Siena, Italy

14 Day Tuscany Itineraries

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Fourteen-day Tuscany itineraries immerse you in the splendor of rolling emerald hills, terraced vineyards, and the quintessential medieval towns that construct the picture-perfect ambiance of Italy. Whether exploring the grand visions of the Medici in Florence or sipping wine in Montalcino accompanied by a panoramic view, visiting the home of Leonardo da Vinci or discovering a charming coastal village, the wonders of history and passion for daily life will emerge in every moment. Zicasso Italy travel specialists have planned thousands of personalized trips and can design your dream Italian vacation with local expertise and recommendations.

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    Describe your dream tour.

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

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    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.

Sunest view of Florence from the Giardino delle Rose

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 in Italy

Iconic Italy: Fast-Paced Exploration from Venice 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.

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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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Vernazza, one of the five centuries-old landmarks where car traffic is prohibited, Cinque Terre National Park, Italy

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. 

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

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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Reviews of Zicasso's Referral Service

4.89 stars based on 4702 reviews.

Italy Travel Review: Tuscany, Cinque Terre, Lake Como, Private...
"Giulio at this travel company did an exceptional job arranging...

Reviewed By Irene P.

Italy Vacation Review: Shopping in Milan, Pompeii Excavations,...
"Start to finish, the outright best travel planning experience...

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Vacation Review: Luxury Italy Tour, Lake Como, Menaggio,...
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Italy Trip Review: Venice, Como, Tuscany, Florence, Rome,...
"Cameron’s attention to details and knowledge of unique...

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Italy Vacation Review: Venice, Florence, Rome, Tuscany,...
"Michela planned a fantastic adventure for our family."

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Luxury Italy Trip Review: Milan, Venice, Porto Venere, Cinque...
"[Our travel agent] created the perfect balance of private...

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