Searching for the ultimate day trip from Florence? On this unforgettable tour through Tuscany, take a guided walk through the medieval city of Siena, visit a Chianti vineyard for a decadent wine tasting and traditional Tuscan lunch, wander around the enchanting town of San Gimignano, and get a close-up look at the Leaning Tower of Pisa! With comfortable, round-trip transportation included and a knowledgeable guide leading the way, this is the best way to discover all that Tuscany has to offer!
Expert, English-speaking guide
Round-trip coach transportation
Guided tour of Siena
Entry to Duomo di Siena
Tuscan lunch at winery
Wine tasting with Chianti, Vernaccia, and Vin Santo
Free time in San Gimignano
Hotel pick up and drop off
Tickets to the Leaning Tower of Pisa
Guide tips
Meet your guide at Santa Maria Novella train station
Your day begins outside Florence's main train station, where your guide will be waiting with a sign. Board an air-conditioned coach and settle in as the cityscape gives way to cypress-lined roads and vineyard-covered hills.
Explore Siena with a guided walking tour
First, you'll arrive in Siena, a medieval city built on three hills in southern Tuscany. Follow your guide through narrow brick lanes to the shell-shaped Piazza del Campo, then step inside the Duomo di Siena—a Gothic cathedral wrapped in green and white marble stripes.
Enjoy free time in Siena
After your guided tour wraps up, you'll have time to explore on your own. Grab an espresso at a café in the piazza, browse artisan shops tucked into ancient buildings, or simply wander the winding streets before lunch.
Savor lunch and wine tasting at a Chianti vineyard
Next, your coach rolls through Chianti's vine-striped hills to a family-run organic winery. Sit down to a Tuscan feast of homemade pasta, prosciutto, aged cheeses, and cantucci cookies, all paired with estate wines like Chianti Classico and sweet Vin Santo.
Wander through San Gimignano
From the winery, you'll head to San Gimignano, a hilltop town famous for its 14 surviving medieval towers that once served as status symbols for rival families. Stroll cobbled streets lined with workshops selling leather goods and ceramics, then climb one of the towers for views over Tuscany's patchwork countryside.
For Reference Only. Itineraries are subject to change
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Start times are in the product’s local time
Free cancellation up to 24 hours in advance!
Tue, 17 Feb 2026
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4.85
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Dash D.
Verified Review
January 22, 2026
A Lovely Day
Hans S.
Verified Review
January 21, 2026
This tour created a lovely day filled with scenery, culture, and relaxation. It was a comfortable way to experience Tuscany beyond Florence.
History Culture And Views
Ottilie R.
Verified Review
January 20, 2026
A great tour that combined history, culture, and beautiful views in a natural way. Each stop added context and depth to the overall Tuscany experience.
Comfortable And Well Paced
Gerrit P.
Verified Review
January 19, 2026
The pacing was excellent for a long day trip. Plenty of time to explore, rest, and enjoy the scenery without ever feeling rushed or exhausted.
Well Organized
Digby R.
Verified Review
January 18, 2026
Everything ran on time and felt well organized. The guide communicated clearly, and transitions between stops were smooth, making the long day feel easy.
Charming Tuscan Stops
Gatik M.
Verified Review
January 17, 2026
Every stop was charming in its own way. Narrow streets, open squares, and beautiful views created a strong sense of place and lasting memories.
Countryside Views Worth Seeing
Juniper R.
Verified Review
January 16, 2026
The countryside views alone made this tour worthwhile. Rolling hills, vineyards, and open landscapes created a peaceful atmosphere that stayed with us long after the day ended.
Authentic Feel
Malte K.
Verified Review
January 15, 2026
The experience felt authentic rather than touristy. The winery visit, local towns, and relaxed schedule helped create a genuine connection with the Tuscan region.
Well Planned Route
Baxter L.
Verified Review
January 14, 2026
The route was well planned, connecting different towns without feeling rushed. Each destination complemented the next, creating a balanced and enjoyable Tuscany experience.
Tuscan Highlights In One
Ekansh W.
Verified Review
January 12, 2026
Seeing several Tuscan highlights in one day was incredibly convenient. Each stop added value, and the overall experience felt complete without sacrificing comfort.
Balanced Day
Clementine K.
Verified Review
January 10, 2026
This tour strikes a great balance between sightseeing, learning, eating, and relaxing. Nothing felt rushed, and the variety kept the day engaging from start to finish.
Namish S.
Verified Review
January 09, 2026
History And Hills
Björn V.
Verified Review
January 08, 2026
Exploring historic towns surrounded by rolling hills was unforgettable. The guide’s explanations added context, making each stop more meaningful and engaging throughout the day.
A Relaxing Travel Day
Fletcher H.
Verified Review
January 05, 2026
This was a relaxing way to explore Tuscany. The calm pace, scenic drives, and time to wander each town made the experience feel balanced and refreshing.
Lasting Memory
Divit S.
Verified Review
January 02, 2026
A day that created lasting memories. From countryside views to historic towns and a peaceful lunch, it captured the essence of Tuscany in a thoughtful, enjoyable way.
Easy Tuscany Experience
Pippa S.
Verified Review
December 30, 2025
Everything about this tour felt easy and well managed. From transportation to timing, it allowed us to focus on enjoying the scenery, history, and peaceful atmosphere.
Posy A.
Verified Review
December 28, 2025
Well Organized Full Day
Axel C.
Verified Review
December 27, 2025
Despite being a full day, the tour never felt overwhelming. Clear planning, smooth transitions, and thoughtful timing made it comfortable and enjoyable throughout.
Beautiful Views
Callum G.
Verified Review
December 23, 2025
The countryside views alone made this tour special. Rolling hills, vineyards, and small towns created a peaceful atmosphere that perfectly matched the slower rhythm of Tuscany.
Sara was super cute, knowledgeable and fun!
Blanca M.
Verified Review
December 20, 2025
We took this trip for the 2nd time but this time we brought out son to his 1st time in Italy. Sara was our tour guide. She has a masters in History and it is a certified sommelier which was perfect for this tour. She gave us a summary of the history of Tuscany and Siena along with a brief and concise explanation of the Chianti Wine and region. We were a large group but she made sure we were all taken care of and on time for our adventure. We loved her! The food (lunch/pranzo) was 5 stars and the wine tasting was enjoyable. I just wished we had more time in San Gimignano (that's my favorite paesino). My son loved everything too.
Scenic Tuscan Journey
Chirag M.
Verified Review
December 18, 2025
The journey through rolling hills and vineyards was stunning. Each town had its own charm, and the overall flow of the day felt natural and easygoing.
Lorenz R.
Verified Review
December 16, 2025
Scenic Towns And Countryside
Hattie S.
Verified Review
December 12, 2025
The mix of countryside views and charming towns made this tour special. Each location offered something unique, and together they created a rich and rewarding Tuscan experience.
Easy And Enjoyable Experience
Roland M.
Verified Review
December 05, 2025
Everything felt easy from start to finish. Transportation was comfortable, stops were well spaced, and the guide helped the day flow smoothly without any stress or confusion.
Pleasant Surprise
Ledger J.
Verified Review
November 27, 2025
This tour exceeded expectations with how smoothly everything ran. The guide was friendly, the locations were stunning, and the winery lunch added a relaxing and authentic touch.
