Best San Gimignano Day Trips in 2026

San Gimignano , Tuscany

From $ 98.90

Visit the beautiful region of Chianti with us and immerse yourselves in the picturesque Tuscan scenery that you have always imagined. The beautiful ruby-red colour and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. You'll join a wine tasting paired with some typical food. Then you’ll move to another winery, in the middle of Chianti Classico Area, where you’ll have a second wine tasting and extra virgin olive oil. The tour will end in San Gimignano, where it started.

San Gimignano , Tuscany

From $ 57.02

Explore the highlights of Pisa on this relaxed half-day trip from San Gimignano, ideal for travelers who want to experience the city’s most famous landmarks without the hassle of planning transport. Travel in comfort on an air-conditioned coach with an expert multilingual guide who will share fascinating insights into Pisa’s history and architecture. Upon arrival, enjoy free time to wander the charming streets or explore the city at your own pace. Visit the iconic Piazza dei Miracoli, home to Pisa’s most famous sights. Admire the Leaning Tower of Pisa, the Cathedral, and the Baptistery from outside—perfect for photos and soaking in the historic atmosphere. After your time in Pisa, relax on the return journey to San Gimignano, arriving in the evening. This tour is perfect for visitors looking for a stress-free, guided experience that combines comfort, flexibility, and the opportunity to see one of Italy’s most celebrated cities in a single afternoon.

San Gimignano , Tuscany

From $ 146.61

Begin your day by meeting your guide at Porta San Giovanni in San Gimignano. From here, head into the beautiful Tuscan countryside for a wine-tasting experience at a local winery, accompanied by typical regional products and a traditional lunch, offering the perfect introduction to authentic Tuscan flavors. After lunch, continue towards the prestigious wine area of Montalcino, world-famous for Brunello di Montalcino. Here, you will enjoy another wine tasting paired with regional specialties, surrounded by breathtaking vineyard landscapes. Following the tastings, enjoy free time in Montalcino to explore the charming historic center, stroll through its medieval streets, and admire spectacular views over the rolling Tuscan hills. Conclude your tour with a return to San Gimignano, completing a day filled with fine wines, local gastronomy, and the unforgettable beauty of Tuscany.

San Gimignano , Tuscany

From $ 138.47

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.