Day Trips from Tuscany to Siena

Immerse yourself in Tuscany’s charm with a tour from Florence! Begin your adventure in Pisa, where you’ll marvel at the Piazza dei Miracoli, Duomo, Baptistery, and the Leaning Tower of Pisa. Next, visit a Chianti Classico estate for a sommelier-guided wine tasting and a delicious lunch featuring local specialties. Continue to Siena for a guided walk through its historic gems like the Duomo and Piazza del Campo. End your day with a stop at Monteriggioni Castle before returning to Florence.

Experience the best of Chianti from its historic hill towns and rolling landscape to its storied wineries in a single day with this private driving tour. Save hours with a dedicated driver, leaving you time to fit in visits to both San Gimignano and Monteriggioni. Break up your sightseeing with a wine-tasting lunch at a Tuscan farm and cap off your day with a Chianti winery tour and 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.

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.

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).

Taste the famous flavors of Tuscany's wines and olive oils on this private tour from Florence. Travel through the Chianti region in a luxury tour vehicle, taking in the sights of the rolling hillsides covered with groves of olives and grapes. Take tours of several vineyards and learn about their production through guided commentary. Enjoy tastings of Chianti varietals and tuck into a tasty 3-course lunch with more wine.

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.

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.

Discover the wonders of Chianti and San Gimignano on a private day tour from Lucca. This customized excursion is perfect for travelers seeking an authentic Tuscan experience. With a private chauffeur at your disposal, you’ll immerse yourself in the charming Chianti countryside, enjoy tastings at renowned wineries, and witness skilled artisans at a terracotta workshop. Later, explore the UNESCO World Heritage site of San Gimignano, with its iconic medieval towers.

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.

Discover the Tuscan countryside and cuisine on a private bike tour from Florence. After a transfer from your hotel, follow your guide as you pedal through the world-famous Tuscan landscape on an electric bike, to avoid becoming fatigued on the famous hills. The scenic journey takes you to a family farm where you enjoy a gourmet lunch prepared using local ingredients. The culinary experience continues with wine and olive oil tastings, before a leisurely ride back to the starting point.

Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.

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.

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.

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.

Ride through the rolling hills of Montalcino on a private e-bike experience for travelers seeking authenticity, exceptional wines, and a deeper connection with Tuscany.Set in the UNESCO-listed Val d’Orcia, the journey unfolds at a relaxed, immersive pace. Premium e-bikes ensure effortless riding, and scenic routes along the Via Francigena offer photo spots, storytelling, and local legends far from crowds. Discover hidden corners and panoramic vineyards on a private, immersive tour for lasting memories.Led by a certified guide, you explore the history, culture, and atmosphere of this region beyond a standard tour.The experience culminates with an exclusive winery visit, followed by a refined Tuscan lunch and curated wine pairing. Savor Brunello and Rosso di Montalcino, both organic certified, in a private, intimate setting. Designed for couples, families, and discerning travelers, this is an elevated, immersive way to discover Montalcino — private, seamless, far from ordinary tours.

Explore Tuscany’s stunning landscapes and rich history on a full-day trip from Florence. Visit the medieval town of Monteriggioni, the UNESCO World Heritage site of San Gimignano, and the historic city of Siena. Enjoy wine tastings at a vineyard, paired with local delicacies and artisanal olive oils, enhancing your culinary adventure. With ample time to wander charming piazzas and cobblestone streets, this tour is perfect for history buffs and wine enthusiasts alike. - Visit iconic medieval towns: Monteriggioni, Siena, and San Gimignano - Savor wine tastings paired with local Tuscan delicacies - Travel comfortably in an air-conditioned minivan - Enjoy free time to explore at your leisure in each town

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.

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.

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.

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

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

Siena and San Gimignano are two of the most beautiful cities in Tuscany, but to visit both in a single day from Florence, private transportation is required. Let someone else do the driving—and the planning—during this full-day private excursion. Stop wherever and as often as you like on a fully customized tour, and enjoy the full attention of a knowledgeable driver throughout the day.

Taste some of Tuscany's most renowned varietals on a full-day private Chianti wine tour from Florence. Visit the charming medieval towns of Montalcino, Montepulciano, and Greve, where historic castles and towers appear untouched by time. In each village, stop at wineries and wine bars to sample pours of Nobile, Brunello, and Chianti Classico wines and learn about the cultivation of these prized grapes.