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.

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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 626 verified traveler reviews.

Italy Trip Review: Venice, Florence, Rome, Wine, Cheese Tasting, Olive Oil, New Pope, 11 Nights

I am so happy we worked with our Zicasso travel agent for our 11-night visit to Venice, Florence, and Rome. We had a wonderful Italian experience. Our agent was everything you hope for in a travel specialist: knowledgeable, thoughtful, helpful, gracious, and kind. 

Upon hearing our initial ideas for the trip, she quickly put together a plan on how best to allot our time. Thereafter ensued exchanges regarding hotels, sightseeing, guides, and transfers. She listened to our thoughts, desires, and questions, making many useful suggestions, including hotel choices. She always prioritized our wants and concerns. She organized the travels quickly, as we contacted her only two months prior to departure. 

Once we agreed to the program, she sent us a brochure PDF laying out details for each day of the trip that included hotel confirmations, transfer details, vouchers for museums, a cooking class, a Tuscany day trip with wine, cheese, and olive oil tasting, a gondola ride, Venice lagoon boat excursion, basilica entrance tickets, and guided tours of each city, the Vatican, and Colosseum. 

Upon arrival in Venice, our agent met us at the airport and escorted us to our water taxi. She kept in touch with us daily, texting a reminder of the next day’s schedule, along with numbers for guides and drivers if applicable. Everything she planned went smoothly, without a single hitch. 

When you begin the process with Zicasso, it feels akin to a shot in the dark. The site provides the names of two companies and you’re left to decide who to work with. I couldn’t be more pleased with the trip our agent designed. Book with her; you will be in the best of hands.

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Italy Trip Review: Rome, Venice, Florence, Opera, Walking Tours, 10 Nights

We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.

I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.

Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.

As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.

I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.

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Italy Tour Review: Tuscany, Florence, Montalcino, Castellina, Chianti, Wine Tasting, Cheese Experience, Local Cuisine, Walking Tour, 9-Day Trip

We loved everything about our trip to Tuscany. We had great, comfortable hotels as bases to explore the beautiful countryside and towns. Our hotels had kind, welcoming staff. Zicasso's travel company provided helpful suggestions and reserved non-touristy restaurants and enjoyable, interesting activities: eating in Florence, wine tasting in Montalcino, and cheese making in Pienza.

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Italy Trip Review: Rome, Florence, Tuscany, Amalfi Coast, Pope Francis’ Funeral, Wine, Cuisine, Culture, Museums, Relaxation, 10 Nights

Zicasso’s tour operator planned the most amazing trip to Italy for us! My requirements were culture, romance, and relaxation. She delivered on every aspect. Although we missed our tour of the Vatican due to the Pope's funeral, my husband and I actually attended his funeral!! Our hotel, though planned many months before, was next to the basilica where Pope Francis was laid to rest. Talk about being a part of history!

We stayed in a beautiful converted villa to boutique hotel in Florence; got whisked away through the Tuscan countryside in a vintage Fiat 500; took cooking classes; sipped lovely wine, accompanied by excellent lunches on our winery tours; soaked in Italy's rich culture and museum scene; and even ticked the relaxation box by spending time by the pool, in the spa, and resting on our large deck overlooking the Amalfi coastline.

Every tour guide was extremely knowledgeable and personable, and it was evident they loved their jobs. Between memories of the boat ride along the Amalfi Coast, tips from the cooking classes I have already started using at home, and the cases of wine we are eagerly awaiting delivery of, my husband and I will forever hold Italy in our hearts and la dolce vita it provided us. 

Talk with our tour operator; you will be glad you did!

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Italy Luxury Anniversary Tour Review: Sorrento, Tuscany, Cinque Terre, Venice, Gondola Ride, 3 Weeks
"Zicasso’s travel agency carefully and creatively designed our dream vacation to Italy and delivered an outstanding compilation of experiences."

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Italy Tour Review: Venice, Tuscany, Rome, Amalfi Coast, Capri, Cooking Class, Ferrari Experience, 2-Week Vacation

We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.

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