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14 Day Italy Itineraries & Vacation Packages

Ratings of Zicasso's Service
<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...

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.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
San Gimignano in Tuscany, Italy

Custom Cultural Italy Tour in 2 Weeks

Places Visited: Rome, Florence +5 more
Places Visited: Rome, Florence, Siena, San Gimignano, Chianti +2 more

14 Day Custom Tour

From $6,300

St Mark's Basilica in Venice, Italy

Luxury Italy Tour in 14 Days

Places Visited: Milan, Como +22 more
Places Visited: Milan, Como, Venice, Florence, Pisa +19 more

14 Day Custom Tour

From $6,200

Siena at sunset in Italy

An Unforgettable Honeymoon in Italy

Places Visited: Venice, Florence +7 more
Places Visited: Venice, Florence, Montelpulciano, Val d’Orcia, Siena +4 more

14 Day Custom Tour

From $6,300

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

Northern Italy to Sicily: Italy Tour for Second Timers

Places Visited: Milan, Bologna +19 more
Places Visited: Milan, Bologna, Perugia, Trani, Ostuni +16 more

14 Day Custom Tour

From $5,700

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

Amazing 14-Day Italy Itinerary with Capri

Places Visited: Rome, Sorrento +11 more
Places Visited: Rome, Sorrento, Vatican City, Capri, Assisi +8 more

14 Day Custom Tour

From $6,300

Italy Tour of the Most Beautiful Towns & Villages

Places Visited: Rome,  Naples +12 more
Places Visited: Rome,  Naples, Pompeii, Amalfi (Amalfi Coast),  Spoleto and Valnerina +9 more

14 Day Custom Tour

From $6,300

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Benefits of Using Zicasso

Plan Your Trip with
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Just for You
Travel with a personalized itinerary and experiences designed for you.
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Every Time
24/7 support and local assistance for every moment of your vacation.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Reviews of Zicasso's Referral Service

4.89 stars based on 5532 reviews.