
3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns
Traveler rating
5.0/5
Based on 2 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns worth booking?
3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns is a 72-hour experience in Florence, Italy, from €1,124 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 2 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 53 / 100
- Rating
- 5/5 (2)
- Duration
- 72 hours
- From
- €1,124 per person
Escape the city and immerse yourself in the timeless beauty of Tuscany on a fully private, 3-day journey through rolling hills, historic villages, and unforgettable food and wine. Starting from Florence, your personal driver-guide will take you through the heart of Tuscany. You'll visit San Gimignano, Siena, Montepulciano, and the Chianti wine region. Enjoy exclusive tastings at family-owned wineries, admire Renaissance art, and relax each evening in hand-picked boutique countryside hotels. This tour is curated for travelers who want to slow down, connect with authentic Italy, and enjoy VIP treatment from start to finish. Highlights: Private driver-guide throughout the tour Visits to San Gimignano, Siena, Montepulciano & more Wine tastings in Chianti and Montalcino (Brunello!) Time to explore, shop, and dine in historic piazzas Option to include truffle hunting or cooking class
What you get
About this experience
Escape the city and immerse yourself in the timeless beauty of Tuscany on a fully private, 3-day journey through rolling hills, historic villages, and unforgettable food and wine. Starting from Florence, your personal driver-guide will take you through the heart of Tuscany. You'll visit San Gimignano, Siena, Montepulciano, and the Chianti wine region. Enjoy exclusive tastings at family-owned wineries, admire Renaissance art, and relax each evening in hand-picked boutique countryside hotels. This tour is curated for travelers who want to slow down, connect with authentic Italy, and enjoy VIP treatment from start to finish. Highlights: Private driver-guide throughout the tour Visits to San Gimignano, Siena, Montepulciano & more Wine tastings in Chianti and Montalcino (Brunello!) Time to explore, shop, and dine in historic piazzas Option to include truffle hunting or cooking class
What's included
Included
- Private transportation
- Lunch
- In-vehicle air conditioning
- Private Guide
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 10 minutes before departure.
Before you book
- Cancellation
- If you cancel at least 6 full day(s) before the scheduled departure time, you will receive a full refund.<br>If you cancel between 2 and 6 day(s) before the scheduled departure time, you will receive a 50% refund.<br>If you cancel within 2 day(s) of the scheduled departure, you will receive a 0% refund.
- Languages
- ru, en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 4 travelers per booking
- Operated by
- Events in Italy
Know before you go
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
Photos






Traveler reviews
2 verified traveler reviews for 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns. Ratings and reviews provided by Viator and Tripadvisor.
Three days in Tuscany
An unforgettable three days in Tuscany. Our private tour from Florence struck the perfect balance between iconic scenery and authentic local flavor. Visiting medieval hilltop towns like San Gimignano and exploring the rolling vineyards of the Chianti region felt effortless thanks to seamless logistics and a knowledgeable, easygoing guide who knew all the best hidden viewpoints away from the crowds. The winery visits were exceptional—not just for the incredible wines, but for the warm hospitality of the hosts who genuinely cared about sharing their craft. Everything was impeccably organized from start to finish, making it a stress-free and deeply memorable highlights reel of the region. Highly recommended for anyone wanting a personalized, unhurried taste of Tuscany.
via Tripadvisor
Fantastic!
Fantastic experience, which allowed us to savor the essence of Tuscany, movie-like landscapes to leave you speechless, unforgettable visits to the cellar with super tastings! Advised
via Tripadvisor (translated)
Good to know
- Duration
- 72 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- €1,124 to €2,108
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Who runs this experience
Operated by Events in Italy, who run 23 experiences we rank across 9 cities, with an average Outty Ranking of 48.3.
See everything Events in Italy runsWhy this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns cost?
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Prices start at €1,124 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 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns take?
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Plan for about 72 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 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 2 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable family friendly in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns?
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No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 72-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns?
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Around 1 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 72-hour experience runs outdoors or after sunset.
Where does 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns 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 -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. 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.
What is included in 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns?
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Included: Private transportation; Lunch; In-vehicle air conditioning; and Private Guide. Always check the voucher for the final list before you travel.
Does 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns include hotel pickup?
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Yes, pickup is offered for every traveler from 682 listed pickup locations in and around Florence. Be ready about 10 minutes before the start time. You can also enter a custom pickup address when booking.
What languages is 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns offered in?
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It is offered in Russian, English and Italian. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns wheelchair or stroller accessible?
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The operator notes: Infants are required to sit on an adult’s lap. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Florence. Standard cancellation terms apply.
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