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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 $6,300

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

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.

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

4.9 stars based on 5841 reviews.

Italy Tour Review: Tuscany, Val d'Orcia, Assisi, Rome, Countryside,...

The Zicasso travel company was outstanding. They provided the exact trip experience we had hoped for. We wanted to avoid crowds and all the tourist hotspots. We wanted to see the countryside and meet people where they lived and worked (as much as possible as tourists). 

During planning, our agent was very patient, supportive, and responsive to our interests and desires. She was very flexible and amazingly helpful in identifying locations and activities that we would like, and another agent did a great job putting all the pieces together for us. 

The vendors they arranged were all top-flight. The drivers and tour guides were always on time, friendly, helpful, knowledgeable, and willing to do whatever we wanted. The lodgings were consistently the best in quality, location, and service. They all included phenomenal breakfasts that ensured I would not lose weight on this trip! Everything went off smoothly and we could not have asked for a better experience.

Reviewed By Robert F.

Northern Italy Family Travel Review: Lake Como, Villages,...

"We had a wonderful family trip. The Zicasso trip planner put together a very thoughtful itinerary. The entire trip was fantastic."

Reviewed By Jeff G.

Travel Review: Amazing Custom Honeymoon in Italy

"The view from our balcony over Positano was breathtaking."

Reviewed By Jennifer M.

Italy Luxury Travel Review: Amalfi Coast, Puglia, Sicily,...

"We recently had an amazing trip in southern Italy, organized by a Zicasso tour company that I can't recommend enough!"

Reviewed By Stephen S.

Italy Tour Review: Rome, Amalfi Coast, Sicily, Capri

"Our travel team members were amazing. Their responsiveness, attention to detail and overall customer service were absolutely impeccable."

Reviewed By John D.

Italy Travel Review: Sicily, History, 2 Weeks

"This was our fourth time using Zicasso. All went well, as we expected, even last-minute changes! We had a great trip."

Reviewed By Ingrid W.