Tuscany Day Trip with Chianti, Siena and San Gimignano with Lunch in Small Group

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Full description Enhance your visit to Florence with an unforgettable day trip to the rolling hills and gourmet charm of the Tuscan countryside. This small-group Tuscany tour from Florence offers a perfect blend of cultural exploration, culinary delight, and scenic beauty. Discover the medieval treasures of Siena, indulge in a Chianti wine tasting paired with a farm-to-table lunch, and stroll the historic streets of San Gimignano, one of Tuscany's most iconic villages. With group sizes limited to just 14 guests, this tour ensures an intimate and personalized experience throughout the day.

Your journey begins in central Florence, where you’ll meet your expert guide and fellow travelers before boarding private transportation bound for the heart of Tuscany. As you leave the city behind, enjoy a photo stop at Florence's most stunning panoramic viewpoint—perfect for capturing the skyline of this Renaissance masterpiece before heading into the countryside.

The first stop on your Tuscany day trip is Siena, a beautifully preserved medieval city renowned for its unique architecture and rich history. Untouched by the destruction of World War II, Siena remains one of the best-preserved historical centers in Italy. As you wander through its winding streets, your guide will share the stories of the city's centuries-old traditions, including the world-famous Palio di Siena, a thrilling horse race that takes place in the heart of the city. You'll also admire the awe-inspiring exterior of the Siena Cathedral, a masterpiece of Gothic design and one of Tuscany’s most impressive landmarks.

From Siena, the tour continues into the Chianti region—famous around the world for its rolling vineyards and robust red wines. Here, you'll be welcomed at a family-run farm and winery for a truly immersive experience. Enjoy a behind-the-scenes tour of the vineyards, wine cellars, and production facilities to learn about traditional Tuscan winemaking. Then, sit down for a seasonal, all-inclusive lunch prepared with fresh, locally sourced ingredients. Each dish is expertly paired with selected Chianti wines, allowing you to savor the full flavor of the region in every bite and sip.

After your wine tasting and Tuscan lunch, the tour heads to the storybook town of San Gimignano, a UNESCO World Heritage Site known for its striking medieval skyline. Often called the “Medieval Manhattan,” San Gimignano is famous for its preserved tower houses, cobblestone streets, and sweeping views of the surrounding countryside. Enjoy free time to explore at your own pace—browse local artisan shops, sample regional specialties, or simply take in the ambiance of this magical hilltop town.

This full-day small-group Tuscany tour offers a carefully balanced itinerary that showcases the best of the region’s art, architecture, history, and gastronomy. From the ancient charm of Siena to the vineyard-covered hills of Chianti and the timeless elegance of San Gimignano, you'll experience the essence of Tuscany in just one day. With expert guidance, small group size, and comfortable transport from Florence, this tour is ideal for anyone looking to discover Tuscany’s most iconic destinations in a relaxed and authentic way. Additional Information Please arrive 15 minutes before your tour start time for check-in. Out of courtesy to other guests, we’re unable to wait for latecomers. No refunds can be provided for late arrivals or no-showsThose with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacsIf you are traveling with a small child, please contact us. We need to confirm space on the vehicle for themLuggage and/or strollers are not allowed on this tour as there is no extra storage space on the vehicleIn order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your guide will assist you. The Cathedral is closed on Sundays and for certain holy days. Please note that due to the religious nature of Siena cathedral, all individuals regardless of gender must cover their shoulders and knees. A scarf or shawl is acceptable. We cannot be held responsible for those denied entryTips/gratuities (for your guide) are always appreciatedUnfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollersThis is a walking tour. Guests should be able to walk at a moderate pace without difficultyMobile tickets will be accepted Inclusions Expert English-speaking guideDesignated professional driverAir-conditioned transportExpertly guided walking tour of Siena and San GimignanoGourmet lunch and wine tasting in ChiantiSmall Group up to 14 people Exclusions Hotel pick-up and drop offEntrance tickets to the Siena CathedralTickets, meals and drinks except if expressly specified in the tour inclusionsOther unspecified service Cancellation Policy Free cancellation up to 24 hours before the service. Cancellations after this time limit or no show, no refund provided Meeting Point Piazza della Repubblica, Florence, IT
Your guide will be holding a green sign. This tour meets by the Carousel in Piazza della Repubblica