Siena San
Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Rated 4.4 Stars, based on 1818 Reviews.
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni – a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.
Florence: Siena & San Gimignano with Dinner in a Boutique Winery

Rated 4.4 Stars, based on 124 Reviews.
Discover the best of Tuscany in one magical afternoon!
Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location.
Looking for the full Tuscan experience?
Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk.
Florence: San Gimignano & Siena Tasting Experience

Rated 4.3 Stars, based on 11 Reviews.
BusVia Firenze invites you to explore the true essence of Tuscany, blending art, history, and the pleasures of wine and food.
We will accompany you to San Gimignano, often referred to as the "Manhattan of the Middle Ages" due to its numerous towers punctuating the skyline. Here, you can savor the finest Tuscan wines paired with light lunch.
The journey continues through the Tuscan countryside to Siena, where your experience begins with a visit to this charming town, renowned as the capital of Gothic art.
In Siena, with a skip-the-line ticket you will enter in the splendid Cathedral of Santa Maria Assunta, with an audio guide on your phone. The Duomo's facade is pure magnificence, but inside it houses masterpieces by Michelangelo, Donatello, Pinturicchio (possibly with a young Raphael), Nicola Pisano, and more.
Siena and San Gimignano Day Tour from Rome

Rated 5 Stars, based on 17 Reviews.
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!
Siena and San Gimignano from the Livorno Cruise Port

Rated 5 Stars, based on 2 Reviews.
Live a different experience from the tours with the ship's bus.
On board our vehicles with permission to enter the historic centers, you will be accompanied within walking distance of the main and famous tourist attractions, just like a VIP!
Our driver will give you a lot of information to better appreciate the places you will visit. Our trusted driver will be able to give you a lot of information to better appreciate the places you will visit. He will be waiting for you at the exit of the ship to start the journey through the beautiful landscape of Tuscany.
First stop will be San Gimignano where you will have free time to visit independently this incredible village.
After this visit, you will continue to Siena where you will be dropped off in the historic center and have free time for your visit.
The driver will show you the time and meeting point for the return
to the port of Livorno in time to resume the ship.
From Florence: Tour to Siena and San Gimignano by Minivan

Rated 4.5 Stars, based on 3 Reviews.
During this small- group tour in a comfortable minivan, you will explore the breathtaking towns of Siena, Monteriggioni, and San Gimignano. All are symbols of Medieval and Gothic architecture, characteristic elements are the historic towers, pointed arches, and narrow streets. Moreover this Tuscan area is full of superb food specialties you will surely have the chance to taste, such as Panforte and Pici. The tour lasts 8 hours with 2 hours spent in Siena, a short visit in Monteriggioni for a photo stop, and approximately 1 hour in San Gimignano.You will also get a detailed description from our expert local guide in Siena.
Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

Rated 5 Stars, based on 8 Reviews.
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.
Day Trip Pisa, Siena, San Gimignano.

Rated 5 Stars, based on 4 Reviews.
Visit the best known Tuscan cities and attractions Pisa, This private tour: will be custom made according to your requirements and it can be adjusted as you go.
Tuscany Tour Siena – San Gimignano – Winery

Rated 5 Stars, based on 4 Reviews.
Our exclusive food and wine tour begins in Siena, one of the most fascinating cities in Tuscany. The day begins with a visit to the majestic Siena Cathedral, known for its splendid Gothic architecture and the artistic treasures it houses.
After exploring Siena, we head towards San Gimignano, the "Manhattan of the Middle Ages", famous for its historic towers and its charming historic center.
The tour continues towards the Chianti hills, the beating heart of the Tuscan wine tradition. Here, an unforgettable gastronomic tour awaits you. We will visit a renowned local winery, where you can taste the fine Chianti Classico wines, accompanied by a delicious lunch based on typical Tuscan specialities.
Siena – San Gimignano Private Tour

Rated 4.9 Stars, based on 11 Reviews.
– Very knowledgeable drivers with explanation about wine, food and general
history of Tuscany.
– Visit the town of Siena a Unesco World Heritage Site.
– Lunch in a typical Trattoria or a wine Estate in the Chianti area.
– Visit San Gimignano, the medieval "Manhattan" frozen in time.
Private Excursion to Siena, San Gimignano and Chianti Landscapes

Rated 4.8 Stars, based on 23 Reviews.
Embark on an unforgettable private tour starting from your hotel. Visit the historic city of Siena, where you’ll enjoy an exclusive guided tour of its charming medieval center. Wander through the narrow cobblestone streets, admire its iconic palaces, and visit the famous Piazza del Campo. You'll also get a chance to see the magnificent Palazzo del Comune (exterior) before taking some free time to relax and enjoy lunch (not included). After Siena, your private driver will take you on a scenic drive through the heart of the Chianti region. Delight in panoramic views of the countryside, including a glimpse of the ancient fortified village of Monteriggioni, known for its remarkably preserved 13th-century walls.
Your journey continues to San Gimignano, a UNESCO World Heritage site celebrated for its medieval architecture and iconic towers. Here, you’ll have free time to explore this fascinating town at your own pace.
The schedule of visits may vary.
Private Tour of Chianti Siena and San Gimignano by Minivan

Rated 4.6 Stars, based on 72 Reviews.
It will be your special day. The driver will be at your disposal and will discuss with you all the possible solutions, so he will be able to customize your day, adapt to your needs and focus only on the attractions that interest you. Start the day with a relaxing visit to the Piazzale Michelangelo where you can take the most beautiful photos of Florence, then after you leave for Siena through the beautiful Tuscan countryside admiring the beauty of the Chianti. Once in Siena we will go directly to the beautiful Piazza del Campo famous all over the world for its beauty, art history and the famous horse race, here in the historic center of Siena you will have free time to. After 2 hours we leave for a visit to the winery where you will discover the secrets of Chianti wine, taste genuine local products. After lunch we continue to visit the medieval village of San Gimignano UNESCO World Heritage Site Famous for its towers ,Here you will have free time to walk in the small old town..
Siena San Gimignano and Chianti Private Tour

Embark on a condensed yet captivating exploration of Siena and San Gimignano. Begin in Siena's heart at Piazza del Campo, marvel at the cathedral, and admire historic landmarks like Palazzo Salimbeni. Conclude your Siena visit to the Basilica of San Domenico.
Transition to San Gimignano, starting at Piazza del Duomo with its iconic Collegiate Church. Climb Torre Grossa for panoramic views and stroll through Piazza della Cisterna. Explore the Civic Museum and meander along Via San Matteo. End the tour at Rocca di Montestaffoli for breathtaking views.
For a more immersive experience, consider an optional lunch at a family winery, showcasing the best of Tuscan flavors. Indulge in farm-to-table dishes and local wine tastings amid the picturesque vineyards. Note that lunch with wine tasting is not included but can be added as an optional and delightful extension to your tour.
Siena and San Gimignano Private Tour with Wine Tasting

Rated 5 Stars, based on 1 Reviews.
Embark on a fascinating private excursion into the Tuscan hills, visiting the historic cities of Siena and San Gimignano.
We will pick you up from your hotel or apartment in Rome. The tour will start with the exploration of Siena, its magnificent Piazza del Campo and its majestic Duomo. Admire the medieval architecture and immerse yourself in the history and culture of this beautiful city. The tour continues to San Gimignano, known as the "Manhattan of the Middle Ages" for its imposing towers. Stroll through the cobbled streets and enjoy the panoramic views of the surrounding hills. After enjoying free time in San Gimignano we will head to a charming wine estate in the countryside where you will have the opportunity to participate in a tasting of local wines accompanied by typical products, tasting the fine Tuscan wines and discovering the secrets of their production. Return to Rome is scheduled for the afternoon.
Florence to San Gimignano and Siena Tour

Rated 5 Stars, based on 1 Reviews.
Your private driver will meet you at the hotel for a fantastic day designed to show you the beautiful Tuscany between San Gimignano and Siena and its most renewed countryside.
You will first reach and visit San Gimignano with its wonderful and medieval historic center with fantastic local shops.
You will then reach the charming village of San Donato for an unforgettable lunch at a typical trattoria where you can taste the real Tuscan cuisine.
After lunch, you will have time to see Siena , with its wonderful medieval buildings around Piazza del Campo, the central square and then return to your hotel.
Private Day-Trip to Siena and San Gimignano

Rated 4.8 Stars, based on 5 Reviews.
Escape from the city for a day-trip out in the countryside and immerse yourself in nature and medieval architecture!
Full Day Tour in San Gimignano, Siena and Chianti

Explore the medieval side of Tuscany, Italy, and enjoy an excellent wine tasting in the Chianti Area.
Begin the tour with Siena, the city of Palio horse- racing. Visit its city center and enjoy the vibrant atmosphere of this picturesque Piazza del Campo. Admire the monumental building of its Siena Cathedral.
As a second stop, enjoy a wine tasting in the Chianti area. Taste fine wines, paired with some typical local food.
Once the winery stop is over, the tour will continue with a visit to the marvelous Monteriggioni castle, a medieval fortress that is really well preserved. You may also recognize it from the Assassin's Creed video game series.
Later, reach the town of San Gimignano, on the top of a low hill at the center of Valdelsa. This wonderful landscape will seduce you with its unique skyline made of towers, built during the 14th century to reflect the growing power of noble families.
Siena and San Gimignano Tour from Florence

Rated 5 Stars, based on 15 Reviews.
A full and relaxing day visiting the most beautiful attractions in the countryside outside of Florence, get an introduction of our lifestyle, explore amazing locations, take hundreds of pictures, breathe the Tuscan atmosphere and most important, spend a day with locals! On this tour we will visit 3 amazing locations: Siena, Monteriggioni and San Gimignano….and we will stop for lunch in a family owned winery for a delicious and authentic lunch combined with a wine and olive oil tasting in the famous Chianti Wine region(optional).
From the Roman city of Siena, to the Medieval Tuscan villages of Monteriggioni and San Gimignano.. a full immersion in art, history, architecture and traditions.
You will have time to explore all the towns on your own and our driver will give you plenty of information to enjoy all the sights and attractions. This is a perfect day trip for any age traveller visiting Tuscany for the first time or even for repeaters.
Private guided tour: Siena San Gimignano and Chianti

Rated 3.5 Stars, based on 6 Reviews.
Get a personalized tour of San Gimignano, Siena and the Chianti region during this 10-hour p excursion from Florence. Travel comfortably with a minivan or a car, with much less walking than on a bus.
With a dedicated driver/guide, explore the middle age stronghold of Castellina in Chianti, deep in the Chianti Classico wine area and the square of Siena and San Gimignano, then pop into a local winery to learn about the local sangiovese grapes and sip some Chianti.
Wine tasting and round-trip private transportation from a meeting point near the Florence train station included.
Highlights 11-hour tour of the Tuscan San Gimignano, Siena and Chianti region from Florence Round-trip transportation from the Florence train station Visit San Gimignano, Siena and Greve Taste Chianti and learn about the cultivation of sangiovese.
Florence Private Day Trip to Siena and San Gimignano

Rated 5 Stars, based on 1 Reviews.
A customized day trip of Siena and San Gimignano for the discerning traveller seeking an authentic Italian experience on a small group tour with only the very best of English speaking driver-guides. Travel from the centre of Florence to discover the one-time capital of Tuscany, Siena and the enchanting hilltop towered town of San Gimignano. Visit Italy close up in a Mercedes minivan for up to 7 people that takes you into the very heart of each of these beautiful Tuscan cities.