Historical Immersion Tour of Tuscany: Siena and Florence

Lucca , Market Square, Piazza dell'Anfiteatro in Italy

What to expect on this itinerary

The alluring heritage of Italy immerses you in its captivating art, intricate architecture, and delicious during this historically-based 7-day Tuscany tour. Bask in the picturesque views of iconic Tuscan landscapes that feature sprawling vineyards, towering cypress trees, and rolling hills, and medieval villages. Whether sipping celebrated wines or viewing priceless Renaissance art, your Tuscany tour will reveal in the region’s illustrious past.

Countries Visited

Italy

Places Visited

Florence, Siena

Suggested Duration

7 Days

Customizable Itinerary

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Day 1

Siena – Introductory Tour of the City

Siena acts as a preserved masterpiece that represents Tuscany, Italy, and the power of individual city-states. Your private transfer will greet you at Florence Peretola International Airport and escort you to your accommodations in the heart of Siena. After settling in to the comforts of your accommodation, your guide will introduce you to the marvels of the city. Your tour will begin at Piazza del Camp and will include the Duomo. After your tour, you will have the remainder of the day to spend at your leisure.

What's Included:

Accommodation
Transfer
Day 2

Siena – Antique Towns and Wine

Day 3

Siena – The Val d’Orcia Wine Region

Day 4

Florence – Power, Prestige, and Preservation

Day 5

Florence – Renaissance and Medieval History

Day 6

Florence – Discovery of Florence’s Past

Day 7

Florence – Departure

Trip Highlights

  • Discover the secret history of San Lorenzo Church in Florence by finding hidden sketches from Michelangelo
  • Embrace the charms of Montalcino during a private tour of the Val d’Orcia with a wine tasting inside an antique wine cellar
  • Witness the treasured sinopie of Pisa’s Sacred Fields that reflect the original sketches of master artists
  • Delight in the enchanting ambiance and welcoming locals of Greve in Chianti during a private tour
  • Wander the winding cobbled lanes of Lucca to explore the exceptionally preserved antique walls and Guinigi Tower
  • Enjoy the point at which history and artistic mastery converge in the Uffizi Gallery
  • Revel in the grandeur and romantic atmosphere of the Renaissance town of Pienza, which is the former home of Pope Pius II
  • Bask in the majesty of Florence’s Duomo during a private tour

Detailed Description

Your 7-day Tuscany tour will combine the marvels of the region’s natural scenery with its splendor of preserved towns and cities. This tour will include private transfers, specialized guides, and unique discoveries. Whether you prefer to linger in the medieval charms of Siena or to explore the often-overlooked museums of Florence, you will have an immersive and authentic experience.

Your historically-based tour of Tuscany will begin with your arrival at the Florence airport, where your private transfer will greet and transfer you to your accommodation in Siena. Here, you can enjoy the medieval ambiance with an introductory tour. A specialist guide will lead you through the Chianti Region and the Val d’Orcia for introductions to the landscapes. You will visit enchanting towns, such as Pienza and Montalcino, to witness the preserved lifestyle of Tuscany’s tranquil villages and to sample remarkable wines, such as Chianti Classico.

You will then transfer to Florence for three nights. Your time here will begin with a fascinating exploration of Pisa and Lucca with a specialist guide. The distinctive cities will reveal their former power dynamics and artwork, from Pisa’s famous Leaning Tower to the dramatic walls that surround the city center of Lucca. Once you have settled into the beauty of Florence, you will have two full days to uncover the artistic treasures of the city, from the Uffizi Gallery to the San Lorenzo Church. Lastly, your private transfer will meet you at your hotel in Florence and escort you to the airport for your flight home.

Starting Price

$2,600 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.

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Verified Traveler Reviews

Based on 1563 reviews

Travel Review: Anniversary Vacation in Italy, Florence, Siena, Tuscany, History, Hiking, Cooking Lesson, Hiking

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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Travel Review: Italy Birthday Vacation, Florence Cinque Terre, Siena, Tuscany, San Gimignano, Lucca, Sailing Pesto Making Class

The 2 weeks in Italy our travel agent planned for us  was fantastic. We has a fantastic schedule with experienced and excellent guides. This was my first time in Italy, a 60th birthday trip with my sisters, we have varied interests and she hit the mark on them all! The hotel location in Sestri Levante was the perfect location. The weather was beautiful for late Sept., we enjoyed the beach and calm Mediterranean waters when we were relaxing back at the hotel.  The guide on our hike in Cinque Terra was very good. We did not know what to expect. His knowledge on the history of the area kept us more than expected. The guide knew the area and was able to rearrange our schedule due to rough winds that cancelled the ferry.

I would have never taken a pesto making class, but it was a highlight!

The sailing day was absolutely perfect. The weather was beautiful, and the skipper was a true sailor!

On our way to Florence we stopped in Lucca and a winery that were fantastic. The driver was prompt and informative. Our hotel in Florence had the perfect location! Close to both sides of the river to explore by foot every day. The 2 days with our guide were fantastic! She was excellent in every way, she knew the history, art and even helped with restaurant suggestions and reservations. Having a guide was the perfect way to not only see the sights but understand the time period and history. The day trips out of Florence to Chianti, Siena and San Gimignano, were perfect with wine-tasting interspersed with visiting the smaller towns in the Tuscany region. The weather was beautiful both a weeks we were in Italy. 

The trip exceeded our expectations in every-way and we will all be repeat customers!! 

Thanks for making my 60th birthday trip, the trip of a lifetime!

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Travel Review: Memorable Vacation to Italy, Florence, Tuscany, Siena, Antinori Winery Tour, Rome, Vatican Tour
Giuliana of this Italy travel company guided us every step of the way and created one of our most memorable vacations. The most impressive thing at the outset was how quickly she responded to our initial inquiry. We had never been to Italy, had not done a great deal of research, and had only a general idea of what we wanted beyond the dates (mid-May) and the cities we wanted to visit (Florence and Rome). Within a day, Giuliana submitted a detailed proposed itinerary based on a recent client request similar to ours. The proposal included various options that provided a great starting point for further discussion. She asked many questions, including our hotel preferences (small boutique, high-rise, how many stars, etc.) and suggested a number of venues that would expose us to Italy’s remarkable history and culture. The result was a vacation specifically suited to our personal tastes and interests. We spent four days in Florence and three in Rome. In Florence, we stayed at the Hotel Lungarno on the Arno River, a lovely small hotel in the heart of the city within walking distance to everything of interest, including the Uffizi and Academy museums, and the famous Duomo. It rained two nights, but we didn’t have far to go for a great dinner. The hotel restaurant was superb. One of the highlights of the Florence leg of the trip was a day tour of the Tuscany wine region that included a stopover in the historic town of Siena. We had lunch at the Osteria di Passignano, a restaurant at the Antinori vineyards where we were treated to a four course lunch and wine tasting and a tour of the winery. Fabulous. In Rome, we stayed at the Hotel Saint George. Another small, well appointed, boutique hotel, centrally located near the Tiber River, it provided access to all the essential venues, including the Vatican, Coliseum, Spanish Steps, etc. As in Florence, everything was in walking distance, including fine dining restaurants, pizzerias, espresso bars, and gelateria—and lots of places to shop. The hotel was comfortable, attractive, with a friendly and efficient staff, but we would not recommend the hotel restaurant. It was nice enough (although too brightly lit) but was virtually empty the night we were there and the food was just O.K. That wasn’t Giuliana’s fault since the hotel restaurant was not on her recommended list. We were just tired (it was our first night) and thought we’d give it a try. The hotel concierge made up for it, however, by recommending two great nearby restaurants for the remaining two nights. Neither was on Guiliana’s list, but they were terrific. A word about the logistical aspects of the trip: we viewed this as critical to the success of a customized tour with multiple venues and connections. We couldn’t have been more pleased. On arriving at Rome’s Fiumicino Airport, we were greeted by Aldo who drove us to the high-speed train to Florence. After sharing an espresso with us in the station café, he made sure we got on the right train, helped us with our bags, and took us to our seats. Similar service greeted us at every connection point during the trip. Our personal tour guides, Enza (Florence), Andrea (Tuscany), and Sylvia (Rome), were exceptionally knowledgeable, personable, and fluent in English. Giuliana telephoned us at several points during the trip to confirm that we had arrived at our destination, that the drivers were on time, and that the accommodations met our expectations. Very reassuring to know she was keeping such close tabs on things. In short, all elements of transportation and personal service were impeccable. Would we visit Italy again? Without doubt. The trip simply whetted our appetites. Would we use this company? We wouldn’t consider any other service. Next time, however, we’ll make more of an effort to visit the restaurants recommended by Giuliana.

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Review: Luxury Italian Vacation, Rome, Venice, Florence, Positano, Siena, Tuscany, Napoli, Amalfi Coast, Pompeii, Duomo, Colosseum

Our trip to Italy proved to be, indeed, 'fantastica'!  We traveled to Venice for 2 nights; by train to Florence for 2 nights where we stayed at the luxurious Palazzo Niccolini al Duomo; by train to Siena for 2 nights.  From there we speed-railed it by "TreniItalia" to Napoli where we were picked up in a private car to take us to the jaw dropping showcase Italian seacoast resort of Positano.  We stayed there for 3 glorious nights at the Covo dei Saraceni with the most breath taking views of the bay and the Amalfi Coast that you could ever see.  Finally, we were picked up in a private car and taken to Napoli for a train to Rome.  But first...we had a 2-hour stop with guided tour of Pompeii's ruins.  Finally, after training to Rome, we stayed at the quietly elegant Residenza di Ripetta hotel near the Piazza del Populo.

I've left out the most important parts which were the incredible tours that this Italy travel agency arranged for us.  We must've seen everything that this trip could offer.  And it was all done over two weeks.  We toured Venice during the calamitous weekend of George Clooney's wedding.  No, we couldn't go to the wedding but we had a fabulous time nonetheless!  Our agent and her team put us up at the quaint yet convenient Hotel Georgioni in Venice quite near the Rialto Bridge.  We had been picked up at the airport and water-taxied to our hotel.  During our fabulous 48-hour stay, we saw every nook and cranny of central Venice anchored by the eye-popping Piazza San Marco.  Included in our stay was a tour of the Doge's Palace with its art treasures galore and a tour of the markets area replete with a 30-minute gondola ride through a memory of photographs that I took that I will never forget.  The Rialto Bridge at night, along with the rest of Venice, is one of the most romantic sights in the world.  The lighting of this magnificent city at night is unforgettable.

From there it was on to the renaissance city and Medici capital of Florence to our luxurious hotel, the Palazzo Niccolini al Duomo right across the street from the magnificent Duomo itself.  We walked and toured everything; from the Accademia Gallery and the "David" masterpiece by Michelangelo to the Uffizzi Gallery and Vasari Corridor to the Ponte Vecchio where I bought my beautiful wife a golden ring the size of Sardinia.  We saw street musicians, vendors, activists and sellers of all kinds.  We even saw a Brahma bull towing a wagon hauling over a 1000 bottles of Chianti up the main street into the square.  The food? Indescribably memorable.  Just like all of Italy.  

On to Siena where the Medieval contrasts with the Renaissance of Florence beautifully.  These 2 cities, once rivals, are now bastions of art and relics dating back centuries...from every genius known to man.  Siena, with its massive "Campo" is the meeting point for all of Tuscany seemingly.  They run their horse race there every year around the Campo.  We didn't see it.  But we did see a huge nighttime sports car rally featuring the finest autos made by Ferrari, Maserati, Alfa-Romeo and others.

Taking the train in Italy is a far preferable way to travel than car.  We had the benefit of traveling in clean cars traveling almost 200 MPH in almost serene silence - with some of the greatest views ever.  It's fun...and grabbing a panini and a water is the perfect way to relax and have lunch aboard the train.  

Positano.  What can we say other than it was a 3-day dream.  Everything that you could possibly photograph is present in this sea coast paradise.  Staying at the singular Covo dei Saraceni provided us with a view out of our bedroom window that could stop time.  It was THAT beautiful!  The views of villas tucked into the mountains; the roads that snake their way down to the beach, the lovely little shops that adorn the narrow streets all make for fantastic photographs so compelling that friends would envy you and your experience.  From Positano, we took a day trip out to the Isle of Capri.  Capri, for us, was like Italy's Catalina Island - kinda honkytonk and overpriced yet still very fun.  Especially when you bus up to the top to take in the wildly sweeping and sometimes scary sights from Anacapri, the island's little town that's 'above it all.'  We toured the historic Villa San Michele with its stories of Axel Munthe, the one time owner and Renaissance man in his own right.

Finally, we finished with 3 days in exciting unstoppable "Roma".  Can there be any more excitement?  Any more history? Any more style?  We saw everything: the Colosseum, the Forum, the Pantheon, the Piazza Navone, the Carra Calla Baths, Circus Maximus, Palatine Hill, The Arch of Constantine, The Villas of Borghese.  We rowed boats, we road bicycle carts, we got lost.  Moreover, we ate gelato at the 150-flavors of Della Palma.  We heard stories about Roman Emperors and the various peccadilloes, their loves (and lovers!) and their battles.  Both won and lost.  

This whole trip will go down in our memory as arguably the greatest trip that we ever took.  We've been together almost 20 years and, thanks to our agent and her team at this travel company, we enjoyed our 2nd honeymoon to the max.  Not once in our 12-day itinerary did we have a hiccup.  Everything that our agency arranged for us from tours, to drivers to train departures and tickets etc went off without a hitch.  All the I's were dotted...all the t's were crossed.  I would recommend this travel agency as a 5-star travel agency to anyone who would ask.  I'd trust them completely.  Indeed, I have the pictures to last a lifetime.  I have memories that will last even longer.  

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Italy Tour Review: Venice, Florence, Rome, Naples, San Gimignano, Siena, Amalfi Coast, Mask & Cooking Classes, Winery Visit, Capri
The majority of the trip was wonderful but there were some issues. The highlights were 1.) In Venice the Gondola Ride with Champagne, the hotel which was a great location, the Mask Class was fun & well organized, the trip to the Islands, the Food Tour with our guide, the promptness of all the transfer guides; these were wonderful.2.) In Florence the Cooking Class was fun however nobody told the chefs most of our group were vegetarians. Luckily they rearranged the menu although we were late because we had to walk over a mile to get to the class which was posted at the wrong location so we paid to take a taxi back to where the class was being held. The tour to San Gimignano & Siena started off a bit strained because of the mile walk (remember 2 people were over 70 years old) to get to the tour office. The guide spoke so softly 2/3 of the bus could not hear her, even asking her to speak up numerous time. Toward the end of the bus ride there she gave us headphones. The trip to the Chianti Winery was fabulous. Maybe even a highpoint. We were dropped off at 11:00 at night in a warehouse looking area with no pick-up. We ask for a taxi. The first taxi kicked us out because he could only take 4 so we waited for a second one. The hotel in Florence was nice with a spa. We checked out & paid any expenses. Later the hotel texted my son in Hawaii regarding 990 euros for the rooms mistakenly asking him to clear it up. 3.) In Rome the Vatican tour was so crowded (we did not know it was Italy's birthday/holiday) glad we had fast tickets. Stopped for lunch & had lunch with the guide (we paid). He was very knowledgeable about the Forum, Circus Maximus & Coliseum. The hotel was nice.  4.) Naples was really nice. Loved our guide who drove us around the various towns & Amalfi coast. The following day we toured Pompeii with another guide. She was also wonderful. Glad we had fast tickets. We didn't know it was another holiday (Armistice Day) so entrance fees were free & very crowded. The boat ride to Capri was the best day. Loved the private boat with the Captain. The only hitch this day was we finished early the guide back at the boat launch told us the Taxi was paid for but the driver said she was wrong so again we paid for another Taxi.   

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Italy Vacation Review: Tuscany, Siena, Florence, Wine Tasting, Cooking Class, 11 Nights

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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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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