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Our 20 Best Italy Itineraries & Vacation Packages

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The cradle of European civilization, Italy is a region that has conquered imaginations since the Ancient Roman Empire and one that has prospered under the Roman Catholic Church. Birthplace of the Renaissance, home to the highest number of UNESCO World Heritage Sites in the world, and a haven for food lovers who treasure the freshest seasonal produce coupled with a fine wine, it comes as no surprise that Italy has many travelers returning for a second and even a third visit.

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Tailor Made Itineraries

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

Walk through the historic city of Bologna to see one of the oldest universities in Europe
First-Time Traveler’s Tour of Italy: Venice, Florence, Rome

10 Day Custom Tour

Dynamic pricing from $3,575

Balance the stories of the ancients with the inspiring art of the Renaissance as you take in the opulent masquerades and intricate delicacies during your personalized Italy itinerary that is perfect for the first-time traveler.  Listen to the echoes of gladiators in the subterranean labyrinth of the Colosseum, and then watch as the gilded frames glisten as they border the masterworks found inside the Vatican Museum. Wander the hidden corridor that connects Florentine palaces and learn how to hand roll delicate pasta to make tortellini. From exploring medieval towns of the Tuscan region to learning the art of glassblowing, whether you are a novice visitor or seasoned vacationer, you will discover something new and exciting around every beautiful corner.  As you refine your own Italy travel itinerary, consider browsing our many tours as you consider your own dreamy vacation.

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The coast of Sorrento in Italy
Italian Adventure to Rome, Amalfi Coast and Sicily

12 Day Custom Tour

Dynamic pricing from $9,199

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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Colosseum in Rome, Italy
Joys of Rome and Southern Italy Itinerary for Seniors

8 Day Custom Tour

Dynamic pricing from $2,595

Whether a lover of art and history, mythology or culture, you will find the majesty of it all as you tour Rome and the Amalfi Coast during your exclusive Italy itinerary for the senior traveler. The treasures of the Vatican span millennia with works displayed that are entangled with the past as the prestige of gladiatorial heroes emanates from the walls of the Colosseum.  The peak of Mount Vesuvius continues to linger above ancient Pompeii as lemon groves overtake the terraced ridges along the coast outside of Amalfi. Your customizable itinerary for seniors will embody the warmth of Italy and provide a masterful exploration of Rome and the Amalfi coast.

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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

Dynamic pricing from $16,375

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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Gondola ride on the Grand Canal in Venice, Italy
Splendors of Italy 17-Day Tour

17 Day Custom Tour

Dynamic pricing from $5,979

From gliding through Venetian canals to exploring the northern jewels of Lake Como and Milan, venturing along the coast of Cinque Terre to discovering the charms of Tuscany, this 17-day highlights tour of Italy showcases beauty and wonder. Uncover the true splendors of Italy when embarking on this trip as you discover the Lakes District and immerse yourself in the world of Ancient Rome.

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Walk through the terraced vineyards of the small town of Corniglia
Exploring Cinque Terre Itinerary: From Levanto to Santa Margherita

8 Day Custom Tour

Dynamic pricing from $2,859

Follow in the footsteps of shepherds and pilgrims, hikers and explorers on the trails surrounding Cinque Terre during your custom tailored Italy itinerary. The majestic turquoise water of the Mediterranean Sea splashes against the mixture of rugged terrain and sandy beaches. Vineyards, olive orchards, and citrus groves grow on precipitous terraces. Fishing boats wade in the natural harbors. Storybook castles and elegant churches decorate medieval towns. Indulge in the unique experience of the culture and landscape along the intimate trails of Italy’s famous five coastal towns.

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Medival Castello di Roccascalegna on a hill surrounded by fields and vineyards in Roccascalegna, Province of Chieti, Abruzzo
7-Day Italian Culinary, Wine, and Gelato Making Tour

7 Day Custom Tour

Dynamic pricing from $2,501

The regions of Italy have perfected their flavors, turning cooking into a cultural statement. Experience the celebration of Abruzzo cuisine in learning the traditional craft on your custom-tailored Italy culinary itinerary. The nutty aroma of olive oil encapsulates a family-owned olive mill. Wines offer bouquets of strawberry and raspberry. Dramatic castles adorn soaring cliffs and the velvety, light texture of gelato beckons you back for another bite. Fishermen cast their nets into the Adriatic. Medieval lanes lead to unforgettable panoramas. Lounge on the beach, learn to make pasta from start to finish and bask in the refined flavors of Italy.

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Vineyards in Montepulciano, Italy
Wine Connoisseur's Dream Tour of Tuscany

8 Day Custom Tour

Dynamic pricing from $2,859

Whether a lover of wine or a self-professed connoisseur, you will indulge in the variety of Tuscan vineyards with this personalized gourmet itinerary of Italy. Medieval towers crown the hilltops, cypress trees line the country roads, and vineyards blanket the verdant knolls. Sample the exceptional wines known as Super Tuscans or leisurely sip the excellent wines of Montepulciano. Savor the familiar flavors of a home-cooked Italian meal and wander the cobbled lanes of a charming, hidden medieval town. Your dreams of a gourmet wine, gastronomy, and art experience come to life in the grandeur of Tuscany with this one week Italy itinerary.

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Ancient town of Matera in Italy
Italy for Second Timers: Puglia and Amalfi Coast Itinerary

8 Day Custom Tour

Dynamic pricing from $2,859

Venture beyond the Colosseum in Rome and the Venetian canals when discovering the marvels between the Adriatic and Tyrrhenian Seas on this custom tailored Italy itinerary for returning travelers. Enjoy the unique baroque architecture in Lecce and the unforgettable troglodyte homes of Matera. Relish the magnificent views of Ravello that encompass the shores of the Amalfi Coast. Sample the flavors of the Puglia region with a private cooking class and delight in refreshing samples of wine and olive oil at a private vineyard. Find fairytale ambiance in Alberobello and handmade shoes in Positano for an unforgettable second helping of Italy.

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Municipal Library of Bologna in Italy

Venice invokes opulence, Rome conjures grace and grandeur, and Florence embodies artistic refinement during your Italy itinerary tailored to offer the finest of Italian luxuries. Lay your head in historical villas once used by nobles and which now contain contemporary comforts. Discover the secret history of the Venetian Republic from within the Doge’s Palace. Follow the Medici across the secret Vasari Corridor in Florence. Experience the opulent artistic tastes of successive Popes in the Vatican Museum. From palaces to ancient arenas, gondolas to glassblowing, you can indulge in exclusive luxury and polished style in Italy.

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Enjoy unique customs in the historic center of Rovinj, Croatia
Jewels of the Adriatic Sea: Croatia and Italy Tour

8 Day Custom Tour

Dynamic pricing from $2,467

The old world charm of Venice and the Istria Peninsula will sparkle like precious gems during your Italy itinerary along the shores of the Adriatic Sea.  Walk in the footsteps of the Roman Empire and in the wake of the Venetian Republic as you delight in a customizable experience of the photogenic woodlands and the crystal clear turquoise of the Adriatic. Ride a gondola along narrow canals and then stroll down the cobbled lanes of a medieval hilltop fortress. Sip wine from a family estate and then discover the enchanting gold mosaics of St. Mark’s Cathedral. Unveil the treasures of the Adriatic Sea found around Venice and Croatia with a week that will bring you to overflowing with delight. For more Italy itineraries, click here for inspiration as you perfect your own vacation along the Adriatic.

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Young girl enjoying a gelato in Rome, Italy
Kid-Friendly Family Tour of Italy's Highlights

10 Day Custom Tour

Dynamic pricing from $3,575

Become gladiators, search for priceless paintings, and indulge in unforgettable adventures with a custom tailored family-friendly Italy itinerary. Relish a chance to blend fun and education with culture that the kids can touch. Knead handmade pasta dough under the guidance of a private chef and then wander through hidden corridors and along the labyrinthine Hypogeum in the Colosseum. Explore extinct volcanic craters and learn the art of making fresh gelato in a medieval town. Your private family Italy tour itinerary will offer flavorful delights, ancient marvels, and secret catacombs to create memories that will last a lifetime.

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Flavors of the Vine & Countryside: Exploring Italy’s Slow Food Movement Tour

10 Day Custom Tour

Dynamic pricing from $3,575

Italy is made for indulgence. Your customizable Italy itinerary will treat you to the culture and cuisine of the north and allow you to experience geography’s influence on history.  Your journey will bring enticing food, wine, and art as you explore Piedmont, Emilia-Romagna, and Tuscany. Scour the woodlands in search of white truffle, and then bask in the beauty of the rolling hills while sampling a Brunello di Montalcino. Stroll through vibrant aisles in a local market and taste the decadent pasta made by your own hands. From rich chocolate to vibrant espresso, enchanting villas to medieval walls, your itinerary in Italy will satisfy your gastronomical and cultural desires.

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Roman Villas and Renaissance Garden Tour of Italy

9 Day Custom Tour

Dynamic pricing from $3,217

Italian villas embody grace and history with gardens that emote beauty, elegance, and tranquility. Your custom tailored Italy itinerary will lend insight into the rebirth of garden splendor and the pure enchantment of traditional estates in and around Rome and Florence. Stroll through orange groves and private greenhouses that grow exotic plants and then explore cypress-lined country roads and opulent homes that are adorned with dramatic terraces. Linger in the scent of hyacinth and discover Roman statues as they reflect in ancient ponds. From delicate fountains to hidden grottoes, renowned parks to classic palaces, you will revel in the artistry and serenity of Italy’s villas and gardens.

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Art, Culture & History of Italy Itinerary

10 Day Custom Tour

Dynamic pricing from $3,575

The Renaissance brought talent and taste, the love of art and architecture, cuisine and history. Your personalized Italy itinerary will bring the perfect balance of knowledge and activity, flavor and discovery for the aspiring modern polymath. Bask in the pristine beauty of Michelangelo’s David and traverse the galleries of the Vatican to reach the Sistine Chapel, and then indulge in the layered flavors of rustic Tuscan cuisine before trying your hand at crafting the perfect gelato. From the natural colors of the Blue Grotto to the gilded frescoes of St. Mark’s Basilica, you can have it all in Italy.

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Secluded Honeymoon in Lake Como and Portofino Itinerary

8 Day Custom Tour

Dynamic pricing from $2,859

Italy is the destination for a perfect honeymoon that combines enchanting history with the endless luxuries of the Italian Alps and Mediterranean Sea. Pastel colors drape over tower homes as elegant vineyards blanket the mountain terraces. Graceful villas clad with trompe l’oeil paintings overlook lakeshores and coastline. Sample the sweet flavor of Swiss chocolate and the succulent tastes of fresh Ligurian cuisine, and then wander hand-in-hand along the captivating esplanades and stunning boutique shops. Wander lavish olive groves and savor the secluded panoramic vistas during your unforgettable time together that will take you from Lake Como to Portofino during your custom tailored Italy itinerary.

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Exploring the Rustic Charm of Puglia Itinerary: Mozzarella to Fairytale Homes

7 Day Custom Tour

Dynamic pricing from $2,501

The charms of the Puglia countryside are rustic and welcoming with locals eager to bring you into their homes, onto their farms, and through the rows and rows of vines of their wineries. Cities radiate with Baroque architecture set against the backdrop of rolling hills and the sapphire waters of the Adriatic Sea. Your 7-day Italy itinerary will offer a perfect week and in-depth exploration of Puglia, from sampling the celebrated cuisine to traversing the fairytale homes known as trulli. Bask in the golden sands of the shoreline and indulge in the culture of the often-overlooked region.

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Cruising Through Italy in a Ferrari Itinerary

8 Day Custom Tour

Dynamic pricing from $6,235

Your customizable 8-day Italy itinerary will take you from Rome to Milan on a self-driving tour and allow you to experience the true beauty of Italian design from the art inside the Accademia Gallery to the cobbled lanes of medieval Siena. Discover Renaissance architecture in Pienza and the gilded coffered ceilings of the Map Room at the Vatican Museum. Treasure the remarkable countryside, bask in the prestige of a personal shopper in Milan, and indulge in the unique opportunity of driving a Ferrari through Italy.

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Essence of Italy: Private Vacation Package to Rome, Florence & Venice

8 Day Custom Tour

Dynamic pricing from $6,235

There is nowhere on Earth that can boast the art of beautiful, bountiful Florence. There’s no city around that can claim the bountiful past that fills all the corners of Rome. There’s no other place where romance and magic are quite so present as in Venice. And there’s no other trip that can take you to Italy and make it feel so much like home.

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Italy Tour of the Most Beautiful Towns & Villages

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 Italy Itineraries & Vacations

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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. 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 ...

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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.

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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.

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7 Best Places to Visit in Italy
A farmhouse sitting in sunny fields in Tuscany.
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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.

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