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14 Day Italy Itineraries & Vacation Packages

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<p>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.</p>

Explore Italy like you never thought possible. Revel in the country’s most iconic...

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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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San Gimignano in Tuscany, Italy

14 Day Trip Idea

From $6,267

Custom Cultural Italy Tour in 2 Weeks

Rome, Florence +5 moreRome, Florence, Siena, San Gimignano, Chianti +2 more
St Mark's Basilica in Venice, Italy

14 Day Trip Idea

From $6,267

Luxury Italy Tour in 14 Days

Milan, Como +22 moreMilan, Como, Venice, Florence, Pisa +19 more
Siena at sunset in Italy

14 Day Trip Idea

From $6,267

An Unforgettable Honeymoon in Italy

Venice, Florence +7 moreVenice, Florence, Montelpulciano, Val d’Orcia, Siena +4 more
Milan Cathedral in Italy, the third largest church in Europe.

14 Day Trip Idea

From $5,693

Northern Italy to Sicily: Italy Tour for Second Timers

Milan, Bologna +19 moreMilan, Bologna, Perugia, Trani, Ostuni +16 more
View of the city of Assisi and the Sacro Convento monastery, nowadays theological seminary, Italy

14 Day Trip Idea

From $6,267

Amazing 14-Day Italy Itinerary with Capri

Rome, Sorrento +11 moreRome, Sorrento, Vatican City, Capri, Assisi +8 more

14 Day Trip Idea

From $6,267

Italy Tour of the Most Beautiful Towns & Villages

Rome,  Naples +12 moreRome,  Naples, Pompeii, Amalfi (Amalfi Coast),  Spoleto and Valnerina +9 more

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Italy Tours by Travel Style

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Italy Tours by Travel Interest

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Popular Italy Destination Tours

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Multi-Region Italy Tours

Southern Italy & SicilyRome & SicilyMilan & Lake ComoMilan & Cinque TerreCinque Terre & Amalfi CoastTuscany & Cinque TerreFlorence & Cinque TerreFlorence & VeniceFlorence, Venice & MilanMilan, Florence & RomeRome, Tuscany & VeniceRome, Florence & VeniceRome, Florence & Amalfi CoastVenice, Florence, Rome & Amalfi CoastVenice, Florence, Rome & SorrentoRome to FlorenceRome to VeniceRome to Amalfi Coast

Multi-Country Italy Tours

Italy & GreeceSpain & ItalyFrance & ItalyItaly & SwitzerlandSpain, France & ItalyFrance, Italy & GreeceFrance, Switzerland & Italy

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