Medieval tour in Tuscany

Go back to the Middle Ages for five days.

Medieval tour in Tuscany: Discover the medieval treasures of Tuscany beyond the bustling city of Florence on this unforgettable 5 day tour. From the iconic leaning tower of Pisa to the charming walled city of Lucca, you'll explore some of the most enchanting towns and villages in Italy. You'll get to experience the fascinating history and culture of San Gimignano as you taste delicious local wines, stroll through the narrow streets of Panzano and admire the stunning views of the countryside in Volpaia. Marvel at the striking beauty of Siena's Gothic architecture before exploring the picturesque hillside town of Cortona. This tour is a perfect blend of stunning landscapes, rich history, and delicious food, allowing you to experience the best that Tuscany has to offer. With our carefully crafted itinerary and expert recommendations, you will enjoy an unforgettable trip that will stay with you long after you leave.

The best time of the year to do the medieval tour in Tuscany is from April till September. (summer season). 

Jump to the first day...View Map

All you need for this 5 day trip.

We assume that you travel from Florence, and that you’re leaving from there, this tour fit well with the 2 days in Florence. In case you’re taking this 5 day tour, we suggest using a car. As it is the easiest and best solution for this 5 day trip. If you stay in a hotel you may bring a packed lunch from there, from brakefast before you leave, it may be nice to have later. 

Recommend time to start from Florence is no later than 08.00 (AM)

To get the best prices and make sure everything is taken care of in advance, we recommend ordering everything you’ll need for the trip according to our suggestions. Booking in advance usually gets you the best price. Add the cost of food and anything else you want after. You get to choose the dates, but we don’t suggest shortening the trip. Longer than five days is fine. Ajust according to your wishes and needs.

The 5 day travel plan for medieval tour in Tuscany.

Highlights of the Medieval Tour in Tuscany.

Starting from Florence, a scenic drive through the Tuscan countryside awaits, with stunning vistas of rolling hills, vineyards, and olive groves. Some of the must-visit destinations along the way are Pisa, Lucca, San Gimignano, Panzano, Volpaia, Siena, and Cortona.

Suggested Highlights of the journey include:

• Pisa – Visit the iconic Piazza dei Miracoli and witness the leaning tower of Pisa, a symbol of Italy’s medieval architecture.

• Lucca – Explore the enchanting walled city and walk or bike around the Renaissance ramparts.

• San Gimignano – Marvel at the 14 medieval towers that dominate the skyline of this hilltop town.

• Panzano – A small Tuscan town known for its Chianti wine, indulge in local gastronomy with some of the best restaurants in the region.

• Volpaia – Take a detour to this lesser-known village, surrounded by vineyards, and enjoy a wine tasting at one of the local wineries.

• Siena – Discover Italy’s Gothic architecture and history, embodied by the magnificent Siena Cathedral and the Palazzo Pubblico.

• Cortona – Immerse yourself in the ancient Etruscan culture and visit the Museo dell’Accademia Etrusca.

Glide through the Tuscany landscape, let the sweet aromas of olive oil and wine surround you, while the sounds of chirping birds and church bells fill the air. The lush greenery changes to shades of amber, orange, and maroon in the fall, enhancing the natural charm of the land. As the sun sets over the horizon, the silhouettes of the medieval buildings become more dramatic and captivating, creating a truly unforgettable experience. 

First day: Leaving Florence

Pick up your car.

We suggest you get the car from Florence Airport as it’s more dependable and has more cars. It’ll save time compared to picking up a car from different places. Plus, if you’re coming from somewhere else, you can get to your 5-day trip straight from Florence Airport. If you’re already in Florence, we have a train ticket for you at Florence SMN to start your journey. (ajust the time and station) If you plan to go by plane to the airport in Pisa, just ajust the pickup destination.

Everything must be adapted to your needs in the order of the car, the size of the car, date, delivery. Book car now , in advance to secure best offer!
When it comes to returning the car, we have preset delivering back to the airport in Florence. But there are also trains, so the car can be delivered other places if you wish. 

Drive from Florence airport to Pisa

The journey from Florence airport to Pisa is a pleasant one, taking approximately one hour. It is recommended to drive on the south ruoute, there are many restaurants and petrol stations along this route. This is particularly useful if anyone in the car is feeling hungry or in need of a restroom break. The drive itself takes you through some beautiful modern Italy.

When you get to Pisa.

Short and efficient stop in Pisa

Find a parkinglot, eat something if needed, and go directly to Campo dei Miracoli. In advance, we recommend that you have purchased one of these tours. You don not save money not to buy it now, and there will be lines. Just buy it now to secure the trip. They have FREE CANCELLATION in case something happends.
In Pisa we don’t have much time it’s past 12 and we only want to take with us the most important experiences from Pisa and “the magical square”.

NB! Buy the tours NOW!

Go to Piazza Delle Vettovaglie.

Located in the heart of Pisa, Italy, Piazza delle Vettovaglie is a must-visit destination that offers a delightful mix of history, culture, and gastronomy. This stunning square was once a bustling food market during the Renaissance period, and today it is home to an array of charming cafes, restaurants, and shops. Visitors can enjoy a leisurely stroll while taking in the vibrant atmosphere and admiring the picturesque architecture of the surrounding buildings. Piazza delle Vettovaglie is also an excellent spot to taste some of the finest Italian delicacies, such as fresh pasta, gelato, and wine. Whether you are a history buff, a foodie, or simply looking for a charming location to relax and unwind, Piazza delle Vettovaglie offers an unforgettable experience that is not to be missed.

Here is a list of suggested restaurants in the area.

If you want you can book a table now, and remember to dress appropriately. If you are perspiring or your shirt is soiled, please consider changing before arriving.

Drive from Pisa to Lucca -Find your stay (book now!)

This 5 day plan says you’ll sleep in Lucca on the first nigth. We suggest different places to stay, based your wishes and needs. Remember to book as soon as you’re sure you’re going. If you wait booking the accomodation till you are there you are in a worse possition for negotiation than the position you have before you go. Pick and choose, wisely  ORDER ONE NIGTH NOW!.

Alla Corte Degli Angeli, Lucca

A nice boutique hotel with, hot tubs and nice shower. This is good place to relax.

The Tuscanian Hotel, Lucca

This hotel is very central inside the city walls of Lucca.

Second Day: Lucca and San Gimignano.

Let the fun begin.... Early!

We suggest that you remind everyone to bring a packed lunch for a long day filled with experiences in the heart of Tuscany. Go to the Dumo in Lucca, look at the Volta Santo and make sure to head to Piazza Del Mercato after, as it has remnants from the Roman amphitheatre that used to occupy the area. It’s highly recommended to take this guided tour for an in-depth understanding of Lucca’s history and architecture. Investing in this tour is worth every penny, especially when you’ve come so far to explore Tuscany. Ensure that you don’t miss out on this amazing experience to gain insights into the landmarks and buildings that make Lucca a must-visit destination in Tuscany.

Jump into the car, start rolling towards the medieval version of New York!

The Medieval tour in Tuscany is all about experiencing the charm and beauty of Tuscany now, you are about to experience the medieval charm of San Gimignano, the town of beautiful towers in Toscana with a fascinating history. You will find yourself amidst the ancient walls of the UNESCO world heritage site, strolling through the narrow streets surrounded by buildings that date back to the 15th and 17th century. The town used to boast of over 70 towers, but today only 14 remain. Remember to park your car outside the city before making your way to explore the town.

As for your lodging, we have selected a charming and beautiful hotel that has an intriguing but horrifying history. The building was once used for executing the women who refused to give the “first night of the bride” to the squire having legal rights, and if declined, the inquisition ensued, and women were hanged in the same building. Nonetheless, the building showcases original 1600s frescoes that are a sight to behold, the rest is history and that is why you came to San Gimignano.

Reguarding food.

If you find yourself in San Gimignano in the afternoon (day nr.2) and in need of some food, there are many great restaurants nearby to choose from. Some popular options include La Vecchia, La Cisterna, and il Pino. However, if you are looking for a more interactive experience, we highly recommend signing up for a local cooking course. This will allow you to learn about traditional Tuscan cuisine, prepare your own dishes, and enjoy a delicious meal at the end of it all. Some cooking course options include those offered by Tuscany Cooking Class, La Mandragola. Whichever option you choose, you are sure to enjoy some delicious Italian cuisine and have a memorable experience in San Gimignano.

Try wine tasting since you are in some of the world's top wine regions!!

Third day: To Siena & Chianti Classico - Land.

It is time to indulge in the world-renowned flavors of Chianti Classico wine – the ultimate temptation for wine enthusiasts. Nestled in the heart of Tuscany, the Chianti region boasts some of Italy’s most picturesque landscapes and is home to nine towns, including Panzano, Volpaia, Radda, Gaiole, and Greve. This area is an irresistible destination for those who want to experience the best of wine, culture and traditional cuisine.

Chianti Classico wine is characterized by intense and complex aromas, with flavors of cherries, blackberries, plums and hints of spices. The famous Chianti area offers visitors plenty of opportunities to taste and explore the different varieties of wine. Wineries are dotted around the rolling hills, offering superb wine tasting experiences, from small family-owned estates to grand modern cellars. Take a tour to see the wine-making process from grape to bottle and enjoy a guided tasting. When you go from San Gimignano to Siena this day, you should make stops at some farms along the road for a wine tasteing. Stop by the town of Panzo and Volpaia on your way. It is worth the stops.  

The beauty of the Chianti region…

is another irresistible temptation. From the medieval streets and castles of Radda and Gaiole, to the stunning landscapes surrounding Panzano and Voplaia, visitors are spoiled for choice. The area is perfect for those who love the outdoors, with countless trails for walking, cycling or horse-riding. You can venture into one of the many vineyards for a picnic amongst the vines or take a cooking class and learn to prepare the traditional dishes of the region.

Chianti Classico is an irresistible destination that will leave wine lovers, foodies, and culture seekers yearning for more. This place is a feast for the senses with its diverse range of flavors, breathtaking scenery and boundless charm from the surrounding towns. Plan your trip now, to feel the magic first-hand.

You will arrive late in Siena due to enjoyable experiences.

Due to the late arrival you and your travel partners probably vill get the third nigth means that you have to have a hotel sorted out before you are there.  We have prepared  some recomened lovly hotels that we have done research about and found to be good. BOOK 2 NIGTHS HERE! For example  in one of the hotels in the city centre, such as these (As shown).

A Hotel with a View.

This hotel is from 1100- modern and comfy.

Reserve this great hotel.

Unforgettable in Siena senter.

Medieval tour in Tuscany, day four; enjoy Siena.

By now the medievalt tour in Tuscany left you with plenty of impressions. The fourth day is t be spendt in Siena.

A day in Siena is a day filled with history, beauty, and culinary delights. The heart of Siena is the Piazza del Campo, a stunning medieval square surrounded by elegant palaces and home to the renowned Torre del Mangia. A climb to the top of the tower offers breathtaking views of the city and its surroundings. Just steps away is the Piazza Pubblico, where you can visit the town hall and the Museo Civico. The highlight of your day will be a visit to the impressive Siena Cathedral, known as the Duomo in Siena. Its intricate facade and stunning interior are sure to leave you in awe. After a day of sightseeing, according to your wishes we hope you had the time to relax proper this day. Siena is a gem of Tuscany that should not be missed, grasp the moment!

Suggested tours in Siena.

Today, the choice is entirely yours to make the most out of your day in Siena. We recommend taking a guided tour that covers the major highlights such as the Dumo in Siena and Piazza del Campo, two must-visit locations. Siena is a beautiful city, so enjoy your time here, relax, eat some delicious food, and take in the medieval atmosphere that Tuscany has to offer. As you step into Siena, you will find yourself in the heart of Tuscany. So, take a deep breath, let yourself feel immersed in the atmosphere, and enjoy your time in this stunning city. Enjoy the hotel, tomorrow we will move on.

Day number 5: Drive to Cortona

The trip around Medieval Tuscany is almost over and will end shortly in Cortona.

Packed up the car to leave the hotel in Siena it is time to move to Cortona. In cortona you don’t want to miss the Museo Dioceano. Beato Angelico is also one of the grate art peaces you should see before the 5 day medieval itineray is over. 

We also reccomend spending some time to learn more about the Etruscan culture, that were strong in the area in the medieval times. 

To wrap up this experience:

When you feel it is time to leave Cortona you can go back to Florence to deliver the car, or move further on to a new travel plan.

Whatever you choose to do we hope above all, that you and your travelpartners have had the travel of a lifteime. However  we hope you, and all patricipants without a doubt can give us a proper feedback online in order to help us and other users. 

With this in mind, give us feed back on all our platforms. Sign up for our newsletter/travel club and leave a comment below or contact us if any questions. 

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