Siena
Neighborhood Tours

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Our most recommended Siena 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: Chianti Hills Wineries Tour with Tasting

2. From Florence: Chianti Hills Wineries Tour with Tasting

Immerse yourself in Italy's renowned winemaking culture on this guided tour by van from Florence. Leave the city behind as you head out into the Tuscan countryside, marveling at the landscape around you. Visit two local wineries and enjoy wine tastings in both of them, learning about the wine-making process from locals. Arrive in the charming town of Radda in Chianti and visit one of the town’s traditional wineries. Enjoy a tasting session of 3 regional wines, then have the opportunity to purchase them. Spend some free time exploring the narrow streets of the town. Continue towards a traditional farm and winery. Learn about the winemaking process from grape to glass. Then enjoy another tasting session of 3 Chianti wines as well as local products. Finally, sit back and relax on the return journey to Florence.

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From Florence: Private Full-Day Jewels of Tuscany Tour

3. 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

4. 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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Siena: Market Tour and Lunch/Dinner at a Cesarina's Home

5. Siena: Market Tour and Lunch/Dinner at a Cesarina's Home

This local partner is home to Italy's first and finest network of home cooks, known as "Cesarina" (a passionate Italian cook and host whose empire is the heart of the Italian home: the kitchen). Since 2004, they have been sharing the joy of regional Italian cuisine with thousands of travelers from all over the world. Visit the local market with your Cesarina, enjoy the distinctive Italian local market and learn how to recognize the best produces from the land. Come back to your Cesarina’s home, and attend a private cooking demo where your Cesarina will share the secret of her family cookbook while finishing one of the dishes in front of you. Sit at an authentic Italian table and enjoy a 4-course seasonal menu including starter, pasta, and main course with side dish, dessert, and drinks included (water, a selection of red and white wines from regional cellars, and coffee). Feel the warmth of Italian hospitality as you connect with local people. If you want to uncover the secrets of Italian family recipes on your travels, the Cesarine are here to share their wisdom, which has been passed down in their families for generations.

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Siena: 2-Hour Food and Wine Tour

6. Siena: 2-Hour Food and Wine Tour

Walk around Siena and discover its best foods while meeting local vendors. Learn about the region's wine production and taste a typical white and red wine. Taste extra virgin olive oil and sample different Pecorino sheep cheeses, from fresh to seasonal, and together with different local kinds of honey. As you tour the town, hear fascinating details about the rare Cinta Senese, an almost extinct pig that is unique to Siena. Learn how local truffles are found and taste black and white truffles. Follow your guide and discover why the Tuscan bread is plain and how it is used in recipes. Hear the history of the recipe behind Siena's medieval cakes and bread. Visit an artisanal ice-cream shop to learn some of its secrets and enjoy the local gelato culture.

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

7. 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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Siena: Private Tour Ideal for Families with Children

8. Siena: Private Tour Ideal for Families with Children

Enjoy a private tour that takes into account children’s attention spans, not one where the young are dragged by their parents on exhausting journeys. With the help of a local guide, keep your children’s attention alive with language that is colorful and lively, and where history is mixed with art, legends, and traditions. By encouraging children to make observations, answer questions, and solve riddles, your guide will reveal the history and secrets of Siena’s monuments in a pleasant way that is sure to prevent children becoming impatient, bored, and complaining. From the meeting point in front of the Basilica Cateriniana San Domenico, you’ll learn about the traditions of the Palio di Siena horse race and admire the magnificent front of the Duomo di Siena cathedral. Next, walk the Via Banchi di Sopra — the former route of pilgrimage to Rome — that will you lead to Piazza del Campo, the principal public space of the historic center of Siena where the tour will end with a souvenir and great memories.

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Florence Highlights Walking Tour from Duomo to Santa Croce

9. Florence Highlights Walking Tour from Duomo to Santa Croce

Start your day by meeting your fun and informative guide at the designated meeting point. From here, your guide will lead you on a fascinating walking tour along the streets and piazzas of Florence, exploring the city’s rich history. At the historical Palazzo Strozzi you can examine the perfectly preserved courtyard, and also see the lesser known, but no less impressive Palazzo Davanzati, a truly marvellous example of a Medieval Palace. Passing by the renowned "Porcellino" (little pig) market, you'll head to the famous Ponte Vecchio, the city’s oldest bridge, built in the 1300s. Whilst appreciating the stunning views of the hills that surround Florence, you will get the opportunity to listen to insights into the bridge’s history, and the famous Vasari Corridor that dramatically changed the shops built on the bridge. You will also visit Piazza della Signoria - the political heart of the city. The Uffizi Gallery, formerly the offices of the Grand Duke, is located on one side of the square and on the other side, Palazzo Vecchio, the former home of the Florentine government. After a pleasant wander through the oldest parts of the city where you can admire tower houses from the 1300s, you'll enter Piazza Duomo where the imposing Duomo (Cathedral of Florence) is located, with its original marble decoration and Brunelleschi's dome, an architectural triumph and a symbol of the Florentine Renaissance, both for its unique design and also the architectural achievement itself. The tour ends in front of the Baptistery with its stunning Porta del Paradiso, along with Giotto's bell tower, a perfect example of 12th-century architecture. You will be totally enchanted by Florence and benefit from your guide’s suggestions to enjoy the rest of your stay.

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From Florence: 4-Day Tuscany Highlights Tour

10. 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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Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.1 / 5

based on 5 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 second winery was really good. We visited in October so the grapes were already harvested and we didn’t get to see them but everything else was amazing!

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