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14 Day Italy Itineraries & Vacation Packages

Explore Italy like you never thought possible. Revel in the country’s most iconic cities, monuments, and cuisines, while also getting the distinct opportunity to uncover hidden treasures from exploring quaint villages to private tastings at countryside wineries. Discover the beauty of Italy and its many enchantments with a personalized 14-day itinerary from Zicasso.

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Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $6,300

Custom Cultural Italy Tour in 2 Weeks

Rome, Florence, Siena, San Gimignano, Chianti +2 more

14 Day Trip IdeaFrom $6,300

Luxury Italy Tour in 14 Days

Milan, Como, Venice, Florence, Pisa +19 more

14 Day Trip IdeaFrom $6,300

An Unforgettable Honeymoon in Italy

Venice, Florence, Montelpulciano, Val d’Orcia, Siena +4 more

Milan Cathedral in Italy, the third largest church in Europe.

14 Day Trip IdeaFrom $5,700

Northern Italy to Sicily: Italy Tour for Second Timers

Milan, Bologna, Perugia, Trani, Ostuni +16 more

View of the city of Assisi and the Sacro Convento monastery, nowadays theological seminary, Italy

14 Day Trip IdeaFrom $6,300

Amazing 14-Day Italy Itinerary with Capri

Rome, Sorrento, Vatican City, Capri, Assisi +8 more

14 Day Trip IdeaFrom $6,300

Italy Tour of the Most Beautiful Towns & Villages

Rome, Naples, Pompeii, Amalfi (Amalfi Coast), Spoleto and Valnerina +9 more

1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
3.Design Your Perfect Journey
Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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More 14 Day Vacations Near Italy

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Reviews of Zicasso's 14 Day Italy Itineraries & Vacation Packages

Based on 2303 verified traveler reviews.

Luxury Italy Group Tour Review: Rome, Tuscany, Chianti, Montepulciano, Montalcino, Siena, Florence, Pisa, Lucca

"...after my first communication with our agent -- I knew that she 'had it.' She understood exactly what we wanted to do."

Luxury Anniversary Vacation Review: Italy, Florence, Venice, Amalfi Coast, Cinque Terre, Tuscany, Verona

"The initial response I received from my agent was immediate and continued right up until our actual trip while we were in Italy."

Review: Italy Family Vacation, Rome, Tuscany, Florence, Amalfi Coast, Sorrento, Positano

"Our agent crafted a set of amazing experiences for our family..."

Travel Review: Luxury Italy Anniversary Vacation, Rome, Venice, Florence, Positano, Ravello, San Gimignano, Tuscany

"Our agent managed to fit in everything we wanted to see and do and some things we hadn't even known we wanted..."

Travel Review: Italy Trip, Rome, Sorrento, Florence, Naples, Pompeii, Herculaneum, Ravello, Siena, San Gimignano, Farm & Food Tour

"We wouldn't hesitate to recommend this company to help others plan the vacation of a lifetime."

Italy Tour Review: Venice, Sienna, San Gimignano, Rome, Revello, Amalfi, Pizza Making Class, Winery

"We were provided first-class treatment every day, our transfers, tour guides, and accommodations were truly amazing!!"