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Siena Cathedral

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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.

Siena: Palio Walking Tour

5. Siena: Palio Walking Tour

Learn about the unique history of Sienna on a walking tour of the medieval old town with an informative guide. Get to know the different "contrade" or districts that make up the city and hear how they date back to medieval times. Stroll through the Piazza del Campo, where the famous Palio horse race takes place every year on July 2nd and August 14th, featuring a contestant from each of the contrade. Visualize the colorful banners and crests of the competing contrade and learn how the competition has defined civic life in the city for centuries. Hear stories about the life and culture of the city from locals and visit the Museum of the Contrada for a more official account. Then head to the Duomo of Siena and check out the characteristic black and white marble interior of the cathedral designed to symbolize the black and white horses of the city's founders. Afterwards, switch gears and enjoy a local tasting experience at a traditional cafe. Try Panforte, Ricciarelli, and Cavallucci, typical sweets famous around the world. Wash them down with a glass of Vin Santo del Chianti.

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What people are saying about Siena Cathedral

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!