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Castellina in Chianti

Nestled in the heart of Tuscany, Castellina in Chianti is a charming hilltop gem! Wander through its narrow cobblestone streets, sip luscious Chianti wines, and feast on delectable Tuscan cuisine. With stunning views of rolling vineyards and olive groves, this picturesque village invites you to explore its medieval treasures and vibrant culture. Grab your camera—this is Instagram gold! 🍷🌄✨

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Recommendations

Culture4.5/5

Parco Sculture del Chianti

Nestled in the stunning Chianti region, Parco Sculture del Chianti is a unique outdoor art gallery showcasing contemporary sculptures. Take a leisurely stroll through the park and admire the impressive works of art set against the backdrop of rolling vineyards. Don't forget your camera for this Instagram-worthy destination!

Eat$$4.3/5

La Chiantina bar bistrò (Tre PORTE) nuova sede

Eat$4.4/5

Bar Pizzeria Italia

Bar Pizzeria Italia in Castellina in Chianti offers a delightful fusion of authentic Italian pizza and exquisite local wines, all within a charming atmosphere that captures the essence of Tuscany—making it a must-visit culinary gem.

Eat$$4.3/5

Pizzeria il Fondaccio

Eat5/5

Tenuta Casanova - Luxury Wine Estate

Nestled in the picturesque Chianti region, Tenuta Casanova offers a luxurious escape with exquisite wines, stunning views, and authentic Tuscan hospitality, making it an iconic destination for wine lovers and travelers alike.

Eat4.3/5

L’angolo del Chianti

Stays

Stay$$$4.35/5

Palazzo San Niccolò

Set in the picturesque town of Radda in Chianti, Palazzo San Niccolò is an elegant hotel offering free Wi-Fi, a large garden and interesting interiors with original frescoes and antique furniture. Rooms at San Niccolò are air conditioned and feature a satellite LCD TV and minibar. All rooms have either a hydromassage shower or bath. Your day at San Niccolò Palazzo begins with a large buffet breakfast featuring homemade pastries and a wide variety of food. Guests can relax out in the garden with tables and chairs and enjoy a drink from the bar. Staff can recommend the best local restaurants and provide useful tourist information. Rates include use of Palazzo Leopoldo's indoor heated pool and of L'Ultimo Mulino's outdoor pool. Set amongst green hills in the Tuscan countryside, the hotel is 40 minutes' drive from Siena.

Stay4.9/5

Agriturismo Rocca

Nestled in the heart of Chianti, Agriturismo Rocca offers breathtaking vineyard views, authentic Tuscan cuisine, and a genuine farm experience, making it an unforgettable destination for wine lovers and nature enthusiasts alike.

Stay4.8/5

Fattoria Poggio al Sorbo

Stay4.6/5

Relais La Costa

Nestled in the picturesque Tuscan hills, Relais La Costa offers a charming retreat with stunning views, exquisite cuisine, and a unique blend of rustic elegance and modern comfort, making it a must-visit destination.

Stay4.6/5

Tenuta Di Ricavo

Stay4.4/5

Hotel Villa Casalecchi

Nestled in the heart of Chianti, Hotel Villa Casalecchi enchants with its historic charm, stunning vineyard views, and captivating Tuscan hospitality, making it an unforgettable retreat for wine lovers and travelers alike.

Things To Do
Provided by

5/5

2 h

Truffle Hunting Experience Siena Tartufi

Ciao, I’m Alessandro, the owner of Siena Tartufi. I’m a truffle hunter from 25 years. I have 3 dogs, Moka and Freddie a Lagotto Romagnolo and Pepita, a black Labrador. I really love going outside with my dogs looking for truffles . In every season there are different types of truffle that will be collected and you can do it with us... My hobby is my job and my passion!

$160.55

5/5

2 h

Private Tour: Siena Walking Tour

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval town and the surroundings with a professional tour guide.

$206.43

5/5

9 h

Volterra and San Gimignano: a taste of medieval Tuscany!

Hi ! About 90% of tourists usually head straight to Pisa and Florence – and yes, they’re amazing – but this tour offers something a little different. It’s a bit more off the beaten path (especially Volterra), and it's a real treat to explore the heart of Tuscany through these two charming villages. Give this experience a try: you won’t regret it! You’ll travel in a comfortable Mercedes van, with a driver/guide who will explain what you're seeing throughout the day. The standard departure time is 8:30am, but it can be customized to fit your schedule.

$1,009.19

5/5

Private Day Tour of Pisa, San Gimignano and Siena from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to the enchanting exploration of the three best-preserved medieval cities in the world (UNESCO World Heritage sites) in Tuscany on a private day trip from Florence. Avoid the stress of renting a car or driving, and let an English-speaking private driver take you directly from the hotel door, through the scenic Tuscan countryside, and into the historic centers of Siena, San Gimignano and Pisa. Travel in premium comfort and at your own pace with invaluable advice and suggestions from your local driver. • 9/10-hr Full-Day private tour of Pisa, San Gimignano and Siena. • Pick-up and Drop-off at your Hotel or address provided. (Florence down town) • Travel in a private luxury Minivan. • Visit three UNESCO World Heritage sites in a single day. • Learn about the area's history and culture from a private driver.

$452.99

5/5

11 h

Private Tour: Siena and San Gimignano Day Trip from Rome

Venture north from Rome to Tuscany on a privately guided day trip, and spend the day in San Gimignano and Siena. As your driver chauffeurs you around the cities, learn about medieval Tuscany and see UNESCO-listed attractions, fine architecture and much more. Check out stunners like the Gothic cathedral of Siena Duomo, and hear about the horse race of Il Palio on an amble around Piazza del Campo. Later, visit San Gimignano where medieval towers and the artisan craft stores of Via San Giovanni await.

$871.58

5/5

Chianti Classico E-Bike Tour

One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines and beauty of the landscapes. Chianti offers a unique landscapes: gentle hills covered by vineyards and olive groves, small stone villages and farm houses. We'll start biking in the hearth of Chianti Classico, only 20 minutes from Siena, during the bike tour we will reach the Castle of Brolio, owned by the Ricasoli family since 1141, and the small villages of Villa a Sesta. We will stop then in a local winery for a Chianti wine tour and tasting. The tour includes also the lunch in local restaurant located at Castelnuovo Berardenga.

$298.17

5/5

10 h

Siena and San Gimignano Day Tour from Rome

We have set high standards for ourselves, which is why we offer you a high quality experience during this full day trip to Siena and San Gimignano from Rome with our luxurious Mercedes Benz Minivans for transportation and the best English speaking drivers! From the very first moment we meet you, you will feel their professionalism; as they have year of experience and will take special care of you at all times! They are also very knowledgeable about Italy, therefore although they are not certified guides, you will get the feeling as they were, as they will always be ready to answer all your doubts! In addition, it’s also good to highlight we are always open to customize our tour according to your preferences, we know for sure this is an added value you will appreciate for making this experience a super special one!

$429.48

5/5

Private Day Trip Siena and Chianti Wine Experience with lunch

• EXPERIENCE FOR YOUR PRIVATE GROUP • Leave behind the bustling city of Florence with a private full-day tour in a luxury Mercedes Minivan. Stroll through the Gothic streets of Siena and discover the black-and-white art and architecture of its historic center, a UNESCO heritage site. Taste renowned Chianti wines and authentic Tuscan cuisine in famous family-owned cellars of local olive oil and aged balsamic vinegar. • 8hr Full-Day private tour of Siena and Chianti from Florence • Pick-up and drop off at your selected hotel/ location (Florence Down Town) • Private transportation by minivan, Air-Conditioned • Tasting of cold cuts and cheeses from the exceptional Falorni butcher shop • English-speaking licensed driver • Learn about local history, food and culture • On request we can organize Lunch in Farm or Winery. (highly recommended)

$372.71

5/5

3 h

Highlights & Hidden Gems of Siena Private Tour - Duomo Included

Siena is a magical place! And with the local host, you are going to experience it all. So get ready; culture, history, and local lifestyle await! Dive into the origin of Siena as you see the city’s main landmarks like Duomo di Siena, Piccolomini Library, and Piazza del Campo. And how about the hidden gems? Oh, you’re in for a surprise! Experience your host's Siena to the max based on his/her passions and expertise! Want to take a break? Leave it up to your host! This is the perfect opportunity to visit that special eatery where only the locals come and your chance to enjoy a local treat hand-picked by your host. Feel free to ask your host more about their life in their city or get recommendations about the top things to do in Siena. Remember, the locals know best. The best part of any city tour is the unique stories. Do you feel like changing the route a bit? No problem, the hosts will be happy to personalize the tour to your wishes and make their Siena, your Siena!

$222.48

5/5

11 h

Private Siena and San Gimignano Tour with Wine Tasting From Rome

Hill towns, Medieval areas and good wine! You will experience all this and more on this wonderful tour from Rome. Begginging with a pickup at your hotel at 7:30am, you will be escorted by your English speaking driver who will show show you this enchanting Region. After a 2.5 hour drive, you will reach Siena and have some free time to explore this quaint town. You will then head to Gimignano, where you will be able to walk about, try some gelato, and take in the sights. Afterward, you will drive down the valley where a nice lunch and wine tasting will be waiting for you. This 11 hour tour concludes with a drop-off back at your hotel.

$584.87

5/5

11 h

Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence

With this personalized tour of Tuscany, you and your friends may see all the area's hidden treasures in a single day. An experience made even better with an extravagant lunch and wine sampling in Tuscany. We're going to leave in a cozy, air-conditioned minivan in the morning for a fast-paced tour. In Siena, as you stroll through the alleyways adorned with Renaissance and medieval architecture, your guide will give you an insider's view of the first bank in history, the exquisitely designed Duomo, and the famous Piazza del Campo. We'll take you to a family-run Chianti estate's vineyards for a laid-back wine-tasting experience and a superlative regional culinary experience while taking in the breathtaking scenery. Then we'll drive you to San Gimignano, one of the area's greatest treasures and one of our favorite stops on this private tour. The final stop will be Pisa, where you will have the chance to discover the Baptistery, the Cathedral, and the world-famous Leaning Tower!

$665.15

5/5

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short journey to the city of Siena. We can reach the heart of the city with our vehicle and you will visit the most important monuments independently. Your driver will also present you the local history and the most important traditions, such as food, since good cuisine is one of the most significant attractions. You'll have time for some shopping and memorable photos. You can choose to have lunch in Siena or into the Chianti hills to have lunch at a wine estate and taste home made Tuscan food paired with local wines. After lunch we will drive you to San Gimignano where, in addition to visiting the city, perhaps climbing up the “Torre Grossa” or entering the Cathedral, you can enjoy a magnificent ice cream. Once the day is over we will take you home while admiring the Tuscan countryside and its charm that will be a memory for a lifetime.

$435.79

5/5

3 h

The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked by your foodie local host. From yummy must-tries like cantucci to unique dishes typical of the city such as gelato; you’re in for a treat, so bring your appetite. This culinary tour in Siena is a cultural journey that takes you further than the food you’ll eat. As you enjoy authentic local bites ranging from savory, sweet as well as drinks, you’ll also discover the city. Stop to admire the Piazza del Campo, Torre del Mangia, and the Public Palace of Siena and hear about their local relevance from your host as you hop from one food hot spot to the other. Want to know what this food tour has in store for you? Your local foodie has you covered! And because sharing is caring, you and your private group will get to try bites of famous dishes. Looking for a vegetarian alternative? It’s possible! Just let your host know!

$247.71

5/5

2 h

Siena private guided tour for families

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets, we will talk about Palio and Contrade, noble palaces, famous painters, Francigena and illustrious characters. Towers, medieval houses, squares and ancient sources. Monte dei Paschi, the famous Duomo with its masterpieces, the Ancient hospital and the noble public palace. I wait for you for a pleasant and interesting private tour of the city of Siena

$263.77

5/5

8 h

Private Tuscany Day Trip from Florence Including the Leaning Tower of Pisa

Take a private amazing day trip through the hills of the Tuscan countryside. Stop to visit the Leaning Tower of Pisa and Sangimignano, the most charming village famous for its towers and medieval look.

$1,099.91

5/5

9 h

Private Shore Excursion from Livorno Port: Tuscany Highlights

Will you arrive at Livorno Port with your cruise ship? It is a great opportunity to enjoy your day visiting one of our destinations in Tuscany. Select your preferred 9-hour excursion among our tour proposals below. You will meet your English-speaking driver on the day of the tour at La Spezia Port and you will enjoy an unforgettable Tuscany Experience!

$498.62

5/5

PolaTour The 17 Fountains of the Contradas of Siena

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and its districts and instant photography will allow you to appreciate the beauties of each district from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends. N.B. During the days of the Palio (29 June-2 July and 13-16 August) the 17 Fontanine di Contrade route is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.

$71.10

5/5

11 h 30 mins

Siena, San Gimignano and Chianti Wine Small Group from Viareggio

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in the beautiful Tuscan countryside. Discover the vibrant local life, the colorful pottery shops and the tallest towes of S. Gimignano. In Siena will you will learn all the secrets about the famous horse race “Palio” and Campo square. A special guided Chianti wine sampling and the visit of a famous wine estate will be reserved for you.

$212.16

5/5

Private Tour Siena San Gimignano and Chianti from Cortona

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.

$470.19

5/5

7 h

Private Tour: Guided Hike in Tuscany with Transport from Siena

Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert guide with a half-day hike through the beautiful rolling hills of Tuscany, between forests, olive groves and vineyards before visiting a local farm for lunch with wine. In the afternoon, visit the medieval hilltop town of San Gimignano for a walk around its UNESCO World Heritage-listed city center. Spend time at your leisure browsing the main sights and boutique stores of local crafts and products before the final, return drive to Siena.