Day Trips from Florence to Siena

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and access to its medieval walls. Continue on to the UNESCO heritage area of Val d'Orcia and stop at the medieval village of Montalcino for an optional taste of local wine and nibbles. Finish your tour with a wander through Pienza before the scenic drive back to Florence.

Discover Tuscany on this private day tour to San Gimignano and Siena from Florence. Explore the hillside town of San Gimignano, known for its many towers, with a guide and enjoy free time for shopping. After lunch with wine tastings near San Gimignano (own expense), visit Siena and discover one of Italy’s finest Gothic churches, the Cathedral of Siena (Duomo di Siena). Hotel pickup is included for added convenience.

Get a taster of Tuscany on this private tour that features a selection of the region's highlights. Visit Siena, the Chianti countryside, and San Gimignano all in the same day, without having to hire your own car. Enjoy an itinerary that includes historic sightseeing and regional wineries, with the option to try local varietals (extra cost). Ideal for travellers who are only in the area for a short time.

Discover Tuscany at its finest in one day, with historical towns, breathtaking views, and stunning art. Avoid transport hassle with a private driver, who will whisk you through beautiful countryside to the historic towns of Pisa, San Gimignano, and Chianti. Learn about the area's culture and see the famous Leaning Tower of Pisa. Experience wine being produced in the renowned Chianti region, with the option for lunch and a tasting of six wines (own expense).

Savor the famous flavors of Tuscany in style with a private wine tour. Start your day with panoramic views over Florence at the Piazzale Michelangelo, before travelling through the Tuscan countryside to the wineries of Chianti, stopping at the charming medieval village of San Gimignano on your way. Wander the vineyards, learn the secrets of local winemakers and stay for an optional lunch and wine tasting.

The day starts with departure from Florence in a private car or minivan. You’ll leave the city and head into the Tuscan countryside, with its rolling hills, vineyards, and medieval villages. The first stop is Montalcino, famous for its Brunello wine. After a visit to the historic center, you’ll tour a renowned winery, walking through vineyards and cellars, and participate in a guided tasting, including local extra virgin olive oil. A farm lunch with traditional Tuscan dishes and estate wines follows. In the afternoon, you’ll travel to Siena. Discover Piazza del Campo, the Cathedral, and other historic sites. You’ll also have free time to explore at your own pace, perhaps enjoying a sweet treat from a local pastry shop. The day ends in Monteriggioni, one of Tuscany’s best-preserved fortified villages. Walk along its intact city walls, then enjoy a wine and local product tasting at an authentic winery inside the village. A perfect blend of history, flavors, and breathtaking views.

Discover Siena, Monteriggioni, and San Gimignano on a day trip from Florence, and indulge in a Tuscan wine tasting, too. The day-long tour starts with a guided walk around Siena’s historical center with admission to Siena Cathedral, the city’s Gothic masterpiece. In the afternoon, you’ll visit Monteriggioni for photos, stop at a Tuscan estate for lunch and wine, then amble the streets of San Gimignano at your own pace.

Explore the charming towns of Siena and San Gimignano on this full-day minivan tour from Florence, with a photo stop at Monteriggioni. Discover the medieval and Gothic architecture of the towns and learn their histories from your informative guide. Visit the main attractions of each city and sample their delicious cuisine—at your own expense—while walking around and absorbing the atmosphere of the cities.

Go beyond Florence and see more of Tuscany with this private day trip to Siena, San Gimignano, and Pisa. Tour these old towns with a guide, discovering their histories and taking in their highlights. Enjoy a balanced itinerary that includes a guided tour of Siena and the Piazza del Campo, along with free time to explore all the towns included in the trip. Don't worry about trying to find something to eat on the go, with lunch, and wine, at a farmhouse included.

Embark on a private excursion from Florence to Siena, to experience the historic towers, pointed arches, and narrow streets of this important Tuscan city. Take in the sights and sounds of Siena and its stunning architecture, plus make a stop for photos in Monteriggioni. Led by an expert local guide, receive a detailed description of the highlights, enjoy exclusive access to the Cathedral, and indulge in the local cuisine.

The best way to see the Tuscan countryside is by car, but renting a vehicle means you have to keep your eyes on the road, instead of on the area’s bucolic beauty. Leave the driving to someone else when you head out on a private excursion to Siena and San Gimignano. Going with a guide also means you learn more about the area than you would on your own.

Swap the busy streets of Florence for the tranquility of rural Tuscany on a private day trip to San Gimignano. A private tour means you can customize your itinerary according to your interests while also receiving the undivided attention of your guide. Plus, letting someone else drive means that you’ll be able to spend less time navigating and more time focusing on the rolling vineyards of Tuscany.

Explore Tuscany's countryside without hiring a car with this private driving tour of the region. Perfect for travelers staying in Florence, enjoy hotel pickup and relax as you are taken to a range of destinations based on your interests. Visit the Florence American Cemetery, the medieval hamlet of Castello di Montefioralle, and take in the view at Piazzale Michelangelo. For wine lovers, opt to visit a Chianti winery (at an additional cost) and enjoy tastings of local varities.

Chianti is not well-served by trains and buses, so exploring by public transportation can be a chore. Navigate around the Tuscan countryside with ease on this full-day private tour to the Chianti wine region from Florence. Enjoy convenient pickup from your hotel and travel by minivan along an itinerary customized to your interests. Admire views of the rolling, vineyard-covered landscape, stop to visit medieval villages, and opt to visit a winery for lunch and a wine tasting (own expense).

Discover the magic of Tuscany on a semi private full-day journey from Florence through the rolling Chianti hills. Explore the medieval splendor of Siena, wandering its charming streets to the iconic Piazza del Campo, home of the legendary Palio horse race, and savor traditional sweets like Panpepato, Panforte, and Ricciarelli. Continue to San Gimignano, the UNESCO listed City of a Hundred Towers, where cobblestone streets and timeless charm create an unforgettable backdrop. Enjoy a wine tasting at a historic estate, sampling 10 exceptional Tuscan wines paired with local delicacies and a traditional lunch. Explore the cellars, learn the secrets of winemaking, and immerse yourself in Tuscany’s rich culture, history, and gastronomy. An intimate, semi-private experience perfect for wine, food, and history lovers.

Discover the magic of Tuscany on a private full-day journey from Florence through the rolling Chianti hills. Feel the sun on your face and the gentle breeze across vineyards as you explore the medieval splendor of Siena, wandering its charming streets to the iconic Piazza del Campo, home of the legendary Palio horse race, and tasting traditional sweets like Panpepato, Panforte, and Ricciarelli. Continue to San Gimignano, the UNESCO listed City of a Hundred Towers, where cobblestone streets, ivy-clad towers, and golden sunlight create an unforgettable backdrop. Delight in a private wine tasting at a historic estate, savoring 10 exceptional Tuscan wines paired with local delicacies, while the aromas of oak barrels and fresh bread fill the air. Explore the cellars, learn the secrets of winemaking, and immerse yourself in the rich culture, history, and gastronomy of Tuscany. An exclusive, intimate experience for the senses, crafted for wine, food, and history lovers alike.

Enjoy a full-day journey from Florence through the rolling Tuscan hills to visit San Galgano, Pienza, and Montepulciano. Immerse yourself in the enchantment of San Galgano, a place where time seems to stand still. Here, nestled among the hills, stands the evocative roofless Abbey—a Gothic masterpiece that has defied the centuries, offering unforgettable views under the open sky. The journey continues with a visit to the nearby Hermitage of Montesiepi, home to the legendary Sword in the Stone. Next, explore Pienza, a splendidly preserved Renaissance village boasting breathtaking views of the Val d'Orcia. Finally, in Montepulciano, stop at a renowned local winery to taste the region's finest wines, perfectly paired with authentic Tuscan specialties.

Visit the charming Tuscan towns of Siena and San Gimignano without the hassle of organizing the trip yourself on this full-day private tour from Florence. Your driver-guide provides insight and recommendations while on the road, but then leaves you with free time to explore, shop, and dine at your own pace. In San Gimignano, enjoy stunning panoramic views of the area.

Experience Tuscany's wine culture on this private wineries tour. Ideal for travelers based in Florence, explore beyond the city without having to hire a car. Travel with a knowledgeable sommelier guide through rolling hills and vineyards, visiting three estates to sample regional wines and olive oil. Enjoy a traditional Tuscan lunch at a family-owned winery paired with wine. Perfect for food lovers looking to immerse themselves in local flavors.

Delight in the flavors of Tuscany on a small-group wine-tasting tour from Florence. Start the tour with a stroll through San Gimignano, a medieval hilltop town with spectacular views. Afterward, continue to two wineries in the Chianti region, where you sample Tuscan wines, food, and olive oils. Group size is limited for a more personalized experience.