Spirit of Tuscany Tour: Highlights of Florence and Siena

What to expect on this itinerary
Indulge in this immersive Italy tour that highlights the splendors of Tuscany. Authentic comforts and traditions emerge through delicious wine-tasting tours, a private cooking class, and the exceptional artwork that has been etched into the churches and displayed in museums. Whether basking in the magnificent design of Michelangelo’s David or indulging in tranquil views from the top of antique walls, you can find authentic beauty in the best of Tuscany.
Customizable Itinerary
Florence – Arrive in Tuscany’s Capital
Florence is a masterpiece of medieval and Renaissance architecture. Wide cobblestone avenues lead to narrow lanes that are nestled between elegant palaces. Your private transfer will greet you at Florence Peretola Airport upon your arrival and escort you to your lavish accommodation in the heart of the city. Visitors and locals stroll down Via de’ Tornabuoni, which is a fantastic shopping street of designer shops. Your guide will introduce you to the remarkable city on a walking tour, beginning with Ponte Vecchio.
What's Included:
Florence – The History and Grandeur of Florence
Florence – The Drama and Heritage of Florence
Florence – Enjoy a Gelato Tour
Florence – The Marvels of Borgo a Mozzano
Florence – Prato and the Town of Mugello
Siena – Chianti Wine Tour
Siena – Traditional Cooking Class
Siena – Wine Tour of the Val d’Orcia Region
Siena – Departure
Trip Highlights
- Witness the magnificent artwork on display in the Uffizi Gallery, including artwork by master artists
- Revel in the intricate detail and stunning focus of Michelangelo’s David when on a private tour of the Galleria dell’Accademia
- Sample the delicious flavors of wines from the Val d’Orcia on a private tour that allows you can taste the layers of celebrated Bruno di Montalcino
- Delight in the elegant and rustic flavors of authentic Tuscan cuisine during a private cooking class taught by an experienced local cook
- Witness the fantastic list of the infamous Leaning Tower of Pisa when wandering the city
- Discover the fascinating artistry and evolution of textiles in Tuscany with a private tour of the Prato and the textile museum
- Revel in the diverse flavors of artisanal gelato throughout Florence on a guided tour that features the best tastes, variety, and originality in the city
- View the tremendous design of the Ponte della Maddalena in the town of Borgo a Mozzano outside of Lucca
Detailed Description
You will discover the picturesque scenery and captivating history of Italy with this 10-day highlights tour of Tuscany. You will have private tours of the magnificent wine regions and specialist guides with insider knowledge of art, architecture, history, and local traditions. Your private transfers, stunning accommodations, and view of Tuscany’s countryside towns will offer you the ultimate luxurious experience.
Your highlights tour of Tuscany will begin with your arrival at the Florence Peretola Airport, where you will meet your private transfer. You will have six nights in Florence with plenty of time to enjoy the fantastic history and artistry on display. Your specialist guides will introduce you to the city, leading you from the Duomo to the Ponte Vecchio and into the galleries of the Uffizi. You will explore the Galleria dell’Accademia to view Michelangelo’s marvelous David and discover the tremendous works of master artists, such as Donatello on a private tour of the Bargello Museum. Afterward, you will meet with local artisans who preserve the traditional handcrafts of Florence, from woodwork to sophisticated furniture.
Your day trips outside of Florence will take you to the likes of Pisa for a magnificent discovery of the former naval powerhouse. Upon returning to Florence, you will explore the diverse and tasty flavors of authentic artisan gelato with a knowledgeable guide. In Lucca, you will wander the elegant streets within the dramatic walls and traverse the arching bridge of Ponte della Maddalena in Borgo a Mozzano. In the city of Prato, you will enjoy a revelation of graceful tranquility among the lush landscape of Mugello.
You will then have a private transfer to Siena for three nights in the medieval city, beginning with a captivating tour that will reveal the historic, eclectic, and intricate architecture of the city. In the Chianti countryside, you will enjoy the distinctive flavors of the local wines with private tastings and tours. Wandering beneath the towers and among the frescoes of San Gimignano will offer you a new perspective of the medieval town and countryside. You will then indulge in a delicious cooking class that will teach you the art of crafting authentic Tuscan pasta. A wine tour of the Val d’Orcia will introduce you to the charming Renaissance town of Pienza and the elegant medieval town of Montalcino. Here, you can sample the famous flavors of Brunello di Montalcino.
Starting Price
$3,600 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.
Verified Traveler Reviews
Based on 1144 reviews
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We had a wonderful trip. "Tuscany in Winter" was my husband's idea to experience this beautiful part the world beating summer crowds. We visited the lovely ancient city of Siena the historic Florence and the Tuscany countryside for a few days in between. We were able to enjoy the galleries, restaurants and other popular sites pretty much on our own and were welcomed very warmly in cold weather by all.
Our guide and driver were very professional and pleasant. They were very concerned about all aspects of the responsibility of providing the very best service possible.
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When we inquired about a trip on Zicasso, they told us a few companies would reach out to us with different offers on our desired location. It only took one reply back from this agent for me to know that we would have a more personable experience with this travel agency. (Mainly because he was straight up with us concerning itinerary ideas, especially regarding weather and how it is unpredictable in March. He patiently worked with my fiance and me for quite a while before we approved the final itinerary filled with transportation to and from hotels, private tours (some meant to be small group, but we ended up being only ones), and pre-planned relaxing train-rides. There wasn’t a moment of our trip that we had to worry or even think about- really. Our first stop was Rome, where we spent 3 days. Upon arrival at the airport in Rome, we had a driver waiting for us, which was a huge relief since we were tired and last thing we wanted to stress about was how to get to our hotel. Our local point-of-contact for the agency also called once we arrived to make sure we had everything we needed. He was great! Once we reached our hotel, we slept off the jet-lag and then our holiday started. March is the early beginning of the tourist season, so we were able to do many things without waiting. Not saying it was empty, but we had room on the sidewalks and were in and out of restaurants in no time at all. I also highly recommend planning free days in each city, as you will want to look around for yourself and take your time in certain parts. Even if you spend a week in every city, you always leave feeling like you needed much more time, as there is so much to do and so little time in a day. We spent 3 days/4 nights in Florence. It was in Florence that we were able to easily tour a good bit of what Tuscany has to offer. Through tours our agent set up for us, we visited the beautiful cities of Siena, San Gimignano (Our Favorite), Lucca, Pisa, and the Chianti Region. We tasted sooooo many wonderful wines and privately ate at local restaurants for lunch. We also took a short train ride to Venice for a day trip, as I craved a gondola ride. Everything was planned so perfectly. The minute we stepped off the train in Venezia our guide to get us to our marked location was there with a water taxi to take us to St Mark’s Square. There, she directed us to our gondola and we spent the day wondering around Venice until meeting up back with her and the water taxi to take us back to the train station. After Florence, we traveled to Sorrento (our other favorite!) along the Amalfi Coast. It was magical and the weather was perfect. We had our own boat to visit the grottos (no wait for the Blue Grotto either!) and to the Isle of Capri; and although most of the shops were closed on the isle (early season still), it was beautiful and we were able to relax on the beach. We saw Pompeii and even hiked up Mount Vesuvius. Sorrento was a quaint and charming city and we made friends with quite a few locals. We truly had a wonderful honeymoon and I would recommend this agency to everyone. We could not be happier!
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Trip was very good. Everything was well coordinated and only a couple of hiccups.
Overall comments:Rome: 4 days in room was perfect, wouldn't want to do more. Can't trust taxis so happy we had drivers and guides. The private guides are the only way to go. We saved hours in lines, had personal feedback and was very cordial and polite. Rome itself is great but it is disappointing to see how much better it could be if the city invested in a few things (toilets!). Again - I'll mention that taxis were there to steal your money. No issues at all with the travel plans and the plans made by zicasso were very good. The boutique hotel was a great choice. Location was excellent, rooms very clean and new. Breakfast was excellent there. In general, all of the hotels we stayed at had a very good breakfast, this is the only way to go as it just takes that meal out of your schedule and starts the day out right. Our biggest snafu was the car rental, we were supposed to have an Audi A3 or equivalent and all the car rental could offer was a ford fiesta... it really took away from our experience in Tuscany to have such a poor automobile on those roads. Again - not zicasso's fault - car rentals are terrible everywhere and in Rome it was very poor service. Our drive and trip to Tuscany was great, we stopped in Orvieto as zicasso recommended and had lunch there - one of the best restaurants during our whole trip. We stayed at the hotel and it was excellent, the food and wine there was excellent - worth staying just for that. It was a little difficult to get to - and a bit of a drive to anywhere from there - but no real complaints and it was worth it to stay there. In all of Tuscany we enjoyed San Gimignano and Pienza the best. We found Siena great but overcrowded, Pienza and San Gimagnano were just as (more) scenic and less hectic. The day trip and guide in Florence was very good but we were glad we only spent 1 day in Florence. This is a personal thing as I understand most people prefer more time in Florence. We really enjoyed Bologna - the food tour was probably the highlight of our trip (the downside is we can no longer eat Parmigiano, Balsamic Vinegar or Prosciutto from any other place, it was THAT much better than anywhere else). We took a day to go to Modena, see the Duomo there (best in all of Italy in our opinion), and we enjoyed the Ferrari museum. I would highly recommend adding Bologna, the food tour and Modena to everyone's trip suggestions.. It is less crowded than the main touristy cities - and just as enjoyable... Loved this part of the trip. The hotel in Bologna was perfectly placed and very very nice, excellent choice.The train to Venice was perfect. The pickup and ride to the hotel was good also. The hotel was ok - but probably the least nice of all the places we stayed. It was very good, just not as nice, more cramped and the breakfast was by far the worst. I equate this to Venice as everything was more expensive and more cramped in Venice. We loved Venice - more than I thought we would. I could see 1 more day in Venice and 1 day less in Rome. Just walking the streets - wonderful!Getting from hotel to airport was good - though it was much further than we'd thought. The airline we used sucks... no way around that - not Zicasso's problem - but flight was 1.5 hours delayed and well - as an airline it isn't very good. I'm still not so sure that taking a full day train ride to get to Puglia wouldn't have been better? (Venice to Naples to Puglia?) Pick up at airport in Puglia was good. The driving service was good - same driver for all our trips in Puglia - but he didn't speak a word of English so that was a challenge. Thank goodness for Google Translate! We had a mix up where we interpreted the itinerary as us having a guide in Alberobello (see itinerary - says private tour - so we were confused). The driver had a friend who gave us a personal private tour of the Trullo homes and some history - that was very nice he arranged that. But it was a little embarrassing and confusing. It could have all been avoided if the driver spoke English as well as the itinerary being more clear.Ostuni and the guide were great. We loved Ostuni as well as Alberobello and the caves. We probably enjoyed those areas more than the renaissance areas of Florence, but that is just us. Note: once we got to Ostuni we told our guide no more going inside churches... at some point - its just another beautiful church - but there is one on every corner in Italy! The Hotel in Puglia is awesome. Seriously this place is amazing. The food was amazing the spa was amazing the service was over the top. What a beautiful part of Italy... We changed our schedule to spend the morning in Bari before catching the train to Rome - we could have easily spent more time there. I probably liked the food in Puglia the best. The focaccia is amazing (just like Grandma made!). In general we loved Puglia though we'd probably have been better served to have a rental car as we were a long way from anything and it would likely have been less expensive than a dedicated driver. We would have had much more flexibility in our schedule and planning if we had our own car. Train back to the Rome train station and pickup was very good - though the Rome train station and driving out of Rome - is never a good experience. The hotel we stayed at our last night was very nice but probably overkill since all we needed was a bed before we caught a flight out. All in all - highly recommend zicasso, they did a great job for this trip. Having guides and drivers on our first trip to Italy - priceless!
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When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.
Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.
Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.
A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.
Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.
When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.
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The travel assistance from Zicasso's company was very helpful. All tour guides were wonderful, as well as the tours, with the exception of the all-day tour into Tuscany, ending in Siena.
As an elderly woman, I found it to be too long. Also, after the lovely lunch and wine tasting, it was difficult to go on a 3.5-hour walking tour, as well as walk a mile into Siena and a mile out of Siena. Also, the bus did not have great air conditioning and did not have a working bathroom.
The other issue I had was with the seven and nine flights of stairs in Venice and Florence in our hotels. With bad hips and knees, I was confined to going up and down the flights only once during the day. I suggest this be a question for guests in the future.
The travel company was very generous in paying for a wonderful dinner for me and my grandson due to my struggles.
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