Isola Bella in the middle of Lake Maggiore, Italy.
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Italy Vacation Ideas

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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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Tailor Made Itineraries

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

Trevi Fountain in Rome, Italy on a beautiful day with blue skies.

Italy Family Vacation: Coastline, History, and Food

10 Day Custom Tour

From $2,745

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

From $3,295

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

From $7,195

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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Nice view of Naples and Vesuvius

10 Days Off the Beaten Path Tour of Southern Italy and Sicily

10 Day Custom Tour

From $2,745

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

From $4,045

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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Admire the splendor of Lucca's walls and the charming central tower with a secluded garden.

Romantic Italy Getaway: Art, Food, Gondolas & More

7 Day Custom Tour

From $1,920

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

From $1,920

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

From $3,570

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

From $2,745

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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Freshly made Italian pizza

Italy Tour for Food Lovers

12 Day Custom Tour

From $3,295

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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Follow in the footsteps of the revered St. Francis of Assisi in his home town

Essence of Italy Tour: Cities, Ruins, Canals, History & Beauty

11 Day Custom Tour

From $3,020

The quintessence of Italy is the combined stories of history, art, and nature that spread throughout the country. On this 11-day custom tailored tour you will be shown Italy’s magnificent spirit through the storied ruins, the Renaissance masterworks, romantic canals, and whispered flavors. From celebrated artists such as Leonardo da Vinci to coveted museums including the Uffizi Gallery, you will be taken into and beyond the cities of Rome, Florence, and Venice finding the allure of architecture, ambiance, landscapes, creating the essence of Italy along the way.

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Siena in Tuscany, Italy

Perfect Italy Vacation for Senior Travelers

17 Day Custom Tour

From $4,245

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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Featured Articles

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 when the weather is ideal for outdoor activities, and the crowds disperse. September through early November are also excellent months for a visit.

Your travel goals, preferences, who you are traveling with, and what you would like to see and do will also affect the best time for your visit. You may wish to plan a skiing vacation on the powdery slopes of the Dolomites with your family or bask on a pristine Sicilian beach with your loved one.

Travelers can immerse themselves in the culinary culture, heritage, and gorgeous scenery year-round, with wine tasting, Roman ruin exploration, and coastal sightseeing always available for your vacation.

Read More    >
Top 15 Things to Do in Italy
Forum ruins in Rome, Italy.
Top 15 Things to Do in Italy

From immersive tours of ancient Rome to the intricacies of artisan crafts, gastronomy to national parks, Italy has an endless number of things to do.

You can witness more UNESCO World Heritage sites than any other country in the world or sample the enticing flavors of celebrated 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 essential things to do in Italy for a majestic, authentic, and unique experience.

Read More    >
10 Best Places to Visit in Italy with Family
Mother and daughter in Piazza San Marco, Venice
10 Best Places to Visit in Italy with Family

Italy is one of the most family-friendly destinations in the world and our 10 best family destinations can inspire how to experience your trip with children of any age.

Italy’s mixture of history and natural scenery, smoldering volcanoes, and preserved ancient ruins create an undeniably captivating ambiance. Whether you want immersive cooking classes or a scavenger hunt through a celebrated museum, wish to sample every flavor of gelato or enjoy physical training like an ancient gladiator, you can discover new and exciting experiences.

The following list offers inspiration for the best destinations in Italy that will allow your family to create life-lasting memories.

Read More    >
Top 10 Most Romantic Places in Italy
Positano at dusk
Top 10 Most Romantic Places in Italy

From castles to ancient ruins, seductive cuisine to lush countryside, glistening lakes to quiet vineyards, the following list offers our recommendations on the ten most romantic places in Italy for your next trip.

Italy is the personification of a romantic destination with elegant cities, secluded charms, scenic coastlines, and exquisite island getaways. Preserved tradition offers authentic beauty, and natural wonder provides the enchanting ambiance of a storybook.

From the elegant shores of Lake Como to the evergreen countryside of Pienza, explore the highlights and the off-the-beaten paths for intimate experiences all around.

Read More    >

Reviews of Zicasso's Referral Service

4.89 stars based on 4217 reviews.

Italy Vacation Review: Rome, Pompeii, Positano, Sorrento,...
"[Our travel agent] learned of our basic interests and took...

Reviewed By Bill T.

Travel Review: Italy, Venice, Florence, Pisa & Rome,...
"...the service was top notch."

Reviewed By Chris I.

Italy Family Trip Review: Matera, Capri, Pompeii, Sorrento,...
"We could not be happier with our experience"

Reviewed By Lilian P.

Italy Travel Agent Review: Luxury 10-Day Family Trip, Venice,...
"[Our travel planner] built us a fantastic itinerary that...

Reviewed By christine G.

Review: Family Tour of Italy, Florence, Venice, Food Tours,...
"Giulia stuck with us throughout [the pandemic] and was...

Reviewed By Karl K.

Travel Review: Italy Family Vacation, Sicily, Siracusa,...
"Daniela was a pleasure to work with as she helped us tailor...

Reviewed By Christopher S.