Tuscany Highlights Guided Small-Group Tour from Florence
Siena, Chianti wine country, San Gimignano, and Pisa in one expertly guided day
This Tuscany highlights tour from Florence takes you through four of the region's most celebrated destinations in a single, well-paced day. Travelling with a small group and an expert English-speaking tour leader, you benefit from a level of personal attention that large bus tours simply cannot offer. From UNESCO-listed medieval squares to a family-owned Chianti winery, every stop has been chosen to reflect the authentic character of Tuscany.
The journey begins in the rolling hills of the Chianti region, where your tour leader sets the scene with stories about the landscape, its history, and its wines. Siena greets you with its narrow cobbled streets and centuries-old architecture, followed by a leisurely lunch at a small estate winery nestled between two of Tuscany's most iconic towns. The afternoon brings the medieval towers of San Gimignano and the world-famous Piazza dei Miracoli in Pisa.
Throughout the day, local specialists and your dedicated tour leader provide context that transforms sightseeing into genuine discovery. The small-group format means you spend less time waiting and more time exploring, tasting, and absorbing the landscapes that have defined Tuscany's reputation for centuries. Easy difficulty and comfortable transport make this suitable for a wide range of travellers.
Tour Highlights
Explore Siena's UNESCO-listed historic centre, including the shell-shaped Piazza del Campo and the Gothic Siena Cathedral with its mosaic floors and gold decorations.
Enjoy a Tuscan lunch of appetizers, pasta, and desserts paired with estate wines at a family-owned Chianti winery between Siena and San Gimignano.
Discover San Gimignano's fourteen preserved medieval towers, its cobblestone lanes, and artisanal shops, earning the town its nickname as the little Manhattan of the Middle Ages.
Taste the award-winning gelato from Gelateria Dondoli at Piazza della Cisterna, a beloved tradition for visitors to San Gimignano.
Visit Pisa's Piazza dei Miracoli, a UNESCO World Heritage Site, and photograph the iconic Leaning Tower alongside the Cathedral, Baptistry, and Camposanto Monumentale.
Travel in a small, semi-private group with an expert English-speaking tour leader available throughout the day to answer questions and share local knowledge.
Itinerary
Meet your tour leader and fellow travellers at Piazzale Montelungo in Florence. Board the comfortable bus and settle in as the route takes you through the vine-covered hills and olive groves of the Chianti countryside, accompanied by commentary from your guide.
A local guide leads your small group through Siena's winding medieval streets, beginning at Piazza del Campo, one of Italy's most admired civic squares and home to the twice-yearly Palio horse race. The guided tour concludes at the Siena Cathedral, a masterpiece of Gothic Romanesque architecture adorned with sculptures, mosaics, and gold detailing. Independent entry to the Cathedral interior is available at your own cost.
A short drive through the Chianti landscape brings you to a family-run estate winery situated between Siena and San Gimignano. Lunch consists of traditional Tuscan appetizers, pasta, and desserts, each course paired with wines produced on the estate. Bottles are available for purchase to take home.
San Gimignano's fourteen intact medieval towers create one of the most distinctive skylines in all of Italy. Your tour leader narrates the town's fascinating medieval history as you walk the cobblestone streets, visit Piazza della Cisterna, and sample the internationally recognised gelato from Gelateria Dondoli. Time is also available for browsing the local artisanal shops.
The final stop of the day is Pisa's Piazza dei Miracoli, a UNESCO World Heritage Site since 1987, where the Leaning Tower, Pisa Cathedral, Baptistry, and Camposanto Monumentale stand together in a setting of white marble and green lawn. Your tour leader guides you to the square, where free time allows for photography and exploration. Note that climbing the Leaning Tower carries an additional fee and is not permitted for children under eight years old.
Reunite with your group for the comfortable return journey to Florence, arriving in the late afternoon. Your tour leader remains available for any final questions during the drive back.
What Is Included
Included
- Expert English-speaking tour leader throughout the day
- Local guided tour of Siena including Piazza del Campo and Siena Cathedral exterior
- Tuscan lunch with wine at a family-owned Chianti winery
- Guided visit to San Gimignano with tour leader commentary
- Visit to Piazza dei Miracoli in Pisa with tour leader guidance
- Comfortable small-group transport throughout the itinerary
Not Included
- Entry to Siena Cathedral interior (optional, payable on site)
- Admission to the Leaning Tower of Pisa (approximately 20 EUR per person)
- Personal expenses and optional purchases
- Gratuities for guides and tour leader
Important Information
Reserve Your Place on This Tuscany Day Tour
Spaces in this small-group tour are limited by design. Secure your spot today and experience Siena, Chianti, San Gimignano, and Pisa with a knowledgeable guide by your side from start to finish.
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