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Siena Cathedral

Day trips

Our most recommended Siena Cathedral Day Trips

From Florence: Tuscany Day Trip with Optional Lunch and Wine

1. From Florence: Tuscany Day Trip with Optional Lunch and Wine

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

2. Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

Discover Tuscany on a guided day tour from Florence to the medieval cities of Siena, San Gimignano, and Monteriggioni. Enjoy views of rolling hills and vineyards, with a stop at a Chianti winery for a traditional Tuscan lunch and wine tasting. First arrive in San Gimignano, a tiny medieval town that has remained intact through the centuries. Sitting upon a hilltop, it is famous for its numerous towers, frescoes, and other art treasures. Enjoy more free time to discover this fascinating city on your own. Next, visit the charming historical hamlet of Monteriggioni, a medieval village enclosed by its famous walls, which remained standing to this day. Afterward, you will cross the Chianti rolling hills and then arrive at a small and typical winery. There, taste 4 wines, and sample balsamic vinegar and other locally produced products. Your final stop is in Siena, where you will have free time to walk along the narrow medieval streets, admiring the splendid palaces, the Cathedral, Libreria Piccolomini, and the famous shell-shaped Piazza del Campo.

Sunset in Siena & Dinner in Chianti Tour from Florence

3. Sunset in Siena & Dinner in Chianti Tour from Florence

On this afternoon and evening tour, you will depart Florence in the early afternoon for the 1-hour drive to Siena. Enjoy the scenic Chianti countryside of delightful hills and vineyards en route. You will have free time in Siena to take in the medieval atmosphere as you wander through its narrow streets. Admire the artistic heritage of this city, exemplified by the Gothic cathedral and the impressive Torre del Mangia in the stunning, world-famous Piazza del Campo. Before leaving Siena, you will have a chance to experience the sunset from a panoramic viewpoint. Then you will continue on to a typical wine estate in the heart of the Chianti region. Nestled between the Tuscan hills and amid vineyards you will be served a delicious dinner that includes typical Tuscan products such as salami, bruschetta, and other unique delicacies. Dinner is accompanied by top-quality local wines personally selected by the owners of the winery. Enjoy this perfect way to end your afternoon in Chianti!

Full-Day Excursion to Siena, San Gimignano & Pisa

4. Full-Day Excursion to Siena, San Gimignano & Pisa

Enjoy Tuscany's top highlights in one day. Take this small-group tour in a comfortable air-conditioned minivan. Explore the breathtaking towns of Siena, San Gimignano and Pisa. Visit Siena’s historic centre with an expert guide, then stop in the medieval town of San Gimignano. At the end explore Pisa and its Leaning Tower. Siena and San Gimignano are the symbols of Medieval and Gothic architectures; characteristic elements are the historic towers, the pointed arches, and the narrow streets. Moreover this Tuscan area is known also  for its superb food specialties, such as panforte and pici, which you will surely have the chance to taste. Then head to Pisa and stand under the Leaning Tower of Pisa and walk through Piazza dei Miracoli, home of many historic sites. You will have free time to stroll around the city before returning to Florence.

Full-Day Excursion to Siena, San Gimignano & Chianti

5. Full-Day Excursion to Siena, San Gimignano & Chianti

Enjoy a full-day excursion by minivan to see the beautiful Chianti area and to visit the cities of Siena and San Gimignano.  Depart at 9:00 AM from Piazza Cavalleggeri, the meeting point located in the city center of Florence. Stop at Piazzale Michelangelo for few minutes to see the splendid panorama and then in one hour you will arrive in Siena. Take a guided tour of the city center, including Piazza del Campo and the Cathedral. There is free time to walk by yourself in the narrow and ancient streets.  Then leave Siena to arrive in Monteriggioni, an old Medieval little village. After a short stop, continue to San Gimignano where you will have free time to explore the city center on your own. San Gimignano is famous for its towers, vernaccia wine and its characteristic craft articles.

Florence: Pisa, Siena and San Gimignano Small Group Day Trip

6. Florence: Pisa, Siena and San Gimignano Small Group Day Trip

Visit three of the most famous and fascinating towns in Tuscany. Enjoy the comfort of a small group tour and learn from your expert English-speaking tour leader. First, discover the nearby town of Siena. Its historical center is considered a UNESCO World Heritage Site. Marvel at Piazza del Campo and the majestic Siena Cathedral. After a short drive through the enchanting countryside, stop in a small, family-owned winery. Enjoy an exquisite lunch of Tuscan appetizers, pasta, and desserts paired with local wines. Next, explore San Gimignano, also known as the town of towers. Discover the fourteen medieval skyscrapers which still remain perfectly preserved. Enjoy the last stop of the day in Pisa. Visit the Square of Miracles, where you can find the iconic Leaning Tower. Spend some time snapping pictures of the famous Italian symbol. After your full-day visiting three of Tuscany’s highlights, return to Florence.

From Florence: Siena & San Gimignano Day Trip with Lunch

7. From Florence: Siena & San Gimignano Day Trip with Lunch

Meet your driver and tour leader in your hotel lobby to embark on a full-day trip to Siena and San Gimignano. Hop aboard a private vehicle for a scenic drive through the rolling hills of the Chianti region, covered with vineyards and olive groves. First up, make your way to the town of Siena, stopping at the Basilica of San Domenico. Inside the church are the relics of Saint Catherine, the patron saint of Siena. Take a stroll to the Piazza del Campo to see the political center of town where the famous horse race Il Palio is held twice a year. From there, meander towards the Gothic Cathedral, which boasts an impressive collection of artworks by Michelangelo, Donatello and Bernini. Along the way, pass by a delicatessen that sells wild boar salami. If you fancy it, you can step inside for a tasting. Then, it’s onward to lunch at a boutique winery surrounded by the Chianti hills and vineyards. Taste the wine and the famous extra virgin olive oil with seasonal produce. Make your second stop at the walled town of San Gimignano, a UNESCO World Heritage site. See the 13 towers that dominate the skyline as you drive towards it. Learn how San Gimignano gained importance during the Middle Ages as a stop on the pilgrim route between Italy and France, known as Via Francigena (the road to France). The townsfolk produced silk and cultivated saffron that still grows around its foothills. Another industry that still exists here is that of Vernaccia di San Gimginano, a white wine. Learn about the region's history and where to find the best artisanal stores, coffee shops and gelato spots from your guide. Check out a selection of artisan stores selling locally made products. Stroll the winding streets, admiring spectacular views of the valley beyond. Afterward, meet your chauffeur for the transfer back to your accommodation in Florence. On the way, stop for one last magnificent panorama at Piazzale Michelangelo, and gaze upon views of the city. Before you leave, don’t forget to ask your local guide for tips on what else to see, do and eat during your stay in Florence.

Rome: Day Trip to Siena & San Gimignano with Wine Tasting

8. Rome: Day Trip to Siena & San Gimignano with Wine Tasting

Full day private tour – food and wine tasting included Enjoy a full-day journey from Rome, through the Chianti hills, to visit the cities of Siena and San Gimignano. Siena, a beautiful medieval city in Italy. You will visit the heart of Siena and the central square known as “Piazza del Campo”, known worldwide for the famous “Palio”, a horse race twice around the square in a medieval style every summer. Siena is famous not only for its wine but also for its sweets: the “Panpepato”, “Panforte”, “Ricciarelli”. Stop for a good Italian coffee and taste a typical sweet of Siena. Continuation to San Gimignano, a UNESCO World Heritage Site, known as “The City of the Hundred Towers” and it still maintains its original features and timeless charm. Furthermore, the name ‘San Gimignano’ is linked to one of the most historical Tuscan wines:” La Vernaccia di San Gimignano”. Arriving in San Gimignano you will explore its charming medieval streets, visit the old center of this wonderful city where the famous Chianti wine is produced. Stop for a wine tasting and local products in a beautiful wine cellar: 10 different types of wine, then visit the estate and learn about the processing of the grapes. Lunch at the restaurant of the estate. Departure for Rome about 4:00 pm.

From Florence: Private GUIDED tour, Siena & San Gimignano

9. From Florence: Private GUIDED tour, Siena & San Gimignano

• Stop At: Siena, Tuscany. Experience Siena through the expert and knowledgeable lens of a professional tour guide! Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore with your guide Siena’s rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts! Duration: 3 hours • Stop At: Castello di Monteriggioni, Tuscany. Make a lovely stop in the small, fortified village, which is still surrounded by its original medieval walls. Located not far from Siena, Monteriggioni is a great spot for a short walk after lunch at one of the local restaurants. Duration: 2 hours • Pass By: Village of Fonterutoli, Siena. Fonterutoli has been an important village ever since the Roman times. The Via Romea passes here, and is still today traveled by pilgrims from all over the world. Location of the historic Mazzei family since 1435 (for 24 generations), the village of Fonterutoli maintains its medieval appearance intact. Stroll in the village to stretch your legs and take some beautiful photos. Duration: 30 minutes •Stop At: Organic Farm/Winery Tenuta Casanova, Tuscany. (*optional) *OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will show you around the property, his wife will prepare a delicious and unforgettable lunch for your private group. The owner will show you to his cellar to admire his Super Tuscans and Chianti Classico wines -Craft Wine- and to the nearby Acetaia, a vinegar cellar, with old vinegar. Afterwards, experience a unique dining setting while taking in an amazing Tuscan panorama. You will taste organic specialties, such as the typical Lasagna with traditional sauces, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses seasoned with an incredible aged balsamic vinegar. Wine will accompany this lunch every step of the way. Each of the four main courses and desserts will be paired with a different and distinctive glass of wine. We will conclude with ice cream and balsamic vinegar or other desserts. (This option will slightly reduce your time to visit the cities of Siena and San Gimignano, and exclude the possibility to visit the fortress of Monteriggioni). Duration: 2 hours •Stop At: Historic Center of San Gimignano, Tuscany. The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany. San Gimignano is a treasure of medieval architecture, frozen in time at 1300 AD. Above all, it is famous for its ancient towers, which still stand out from its skyline, earning it the nickname Manhattan of the Middle Ages. This is the last destination of the day, before returning to Florence. Duration: 1h30m

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What people are saying about Siena Cathedral

Overall rating

4.5 / 5

based on 1,688 reviews

Sara (guide) and Fabio (driver) were excellent. We never felt lost, even though each stop went by very quickly. Sara kept us engaged to whichever degree we wanted, and read the room to keep our energy up or let us rest. She was extremely kind, informed, and personable. English speakers will be able to communicate with Sara seamlessly! Other travelers: 1) Eat breakfast before you board! Our group was hungry; 2) Bring sunscreen - the Tuscan sun is no joke!; 3) Pack snacks; 4) Come prepared with lots of 1 Euro and 50 cent coins for public restrooms and factor in wait time; 5) You're able to keep items on the bus, so bring a bigger bag to store your souvenirs and a smaller bag to carry with you; 6) You'll have time to nap and relax on the bus, but never longer than 2 hours at at time; 7) You may think you won't have enough time in Pisa, but for real you only need 30 minutes so this is the perfect way to see it; 8) The meeting point at the train station uses "Walkabout" NOT "GetYourGuide."

We really enjoyed this excursion. Manolo was an excellent guide. Very knowledgeable but also just good at keeping the group together and moving along on the itinerary. I enjoyed all of our stops, but I especially liked Siena where the local guide shared a lot of fun details about Siena’s history and their church was absolutely beautiful. We also really enjoyed the winery and lunch - it was worth paying the extra for this part in my opinion! It is a lot of walking, including to the pick up and drop off locations for the buses since they can only get so close to city centers, so be sure to pack comfortable shoes!

This was fantastic. Out of our two week trip in Italy this was up there in terms of our favorite activity for myself and my husband. Our tour leader was Alessandro, who was funny, personable, very informative and kept our large group together and moving seemingly with ease. And our bus driver Nando was fantastic as well! We loved all of the stops and the lunch and wine were delicious plus a very fun time to meet the other travelers. If you are considering booking this, definitely go for it, especially if this is your first time in the area, you’ll have a great time!

What an amazing trip this was. Special thanks go to Elizabetta (Amazing, Funny, Joyful, and a friendly Tour Guide) and Giancarlo (Super Driver) for making this a memorable trip. Although I experienced so many tours in so many countries, I never wrote a review. However, this is just something special and I confidently can say this is the best tour I’ve ever had. Yes, “ever”.

Totally worth going to get a glimpse of Tuscany beyond Florence. Lunch with wine tasting is great. Sienna is a very interesting city and would love to return on a road trip in future!