Siena, Italy
30,000+ Verified Traveler Reviews

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
Mount Etna in Sicily, 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 6198 verified traveler reviews.

Bill R.
Italy Travel Review: Rome, Florence, Tuscany, Food Tour, Wine Tasting, 9-Day Trip

Zicasso’s travel company did a great job and was very responsive. The guides and drivers were excellent. It was a wonderful family trip.

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Paige A.
Italy Travel Review: Sicily, Taormina, Valley of the Temples, 5-Day Trip

Aside from the delay because of the time change, working with Zicasso’s travel specialist was great. She took care of all arrangements in Sicily once our decisions were made. She confirmed with every hotel, driver, and guide, making sure our travel was effortless.

The guides were great, adding so much historical information to our attractions. Our drivers were friendly, providing us with clean, comfortable vehicles, safe driving, and interesting conversation about modern life in Italy. Our hotels were high-end, in city centers, with amazing breakfast buffets and professional, kind staff.

We used a reputable tour group for our first week of mainland Italy travel, but our experience with this travel specialist far surpassed the tour group experience and our expectations. I would not hesitate to use her again for any travel plans in Italy. She checked in with us pre-, mid-, and post-travel. There wasn’t one hiccup with the plans she made for us.

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Renee P.
Italy Vacation Review: Rome, Florence, Vatican, Colosseum, Roman Forum, Trastevere, Private Guide, Food Tour, 7-Day Trip

Zicasso’s travel company helped us plan a trip that exceeded our expectations. From the hotels to the guides to the scheduling of events, things could not have gone smoother. We visited all the sites and did all the things we wanted to do, and still had free time to roam on our own. This team is top-notch and we highly recommend them.

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Mitzi M.
Italy Vacation Review: Venice, 1 Week

The trip was fantastic. Zicasso’s travel specialist was so helpful every step of the way. She made sure even the smallest details were perfect. I would definitely use her again.

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Marc Z.
Italy Tour Review: Rome, Florence, Venice, Private Tours, 12 Nights

Our recent trip to Rome, Florence, and Venice, planned by Zicasso’s travel specialist and her team, was nothing short of exceptional. Every detail was handled with care, precision, and an obvious commitment to excellence. The hotels were truly top rate, perfectly located, and impeccably chosen to enhance the experience of each city. The tour guides were extremely knowledgeable, engaging, and clearly passionate, adding depth and context that made each destination come alive.

What truly set this trip apart was the level of service. From seamless transfers to on-the-ground assistance, everything felt effortless. The recommendations and tips provided along the way were incredibly useful and allowed us to experience each city with confidence and ease. The assistants who helped guide us through logistics and navigation were attentive, professional, and reassuring, making the entire journey feel like true white-glove service from start to finish.

The travel specialist and her team exceeded every expectation. Their planning, responsiveness, and attention to detail transformed an already incredible itinerary into an unforgettable experience. I would recommend them without hesitation to anyone looking for a flawlessly executed, high-end travel experience.

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Leah B.
Italy Travel Review: Verona, Bolzano, Food Tour, Wine Tasting, 1-Week Trip

Zicasso’s travel company was amazing to work with! They really took care of every detail for a worry-free experience! They were very responsive during planning and the trip. All of the locations and accommodations were exactly what I wanted. I cannot recommend them enough!

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