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
14 Day Trip IdeaFrom $13,700
A Perfect Private Tour of Tuscany in 2 Weeks
14 Day Trip IdeaFrom $6,200
Iconic Italy: Fast-Paced Exploration from Venice to Sicily
14 Day Trip IdeaFrom $13,700
All Star Italy Luxury Tour: Milan, Como, Tuscany & Amalfi
13 Day Trip IdeaFrom $5,900
Treasures of Italy Tour: Venice, Florence, Rome & Positano
14 Day Trip IdeaFrom $5,100
Best of Italy in Autumn: 14-Day Romantic Tour
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
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.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.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.
Reviews of Zicasso's 14 Day Tuscany Itineraries & Tour Packages
Based on 2455 verified traveler reviews.
Our family of five just got back from the most wonderful vacation in Tuscany and Rome. Our agent crafted a set of amazing experiences for our family from the private tour guides to Florence, Pisa and Lucca; a private wine tasting lunch at the Capannelle Winery and vineyards in Chianti; tickets to the Papal mass at the Vatican; to a tour beneath the church of San Clemente to see the excavations of a byzantine and then a Roman street neighborhood; a day excursion to the Amalfi coast to visit Positano, Sorrento and Pompeii; and more! Our agent and the guides found excellent restaurants from a simple salumeria where the locals ate to some high end restaurants. The hotels were right in the center of Florence – on the piazza della Repubblica - and Rome – between the Piazza del Popolo and the Spanish Steps. Our agent was attentive to our plans and made excellent suggestions. Everything went extremely smoothly. All the guides drivers were very friendly, spoke English and were very knowledgeable about art, history and the local culture. We saw so much every day because everything was so well planned. Simply the best travel experience ever!
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Planning a trip overseas with young children can be overwhelming when you don’t know all of the customs, the area, or how to get your little one safely from one place to the next. For those reasons, we considered a group tour of Italy for our first trip, but they just seemed to all be designed in the same cookie cutter fashion and without the kind of flexibility we hoped to enjoy. Thankfully we found our way to our agent with this Italy travel company who put together a custom itinerary that truly enabled us to experience several parts of this beautiful country—Venice, Florence, Rome, and The Amalfi Coast. From the individualized planning, the well-coordinated transportation, the lovely accommodations, knowledgeable guides, unique experiences, and especially the little details such as a local cell phone pre-loaded with all of the numbers and documents we would need during our trip, she went above and beyond in designing a trip that was unforgettable in all of the right ways. For these reasons and those discussed below, I enthusiastically recommend this company to anyone planning an Italian vacation.
From the start, we worked with several travel agents at different companies, trying to design an itinerary that fit our needs, interests, and budget. Our agent was the only one that seemed to truly listen to us and select not only hotels and transportation that would accommodate a toddler, but also experiences that would include her and were unique to our interests, even including a trip to my family’s hometown that was far off of the beaten path. She also offered us advice on best ways to get around with children in each city, provided a list of restaurants that would welcome our daughter, and, when I unexpectedly learned I was expecting another child, she offered to let everyone involved with our trip know of any special needs or food aversions I might have. While the individualized service and transportation would seem to come with a hefty price tag, the cost was actually the same as the hokey bus tours and very competitive with all of the other offers from travel agents we received, making the choice of this company a no brainer.
And the transportation alone was well worth the price. Everything was so beautifully choreographed: for instance, we walked out of our hotel in Venice and boarded a water taxi, which took us to a Mercedes van with child seat installed that was waiting for us, which took us to the train station where we boarded and took our first class seats. All of our transportation ran this smoothly, and we know there is no way we could have seen everything we did see had we tried to navigate Italy on our own. We always rode in luxury vehicles. Some were even equipped with DVD players for our little one. The drivers were excellent. Each English speaking driver was waiting for us at the airport or train station with a sign, handled all of our luggage, and acted as our first guides to each city as well. Additionally none of them pushed for any of the tips they definitely earned.
The hotels also exceeded our expectations. All of the accommodations were well-located, four star properties, and were the same hotels our agent included in her original price quote. When we were planning our trip, people kept telling us of the small quarters you’re forced to stay in in Italy and other European cities, but we did not find this to prove true in the hotels our agent chose for us. Every room had at least a queen size bed and a full size bed for our toddler, a sitting area, as well as a decent sized bathroom—one even had two bathrooms, another even had a bathtub, which is quite rare in Italy. Each hotel offered an exceptional free breakfast with a mixture of hot and cold entre choices and fresh local produce. Plus every hotel offered something different. In Venice we stayed at a boutique hotel with a long history that was in an area all of the locals agreed had the best restaurants and cafes. It had a lovely courtyard with a pool. In Florence we stayed in a sleek, modern hotel that featured a rooftop pool and bar with stunning views of the city. In Rome we stayed at a modern boutique hotel that greeted our child with a t-shirt, coloring book, and candies. And finally in Positano we stayed in a hotel that had terraces overlooking the bay and city, a pool that looked out to the water and mountains, and an excellent restaurant. The hotel staff at each place was quite friendly, and I doubt we could have selected better places on our own.
All of our local guides had specialized knowledge that made them an excellent fit for the service they provided. In Rome we visited the ancient sites with a sculptor who spent his childhood at the ruins with his father, a famous archeologist involved in the digs and study of the ruins. In Venice we got to know the city by spending the day walking and boating with a woman who spent nearly her entire life there, who gave us excellent recommendations for restaurants and things to do, and knew almost each person we passed. Similarly in Pisa, we were introduced to the city by a woman who lived there and whose husband operated a local winery. They were all so knowledgeable and friendly, and having them to ourselves for much of the day was invaluable, as we were able to ask questions and visit some places not accessible to large groups.
Once we were introduced to the city, our agent also planned unique experiences to help us experience the place. We toured Venice by water. We biked our way through the narrow streets and beautiful countryside of Florence. We toured a winery and had a private six course lunch with wine pairings. We let our toddler run through an amazing Sculpture Park in Chianti. We shopped, cooked, and dined with a chef in Rome. We sampled foods at specialized eateries in a neighborhood that pre-dates the Coliseum. We visited the abbey at Monte Cassino, rebuilt after being destroyed during WWII. And we travelled the entire Amalfi Coast by boat, visiting the Emerald Grotto, the Blue Grotto, swimming in caves, and enjoying Positano, Amalfi, and Capri. In two weeks we saw, experienced, and tasted so much that we will continue to relive this trip for a lifetime.
In all ways, as I hope is clear, this trip was exceptional because of our agent's hard work and the work of all at our travel company. This showed not only in the ways already described, but also in all of the small details. We were greeted upon arrival with a welcome package and were given a phone that had all of our tickets, our itinerary, and everyone’s phone number loaded onto it. Our agent checked in with us periodically while we were there and made it clear that we could call at any time if we had questions, concerns, or if something was not up to par. When our boat tour was late, for instance, she called to change our dinner reservations. And she even educated us about some Italian customs before we arrived.
A trip like this one is a financial investment for many of us, and I know from experience that putting your trust and your hard-earned money into the hands of someone you only communicate with via email or phone is scary. But believe me, if you choose this company, you will not be making a poor decision. There is literally nothing more I could have asked for, no other way this trip could have been more spectacular, and no better way I could have spent every one of my pennies. Thank you to our agent for making us the envy of all of our Facebook friends, for truly making this an awesome family vacation, and for making one of my ultimate dreams come true.
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My husband and I just returned from a two-week vacation in Italy. With the help of Zicasso and our travel company, we were able to fit every wish into this short time.
We started out in Rome, then went on to Florence for some amazing history. We then traveled to the Tuscany and Chianti countryside for private cooking and wine experiences. We loved the small villages we explored and the little family-owned wineries and olive farms.
A highlight was staying in a bed and breakfast in Ponzano that overlooked the beautiful olive gardens and countryside. We explored the small villages of San Gimignano, Montepulciano, and Montalcino, and felt like we had discovered authentic local life.
The tail of our trip was spent in the beautiful Lake Como area, with a day trip to Lugano, Switzerland.
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THE BEST VACATION EVER!!!!
I must admit that I was somewhat uncomfortable arranging a group tour to Italy with someone I communicated with only via the Internet and telephone. However, after my first communication with our agent -- I knew that she “had it.” She understood exactly what we wanted to do. She was right-on in both concept and execution.
Our ten-day adventure in Italy began with a private transfer with an English speaking local driver from the Rome airport to our fantastic 3 star boutique hotel located right in the historical center of Rome. During our three days in Rome, we had fantastic private tours of Ancient Rome, the Coliseum, and the Vatican Museums. Extremely knowledgeable, English-speaking guides led all of our tours. Sense of Italy had arranged for VIP, skip the line, priority entrance for all tours -- saving us from long waits in long lines.
After our busy 3 days in Rome, we departed via private van transfer from our hotel in Rome to the Chianti Region of Tuscany. The transfer included stops on the Val D’ Orcia to visit the amazing Villages of Montalcino and Montepulciano. The “light lunch” and wine tasting we enjoyed in Montalcino was one of the highlights of our trip. In Tuscany we stayed 7 Nights in a beautiful, historic villa located on one of the best wine estates of Chianti (Villa Le Corti near San Casciano) where we were met with a fantastic welcome dinner. During our time in Tuscany we were transported by private van from our villa to private tours of Siena, San Gimignano, Florence, Pisa and Lucca. On each of our stops we were met by knowledgeable English speaking guides that clearly were proud of the history of their country, and were anxious to share it. Interspersed in all of this activity were numerous exceptional meals with opportunities to taste (and drink) very fine Italian wines.
When we finally were forced to leave Italy, our agent arranged for private transport accommodating our varying departure times from the Florence airport and train station.
Thanks to this travel company and our agent for designing the perfect vacation for our group. The only complaint that I heard was that we ate too much — wow was all the food delicious. I really don’t know how she did it. All of the tours were great — the van drivers friendly and helpful, the guides knowledgeable, and the sites spectacular. Our stay in the villa was a great experience. We were treated royally everywhere. We all marveled at our agent's ability to get us, the vans, the guides, the food and wine, etc. all at the right place at the right time. She is a genius!!!!
Jeff E
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My husband and I, along with our 2 children (age 20 and 17), enjoyed a wonderful Italian vacation booked through Zicasso and this travel agency. Our travel consultants listened to my ideas and arranged for us a fantastic custom itinerary. They stayed within the budget allotted, offered choices for beautiful hotels and private tours, and made several revisions as per our request. We departed from New York on our 25th anniversary, and spent 10 days traveling the country within the month of November. This off-season time proved to be a great decision as reservations were easy to obtain, crowds were minimal (mostly all locals), and the weather was conducive for walking and sightseeing (average 60 degrees F). Transportation and the personal drivers were top notch; with Mercedes SUVs or minivans to take my family from Milan-Chianti-Florence-Verona-Venice and then the high speed train down to Rome. Accommodations arranged for us were phenomenal! We stayed in a 12th century castle in Chianti, in the heart of the city center in Florence, and near the Spanish Steps in Rome. The personal tour guides were friendly and knowledgable, and were happy to recommend eateries preferred by locals. All in all, everything was flawless. We plan to return some day to see the Amalfi coast, Positano and Capri. We would absolutely recommend these travel consultants, and the travel company team to anyone who is looking for a personalized Italian vacation.
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