Day Trips from Tuscany to Siena

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.