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Luxury Italy Tours & Vacations

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Italy is a beacon, beckoning to those in search of an immersive cultural experience. Be provided with the most exclusive access, from Milan’s fashion week to private dining experiences hosted by top-tier chefs. Elevate the quintessential Italian vacation to an entirely different level with Zicasso’s luxury Italy tours, where your travel dreams will be made a reality.

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Tailor Made Itineraries

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

Val d'Orcia in Tuscany, Italy

Best of Luxury Italy for 2022-2023

12 Day Custom Tour

From $7,195

Your 12-day luxury Italy highlights tour immerses you in elegant art, pristine nature, and the legendary dolce vita. You will celebrate history and heritage with exclusive tours that take you away from crowds from the Vatican Museum to Tuscany’s hilltop towns. From islands in the Venetian Lagoon to the Amalfi Coast’s panoramas, you will find flavor, glamour, and a zest for life during your Italy tour specifically designed for you.

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Vineyards in Langhe region of Piedmont, Italy

Luxury Italy Wine Tour of the Top Regions

9 Day Custom Tour

From $5,395

Embrace the marvels of Italian flavor and the splendor of Italy's scenery during this 9-day luxury Italy wine tour. You will have an immersive experience of the wine culture and Italy's fabulous history of wine consumption, which will reveal sumptuous vines, elegant tastings, and exclusive excursions. From regal estates to stately panoramas, you will wander through antique cellars, stroll through medieval towns, and sample the spirit of Italy through its illustrious wines.

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The coast of Sorrento in Italy

Italian Adventure to Rome, Amalfi Coast and Sicily

12 Day Custom Tour

From $7,075

The wonders of Rome, the coastal Campania region, and Sicily come alive on this 11-day tour of Italy's southern half. From the Italian capital to the bustling port city of Palermo, enjoy a balanced itinerary that combines guided excursions, food tours, and ample free time to bask in all that is best of the regions you visit.

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La Morra surrounded by vineyards

Italy Honeymoon Indulgence: Romance, Food, and Wine

10 Day Custom Tour

From $5,895

From the bustling historic neighborhoods of Bologna to the illustrious Piedmont farmlands surrounding La Morra, explore and adore boundless beauty as you breeze through the countryside on your 10-day Italy tour. Farm-to-table lunches paired with award-winning Italian wines, Ferrari test drives through ancient streets, and evenings exploring the local culture of medieval communes all feature on this luxurious honeymoon vacation to Bologna, Florence, and La Morra in Italy.

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Saint Peter Basilica in Rome at Christmas

Christmas in Italy: 14-Day Luxury Celebration

14 Day Custom Tour

From $8,115

With atmospheric light, enticing aromas, and a festive ambiance, you can bask in captivating traditions and alluring charm during your 14-day luxury Italy Christmas tour. Sample delicious pastries, witness the Colosseum, and stroll down a medieval alley that leads to historical shops. From Mass at the Vatican to learning how to make seasonal dishes, viewing the David to exploring Christmas Markets, Italy immerses you in the true joys of the holiday season.

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Luxury Italy Family Vacation

16 Day Custom Tour

From $9,595

From the pleasures of high culture to the joys of adventure, this is an Italian excursion that offers something for all ages. Taste buds will revel in the joys of Bologna, eyes will feast upon the immaculate detail of the Sistine Chapel, and your skin will glory in the soft sun and gentle breeze on the shores of the Med. Be you father or daughter, brother or mother, sister or husband or wife, there is something in Italy just for you.

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Sforza Castle Castello Sforzesco is one of the symbols of Milan, Italy

High-End Northern Italy Tour: Venice, Lake Garda, Milan

11 Day Custom Tour

From $6,045

North Italy captivates visitors with its lush countryside and elegant cities, and this 11-day tour of Venice, Lake Garda, and Milan will offer you a splendid balance of natural beauty as well as the thrills and culture of big-city life. From active walking tours of the many renowned cities and towns you visit to the sublime surrender of a leisurely day, this tour ensures an unforgettable Italian visit.

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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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Inlet and beaches in the Maddalena archipelago in Sardinia, Italy

Fully Immersive Tour of Italy: Highlights and Hidden Gems

21 Day Custom Tour

From $12,595

The perfect balance of leisure and adventure is available on this 21-day tour of Italy. With destinations, such as Venice and Bologna, you will get a sound introduction to Italy's urban charm that can then be compared to the rustic countryside of Tuscany and the Costa Smeralda. No matter your preference, by the tour's end, you will be well acquainted with the culture and history of this unique Mediterranean world.

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Runway model in a red dress at a fashion show. Credit: Ahmad Ardity

Italy in Vogue: Exclusive Access to Milan Fashion Week & Italian Style

10 Day Custom Tour

From $9,895

Blend high fashion and exclusivity on this 10-day Italy tour that includes insider access to Milan Fashion Week. Showcasing some of the most iconic works of Italian fashion houses specializing in everything from haute couture to fine jewelry, this tour explores the fashion realms of Armani, Fendi, Ferragamo, Prada and the famed jeweler Bulgari in Milan, Florence, Tuscany, and Rome. Go behind the scenes of the world of Italian fashion and style, and get unparalleled access to world-renowned luxury couturiers and their private collections on this exclusive Zicasso experience.

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Photo courtesy of Museo Lamborghini

Prestige & Passion of Italy Tour: The Italian Racing Tradition

10 Day Custom Tour

From $5,995

Journey through Italy's Motor Valley on this 10-day luxury tour celebrating the region of Emilia-Romagna. High performance and craftsmanship blend as engineers turn into artisans as you visit the home of the world’s most revered motor brands: Maserati, Ducati, Ferrari, Lamborghini, and Pagani while enjoying the traditional food, wine, and culture that overflows in Italy.

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The dome ceiling inside Santa Maria del Fiore in Florence, Italy.

Italy: The Gold Standard Tour

10 Day Custom Tour

From $5,995

Succumb to the beauty and savor the wealth of culture on your 10-day Italy tour. This Italian journey sets the gold standard. From gilded palaces and gold-plated art to the golden rolling hills of Tuscany, this trip offers some of the most authentic and luxurious experiences Italy has to offer. It's a treasure hunt for the finest Italian travel experiences, especially in food, wine, art, and natural beauty.

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Pontine Islands, Ischia and South of Naples Sailing Tour

8 Day Custom Tour

From$4,795

Spectacular vistas and attentive service will be your constant companions on this 7-night cruise through the coastal paradise of Italy's Pontino and Phlegraean islands. From Ponza to Capri, hop your way between islands that engage with local culture and enjoy the delights of authentic cuisine. By the time the sun sets on your tour, you will have memories that are missed by many that never leave the mainland.

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Perfect 9-Day Puglia Exploration

9 Day Custom Tour

From$3,145

Situated in Southern Italy, Puglia remains well off the beaten path for visitors to this famous peninsula, and this 9-day tour of Puglia aims to capitalize on this by leading you to all the main attractions as well as ensuring an exclusive feel throughout its entirety. From Savelletri to Lecce, this rural region of Italy will come to life through visits to olive groves, picturesque beaches, and charming city centers.

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Unexplored Northern Italy Tour: A Different Side of Italy

8 Day Custom Tour

From$4,795

Far from the bustling crowds of Rome and Florence, this 7-day tour of Northeast Italy will provide travelers with a refreshing introduction with the rural beauty and cultural brilliance that attracted visitors to Italy for centuries. From the elegant stateliness of Udine to the brisk boardwalks of coastal Trieste, you will have a chance to see a side of Italy missed by many, while enjoying all the comforts of modern resorts and accommodations.

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Honeymoon Highlights: Rome, Florence, Venice Tour

12 Day Custom Tour

From$3,295

Little is left to the imagination on this 12-day tour of Italy that is handcrafted to bring you as close to the country as possible. As you make your way through Rome, Florence, Venice, as well as the regions of Lazio, Tuscany, and Veneto, you will enjoy a unique balance of rural leisure and urban thrills. This tour is designed to maximize your enjoyment of this colorful corner of the Mediterranean world.

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Heart of Italian Cuisine: 10-Day Gastronomy and Culture Tour

10 Day Custom Tour

From$2,815

This 10-day journey through Italy presents a feast for the senses as you encounter new sights, flavors, and smells in this rich landscape. Your tour of the Italian culinary legacy will begin in Palermo and then to Rome, both revealing Italy’s diverse character in the open-air markets, kitchens, and regional ingredients. Finally, the rolling hills of Tuscany will beckon to you as you bask in the vibrant neighborhoods and charming countryside of Florence.

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Food-Lover's Tour of Tuscany and Umbria

9 Day Custom Tour

From$2,470

Along with the rich culture and abundant historical sites, this 9-day tour of central Italy is designed to showcase the gastronomic greatness of the places you visit. From Umbria to Tuscany, the beating heart of Italian olive oil and wine production will be yours to enjoy along with the many other culinary delights. By the time you depart, you will have a better understanding of Italy's love affair with food.

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Best Of Luxury Emilia Romagna in Two Weeks

12 Day Custom Tour

From$3,175

Mouthwatering food and wine, remarkable history, and natural beauty immerse you in luxury on this 12-day best of Emilia Romagna tour. Tour through scenic country streets in a pristine Ferrari. Sample the culinary prowess of notable chefs in Italy’s most notable food region. Explore the surreal ideas of a master filmmaker. From medieval arcades to stunning gardens, gilded mosaics to Michelin-starred restaurants, you can embrace endless grandeur and timeless style as you discover it all.

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Luxury Italy Vacation: Rome, Florence & Venice in a Week

8 Day Custom Tour

From$4,555

Together, these three cities are calling you to join them, and there are an infinite number of reasons to answer with this 8-day tour. Rome is beckoning, singing to you the triumphs of her past and the incomparable splendor of her present. Florence is begging, enticing you with her world-class art scene and spectacular shopping. Venice is waiting, promising the treasures of a city that is truly unlike anywhere else on Earth.

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Enticing Flavors of Italy Tour: Private Cooking Courses, Wine & Olive Oil Tasting

8 Day Custom Tour

From$4,795

Your custom tailored Italy tour of private cooking courses, wine, and olive oil tasting takes you through the sites and flavors of Italy, exploring illustrious dishes every step of the way. The enticing aroma of fresh pasta emanates from a small restaurant in an antique building. Wander a medieval town with a chef as your guide, stepping into historic cheese and butcher shops to find the perfect ingredients to use for cooking. Michelangelo’s David stares down at you from a stunning perch etched in brilliant marble and eternalized in a gallant pose. The Colosseum lights up the night with powerful arches standing as a reminder of Rome’s continuous history.

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VIP Tour of Sicily: Beauty, Culinary & Luxury Experience

11 Day Custom Tour

From$6,595

Treat yourself to the luxury and romance of Sicily, from the crystal clear azure sea to the inspiring ancient ruins scattered across the hillside; the splendors of the island await. Baroque palaces decorate historic cities. Private vineyards overtake the hillside of a secluded island getaway. Cobblestone streets lead to remote vistas with immaculate views of the countryside. You can indulge in the pure essences of the cuisine and bask in the alluring flavors of celebrated vineyards on your custom tailored luxury Sicily tour.

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Royal Italian Vacation: Luxuries of the Italian Riviera and Amalfi Coast

8 Day Custom Tour

From$4,795

Kings and queens, emperors and aristocracy once roamed the cobblestone-framed loggias and marbled hallways of preserved villas and opulent palaces across Italy. Follow in the footsteps of Bourbon royalty and witness the lavish collections of nobility in the Genoese Republic. Bask in the sunlight on private boats for views of the coastline and delight in the culture of secluded towns carved into the sloping maritime mountains. Your custom tailored tour immerses you in the luxuries of the faded aristocracy, indulging in the grandeurs of castles and the antique rooms of remarkable palaces overlooking Italy’s shimmering shoreline along the Mediterranean Sea.

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Paradise Tour of Italy: Sicily and Puglia Vacation

19 Day Custom Tour

From$11,395

Welcoming temperatures, coastal communities, and picturesque beaches appear in abundance on this 19-day tour of Sicily and Puglia. Lacking the icy elegance of Italy's Northern region, Southern Italy has long attracted those in search of rich culture and compelling history. From the bustling port of Palermo to the mysterious origins of the Trulli in Puglia, this tour ensures your full immersion into the warmth and vitality of Southern Italy.

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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.

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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 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.

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Reviews of Zicasso's Referral Service

4.89 stars based on 4520 reviews.

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

Reviewed By Alvin Y.

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

Reviewed By kathleen v.

Italy Family Trip Review: Tuscany, Emilia-Romagna, Truffle...
"[Our travel agent] listened to what we were looking for...

Reviewed By Luisa D.

Italy Trip Review: Venice, Como, Tuscany, Florence, Rome,...
"Cameron’s attention to details and knowledge of unique...

Reviewed By Madison S.

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.