Small Group Tuscany Highlights Tour with Lunch & Wine Tasting
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.6/5
Based on 47 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Small Group Tuscany Highlights Tour with Lunch & Wine Tasting worth booking?
Small Group Tuscany Highlights Tour with Lunch & Wine Tasting is a 11.5-hour experience in Florence, Italy, from $129 per person. It scores 69 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.6/5 rating across 47 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 69 / 100
- Rating
- 4.6/5 (47)
- Duration
- 11.5 hours
- From
- $129 per person
Discover the highlights of Tuscany on a small group tour from Florence, visiting Siena, San Gimignano, and Pisa. Travel in a cozy atmosphere with a maximum of 25 participants and enjoy the experience with an expert local
What you get
About this experience
Discover the highlights of Tuscany on a small group tour from Florence, visiting Siena, San Gimignano, and Pisa. Travel in a cozy atmosphere with a maximum of 25 participants and enjoy the experience with an expert local Tour Leader. Explore Siena’s medieval streets, famous for the Palio horse race, its elegant brick buildings, and the stunning Gothic Cathedral. Then, enjoy an authentic Tuscan lunch at a family-run estate, featuring traditional local dishes paired with excellent red wines. Continue to San Gimignano, the charming hilltop village known for its medieval towers and breathtaking views of the Tuscan countryside. Finally, visit Pisa and the iconic Piazza dei Miracoli, home to the world-famous Leaning Tower. A perfect day combining history, culture, local flavors, and the timeless beauty of Tuscany.
What's included
Included
- Monolingual tour Experience
- Free time in Pisa and San Gimignano
- Round-trip transportation by an air-conditioned minibus or minivan
- 1 Hour Guided Tour of Siena with a Professional Local Guide
- Professional English-speaking Tour Leader throughout the day
- Free Wi-Fi and advanced sound system onboard
- Lunch and wine tasting at a Tuscan winery
Not included
- Admission fees
- Admission fees
- Hotel Pick up and Drop Off
What you'll see and do
Florence
Meet your fellow travelers and the tour leader at the starting point in Florence (Piazzale Montelungo) and find a comfortable place on your bus. As you pass through the rolling hills, vineyards, and olive groves of the Chianti region enjoy the anecdotes shared by your tour leader. With great passion and deep knowledge of the territory, your guide will make your trip entertaining and interesting!
15 minutes here
Siena
Built upon hills, Siena is likely Italy's loveliest medieval city whose historic centre is listed as a UNESCO World Heritage site. Follow your local guide through the winding, narrow cobbled streets and discover the magnificent architecture from the 13th Century.
120 minutes here
Piazza del Campo
Our guided tour starts from Piazza del Campo, which is widely regarded as one of the most beautiful squares in Italy thanks to its architecture, the Mangia tower and its unique shell shape. Piazza del Campo is the civic heart of Siena, and the place where the famous Palio horse race takes place twice annually.
60 minutes here
Torre del Mangia
Dominating Piazza del Campo, the Mangia Tower is a symbol of Siena's grandeur with its striking 87 metres in height.
Pass by without stopping
Duomo di Siena
Our guided tour ends in front of the impressive Siena Cathedral, a stunningly beautiful building of Gothic Romanesque architecture.
Pass by without stopping
Strada Statale 222 Chiantigiana
Afterwards, take a break for a 3-course lunch at a delightful, family-run estate. Savor the delicious Tuscan products paired with fine wines produced by the estate itself.
120 minutes here
San Gimignano
After lunch, we move to San Gimignano, the little Manhattan of the Middle Ages. The numerous medieval towers form an unforgettable skyline and offer an impressive view of the town from the surrounding valley.
60 minutes here
Piazza Della Cisterna
Head to Piazza della Cisterna, at the heart of San Gimignano’s historic old town, and taste the world-famous and award-winning gelato from Gelateria Dondoli.
20 minutes here
Pisa
The last stop of your memorable day trip is Pisa with its uniquely beautiful Piazza dei Miracoli, a UNESCO World Heritage site since 1987.
60 minutes here
Leaning Tower of Pisa
Before heading back to Florence, don't forget to take a funny posing photo "holding up" the Leaning Tower of Pisa! The admission fee to the Leaning Tower of Pisa is not included, it costs approximately €20 per person. Children under 8 years old are not allowed to climb the Tower.
30 minutes here · Admission not included
Piazza dei Miracoli
The square is dominated by four great religious edifices: the Pisa Cathedral, the Pisa Baptistry, the Campanile, commonly known as the Leaning Tower, and the Camposanto Monumentale
60 minutes here
Florence
At the end of the day, reunite with your travel companions and return to Florence in the late afternoon.
5 minutes here
Where it starts and ends
Meeting point
Florence
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Mon, Fri, Sat
- Group size
- Up to 12 travelers per booking
- Operated by
- Ciao Florence Tours Srl
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Infants are required to sit on an adult’s lap
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- With prior notice, we can accommodate Vegetarian and Gluten free customers for lunch
Photos
What travelers are saying
Outty’s summary of the themes that recur across 47 traveler reviews. Written by us, not quoted from reviewers.
The guide
9 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
47 verified traveler reviews for Small Group Tuscany Highlights Tour with Lunch & Wine Tasting. Ratings and reviews provided by Viator and Tripadvisor.
Day Tour of Tuscany Review
As the first time travelling to Italy, the tour provided an informative experience for us. Samuele was our tour guide and was very friendly and helpful as a Tuscan native.
via Tripadvisor
A fab day out for seeing the highlights of Tuscany!
My Grandma and I had a lovely tour seeing the highlights of Tuscany with put fabulous tour guide Sam and driver Nicola. Beautiful towns, delish lunch, fab views! Not too much walking but not too much time on the bus either. A very lovely day out!
via Tripadvisor
AMAZING!!
Absolutely so amazing. We had a group of 14 with Sam as our guide and despite it being such a long tour in such intense heat, they were both amazing. Sam was so funny and made everything really smooth. He always made sure we were all there and kept the trip from getting boring despite spanning a full 11—almost 12!—hours.
via Tripadvisor
Use this guide!
Our tour guide was very nice and did a great job explaining everything we had a very good time.
via Tripadvisor
Bus tour
We had a wonderful time and our guide Cecelia was amazing. A bit hot for all day but absolutely worth it.
via Tripadvisor
Good to know
- Duration
- 11.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Fri, Sat
- Price range
- $129 to $159
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 16
- Verdict
- Solid Choice
Why this scores 69
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Small Group Tuscany Highlights Tour with Lunch & Wine Tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Small Group Tuscany Highlights Tour with Lunch & Wine Tasting cost?
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Prices start at $129 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Small Group Tuscany Highlights Tour with Lunch & Wine Tasting take?
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Plan for about 11.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is Small Group Tuscany Highlights Tour with Lunch & Wine Tasting worth it?
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It holds an Outty Ranking of 69 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.6/5 across 47 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Small Group Tuscany Highlights Tour with Lunch & Wine Tasting?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Small Group Tuscany Highlights Tour with Lunch & Wine Tasting suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 11.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Small Group Tuscany Highlights Tour with Lunch & Wine Tasting?
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Around 16 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 11.5-hour experience runs outdoors or after sunset.
Where does Small Group Tuscany Highlights Tour with Lunch & Wine Tasting start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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