, Ponza, and Ventonete islands. Those seeking to escape the crowds and bask in seaside intimacy will enjoy glamorous suites that overlook the sprawling Mediterranean Sea, enjoy therapeutic treatments at coveted wellness spas, and savor signature Mediterranean dishes served up at Michelin-starred restaurants. Book your elegantly curated experience today.

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Couple taking sunset gondola ride on the Grand Canal in Venice, Italy
Romantic Italy Getaway: Art, Food, Gondolas & More

7 Day Custom Tour

Dynamic pricing from $2,501

Italian masterpieces embody love and grace. Romance and spirit passed through the ages and experienced during your customizable, couple’s tour of Italy that celebrates storybook architecture and immerses you in the treasured culture. Sample incredible cuisine that captures the essence of passion, and cruise down candlelit canals. Delight in delicious wines that have been produced on scenic, coastal cliffs, and stroll along remarkable medieval fortifications. Whether discovering ancient foundations in Florence or sophisticated, Renaissance villas in Venice, you will enjoy the pleasures of Italy that can be found in the endless romance that is highlighted through Italy’s classic ambiance.

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Explore the ancient Roman city of Pompeii, near Naples
A Serene Senior’s Tour of Southern Italy and Sicily

7 Day Custom Tour

Dynamic pricing from $2,501

Discover the breathtaking towns, stunning landscapes, and the delicious cuisine of Southern Italy and Sicily during this amazing week-long vacation crafted especially for seniors. Exclusive experiences and private tours await at every destination as you uncover the history, culture, and ideal lifestyle of the area. Wander through the historic streets of Palermo, venture to the majestic island of Capri, and experience the fascinating city of Pompeii.

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Explore the streets of Renaissance Florence, Palazzo Vecchio.
Highlights of Italy Tour: Venice to Sorrento

13 Day Custom Tour

Dynamic pricing from $4,649

The endless variety of Italy is highlighted on this custom tailored tour along the country’s best sites, within marvelous cities and magnificent landscapes. Witness the intricate detail of Michelangelo’s David. Wander through the antiquity of Rome, where the sensational Colosseum continues to tower over the columns of the Forum. From the romantic canals of Venice to the astounding remains of Pompeii, you will wander along Italy at its best, immersing yourself in exceptional coastline and breathtaking cliff sides, and a different world of which many have only dreamed.

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Statues of saints on top of St. Peter's Basilica in Rome, Italy
10-Day Italy: Rome, Florence and Venice

10 Day Custom Tour

Dynamic pricing from $3,575

Inspiring art and mouthwatering cuisine offer a glimpse of the cultural majesty that you will experience during your custom-tailored 10-day Italy tour that immerses you in the splendor of bustling Rome, Florence, and Venice. Marvel at these breathtaking cityscapes while also indulging in the majesty of the Tuscan countryside. You will wander beneath the gilded mosaics of St. Mark’s Cathedral, sample the bold and layered flavors of the celebrated Brunello di Montalcino wine, and gaze up at the masterful ceiling of the Sistine Chapel. Throughout your once-in-a-lifetime journey, you will undoubtably discover the unparalleled treasures of Italy’s captivating highlights.

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Italy Tour for Food Lovers
Italy Tour for Food Lovers

12 Day Custom Tour

Dynamic pricing from $4,291

Your custom-tailored food tour of Italy provides insight into the importance and diversity of the gastronomy of the Italian peninsula, immersing you in the luxury of culinary excellence, authenticity of regional cuisine, and splendor of traditional culture. From the canals of Venice to the maritime cliffs of the Amalfi Coast and the charming hills of Tuscany to the dramatic walls of Rome’s Colosseum, you will travel between illustrious cities and across the enchanting countryside. You will also transform cuisine into artistic pleasures, which derive from a black truffle pasta that is coated with guanciale wine that also emits aromas of sweet tobacco and gelato, erupting with fresh strawberries.

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Frediano castle in Florence, Italy
Essence of Italy Tour: Cities, Ruins, Canals, History & Beauty

11 Day Custom Tour

Dynamic pricing from $3,933

The combined stories of history, art, and nature that spread throughout the country will show you the quintessence of Italy on this 11-day highlights tour.  Storied ruins, Renaissance masterworks, romantic canals, and whispered flavors will come to life beyond the cities of Rome, Florence, and Venice, where you can find the allure of architecture, landscapes, and ambiance creating the essence of Italy along the way.

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St. Francis of Assis Basilica in Umbria, Italy
Perfect Italy Vacation for Senior Travelers

17 Day Custom Tour

Dynamic pricing from $5,520

The sights of Italy abound with mystery and legend throughout the breathtaking odes to history. Begin with Da Vinci in Milan, and then explore Michelangelo in Florence and the Vatican, continue to Assisi, Venice, Pisa, and Siena.  See Signorelli’s frescoes, Brunelleschi’s Dome and Bernini’s baroque, the canals of Venice and Bellagio on Lake Como. All of these are just the start on this handcrafted sightseeing tour for seniors as you will delve beneath the surface with expert guides to living the history that is often felt far beyond what any words can explain.

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Grand Tour of Sicily's Extraordinary Highlights

16 Day Custom Tour

Dynamic pricing from $5,403

Uncover hidden gems, breathtaking beauty, stoic monuments, natural wonders, and delectable cuisine on a 16-day grand tour of Sicily. Just off the coast of southern Italy, Sicily is the largest Mediterranean island, steeped in history and tradition. Venture off the beaten path of Italy's mainland for an unforgettable discovery that blends the ancient world and contemporary life.

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11-Day Luxury Trip to Venice, Florence, and Rome for Families

11 Day Custom Tour

Dynamic pricing from $9,719

From gliding through Venice on gondolas to crossing the Ponte Vecchio in Florence and uncovering ancient ruins in Rome, this 11-day Italian adventure guides you through the classic sites of Italy’s three major cities.

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Get Your Dream Vacation In 3 Simple Steps

  1. 1

    Describe your dream trip.

  2. 2

    We match you with top travel specialists. They compete to plan your vacation.

  3. 3

    Book the trip when you are satisfied.

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