Day Trips from Tuscany to Siena

Explore the best of Tuscany in a single day on this private tour from Florence. Travel along scenic countryside roads to reach iconic destinations, including Siena, Pisa, and the UNESCO-listed hilltop town of San Gimignano. See famous landmarks such as the Leaning Tower of Pisa and Piazza del Campo without the hassle of planning your route. Enjoy private transportation and accommodation pickup upon request for added comfort.

There are no direct transport links between Florence and San Gimignano, so the best way to explore this UNESCO-listed hilltop village is by private car. Embark on a deluxe visit during this half-day, group tour, and visit key landmarks like the Duomo, San Agostino Church, the Museum of Holy Relics, and the 13 towers of its skyline. Tours stop at a wine estate, where travelers can opt for a tasting.

When your boat docks at the Livorno Port, don’t waste time at the port. Book a private Tuscany day trip in advance, and head out with a guide who also drives to discover the region’s highlights such as the hill town of San Gimignano, the Chianti wine region, and Piazzale Michelangelo in Florence, the city’s beloved vantage point. Gelato, wine tasting, and lunch are among the perks.

Pair the beauty of San Gimignano, a UNESCO World Heritage Site, with the classic flavors of Italian cuisine on this private adventure. Discover the walled city, home to some of the world’s best ice cream at Gelateria Dondoli, then head to a country farmhouse. Choose whether to make pizza, lasagne, or fresh egg pasta, then prepare and enjoy your Italian lunch with local Chianti wine.

Experience the very best of Tuscany on an unforgettable full-day journey from Florence, visiting four of the region's most iconic destinations in one seamless itinerary. Marvel at the world-famous Leaning Tower of Pisa, wander through the medieval streets of San Gimignano, explore the historic charm of Siena, and travel through the rolling vineyards of the renowned Chianti countryside. Savor the authentic flavors of Tuscany with a light winery lunch featuring regional cheeses, cured meats, local wines, and traditional Cantuccini biscuits. Along the way, enjoy spectacular landscapes of vineyards, olive groves, and picturesque hilltop villages that have made Tuscany one of Italy's most beloved destinations. Perfect for first-time visitors and lovers of history, culture, food, and wine, this expertly planned day trip lets you experience Tuscany's most famous highlights without the hassle of planning transportation. Reserve your place today and create unforgettable memories.

Escape the city and experience the very best of Tuscany on a full-day journey through its most iconic destinations. Travel comfortably from Florence to discover the medieval charm of Siena, the famous towers of San Gimignano, the rolling vineyards of the Chianti countryside, and the world-renowned Leaning Tower of Pisa. Stroll through UNESCO World Heritage Sites, admire spectacular Renaissance and medieval architecture, taste authentic Tuscan wines and local specialties at a traditional winery, and capture unforgettable views of Tuscany's picturesque landscapes. Whether you're fascinated by history, passionate about Italian culture, or simply looking to experience Tuscany's timeless beauty, this tour offers the perfect combination of historic cities, scenic countryside, and authentic local flavors—all in one unforgettable day.

Explore the medieval town of San Gimignano before heading into the scenic Chianti hills on this private Tuscan experience, which includes lunch and wine tasting. Walk through cobblestone streets, enjoy a gelato or glass of Vernaccia, then travel to local wineries for a traditional Tuscan lunch and guided wine tastings. This tour blends cultural heritage with countryside charm and regional flavors for a well-rounded day in Tuscany with hotel pickup included.

Reaching Siena and San Gimignano from Florence by public transport requires separate connections to two different destinations—and coordinating a return journey from both in a single day takes planning that most visitors don't have time for. This full-day tour covers both UNESCO World Heritage-listed towns and offers free time in each to explore Piazza del Campo and San Gimignano's medieval towers independently.

Escape the crowds and experience the best of Tuscany with this private shore excursion from Livorno or Florence. Travel in comfort from your ship or hotel with a private driver and enjoy a small-group walking tour of San Gimignano, led by a local expert. Discover medieval towers, artisan shops, and breathtaking views in this UNESCO-listed town. Enhance your day with an optional wine tasting and Tuscan lunch at a renowned Super Tuscan winery, where you’ll sample Vernaccia di San Gimignano and other local labels in an authentic countryside setting. After lunch, continue to Siena, one of Tuscany’s most enchanting cities. Enjoy free time to explore Piazza del Campo, admire the Siena Cathedral from outside, and stroll the historic streets at your own pace. This flexible experience can be tailored to your cruise schedule, with guaranteed on-time return. Perfect for travelers seeking a mix of history, beauty, and flavor in a single day.

Explore Siena and San Gimigano on our private Shore Excursion, travelling in the comfort of an air-conditioned vehicle. Discover the highlights of Siena, admire the marvelous Tuscan landscape, relax in the hilltop village of San Gimignano and taste ocal wine. Your english speaking driver greets you at your cruise ship at Livorno Port and chauffeurs you to your first destination, Siena. You will have about 2 hours of free time to explore the town, a true jewel of Tuscany. Continue your day visiting San Gimignano. Famous for its skyline of tall Medieval towers, here you will have free time to explore the main street full of typical shops, have a look at its splendid Cathedral and medieval palaces, and enjoy a wine tasting! At the end of the wonderful Siena and San Gimignano Shore Excursion, your driver will chauffeur you back to your cruise ship at Livorno Port. Get on board and enjoy the tour!

This tour ticks off two must-sees in Tuscany's collection, Siena and San Gimignano. You'll be picked up from your accommodation in Florence and taken for a full-day tour of these two cultural hotspots. You'll start with a walking tour of the old town of Siena. Siena Cathedral, one of Italy's most popular Romanesque-meets-Gothic churches is here, too, and you'll head inside it before heading into the city centre. In this part of Siena, the Piazza del Campo is the biggest draw. Shaped like a seashell, you'll find everything from a big water fountain to City Hall here. Then you'll hop back on your transport and make your way to San Gimignano, which is often known as the Manhattan of the Middle Ages because of its line-up of ancient towers. You'll head to a gelateria for a chance to try some ice-cream made by a master whose creations have won international championships. When you've had your fill and looked around San Gimignano, you'll be taken back to your accommodation in Florence.

This experience is suitable for everyone, even children. We will be in an open area admiring the wonderful Tuscan hills. We will stop at all the most scenic places to take beautiful photos.

This tour combines two of Tuscany’s most authentic medieval towns in a single day. In Volterra, you’ll enjoy a live alabaster carving demonstration in a traditional artisan workshop before exploring the historic center at your own pace. The experience continues in the perfectly preserved walled village of Monteriggioni, one of the most iconic sights in the Tuscan countryside.

Welcome to a unique experience in the heart of beautiful Tuscany! Our Chianti tour invites you to discover the essence of this legendary wine region, all with the luxury and comfort of our exclusive chauffeur service included. From the moment we pick you up at your accommodation, you will immerse yourself in a dream journey through the most impressive landscapes in Italy. Our expert drivers, knowledgeable about the area, will guide you through the winding roads between hills, dotted with vineyards, olive groves and cypress trees, giving you panoramic views that will leave you breathless. During the tour, you will have the opportunity to see family-owned vineyards, where you will be greeted with warm Tuscan hospitality and have the opportunity to taste some of the most exquisite wines in the region. From the iconic Chianti Classico to other local varietals, each sip will transport you to centuries of wine tradition.

we will make you experience Chianti as we do, in its beauty, goodness and simplicity, with fun and light-heartedness

Departure from your Accommodation or Hotel, travel in a van maximum 6 people , English speaking driver, each vehicle is equipped with fresh water. 1 stop city of Siena where you will have 1.5/2 hours to visit the city of the Palio, and those who love wine can visit the wine cellar in the tufa cave under the baptistery of Siena, with the possibility of wine tasting for a fee 2 stop town of San Gimignano where you will have 1 hour of time for Visiting and Shopping in the City of 7 Towers. stop at the local winery for tasting of local wines and visit of the company. Return to Florence where you were picked up, it is possible on your request to do a wine test and lunch in a winery in the San Gimignano area

Lilium Travel Florence offers a full-day, 9-hour journey through the heart of Tuscany with a private van tour (max 8 pax) from Florence. First, you’ll visit San Gimignano, the "Town of Towers," a stunning medieval gem and UNESCO World Heritage site. Explore its narrow streets, admire the well-preserved towers that once symbolized wealth and power, and soak in panoramic views of the surrounding Tuscan countryside. Next, head to the village of Monteriggioni, a perfectly preserved medieval fortress with its iconic walls and towers still standing proudly. Wander through the town, feeling as if you’ve stepped back in time. The final stop is Siena, famous for its unique medieval architecture and the breathtaking Piazza del Campo, home of the historic Palio horse race. Enjoy time to explore its cobbled streets, visit the stunning Siena Cathedral, and relax in one of its charming cafes. With ample free time at each location, this tour offers a perfect blend of history, culture, and relaxation.

Experience Tuscany’s highlights on a private day trip from Florence to Siena, San Gimignano, and Pisa. In Siena, explore the UNESCO-listed historic center, admire its Gothic cathedral, and visit the famous Piazza del Campo, home of the Palio horse race. Continue through the rolling hills to San Gimignano, the “Town of Towers,” where medieval skyscrapers, cobbled streets, and artisan shops await. Finish in Pisa, marveling at the iconic Leaning Tower and the stunning monuments of the Piazza dei Miracoli. With comfortable transport, a private guide, and flexible pacing, this exclusive Florence day tour offers a personalized way to see Tuscany’s most famous landmarks.

Explore the charming medieval town of San Gimignano, known for its iconic towers and rich history. After soaking in the sights, savor a delightful lunch at the Torciano estate, where you can also enjoy a guided tour of the winery and taste exquisite wines. The journey continues to Siena, a city filled with stunning architecture and vibrant culture. Ideal for travelers looking to immerse themselves in Tuscany's beauty and flavors. - Visit the enchanting town of San Gimignano, famous for its towers - Enjoy a delicious lunch and wine tasting at the Torciano estate - Experience the rich culture and stunning sights of Siena - Perfect for wine lovers and cultural enthusiasts alike

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.

Enjoy a half-day journey from San Gimignano to the picturesque wine region of Chianti. Begin your adventure with a visit to the charming village of Castellina in Chianti, followed by a delightful wine tasting at a nearby vineyard. Stroll around Monteriggioni, a medieval village where you can admire the ancient walls. At a beautiful wine estate, take part in a wine tasting savoring the rich aroma and ruby-red tones of Chianti wine crafted from Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes.

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine (tasting included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition, the experience includes a guided tour of one of Chianti's most characteristic castles, the castle of Brolio, from which you can take in magnificent panoramic views to the vineyards and the city of Siena. To experience the most out of the territory, we'll book lunch at a local family owned restaurant where you, in addition to enjoying its tranquility and warm welcome, can savour the dishes of the Tuscan tradition. The way back is mainly descending and the guide will stop in magnificent sightseeing spots before getting back to the starting point.

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition to it, this tour has an Arts footprint. We'll lead you through some hidden sculptures, located throughout the landscape, as a warm up to our stop at the Chianti Sculpture Park, where you'll visit some contemporary sculptures and installations. We'll build on to the arts experience by stopping at the hamlet of Scopeto, where the film "Letters to Juliet" has been shot. Least, but not last, it will be wine time right after at the Scopeto Winery, where you can further develop your reconnaissance of the territory by tasting one of its maximum expression: the Chianti Classico. We then, climb back to our comfortable ebikes to return to Siena