Fourteen Day Tuscany Itineraries

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Zicasso’s unique process connects you to the best travel specialists around the world. When you plan your dream vacation to Italy with Zicasso you will make discoveries that will last a lifetime.

How Zicasso Works

  1. 1.

    Describe your dream tour.

  2. 2.

    We match you with up to 3 top travel specialists. They compete to plan your trip.

  3. 3.

    Book the trip when you are satisfied.

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Tailor Made Itineraries

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

Devil's Bridge, a thousand-year-old stone bridge over the Serkyo River, Tuscany.

A Perfect Private Tour of Tuscany in 2 Weeks

14 Day Custom Tour

From $8,395

When every day is personalized to your preferences, you can be certain that each moment will be captivating. Stand in front of Botticelli’s Birth of Venus on a private tour of the Uffizi Gallery. Stroll along cavernous halls in labyrinthine abbeys with views out to vast valleys. Sip wine in a private villa with a boutique vineyard and discover tiny towns untouched by time with locals who welcome you like beloved family. Your 2 weeks in Tuscany tour provides you with a unique view of Tuscany, tailored by our Tuscany travel agents, to ensure that every day is made specifically for you.

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View of Capri Island from Mount Solaro.

Iconic Italy: Discovering Italy's Delights from Tuscany 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. Book your dream Italy tour today.

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The village of Montefioralle is one of the most beautiful in the Chianti Valley, Tuscany

All Star Italy Luxury Tour: Milan, Como, Tuscany & Amalfi

14 Day Custom Tour

From $8,395

Dream big, and vacation even bigger! This private tour is almost too good to be true, as every day is an over-the-top once-in-a-lifetime experience and it's designed just for you. You will have private museum visits and designer label trunk shows. Relax and sip wine at Chianti estate vineyards. A highlight will be a scenic drive through Tuscany in a Ferrari! Visit the glamorous island of Capri by private yacht and sunbathe while sipping Campari at an exclusive beach club. Foodies will enjoy Michelin-star fine dining on the Amalfi Coast. It’s all beyond amazing!

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Enjoy beautiful views of the Tuscan hills.

Tuscany & Cinque Terre Tour

13 Day Custom Tour

From $3,570

From the lush green of Tuscany’s hills to the pearl blue water of Cinque Terre’s coastline, experience why Italy is one of the world’s top destinations. Tuscany and Cinque Terre are works of art that everyone can enjoy. In Tuscany and Cinque Terre you do not just view the art, you become a part of it. Find out for yourself what all the great reviews are about!

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Positano on Italy's Amalfi Coast

Treasures of Italy Tour: Venice, Florence, Rome & Positano

13 Day Custom Tour

From $3,570

Treasures abound on this 13-day Italy tour through Venice, Florence, Rome and Positano that will fill your trove with riches. There is endless art and history along the storied Venetian lagoon, within the walls of Florence, around the ruins of Rome, and along the shores of the Amalfi Coast. Each day will bring you another spectacular gemstone to gather until you are brimming with memories and experiences that build tremendous wealth. You will see art and architecture, hear legends that have shaped history, and witness the grounds of which so much of Western Civilization has been based. From pastel buildings to luxurious train rides, towering domes and luscious apartments, you will fill your treasure chest with riches that you will always carry.

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Trod the paths that were once walked by Cicero and Caesar during a visit to the Roman Forum

Best of Italy in Autumn: 14-Day Romantic Tour

14 Day Custom Tour

From $3,845

This 14-day tour of Italy is designed to reacquaint you with the benefits of journeying at this time of year. Enjoy the November light as it reflects off the mirror of Lago Maggiore, truffle hunt through the changing colors of the Piedmont countryside, and indulge in a multitude of other adventures designed to capitalize on this bracing time of year. Autumn in Italy creates the perfect setting to enjoy the quieter and cozier side of this storied country.

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Helpful Content

Reviews of Zicasso's Referral Service

4.92 stars based on 1345 reviews.

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"We appreciated the ability to customize the trip to our...

Reviewed By Steven B.

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"We are truly happy with our honeymoon"

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Italy Travel Agent Review: Venice, Cortina, Dolomites, Lake...
"The staff was wonderful work with, immediately responsive,...

Reviewed By Josh R.

Italy Vacation Review: Cinque Terre, Venice, Tuscany, Cooking...
"We really felt like our itinerary was personalized for...

Reviewed By Robert D.

Italy Travel Review: Venice, Florence, Pienza, Tuscany,...
"I would recommend this travel company to my friends"

Reviewed By Albert A.

Travel Review: Italy Vacation, Rome, Florence, Ravello,...
"[Our travel planner] listened to my requests of having...

Reviewed By Heather H.