Itinerary 1 itinerary
Day 1
Meet at meeting point: Piazzale Montelungo Firenze,Città Metropolitana di Firenze,Toscana,Italy Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.Attractions and Activities: San Gimignano (Free entry) Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence. 2 hr(s)
Attractions and Activities: Piazza della Cisterna (Free entry) The atmospheric heart of San Gimignano, framed by tower-houses and a medieval stone well that anchors the square. A short, curated stop for photos and storytelling that brings the town's merchant past to life. 10 min(s)
Attractions and Activities: Mura di San Gimignano (Free entry How to visit:No indoor visits) Glide past the 14th-century fortifications and the most iconic gate, imagining pilgrims and traders entering centuries ago. Your tour leader shares context and highlights so you can appreciate the engineering and defense of a Tuscan walled city.
Attractions and Activities: Monteriggioni (Free entry) Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier 40 min(s)
Attractions and Activities: Chianti Road (Ticket included) Travel the legendary wine route through rolling vineyards, stone farmhouses, and cypress-lined ridges—classic Tuscany in every direction. Stop at a welcoming Chianti winery for a tasting of three wines and a farm-to-table 3-course lunch, ending sweetly with cantucci e vin santo. 1 hr(s)30 min(s)
Attractions and Activities: Siena (Free entry) Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena's golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace. 2 hr(s)30 min(s)
Attractions and Activities: Piazza Salimbeni (Free entry) Admire refined Renaissance architecture and hear how the world's oldest operating bank shaped Siena's wealth and culture. It's a concise stop with rich history and elegant façades perfect for quick photos. 15 min(s)
Attractions and Activities: Piazza del Campo (Free entry) Stand in Siena's shell-shaped stage, home to the legendary Palio horse race, and take in Palazzo Pubblico and Torre del Mangia. Your guide unpacks centuries of tradition so the square's drama and design truly resonate. 15 min(s)
Attractions and Activities: Siena Cathedral (Ticket included) Gaze at the striped marble exterior, a Gothic marvel that crowns the city; (if option selected) interior visit to admire polychrome floors and masterpieces. A powerful highlight that pairs art history with unforgettable visuals. 15 min(s)
Attractions and Activities: Biblioteca Piccolomini (At your own expense) Step into a jewel box of vivid Pinturicchio frescoes and illuminated manuscripts that glow with Renaissance color. A quick but dazzling stop that rewards art lovers and casual visitors alike. (if cathedral option selected) 10 min(s)
Return along vineyard-draped hills and ancient hamlets, the perfect finale for golden-hour photos across the Tuscan countryside. A smooth, scenic drive back to Florence rounding off a day of towers, wine, and medieval splendor.
Guests leave on their own: Piazzale MontelungoEnd the tour on your own and bring your trip to a happy conclusion Firenze,Città Metropolitana di Firenze,Toscana,Italy Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
*Itinerary times are in the local time of the place of visit and may be subject to changes due to weather conditions, road conditions, and other factors. We appreciate your understanding.