Florence, Italy
country flag

Italy Trip Planner

Ratings of Zicasso's Service

Whether you are searching for the most delicious fare, the finest art, or the grandest cities, Italy is full of experiences that will revitalize your senses. Zicasso’s Italian Trip Planner possesses a wide variety of authentic, Italian experiences, and our custom itineraries cultivate the opportunity for travelers of all ages and interests to find an Italian experience that is best suited for them. Inspiration starts here.

How Zicasso Works In 3 Simple Steps

  1. 1

    Describe your dream trip to Italy.

  2. 2

    We match you with top Italy trip planners to plan your vacation.

  3. 3

    Book the trip when you are ready.

Ratings of Zicasso's Service

Tailor Made Itineraries

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

View of Capri Island from Mount Solaro in Italy

Iconic Italy: Fast-Paced Exploration from Venice to Sicily

14 Day Custom Tour

From $3,845

Discover Italy's diverse history, pristine nature, and contemporary culture on this 14-day journey. From hiking Mount Etna to zooming around Rome on a Segway, witness this magnificent country from many different vantage points. Be immersed in Italy's renowned cuisine, discover the wines of Chianti and Sicily, and attend a cooking class in Florence.

View Custom Itinerary
Val d'Orcia in Tuscany, Italy

Best of Italy Vacation in 12 Days

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.

View Custom Itinerary
Gran Sasso e Monti della Laga National Park, Italy

Soulful Italy: Umbria, The Marches, and Abruzzo Tour

8 Day Custom Tour

From $2,195

Discover central Italy's hidden gems on this 8-day tour. Often overshadowed by Lazio and Tuscany, the regions of Abruzzo, Marche, and Umbria are stars in their own right. From the natural beauty of Gran Sasso National Park to small squares of towns like Ascoli Piceno, there is much to seek and enjoy on this journey. Book your memorable tour today.

View Custom Itinerary
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.

View Custom Itinerary
Gondola on a sunny street in Venice, Italy

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.

View Custom Itinerary
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.

View Custom Itinerary

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.
The ruins of Pompeii in Italy.

Family Trip to Italy: Nature, Ancient Temples, and Cuisine

12 Day Custom Tour

From $3,295

Bask in the splendor of La Dolce Vita from the Amalfi Coast to ancient Sicilian temples during your 12-day family Italy tour. Stroll cobbled lanes where ancient Rome presses against medieval walls. Wander the lush volcanic base of Mount Etna where grapevines thrive. Uncover ancient Greek theaters and recently excavated Roman mosaics. Your family-friendly tour reveals artistic splendor and as you celebrate the simple pleasures for which Italy is known.

View Custom Itinerary
Sun rising over Roman ruins in Italy

Hidden Beauty Tour of Rome, Venice, and Florence

9 Day Custom Tour

From $2,785

An exploration of the hidden gems of these iconic cities, this 9-day sample tour of Rome, Florence, and Venice presents travelers with a unique cocktail of national pride and regional charm. As you make your way from the bustle of landlocked Rome to the sunny facades of Venice, enjoy luxurious encounters with what is best of each city and form your own memories in cities that have inspired generations.

View Custom Itinerary
Rolling hills in the Tuscan countryside

One Week in the Tuscan Countryside Tour

7 Day Custom Tour

From $1,920

Italy’s countryside is teeming with hilltop towns that are speckled across the breathtaking region of Tuscany, which you will explore on this handcrafted 7-day tour. Under the Tuscan Sun, you will appreciate the endless beauty of the emerald hills that roll from Montepulciano in addition to admiring the ancient architecture of the cultural heritage sites in San Gimignano. From town to town, you can find beauty in every charming destination against the beautiful countryside backdrop.

View Custom Itinerary
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.

View Custom Itinerary
Colosseum in Rome, Italy

Joys of Rome and Southern Italy Itinerary for Seniors

8 Day Custom Tour

From $1,995

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.

View Custom Itinerary
Cheese wheels parmesan, cheese dairies Tuscany, Italy

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

10 Day Custom Tour

From $2,745

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.

View Custom Itinerary
Secluded Honeymoon in Lake Como and Portofino Itinerary

8 Day Custom Tour


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.

  Read More

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

7 Day Custom Tour


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.

  Read More

Exclusive Sicily Tour of Ancient and Contemporary Charm

11 Day Custom Tour


Experience the essential culture and remarkable history of Italy during this 11-day Sicily tour. This adventure immerses you in the hidden splendor of the island’s western edge. Indulge in secret splendor by sampling the customary flavors of diverse cuisine and basking in the elegant magnitude of glistening mosaics. Sample celebrated wines, witness preserved ancient architecture, and dig your toes into the golden sands of the Mediterranean coastline during this magnificent Sicily tour.

  Read More

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

8 Day Custom Tour


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.

  Read More

Serene Days of Milan and Lake Como Tour

7 Day Custom Tour


Once dominated by massive glacier formations, the diverse terrain of the Alps and Northern Italy will be your to explore on this 7-day tour of Lake Como and Milan. Como provides you with a rustic introduction to the region, and panoramic views of the nearby lake and humbling trips into the mountains reveal a quieter side of Italy. Once you experience Lake Como, you will make your way to the exhilarating expanse of Milan.

  Read More

Iconic Florence and Venice Tour with Countryside Culture

12 Day Custom Tour


Enjoy the perfect balance of rural charm and urban thrills on this 12-day tour through Tuscany, Umbria, and Venice. Savory cuisine and local wines provide the refreshment. As you make your way through these regions, expert guides will make sure that you experience what is best of each destination, history, and culture you encounter.

  Read More

Show More(6 itineraries)

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    >

Reviews of Zicasso's Referral Service

4.89 stars based on 4702 reviews.

Italy Trip Review: Tuscan Countryside, Private Wine Tasting,...
"Our 12-day trip to Italy was amazing, in no small part...

Reviewed By Jill M.

Vacation Review: Luxury Italy Tour, Lake Como, Menaggio,...
"We would absolutely use this travel company again!"

Reviewed By Helen C.

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

Reviewed By Alvin Y.

Luxury Italy Trip Review: Rome, Porto Ercole, Florence,...
"Dominick listened to our needs and what we like on a couple...

Reviewed By Alice J.

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

Reviewed By Madison S.

Luxury Italy Trip Review: Venice, Florence, Volterra, Venetian...
"Chiara was very responsive to our needs and a great communicator."

Reviewed By Carl P.