San Gimignano
Neighborhood Tours

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Our most recommended San Gimignano Neighborhood Tours

From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

1. From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside, followed by a stop in Siena. Here, a specialist guide will lead you on a walk through the city's historical center. Skip the ticket line to see the interior of the magnificent cathedral, and pass through the shell–shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

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From Florence: Private Full-Day Jewels of Tuscany Tour

2. From Florence: Private Full-Day Jewels of Tuscany Tour

Be seduced by the eternal charm of Tuscany’s jewels on this 12-hour tour. What are Tuscany’s jewels? The beautiful cities and villages, as well as art and the historical monuments that call this unique region of Italy home. Falling in step with the more ‘human’ way of life in Tuscany, this relaxed tour begins when you want it to. You determine the pick-up time from your centrally-located Florence hotel. You will also enjoy the transportation, which is provided by a private vehicle operated by an English-speaking driver. After pick-up, you will drive through the Tuscan countryside until your first stop, Siena, is reached. Siena is a medieval city known for its artistic treasures, which have been recognized by UNESCO. In Siena you will visit the shell-shaped Piazza del Campo. Here you will find the Palazzo Comunale flanked by the Torre del Mangia. Every year the famous Palio takes place here. You will also have free time to visit the cathedral, built in the Middle Ages and admire the splendid buildings and narrow streets. From Siena, you will enjoy a drive through Chianti territory on your way to Monteriggioni. The drive boasts a panoramic view of the vineyards and olive groves. Monteriggioni is a small 13th-century town which is still surrounded with its original town walls. Here you will take a walk within the restricted perimeter of the walls, which have eleven towers with spectacular views. This is a Tuscan gem that will transport you back in time. Only a short distance away, in a pleasant country estate you will be served a typical Chianti-region lunch. You will also enjoy a guided tasting of Chianti and Vernaccia wines. After lunch you will leave the estates and go to San Gimignano, another beautiful town and UNESCO world heritage site. Famous for its signature medieval town planning, it is called the “Manhattan of the Middle Ages”. On a stroll through the town center you will discover the Piazza della Cisterna, the Dome, the Palazzo del Podestà and the Church of Saint Agostino. Your final stop will be at the famous town of Pisa, which is also a UNESCO world heritage site. In the Piassa dei Miracoli the masterpieces in marble rise from the green lawn, including the famous Leaning Tower of Pisa, the magnificent Baptistery, the stunning Cathedral and the Monumental Graveyard Tuscany is a one-of-a-kind region of boundless natural and cultural beauty. This small, personalized tour is an authentically Tuscan experience.

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From Rome: Full-Day Trip to Tuscany with Wine Tasting

3. From Rome: Full-Day Trip to Tuscany with Wine Tasting

This tour has been designed to showcase the very best of Tuscany in just one-day and is perfect for travelers who only have a short amount of time. The day begins with departure from Rome at 6:45am on a fast speed train to Florence. Upon arrival in Florence, head to the meeting point sent to your email to meet your guide and set out on your sightseeing adventure. The first stop of the day is the historic city of Siena, which is bursting with rich architectural styles, best showcased at the cathedral and the old palace. After a brief guided walking tour of Siena, enjoy free time to explore on your own. Wander around the quaint streets of this magical town, have a traditional Italian lunch at one of the many cafés, or shop for handmade crafts and souvenirs. Continue the tour to the walled town of Monteriggioni next, which was the filming location of the blockbuster movie, Gladiator. Arrive at the UNESCO World Heritage Listed San Gimignano next, which is the most famous walled medieval town in Tuscany, and nicknamed the ‘Manhattan of Tuscany’ due to its many towers. Armed with tips and recommendations from your guide, head out on your own adventure in the town and visit the sights and attractions that interest you most. Don’t forget to stop by the store of the world-champion gelato maker, and treat yourself to a seriously sweet treat. Finally, ride through the rolling countryside of Chianti and soak up the charming scenic views on the way to an authentic Tuscan winery. Against the backdrop of luscious vineyards and olive groves, enjoy a spectacular wine and olive oil tasting session. At the end of a truly unforgettable day it’s time for the return journey to Rome, arriving at approximately 8pm.

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From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

4. From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

Start your experience at 11:00 AM and explore the scenic hills of the Chianti region where some of the most famous Tuscan wines are produced. Ride through the beautiful fields of vines, cypresses, and Tuscan rural houses. Enjoy plenty of stops for beautiful photo opportunities throughout your experience.  Stop at a local winery where the kind owners will escort you around their property before serving an authentic Tuscan meal, followed by wine and olive oil tasting. Hop on your scooter once again and follow your guide through the final part of the scenic ride, arriving back at the meeting point at approximately 3:30 PM.

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San Gimignano: Private Winery Tour, Wine & Oil Tasting

5. San Gimignano: Private Winery Tour, Wine & Oil Tasting

Podere la Marronaia is a small family-run farm in San Gimignano dedicated to the cultivation of grapes and olives with production of organic wines and extra virgin olive oils and farmhouse rentals. The story will begin in the year 2000 when Silvia and Luigi Dei, together with their young children Pietro and Corrado, bought a property called Podere la Marronaia to make of it their home and follow the dream of a new life. The old vineyards and olive yards were immediately converted into the organic method of cultivation, while a long restoring of the house began. Now the whole family works in the farm business. Pietro and Corrado grew up following the dream to continue the family tradition. In the year 2000, the production was converted into the organic ethos of cultivation and recently in 2016, following the idea of a more sustainable agriculture and the respect of the environment, the fields have been converted into biodynamic agriculture. The purpose will be to produce wines and extra virgin olive oil that are the expression of the local tradition, using authentically produced grapes and olives. The cellar and the tasting venue, Sosta Alle Colonne, is situated within walking distance from the town center of San Gimignano, surrounded by a beautiful countryside with a view of the towers and the Vernaccia vineyards. Different options will be to introduced to guests of the Tuscan farming world and local traditions. The aim is not to offer just a wine tasting, a lunch or a visit but to introduce guests to a full immersion personalized experience and share soul and passion for the land and products.

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

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

Your day starts in the morning with a free tour of Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous Leaning Tower. Afterwards, you'll move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. There you will enjoy a typical Tuscan lunch accompanied with a good local wine tasting. Following lunch you will 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. Your exciting day continues with a panoramic view of the true Chianti countryside before arriving in Siena, where if desired, your professional guide will let you discover 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, you can choose to have some free time to enjoy a cup of coffee or a pan forte (a typical local cake), and to go shopping in the typical local stores. Your return to Florence will have a magnificent sunset as a backdrop, which will make for a perfect ending to an unforgettable day spent in Tuscany.

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Poggibonsi: Pizza & Ice Cream Cooking Class with Wine

7. Poggibonsi: Pizza & Ice Cream Cooking Class with Wine

Experience the joy of freshly baked Italian pizza and delicious gelato with a 2-hour expert-led cooking class near San Gimignano. Listen to the history behind one of the world's best loved foods and the techniques to make the perfect pizza base, tasty homemade tomato sauce and fresh fruit gelato. Sit down to indulge in your creations with your fellow chefs, accompanied by a tasting of Tuscan wines and olive oils. After Pizza it’s time for Gelato, the chef will tell you why gelato remains Italy’s favorite dessert while giving an insight to the ‘gelato culture’ that continues to grow. Through a demonstration, you will get to know the basic raw ingredients, how to select the best products available and enjoy tasting of some of the flavors used in gelato making.

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From Florence: 4-Day Tuscany Highlights Tour

8. From Florence: 4-Day Tuscany Highlights Tour

Day 1: After checking in to your hotel, begin your day with a guided tour of the Uffizi Gallery and learn more about the oldest and most famous art collection in the world.  Following the Uffizi, join a tour of Florence's most iconic streets and squares with a professional guide. Stroll through the stunning Santa Maria del Fiore Cathedral, the Old Bridge, the Signoria Square with its replica of Michelangelo’s David, the Republic Square and more. Day 2: Crossing the beautiful Chianti hills, arrive at the walled town of Monteriggioni. Drink in the town's century-old history and relive the Medieval atmosphere before continuing to Siena, famous for its splendid examples of Gothic architecture, and enjoy a light lunch in a cozy restaurant where you can try traditional Tuscan products.  Next, drive to San Gimignano, a UNESCO World Heritage Site famous for its wine. At the end of the day, head to the Chianti area and marvel at its picture-perfect landscapes. Sample the region's best red wine in a rustic wine estate along with home-made aperitifs and olive oil tastings. Day 3: After breakfast, begin the journey to Cinque Terre National Park for an unforgettable day in one of the most enchanting landscapes in the world. Discover five villages suspended between sea and land, where you can sunbathe or swim in one of the area's many beaches before taking the boat to Vernazza, a seaside town surrounding a small natural port. Day 4 Today, enjoy a guided tour of the Florentine Dome and enjoy panoramic views of the entire city from its peak. Afterward, enjoy a guided tour of the Accademia, where you can see Michelangelo's masterpiece, David.

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From San Gimignano: Half-Day Chianti Wine tour

9. From San Gimignano: Half-Day Chianti Wine tour

Go on a sweet escape in Tuscany. Raise your glasses to this amazing winery tour in the charming landscape of Chianti. Visit a wine tasing school and a local winery. Taste 9 different types of wines in a single day. Kick off your grape escape by meeting your friendly and knowledgeable tour guide who will lead the way to Chianti countryside, Tuscany’s region for delicious wines. As you reach Chianti, make your first stop at the Tuscany Wine Tasting School. Taste 4 different types of wines, the Chianti Classico D.O.C.G., the Super Tuscan wine, a 30-year-old balsamic vinegar, and the truffle extra virgin olive oil. Next, head over to a local winery in the area for a guided tour through vast vineyards. Savor the taste of 3 sumptuous wines, the Vernaccia white wine, a rosè wine and a Chianti colli senesi D.O.C.G. After a heavenly trip to the wineries, drive back safely with your driving guide.

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From Livorno: Shore Excursion to Chianti and San Gimignano

10. From Livorno: Shore Excursion to Chianti and San Gimignano

Discover the beauty of the Chianti wine region on this shore excursion from Livorno. After getting picked up from the port, enjoy a relaxing 1.5-hour drive through the picturesque Chianti countryside to reach your first stop, the charming market town of Greve-in-Chianti where you can visit Macelleria Falorni, a specialist in wild boar and pecorino cheeses and one of the best butchers in Italy. Later, as you cross the hills to Montefioralle, the tiny hamlet where Amerigo Vespucci was born, enjoy a wine tasting tour at a small family-owned estate. Your journey will then take you through the Antinori vineyards at Badia a Passignano to relax over a convivial Tuscan lunch at a little osteria hidden away amongst these rolling hills. After lunch, stop at the World Heritage site of San Gimignano with its unforgettable skyline of towers. The town is renowned for its white Vernaccia di San Gimignano wine and the Gelateria di Piazza, where Sergio Dondoli creates award-winning gelato with flavors including Vernaccia wine sorbet. Get dropped off back at your ship in the afternoon with plenty of time before departure.

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Other Sightseeing Options in San Gimignano

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What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 10 reviews

Amazing trip that made our dreams come true.! We love so much the kindness and understanding of Sia who found us as we were lost and the trip would not have been. Sia was so knowledgeable and spoke both In English for us and Italian for others. We liked this trip as it was less people and that’s where we ended up making great friends. Recommend it highly!!

We really liked the tour. The guides Oscar has been wonderful, with very interesting and timely explanations. He has also given us good advice to move around the city and discover other points.

Highly recommend this for any tourist who wants to explore more of Tuscany but not sure on how to get around. You get a taste of everything in one day and definitely get your money's worth.

The guide, Sonia, was very knowledgable and told us about interesting history everywhere we went. The free time was great and being in a group made it better

everything left on time… ..well organized …… enough time to visit the places… ..comfortable trip… ..