Day Trips from Tuscany to Siena

Navigating Tuscany’s rolling vineyards and medieval towns by public transportation or rental car can be stressful and time-consuming. With this private day trip, leave the driving to a professional and relax as you take in views of the Crete Senesi, Montepulciano, and Siena. Stop at a winery to taste Tuscan reds and whites and enjoy free time to explore the old towns of these two iconic destinations with included hotel pickup.

Soak up the Tuscan sun, and delve into Chianti's cuisine, without the hassle of navigating on this open-top minivan tour. Enjoy a scenic drive through the countryside, stopping for a tour and tasting at a local cellar. Take a stroll through the villages of Montefioralle and Greve in Chianti before sitting down to a Tuscan lunch at a second cellar featuring a multi-course meal with wine pairing.

A fantastic private tour, to discover the medieval villages of Chianti. Thanks to our unique minivan specially modified to fully appreciate the landscape. Enjoy the journey like the destination The last stop will offer you the perfect opportunity to buy and ship excellent wines directly from the producer

Ideal for travelers looking for off-the-beaten-path adventures, Italian-style, this tour pairs an all-terrain vehicle (ATV) off-road session with wine tastings and medieval village visits. After a quick lesson, explore the Chianti countryside riding your own ATV or on the back of someone else's. Then, hop on the tour minivan and head to the Tuscan hill towns of Montefioralle and Piazza Matteotti for exploring and shopping. Finish the day with a generous lunch and six wine tastings at a classic Tuscan winery.

The best of the best - Unique opportunity to combine adventure (e-bike tour in one of the best Tuscany bike roads), art&history (visit to medieval town), and wellness (wonderful SPA with an amazing view). A once in a lifetime experience in one of the most beautiful areas of Tuscany. Dedicated tour leader, small group (max 8 pax) will allow you to have an intense experience. Free transportation, free e-bikes, free best moments video collection (by drone) and free WIFI during the tour.

Explore the wonderful Chianti wine region and its rolling hills! Get away from the noise and crowds of the city and enjoy a relaxing day tour in the Tuscan countryside, famous all over the world for its fairytale villages. Our Chianti Wine Experience tour includes two visits with tasting at two cellars located in the heart of Chianti, where you will discover all the secrets of the wine production process. Afterwards, you can taste the excellent Chianti accompanied by typical Tuscan products.

Spend a day in Tuscany visiting the city of Siena, the castle of Monteriggioni and the medieval village of San Gimignano. With a private English speaking driver, you will enjoy greater flexibility in your itinerary with plenty of free time. Enjoy a walk through the historic center of Siena then have fun tasting the famous Chianti wine with a lunch in a family-run winery (tasting and lunch not included in the price) and then admire the view of the Tuscan countryside from San Gimignano where you can taste the best ice cream in Italy. Finish the tour with a visit to Piazzale Michelangelo before returning to Florence.

On this tour we will visit two of the most beautiful cities in Tuscany, important both for art and culture and of considerable historical importance. This tour will allow you to discover what is inside two such important Renaissance cities and walking through the streets of their historic centers you will feel like taking a leap in time and you will find yourself immersed in the Middle Ages; furthermore, we could stop in a family winery to taste the fantastic Chianti wines and have lunch or light lunch(winery cost included)

Discover two of Tuscany's most beautiful cities, Montepulciano and Siena, in just one day on this private trip. From Florence, journey in an air-conditioned vehicle to Montepulciano, with time to take in hilltop views from the Torre di Pulcinella. Next, visit Siena, where you can explore a medieval square and the local Gothic cathedral—climb to the top for views over the city.

Exploring the Chianti countryside and its historic hill towns by public transportation is virtually impossible. With this private day trip, relax and enjoy the views as an expert local driver takes you across the rolling hills to San Gimignano and Monteriggioni. Explore the medieval towns at your own pace and relax over a wine tasting at a Chianti cellar before the ride back to Florence.

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • San Gimignano • Siena Wine and Light Lunch in the Tuscany countryside included! Upgradable with licensed local guide in Siena (if option selected) Pickup and dropoff will be at your accommodation. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

The mountainous Tuscan region of Chianti is home to vineyards and wineries that produce some of Italy’s most popular vintages, but they can be difficult to reach without a car. On this full-day private tour, your driver transports you to several dispersed towns and villages in the region, all with a unique attachment to winemaking. Opt to join wine tastings (own expense) and explore each location on short walks.

- 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.

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.

Discover the best of Tuscany on a private journey through its beautiful towns and landscapes. Travel from Florence with a professional English-speaking driver who takes the stress out of navigating. In Siena, meet a licensed local guide for a walking tour through medieval streets. Along the way you'll learn about the majestic cathedral and famous Palio horse race. Then, savor a leisurely Tuscan lunch with wine pairings at a family-run Chianti farmhouse, surrounded by vineyards and olive groves. End your day in the hilltop gem of San Gimignano, a UNESCO-listed village, where you’ll enjoy free time to explore artisan shops, climb the towers, or simply soak in the views. With private transport and a relaxed pace, this day offers an intimate and authentic way to experience Tuscany.

The Tuscan countryside is a gourmet paradise, but few transportation options keep many travelers limited to Florence. Explore Siena, home to a magnificent cathedral and the famous Palio horse race, and the storybook village of San Gimignano (a UNESCO World Heritage Site) during this small-group tour. A seasonal lunch and Chianti wine tasting at a family-run vineyard are included.

Seeing both San Gimignano and Siena in one day can be difficult to coordinate on your own. This guided day trip from Florence simplifies the journey, combining two of Tuscany’s most atmospheric towns into a single, well-paced itinerary. Travel through the Tuscan countryside with a guide providing insight along the way, then enjoy free time in each destination to wander medieval streets and take in the scenery at your own pace.

Getting around Tuscany by public transport can be daunting. Skip the hassle of coordinating train and bus schedules and cover two top Tuscan towns in a single day with this San Gimignano and Siena tour. Explore the medieval old town of San Gimignano and enjoy a wine tasting before continuing on to Siena. Skip the line to enter the magnificent cathedral and explore the sights, shops, and eateries at your own pace.

Discover the essence of Tuscany on this immersive tour that combines history, stunning landscapes, and exquisite flavors. Departing from Villa Costanza, journey to Monteriggioni, a medieval fortress town where cobbled streets and artisan shops await. After exploring its historical charm, indulge in a guided wine tasting at a picturesque Chianti winery, savoring local varietals and regional delicacies. Continue to a renowned family-run winery in San Gimignano for another rich tasting experience that reflects the region's winemaking passion. This tour promises a blend of cultural immersion and culinary delight, perfect for history buffs and wine enthusiasts alike. - Depart from Villa Costanza at 14:45 for a half-day adventure - Explore the medieval fortress-town of Monteriggioni with free time - Enjoy guided wine tastings and cellar tours at two charming wineries - Experience the richness of Tuscan terroir with local cuisine pairings

Begin your adventure in Pisa, where you'll have free time to explore the UNESCO-listed Piazza dei Miracoli. Marvel at the Leaning Tower, one of the most iconic landmarks in the world. Admire the Cathedral and the Baptistery, and take plenty of time for photos and local souvenirs. Head into the Chianti hills to enjoy a Tuscan lunch at a traditional winery. Your meal will be accompanied by a guided wine tasting of local varieties, offering a true taste of Tuscany's winemaking heritage. Enjoy free time in Siena, where you can stroll through medieval streets and admire the stunning Piazza del Campo, one of Europe’s most beautiful squares. Known for its shell shape and unique charm, it’s also home to the Palio di Siena, a famous bareback horse race held twice a year. Conclude your day in San Gimignano, a breathtaking hilltop town famous for its skyline of medieval towers. Explore its cobbled streets, artisan shops, and panoramic views. Don’t miss the chance to try its world-champion gelato!

Discover the flavors of Tuscany on this half-day private tour to Chianti. Relax in a comfortable luxury car as you’re driven around the vineyards of Chianti. Visit a winery and sample two wines, before enjoying some free time to explore Panzano. You’ll also have the chance to meet a famous butcher, Dario Cecchini, before heading back to Florence.

Chianti wine country is known for its magical scenery, but exploring the area can be tricky for out-of-town travelers. Leave traffic and navigation to your private driver as you sit back and enjoy the ride on this half-day wine-tasting tour. Savor both red (Chianti Classico) and white (Vernaccia) wines, capped off by the chance to explore the beautiful medieval town of San Gimignano.

The logistics of getting around Tuscany from Florence can be a hassle. With this small-group day trip, skip figuring out public transport and visit Siena and the Chianti countryside with a private van. Set off from Florence and stop in Siena for free time to sightsee and shop. Afterward, enjoy a scenic drive through the countryside to a boutique winery for a generous wine tasting paired with a 3-course lunch.