Day Trips from Tuscany to Siena

The historic winemaking region of Chianti is tough to reach without private transportation. But on this full-day wine-tasting excursion, which includes round-trip transfers, you’ll swap the crowded sights of Florence for rolling hills and traditional villages. Meet local producers and savor seasonal produce over a guided tasting at two wineries. Then, sit back and enjoy a tasty Tuscan dinner with the vineyards of Chianti as your backdrop.

Explore the peaceful hills of Chianti hassle-free with this group wine tour that includes transportation directly from the city center. Take in views over the rolling vineyards during the drive and stop for tastings at two different independent wineries. Connect with the winemakers as you stroll through the estates and sample a number of Tuscany wines paired with local nibbles while relaxing on panoramic terraces.

Travel by coach with an expert guide from Florence to three of Tuscany’s hidden gems. This day trip takes you to the medieval town of San Gimignano to explore its famously preserved towers, Piazza della Cisterna, and the Piazza del Duomo. Next, you’ll travel to the Gothic-style San Galgano Abbey nestled in the Tuscan hills, and then Volterra, a walled medieval city atop a mountain. You will have free time at each stop and your guide will provide their expertise.

Get more familiar with the Chianti wine region, without the hassle of figuring out how to visit it from Florence, on this group tour. Well-suited for travelers looking for a streamlined experience, relax knowing your transportation and activities are all pre-arranged. Enjoy visiting two winery estates and their vineyards, local wine tastings, and the opportunity to try regional snacks including bruschetta and cheese.

Florence might be the capital of Tuscany, but there’s lots more for curious travelers to discover in the Tuscan countryside. On this full-day tour, board a coach for a trip to the historic streets of Siena and the medieval town of San Gimignano, stopping along the way to indulge in a few glasses of locally made wine at a Chianti winery.

Combine medieval history, regional wine, and UNESCO-listed monuments on this full-day tour from Florence. This is an ideal choice for anyone who wants to experience wine tasting without getting behind the wheel afterwards. Visit Monteriggioni's medieval castle, explore Siena's historic architecture, and admire San Gimignano's skyline. End with a tasting of three Chianti wines and an opportunity to savor authentic, local flavors.

Knowing where to visit in the Tuscan countryside can be daunting for first-timers, especially if you're starting off in Florence. Simplify your day out with this group tour. Once you've boarded your coach, sit back knowing the transportation and activities are covered, meaning you can fully immerse yourself in the experience. Enjoy visiting Pienza, Montalcino, and Montepulciano, the Orcia Valley, and taking part in a wine and cheese tasting.

Venture to the notable wine regions of Tuscany on this private day trip from Florence. Enjoy the scenic drive through the Tuscan countryside and hop out to capture photos along the way. Venture into Siena and San Gimignano to explore must-see medieval landmarks at your own pace and finish your experience in Chianti with an optional wine tasting at a local winery.

Discover the beauty of Tuscany on this evening tour from Florence, featuring a visit to the Chianti countryside and a 4-course dinner. Head to a charming farmhouse winery to sample up to three glasses of Tuscan wine. Then head to a second estate to enjoy a relaxing evening of wine, dinner, and stunning views before returning to Florence.

See what Tuscany has to offer without breaking the bank on this budget-friendly day trip to the region's highlights from Florence. Save hours with coach transportation and enjoy free time to explore the medieval old towns of Siena and San Gimignano, plus the sights of Pisa. Upgrade to a guided tour of Siena, or add-on a 2-course lunch with wine pairing for a hassle-free, all-inclusive day.

The Chianti hills are home to some of Tuscany's most prestigious wineries and picturesque villages, but getting around by public transportation is practically impossible. On this wine tour, leave the driving to the professionals as you travel on a comfortable coach directly from Florence. Visit two traditional wineries for guided tours and tastings to learn more about local wine history and production, plus stretch your legs with a stroll through San Gimignano or Monteriggioni (depending on the departure time) to sightsee and shop at your own pace.

Experience the best of Tuscany on a full-day tour from Florence. Begin in Pisa at the UNESCO-listed Piazza dei Miracoli to admire the legendary Leaning Tower, the Cathedral, and the Baptistery, with plenty of free time for your bucket-list photos. Next, journey into the rolling hills of the Chianti wine region for an authentic winery lunch paired with a guided tasting of fine local blends. Continue to medieval Siena to stroll its historic streets and the unique, shell-shaped Piazza del Campo, soaking in the atmosphere of one of Italy's most beautiful squares. In the Full Tour option an official English-speaking guide will lead you through a city tour of Siena. Conclude your Tuscan adventure in the hilltop town of San Gimignano, famous for its skyline of medieval towers, panoramic views, and award-winning gelato, before a comfortable ride back to Florence. Please note: The order of the itinerary may vary to optimize your experience, but all scheduled destinations will be visited.

Make the most of your time in Livorno with this private day trip that includes round-trip transport to Florence plus a stop at a winery in the Tuscan hills for a wine-tasting lunch (own expense). Skip the hassle and delays of public transportation and head straight from the cruise port to Florence so you have more time to explore on your own, then break up the return drive with a winery visit.

Discover the art, history, and culture of Siena, Monteriggioni, and San Gimignano on a private tour. Listen to in-depth commentary from your driver, then explore each location on your own. Because it’s a private tour, you get to travel in comfortable transportation and enjoy a completely immersive experience without spending a moment waiting on other people.

Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.

Get an extra boost from your electric bike on a half-day bike tour of the Chianti region. Follow your guide through a picturesque landscape of gentle hills with vineyards, olive groves, and small villages, stopping at a 12th-century castle and a winery. Your tour includes a wine tasting, bottled water, and use of all necessary equipment.

Enjoy an unforgettable half day e-bike guided tour in Chianti region, one of the most known wine region in the World. You’ll cycle surrounded by vineyards and olive groves, while enjoying the amazing views of the Tuscany countryside. The bike tour will take you to PIevasciata before to come back to Siena along the Eroica route, on paved and gravel roads. During the ride we’ll stop in a winery for a Chianti wine tasting.

When your cruise ship docks at Livorno, don’t miss the chance to experience the famous flavors and towns of the Tuscan countryside. Travel inland aboard a private minivan to the UNESCO-listed medieval towns of San Gimignano and Siena, home of the famed Palio horse race. After leisure time to explore the cobblestone streets, impressive cathedrals and charming piazzas, visit a local winery to taste different varietals of renowned Chianti wines.

Leave your cruise ship in Livorno, and head to the Tuscan hills for a day of tasting wine and food. With a private guide, you’ll enjoy undivided attention and a flexible itinerary with timings to suit your schedule. Head to the Chianti region where the prestigious Chianti Classico wine is produced, and visit two wine estates. Tour the cellars, meet an owner, learn about cheese making, and enjoy a light lunch with Tuscan wine.

Immerse yourself in the scenic Chianti Classico hills, without the hassle of driving, on a full-day private wine adventure from Florence. Discover the heart of Tuscany’s famous wine district, savoring organic wine tastings and enjoying a light lunch of authentic Tuscan delicacies at a typical farmhouse. Led by a guide, this tour is perfect for wine lovers eager to experience the charm and flavors of Chianti.

Head deep into Tuscany's picturesque vineyards and ancient towns on this private tour, blending art, history, and wine to immerse you in the region's rich traditions. Stroll the captivating medieval stone pathways of San Gimignano and savor two wine tastings at renowned wineries, learning about the craft and passion behind Tuscany’s world-class vintages with rolling hills as your backdrop.

Refine your palate by tasting a variety of Chianti and other Tuscan wines—without the hassle of navigating unfamiliar roads or designating a driver—on this private wine tour. Along with a tasting, get a behind-the-scenes look at regional wine production and sample other local specialties, such as olive oil and bruschetta.

Explore two charming Italian towns, Siena and San Gimignano—without having to rent a car or tackle public transport—on this full-day trip from Pisa. Travel through the picturesque Tuscan countryside to your first stop, San Gimignano, and enjoy free time to shop, eat, or explore. Continue to Siena—known for its well-preserved medieval architecture—and choose whether to wander historic streets, sample gelato (own expense), or visit one of its UNESCO World Heritage-listed monuments. End the day back in Pisa.

Immerse yourself in the unique history of this pristine territory and taste some of the most excellent wines ever bottled. We have selected for you the "best of the best", no discussion. Visit an excellent Chianti wine producer and taste its great wines with a private tour of the winery. Spend the afternoon in a historic boutique winery of Chianti. Learn from the staff of this famous Chianti Winery where the story of this wine began, and the atmosphere of the old cellars will be an indelible memory of your once-in-a-lifetime wine tour Luxury transportation is included.