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PisaWine tasting & winery tours

Our most recommended Pisa Wine tasting & winery tours

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

1. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and choose a guided tour in your language to learn even more about the historic area. Begin with Pisa and visit its stunning Piazza dei Miracoli. Admire the Baptistery, the Cathedral of Santa Maria Assunta, and, of course, the famous Leaning Tower of Pisa. After your free time in Pisa, head to a typical Tuscan winery in the Chianti Area and enjoy a delicious lunch with some local wine. Explore the city of Siena and visit to Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. Enjoy your last stop in San Gimignano, a UNESCO medieval town, world-known for its Vernaccia di San Gimignano. The system of towers of San Gimignano tells the glories of the powerful families. Between saffron fields and typical indigenous vineyards, the city knows how to offer postcard views.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

2. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Start in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch discover one of the most beautiful medieval villages of San Gimignano, or the "Medieval Manhattan, where you can explore the maze of cobbled streets, small squares, and many local craft stores. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that characterizes this city. At the end of the guided tour, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

3. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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.

Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

4. Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

Spend the day discovering many of the main highlights of the Tuscan countryside on this guided tour with a traditional Italian lunch included. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena. Your first stop will be Pisa and the Square of Miracles. See the cathedral, baptistery, and, of course, the famous Leaning Tower. The Leaning Tower is almost 56 meters tall, about 183 feet, and leans at about 4 degrees, making it one of the most famous and iconic buildings in the world.  From Pisa, drive past hilltop hamlets scattered across some of the most beautiful and enchanting areas of the countryside. Arrive at San Gimignano where a traditional Tuscan lunch with wine tasting will be served, if the option is selected. Continue to the preserved medieval village of San Gimignano, a UNESCO World Heritage site often nicknamed the “Manhattan of the Middle Ages” because of its famous tall, narrow towers. Explore the town center and the charming craftsmen shops along the cobbled stone streets and small squares. End the tour in Siena, a hilltop town rich in art and traditions. Stroll the pedestrian historical center and visit the beautiful local cathedral. Take a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo. Sample Lunch Menu - Appetizer: cold cuts ( prosciutto, finocchiona, salami ) bruschetta olive oil and truffle oil pecorino cheese with balsamic vinegar and green salad - Main Course: penne with meat ragout and parmesan cheese - Dessert: homemade tart with jam and vinsanto - Tasting of 3 different wines

From Pisa or Lucca: Half-Day Tuscany Chianti Wine Tasting

5. From Pisa or Lucca: Half-Day Tuscany Chianti Wine Tasting

Explore the glorious hills of Tuscany on a 4-hour tour of a picture-perfect landscape just moments from the city centers of Pisa and Lucca. Following a pick-up from either city, travel to the picturesque countryside surrounding Pisa and stop at the winery. The owner will give you an insight into the various methods that go into producing the wines and extra-virgin olive oils of the estate. After a short introduction, go to the cantina to see where the wine is aged. Then, enjoy tastings of the delicious wines. Relax on the transfer back to the city, enjoying views of the Tuscan landscape along the way.

Pisa Cathedral Guided Tour & Wine Tasting + Leaning Tower

6. Pisa Cathedral Guided Tour & Wine Tasting + Leaning Tower

Your informative guide will take you to the Piazza dei Miracoli, discovering its monuments which are known as “miracles” because of their incredible beauty and uniqueness. Be dazzled by this marvelous square which is dominated by the Cathedral where you will visit the interior, which is typical of the distinctive Pisa Romanesque architecture. Admire the celebrated Leaning Tower, the round-shaped Baptistery surrounded by its suggestive columned arcades and its “Camposanto”, originally a cemetery, an extraordinary quadrangular cloister. The commentary of your guide will be particularly focused on the Leaning Tower, one of the wonders of the world. Be enthralled by the history and the leaning structure of the Tower which stirs the imagination of all visitors. After about 1 hour of guided tour in the Square, you will have a wine tasting near the Leaning Tower, where a local expert will explain everything about the local wines. With this tour you'll have the opportunity to climb the Leaning Tower as well, if option selected. Remember that all tourists have to go to the proper left-luggage office to hand in bags/luggage before starting the visit. Kids under 8 are not allowed inside the tower.

From Pisa: Winery Tour in the Tuscan Countryside

7. From Pisa: Winery Tour in the Tuscan Countryside

Benefit from pick-up at your hotel or the railway station in Pisa, and then journey into the rolling hills of the Tuscan countryside. Head to a typical medieval village on the hillside, and then go to a local winery to take a tour with the owner or a qualified guide. Learn about life at the wine estate, and hear about the ancient techniques of producing wine in one of Italy's most notable wine regions. Investigate the process of producing olives, and then taste a selection of wines with salami and more. Sample the local extra virgin olive oil with bread, along with bread baked in a wood oven and served with jams. Vegetarian diets and food for children can be catered for on request. 

From Florence: Pisa and Siena with Wine Tasting in Chianti

8. From Florence: Pisa and Siena with Wine Tasting in Chianti

Spend a day surrounded by the Renaissance beauty and rolling hills of Chianti, visiting Pisa and Siena with our private driver. A wonderful experience between art, wine, Tuscan legends and local food to discover vineyards, leaning towers, sunflowers and typical Tuscan farms. Meet your driver at your hotel, B&B or private apartment in Florence and set off on a discovery tour of Tuscany with stops in Pisa, a rural Tuscan farmhouse, and in the afternoon in Siena. First stop in Pisa to admire "Piazza dei Miracoli" and the famous Leaning Tower. Visit the other buildings that surround the area, including the Baptistery and the Cathedral. Depart from Pisa, driving through one of the most beautiful Tuscan wine roads. You can also request an extra stop at the famous village of San Gimignano. Stop for lunch in a Tuscan farm: visit, 3-course lunch and wine tasting. This farm promotes genuine Italian food and wine culture all over the world. A beautiful Italian experience to learn the best pairings between wine and food, the etiquette of the glass, the secrets of Italian cuisine, Tuscan winemaking techniques and more. Three-course lunch, with homemade pasta, bruschetta, salami, pecorino cheese, ham, salami and more. Wine tastings with: Chianti, Chianti Riserva, Sangiovese, Vernaccia and Super Tuscan, and also Extra Virgin Olive Oil Tasting Pepper Olive Oil Tasting Balsamic vinegar tasting Truffle Olive Oil Tasting After lunch, the tour continues with the visit of Siena to the historic center of this city, declared a World Heritage Site by Unesco, known for its splendid architecture and the beautiful main square, Piazza del Campo. Furthermore, Siena is also known for its legendary Palio horse race, which takes place twice a year and attracts hundreds of spectators. The most interesting things to see in Siena are: the famous Piazza del Campo, the Duomo, the Baptistery, the Church of San Domenico and the wonderful narrow streets of the historic center such as the "Via di città". At the end of the visit, we will return to your location/address in Florence.

Florence: Truffle Hunting Tour, Wine Tasting, and Lunch

9. Florence: Truffle Hunting Tour, Wine Tasting, and Lunch

Enjoy the charming Tuscan countryside and the haunting beauty of the Tuscan forests on a day spent hunting for truffles in the woods. Take a trip from Florence out into the countryside and visit San Miniato, a small town in Tuscany that supplies nearly 80% of the world's precious white truffles. Follow the dog hurriedly through the forest as he sniffs about and experience the surge of excitement as he starts digging for these edible treasures. Once some truffles have been found, you will be treated to a delightful meal that incorporates the fresh truffle you just discovered along with a wine tasting of local area wines.

From Florence: Pisa/Chianti Half Day Tour with Wine Tasting

10. From Florence: Pisa/Chianti Half Day Tour with Wine Tasting

Explore the Chianti wine region and visit the famous "Leaning Tower" of Pisa, tasting 5 of the best Chianti wines in a beautiful farmhouse located along a wonderful wine route. Itinerary: • Our driver will pick you up at your hotel, B&B or apartment at 8.00 am • In the morning, we will visit the city of Pisa and the incredible Leaning Tower. We will also see the great Baptistery and the Cathedral, which are located in the same square as the Tower. • Afterwards we will drive within the famous Chianti region, which includes the iconic landscape of rolling hills, sunflowers, cypress avenues and medieval villages. • We will drive through the Chianti vineyards, along a beautiful wine route. • Later we'll visit a typical farmhouse, its vineyards, the cellar, and we'll discover the secrets of the production of Chianti wine. • We will have a tasting experience of 5 wines with explanation of the basic characteristics. • The return is scheduled for 2 pm. This is our secret Tuscany for you!

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Frequently asked questions about Pisa Wine tasting & winery tours

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What people are saying about Pisa

Overall rating

4.4 / 5

based on 1,085 reviews

Stefono was an amazing tour guide: great knowledge of the area, just the right amount of wit, and he cared about us having a good experience! We also had a local guide in Sienna, who was amazing in her own right. The lunch was absolutely delicious with a variety of wines, good food, and a great view! The whole day was a whirlwind and left you ready for a nap on the drive back to Florence, but it was a fantastic experience well worth the price!

I got really excited! It was a beautiful sunny day in Tuscany. Not only the leaning tower, there is so much to discover and I was very surprised by Saint Gimigagno!

Alex was such an amazing tour guide. He was friendly and really made the experience the best of tuscany. the tour was beautiful and so informative

Everything was perfect, really enjoyed the tour. Beautiful Sienna I hope to be able to visit it again

Great day out. Really knowledgeable and engaging tour guide