Day Trips from Tuscany to Siena

Tick off more highlights of Tuscany in less time—and enjoy a more personalized way to travel—on an activity-packed day trip great for first-time visitors. With just your guide (or small group, if option selected) for company, zip between highlights from Siena and Monteriggioni to San Gimignano and the Chianti wine region. Benefit from the included transit and your guide's insider knowledge along the way, and even enjoy a wine tasting and lunch.

Immerse yourself in Italian wine culture on this half-day tour around the revered Chianti Classico wine region. There’s no crowding into cellar doors on this small-group tour of the region. Instead, spend your afternoon exploring the cellars and sampling the products of some of the region’s vineyards. All transport is provided, so you can fully enjoy your tastings.

Tuscany has played backdrop to countless movies, but getting around the stunning region—and knowing where to find filming locations—takes local know-how. Discover a hand-picked selection on this full-day, small-group adventure. From the vampires of the Twilight saga to Diane Lane in "Under the Tuscan Sun," you’ll enjoy free time to explore iconic sites in Siena, Montepulciano, and Cortona. Even better, a light lunch and wine tasting are included.

Explore the rolling hills, sun-blushed vineyards, and winding country lanes of Tuscany from a classic Italian Vespa. Hop aboard your own 50cc Original Piaggio Vespa scooter or share one with a friend, and follow your guide on a scenic tour of the Chianti region. Enjoy the views of the skyline of the Medieval walled city of San Gimignano, jump off to admire the views, and enjoy a delicious wine-tasting lunch at a Tuscan winery.

Experience the allure of Tuscany without the hassle of tricky logistics with this all-inclusive day trip from Rome. Save time with a high-speed train to Florence, where you’ll hop on a minibus with your tour leader and small group to visit Monteriggioni, Siena, and San Gimignano. End your Tuscan adventure with a wine and olive oil tasting in Chianti before heading back to Florence for the return train to Rome.

Your experience begins early in the morning with a free tour of Pisa, here you will have time to admire the magnificent Cathedral, the Baptistery, the Monumental Camposanto and of course the famous Tower of Pisa. Afterwards, we will move to a rustic winery in Chianti, on the slopes of San Gimignano, where you will be waiting for a typical Tuscan light lunch enriched by a tasting of good wine. After lunch you will discover one of the most beautiful medieval villages perched, San Gimignano, also known as the Medieval Manahattan for the many towers that distinguish it. We will then arrive in Siena, where our expert guide will lead us from Piazza del Campo, up to the Cathedral, crossing the most beautiful Contrade that characterize this city. At the end of the tour, there will be free time to enjoy a coffee and some shopping in the typical local shops. Our return to Florence will have as its scenery a magnificent sunset, a perfect conclusion to an unforgettable day spent in Tuscany.

If you want to discover Chianti and fully enjoy its flavors whether you are a wine lover or not our tour will involve you at 360 °! Our afternoon excursion Depart comfortably from Florence together with a tour leader who during the bus journey will introduce you to the history and curiosities of this enchanting area of Tuscany, rich in vineyards and verdant hills that you can admire during the journey comfortably seated in minivan. Once you arrive in Chianti area you enjoy in two different typical farms, visits and wine tastings of selected wines, including fresh whites, important reds, elegant sparkling wines and a precious vin santo. Each glass is accompanied by typical local products: the ingredients and dishes vary according to the season, so you can find among others local cold cuts and cheeses, organic extra virgin olive oils flavored with white truffle and chilli, aged balsamic vinegar. At the end, for those who wish, there will be the possibility to buy the tasted products.

Make the most of your day in Tuscany with this all-in-one adventure from Florence. Skip the hassle of planning and enjoy a curated route through Pisa, San Gimignano, Siena, and the Chianti Hills. Get up close to the Leaning Tower, sip wine and tuck into lunch at a rural vineyard and wander quaint medieval towns your own pace. Upgrade to add a guide or tower climb if you want to go all in.

Take a breather from the hustle and bustle of Florence on this trip to Chianti. Perfect for foodies and wine enthusiasts, this itinerary includes stops at a local vinegar distillery and a winery that includes multiple wine tastings. Don't worry about finding a designated driver; a coach driver will take on travel duty. Relax in the rolling countryside and take in the picturesque scenery throughout your trip.

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.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

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).