Siena, Italy
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14 Day Tuscany Itineraries & Tour Packages

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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Sunest view of Florence from the Giardino delle Rose

14 Day Trip IdeaFrom $13,700

A Perfect Private Tour of Tuscany in 2 Weeks

Florence, Siena, Pisa, Lucca, San Galgano +11 more
View of Capri Island from Mount Solaro in Italy

14 Day Trip IdeaFrom $6,200

Iconic Italy: Fast-Paced Exploration from Venice to Sicily

Venice, Milan, Sorrento, Chianti, Amalfi Coast +4 more
The village of Montefioralle is one of the most beautiful in the Chianti Valley, Tuscany

14 Day Trip IdeaFrom $13,700

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

Milan, Lake Como, Amalfi Coast, Florence, Siena 
Vernazza, one of the five centuries-old landmarks where car traffic is prohibited, Cinque Terre National Park, Italy

13 Day Trip IdeaFrom $5,900

Tuscany & Cinque Terre Tour

Tuscany, Cinque Terre 
Positano on Italy's Amalfi Coast

13 Day Trip IdeaFrom $5,900

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

Venice, Florence, Rome, Amalfi Coast 
Trod the paths that were once walked by Cicero and Caesar during a visit to the Roman Forum

14 Day Trip IdeaFrom $6,300

Best of Italy in Autumn: 14-Day Romantic Tour

Turin, Florence, Rome, Stresa, Vatican City 

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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4.9

Reviews of Zicasso's 14 Day Tuscany Itineraries & Tour Packages

Based on 5642 verified traveler reviews.

Grace B.
Italy, Greece Honeymoon Review: Culture, Cuisine, Snorkeling, Cooking Class, 12 Nights

My husband and I went through Zicasso to plan our honeymoon to Italy and Greece. This was the best decision ever! We worked closely with our travel specialist to plan our trip and she was absolutely phenomenal. This was our first international trip outside of the US, so we were a bit nervous at first! However, our specialist ensured every aspect of the trip was organized and that we were taken care of every step of the way.

The biggest relief was transportation. We did not have to give a second thought as to how we were getting places; we had drivers set up at every destination and for nearly every activity. Also, we had 24/7 support if anything were to go wrong, which gave us peace of mind.

If you are hesitant to use Zicasso for your next trip, I want you to know that I was too, but it was the best decision! We were able to personalize and tailor our trip to our needs without the hassle of dealing with the details.

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komal P.
Italy, Malta Trip Review: City Tour, 20 Days

I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.

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Mitch A.
Italy, France Travel Review: Scenery, 10-Day Trip

The trip was amazing all around. Incredible. The service and itinerary were perfect. We highly recommend Zicasso's travel company.

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Helena H.
Greece, Italy Travel Review: Rome, Athens, Santorini, Local Cuisine, 14-Night Trip

Our trip was absolutely amazing! This was the trip of a lifetime. Zicasso and our trip planner were incredible. He was repeatedly helpful, offering personalized attention to our needs. He booked amazing tours for us and seemed to really grasp what we wanted. Everything was incredible.

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Robert K.
Italy Vacation Review: Ravenna, Padua, History, Art, Scrovegni Chapel, 13 Days

It was a great pleasure working with Zicasso's tour agency. Our travel designer and her staff were attentive to the kind of trip we wanted and planned a great itinerary. The hotels, restaurants, and drivers were all top-notch. For us, the acid test was the quality of the guides, and they excelled there as well. We would happily have them plan another trip for us.

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Danielle S.
Italy Tour Review: Ravenna, Verona, Rimini, Scrovegni Chapel, Private Tours, History, 12 Nights

My husband and I had a great time on our trip to the northeast Adriatic Coast of Italy. We have very specific tastes as far as where we like to stay and the private tours we like to have during the trip. Zicasso's travel company did a great job, giving us fantastic hotels, and all of our tour guides were top-notch.

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