The road to Rome remains unchanged in parts of Tuscany, leading across the unspoiled landscape. Vineyards decorate hillsides. Cypress trees shade unpaved country lanes. Medieval towns that were built around historic churches maintain strong connections to their roots. Your custom tailored Tuscany tour takes you on the route of pilgrims known as Via Francigena. Stroll alongside historic walls; meander around ancient burial grounds;...
Customizable Itinerary
Day 1
Florence – The Route of Pilgrims
Via Francigena once led pilgrims from France to Rome during the Middle Ages. The route connected abbeys throughout the countryside, linking sacred places across Europe’s Christian world, followed by merchants and travelers alike. A large portion of the road, 250 miles worth, winds along the Tuscan landscape and connects small villages that once settled around the historic churches. When you arrive at Florence International Airport, your private transfer greets you.
Your first introduction to the province is the lush greenery draping over the undulating hills. Cypress trees line unpaved roads, and oak trees flourish in the distance. You make your way to the Pontremoli, a stunningly preserved medieval town set against the lushness of Tuscany’s northern region of Lunigiana. The castle was erected in the 11th-century and continues to watch over the streets. The marketplace still brims with energy along the cobblestone streets on Wednesdays and Sundays. The 17th-century cathedral stands in the center of town with a rich Baroque interior. You easily settle in town with the aroma of pesto drifting out of the local restaurants.
What's Included:
Day 2
Florence – On the Winding Road
Day 3
Avenza – Rediscovering Tuscany
Day 4
Pietrasanta – Along the Castle Walls
Day 5
Lucca – Finding A Little Italian Athens
Day 6
Altopascio – Outside of the Seasoned Walls
Day 7
Castelfranco di Sotto – Following the Medici
Day 8
Elsa Valley – The Hills of Val d’Elsa
Day 9
San Gimignano – Towers in the Distance
Day 10
Monteriggioni – Roots of the Road
Day 11
Siena – Traveling to Traditions
Day 12
Siena – End of the Road
Trip Highlights
- Visit a number of medieval and Renaissance villages off the beaten path of visitors, taking you into the heart of Tuscany
- Travel along an ancient road that has guided pilgrims from France to Rome for a millennium
- Discover remarkable churches, abbeys, and monasteries overlooking lush valleys and stunning hills
- Stroll along antique city walls that have protected art and culture for centuries
- Witness the marvels of Roman and Etruscan ruins, along with the remains of their culture in archeological parks
- Wander through fortresses, castles, and towers that offer unparalleled views of Tuscany and the magnificent coastline
- Revel in physical activity while simultaneously slowing down to experience the beauty of Tuscany’s culture, traditions, and natural wonder
Detailed Description
The pilgrim’s route in Tuscany through Via Francigena, shows you the unique charms of the Italian province, from olive groves to medieval alleys, leading you into the enchantment of lesser-known villages and often overlooked artwork. On your 12-day journey along via Francigena, you can walk, mountain bike, or horseback ride along the historic pathway, leading you from the province’s northern edge to its southern borders. Part of the beauty of the modern pilgrimage route is that you can begin and end your travels at any town along the way.
When you arrive at Florence International Airport, your private transfer welcomes you to the region. Soon you can settle in the small northern Tuscan town of Pontremoli. The following day, your guide meets you at your hotel with a bicycle and hands you a Pilgrim’s Passport, where locals in each city can stamp your document as a testament to your unique journey. You leave Pontremoli en route to Aulla, visiting the towns of Ponticello, Filattiera, Filetta, and Villafranca in Lunigiana. Each town brims with Romanesque churches and sensational castles that lend a storybook ambiance to the countryside.
On your way to Avenza, you have views of the seaside while biking alongside abbeys and fortresses. Your view of the Apuan Coast leads to Sarzana and Luni before you continue to Avenza. After breakfast, your guide leads you into the countryside to the Ducal Palace of Massa and the Aghinofli Castle of Montignoso. You settle in for the night at Pietrasanta. After exploring Pietrasanta in the morning, you set out for Valdicastello and Camaiore, both invoking an ethereal charm emanating from the historic churches. Montemagno has remnants of a historic hospital dating back to the 11th-century. Once in Lucca, you can relax inside the celebrated antique city ramparts.
The route continues, lined with cathedrals and churches in the towns of Segromigno, Capannori, Lunata, and Rughi. In Montecarlo, you find a quiet, preserved 12th-century town before reaching Altopascio. The path to San Miniato has you visiting the Hospice of Tau. En route to Gambassi Terme, you witness castles and decadent religious artwork, including the wonders of an Etruscan Tomb in Elsa Valley at Montaione. You have a short journey to the medieval hillside town of San Gimignano, known for its tremendous towers.
The road winds across the hilltops where you can take in the Roman Ruins and Etruscan tombs at Poggibonsi and Colle Val d’Elsa on your way to Monteriggioni. The final leg of your tour takes you from the fortified town of Monteriggioni to Siena, a medieval city that once rivaled the beauty and power of the provincial capital of Florence. After breakfast on your final morning, your private transfer will meet you at your hotel and escort you back to Florence International Airport. However, you can always stay in Siena and continue the path of the pilgrim, making your way all the way to Rome. For trip extension ideas, browse the reviews for Italy tour operators on Zicasso.
Starting Price
$5,400 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 5984 reviews.
Zicasso's travel agent created an itinerary and experience that was simply perfect. Every hotel experience, guide, and driver was excellent. She was kind, patient, knowledgeable, and made the perfect suggestions. I loved working with her! Thank you to our agent, the tour operator, and Zicasso for a wonderful trip!
Reviewed By Anita L.
The trip was wonderful. Zicasso's travel agent and her staff planned the perfect 10-day trip. The accommodations, the drivers, the guides, and the restaurant recommendations were perfect. The communication was excellent and timely. They went above and beyond to make sure we were comfortable and happy. The staff were very attentive and flexible, even when we wanted some small changes, such as pick-up times for the drivers. They adapted and made it all work. This travel agent is absolutely terrific.
Reviewed By Marci M.
Our Italy trip with Zicasso’s travel partner was nothing short of spectacular! Referred by a friend who had an amazing experience, we decided to give it a try and were not disappointed. Our agent was fantastic, always ready with answers to our questions and providing excellent support throughout our journey.
In Tuscany, we visited beautiful wineries and enjoyed a delightful lunch with the vintners, who were incredibly warm and welcoming. Her attention to detail was evident when she adjusted our plans due to weather changes and even checked in on us when we were slightly delayed for a tour.
Siena was breathtaking and our hotel in Rome was perfectly located, allowing us to walk to all the major sites. One of the highlights was a small boat tour around Capri from Amalfi—perfect weather and stunning waters made it unforgettable. The cooking class on the Amalfi Coast, set on the side of a cliff, was exceptional and having personal tours just for the two of us was an unexpected and delightful bonus.
We can't express enough how much we enjoyed our Italy trip. The travel partner exceeded our expectations and we highly recommend them for a truly memorable experience!
Reviewed By Kent S.
Zicasso’s trip coordinator and her team did a fantastic job, not only in planning the trip to meet our needs and wants, but also in personalizing it as needed. They were also available as we needed them to adjust things, such as pickups, and even made some dinner reservations for us. With our budget, they set us up in excellent hotels that fit our desire for the trip to be a wonderful anniversary getaway. Her staff were also very helpful. We would strongly recommend them for a trip to Italy!
Reviewed By Rajesh J.
Zicasso's travel planner and her staff did a perfect job for our family of six. She made our trip seamless!
Everything she planned was perfect and no detail was left out. I would use them again and again for my travels to Italy.
Reviewed By Sally F.
My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.
Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.
Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.
Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.
What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.
Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.
As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.
Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.
The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.
This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.
Reviewed By tasmia S.