When you think of Tuscany, you can already imagine the green hills and practically taste the lingering pleasures of Chianti wine. Your custom tailored Tuscany tour of Medieval cities shows you the celebrated Italian province by taking you deeper into the cities you already know, and into the countryside towns protected from the toils of time like a secret. Let your private guide lead you to Renaissance artwork and down preserved streets of medieval villages holding close to heritage and tradition....
Customizable Itinerary
Day 1
Florence – Familiar Florence
The city of Florence is at once newly exciting and wholly familiar. When your private transfer greets you at the airport, you can feel your heart racing, eager to set your eyes on a city known for art, architecture, and legendary leaders. The old city walls layer various districts of the city, culminating with the 13th-century walls that continue to encircle the historic center. In the heart of the city, you can see the towering red brick dome of the Florence Cathedral, the largest brick dome in the world, set behind the pink and white marble façade. Renaissance and medieval palaces continue to line the streets, now filled with boutique shops and apartment complexes. The city’s officials fill the halls and rooms of the Old Palace located in Piazza della Signoria. Statues vibrant with detail decorate the large plaza, each telling a story of its Renaissance designer and ancient content.
After your settle into your centrally located hotel, your guide meets you in the lobby, enthusiastic to lead you on a private tour of Florence’s luxurious sites. The scent of freshly made gelato drifts out of elegant gelaterias. You can see the influence of the Medici’s in much of the city, including inside the family’s church, the Basilica of San Lorenzo. The church was erected in the 15th-century and has maintained a graceful interior. The polished marble floors lead to the high altar, flanked by tall-pillared archways. The design is unique and fits the elaborate tales of the historic wealth and exuberance of the family that helped shape much of Tuscany.
What's Included:
Day 2
Florence – Essence of the Pisan Republic
Day 3
Florence – Leisurely Lucca
Day 4
Florence – Over the Etruscans
Day 5
Siena – Medieval Towns and Lunar Landscape
Day 6
Maremma – Slice of Life
Day 7
Maremma – The Maremma
Day 8
Florence – Preserving Memory
Trip Highlights
- Enjoy a private tour of the Renaissance artwork and architecture in the vibrant city of Florence
- Experience the celebrated flavors of a local Pecorino cheese farm with a private visit to see the process of cheese-making from start to finish
- Witness the marvelous landscapes of Crete Senesi, an overlooked, yet, sensational region outside the city of Siena
- Discover the charms of Pisa, from its Roma roots to the Piazza dei Miracoli where the Leaning Tower stands
- Climb to the top of the Guinigi Tower for an unparalleled view of the Tuscan countryside and the medieval city of Lucca
- Revel in hard to reach historic towns filled with culture and unspoiled by time
Detailed Description
Cypress, oak, and olive trees rise and fall with the hillsides. Vineyards carpet the valleys. Historic towns watch over the landscape. These are the quintessential images of Tuscany. On your 8-day Tuscany tour of Medieval cities, you will witness gardens and towers, preserved ramparts and breathtaking cliffs. Each moment takes you one step beyond the classic splendor and immerses you in the past, present, and future wonders of the towns, cities, and countryside.
Your luxurious tour in Tuscany begins with your arrival at Florence International Airport. Your private transfer greets you at the airport and escorts you into the Renaissance city of Florence where you have the remainder of the day at your leisure. After breakfast the following morning, your guide meets you at the hotel for a private tour of Florence’s best-known, and lesser-visited treasures, for an all-encompassing exploration. Travel to Pisa where you can discover the remnants of the Pisan Republic, from Piazza dei Miracoli to the Church of Santa Maria della Spina.
In Lucca, you can stroll around the historic city walls and climb to the top of the central tower, which offers views of the red-tiled rooftops and surrounding lush landscape. The following day, you venture to the towns of Arezzo and Cortona, both providing enchanting characteristics of historic Tuscany dating back to the Etruscans. When visiting Siena and Monteriggioni, you find the captivating architecture of the Middle Ages and the exquisite landscape of Crete Senesi. Travel to Volterra for a day to traverse the cobbled streets of the medieval hillside town, followed by a private guided tour of a local Pecorino cheese farm.
When you arrive in Val d’Orcia, your guide leads you through numerous villages often overlooked by visitors both foreign and domestic. You can sip on famous wines in Montepulciano and Montalcino or venture into the stunning region of Maremma to visit towns such as Pitigliano and Castiglione della Pescaia. On your final morning in Florence, your private transfer meets you at your hotel after breakfast and escorts you to the airport for your flight home.
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
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Reviews of Zicasso's Referral Service
4.9 stars based on 5790 reviews.
The trip was very well planned by Zicasso's travel company and all of the stops and pick-up points, cars, trains, boats, etc., were there and reliable. We had a fantastic time.
Reviewed By Jeffrey C.
I am writing to express my immense gratitude to the entire team at Zicasso’s travel partner for curating the most spectacular trip to Italy for my family. From start to finish, the level of service was beyond impeccable and truly set a new standard for what we consider luxury travel.
The planning process was an absolute pleasure. Communication was one of their greatest strengths; our contact was consistently available and responses to our questions were nearly instantaneous. This travel company made us feel like we were their only clients. They took the time to understand the different ages and interests within our family, and built a bespoke itinerary that perfectly balanced history, leisure, and unique local experiences.
This was genuine white-glove service in every sense of the word. From the moment we landed, every detail was flawlessly executed. Private drivers were waiting for us, guides were engaging and knowledgeable, and our accommodations were magnificent. We never once had to worry about a single logistic, allowing us to be fully present and enjoy our time together.
If you are looking for a travel partner that offers unparalleled personalized service and flawless execution for a trip to Italy, look no further. Thank you for giving our family memories we will cherish forever.
Reviewed By Christopher L.
My husband and I were thrilled with our recent trip to Italy that Zicasso’s travel designer put together. We began by attending a family friend’s wedding, held in Ravello, on the Amalfi Coast. Due to my husband’s mobility issues, we were met by a driver and headed to the Amalfi Coast. The driver was first class and the trip was very comfortable.
After the wedding festivities, we were able to have the most wonderful experiences visiting the towns of Amalfi and Positano, and our base for one week was in beautiful Sorrento. We attended a cooking class and enjoyed eating what we prepared. We had in-depth learning opportunities in Naples and Sorrento. Every guide we had spoke excellent English and was so knowledgeable. We especially enjoyed Pompeii! A super-fun day was had on the small group tour of Capri. The crew was fantastic and very accommodating in consideration of my husband’s mobility issues.
From beginning to end everything went well. The use of a messaging app was great for making sure everyone was on the same page.
The only thing that was a disappointment was the pizza in Naples. It wasn’t the best.
The hotel in Sorrento was phenomenal - it couldn’t have been better. The view of Mt. Vesuvius from our balcony helped create memories we will have forever. The hotel in Rome was also very nice. It was right in the middle of the main attractions.
We are very happy with our experience with this travel company and would not hesitate to recommend it!
Reviewed By Anne F.
Our trip was a family one, two grandparents over 70, two parents and one adult son, one teenage girl, and one younger girl, 12. Three of us had been to Italy while the others had not. We wanted as complete a trip as we could in 14 days, so we included all the traditional places, Venice, Florence, Rome, and Naples/Pompeii. We spent three days in each and one day in Ferrara. While it was a lot for 14 days, we did not feel rushed.
What I like about Zicasso is they give you options to pick the best fit for your trip—we worked with two other agencies before we picked Zicasso’s travel partner. This travel partner took the time to understand our needs: three hotel rooms, all different in sizes, and tours and timing. Very important was the degree of coordination before the trip with the travel agent; she was available and knowledgeable, and took the time to adjust our needs. One of the best things about this travel partner was they used a van for all the travel, except from Rome to Naples. This was a much better option than the train for seven people and baggage.
During the trip, we were met on time by every driver and every guide. The hotels were excellent and the whole trip went well. When we had a delay on the train, the driver knew it and adjusted our pick-up.
Reviewed By Fred S.
Zicasso’s travel company was wonderful in planning our trip on short notice and in line with our requests and preferences. Their suggestions of what to do and where to stay were perfect. And when we accidentally got off on the wrong island, the travel company quickly got us new ferry tickets to get to the right place. It was all seamless.
Reviewed By Sherry G.
This trip was the greatest week of our lives! Everything planned was better than I could have imagined. The private drivers being coordinated behind the scenes made the trip so easy and removed all the stress of trying to navigate a new country. Every driver and our tour guide was so nice and I feel like we made friends with all of them.
My favorite part of the trip was definitely the cooking classes and that every tour was private and intimate for my wife and I. The connections Zicasso’s travel agent hooked us up with made the trip the most memorable experience. Our travel agent and the travel company took special care of all the tiny details of the trip; our hotel knew it was my birthday and had a special surprise for me! I’m beyond thankful for the perfect honeymoon they provided my wife and I.
Reviewed By Branson S.