Tour of San Gimignano and Private Wine Experience in Chianti in Florence
Florence, Italy

Tour of San Gimignano and Private Wine Experience in Chianti

Outty Ranking 60 5.0 · 2 traveler reviews5 hoursFrom $100

Pick your date

Highlighted days have spots open. Grey days are sold out or not running.

September 2026

SMTWTFS

Loading live availability

Who is going?

Adults

Age 13 and over

2

Children

Age 12 and under

0

Select a highlighted day to see live departure times and the exact price for your group.

From, per person$100
View availability on Viator

Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.

Instant mobile ticketSpots available today

Outty Ranking

60/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 2 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Tour of San Gimignano and Private Wine Experience in Chianti worth booking?

Tour of San Gimignano and Private Wine Experience in Chianti is a 5-hour experience in Florence, Italy, from $100 per person. It scores 60 out of 100 on the Outty Ranking, which we label “Solid Choice, based on a 5/5 rating across 2 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
60 / 100
Rating
5/5 (2)
Duration
5 hours
From
$100 per person

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in the hills of San Donato in Poggio. Enjoy hotel pick-up and drop-off services

What you get

  • Local expert driver
  • Private transportation
  • Bottled water
  • In-vehicle air conditioning
  • Alcoholic beverages

About this experience

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in the hills of San Donato in Poggio. Enjoy hotel pick-up and drop-off services so you can sit back, relax, and enjoy the landscape while we drive you through the gorgeous Tuscan roads. Our first stop will be in San Gimignano, a medieval village well-known for its castle towers and for producing one of the first DOCG wines in Italy: Vernaccia di San Gimignano DOCG, which you will taste later on at our tasting room! Our second stop is at our Family Winery, located in the Chianti Classico area, surrounded by olive trees and vineyards. What will you do? At this estate winery, our clients have the opportunity to tour a cellar, taste and enjoy at least 5 different Family wines, from the Vernaccia di San Gimignano to the Chianti Classico Riserva wines as well as Super tuscans. You will also have a chance to try our exclusive extra virgin olive oil.

What's included

Included

  • Local expert driver
  • Private transportation
  • Bottled water
  • In-vehicle air conditioning
  • Alcoholic beverages

Not included

  • Everything that is not mentioned in the inclusions.

What you'll see and do

  1. Province of Florence

    Customers will be picked up by our driver at the location of their choice, and it will take approximately 1 hour to reach the beautiful medieval town of San Gimignano.

    60 minutes here

  2. San Gimignano

    After our driver has completed the personalized pick-up at your address, we will embark on a journey to the gentle hills of Chianti, amidst avenues of cypress trees, olive groves, sunflower fields, and long rows of vineyards until we reach the famous medieval town of San Gimignano. There, we will stop for approximately 1 hour for a self-guided tour. San Gimignano is a beautiful medieval town located in the Tuscany region of Italy. It is famous for its distinctive skyline characterized by medieval towers, earning it the nickname "the Manhattan of the Middle Ages". These towers, mainly dating back to the 12th and 13th centuries, were a symbol of power and wealth for the noble families of the city. The town is also famous for wine production, particularly the renowned white wine Vernaccia di San Gimignano. Visitors can enjoy wine tastings at the numerous wineries in the area.

    60 minutes here

  3. San Donato in Poggio

    After visiting the towers of San Gimignano, it's time for a tasting. We will head to Chianti Classico (abt. 30mins from San Gimignano to San Donato in Poggio) to sample the finest wines of our region: Vernaccia di San Gimignano, Chianti Classico, Chianti Classico Riserva, and Supertuscan, along with excellent olive oil, all produced by a historic winery founded in 1929, Cantine Guidi. At the end of the tasting, we will return to your address.

    120 minutes here

  4. Province of Florence

    After the wine tasting experience, we will return to the location where the pick-up was made.

    30 minutes here

Where it starts and ends

Hotel pickup

Pickup is included for all travelers.

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
Every day
Group size
Up to 7 travelers per booking
Operated by
CANTINE GUIDI 1929

Know before you go

  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available
  • Suitable for all physical fitness levels

Photos

Tour of San Gimignano and Private Wine Experience in Chianti in Florence, photo 2Tour of San Gimignano and Private Wine Experience in Chianti in Florence, photo 3Tour of San Gimignano and Private Wine Experience in Chianti in Florence, photo 4Tour of San Gimignano and Private Wine Experience in Chianti in Florence, photo 5Tour of San Gimignano and Private Wine Experience in Chianti in Florence, photo 6Tour of San Gimignano and Private Wine Experience in Chianti in Florence, photo 7

Traveler reviews

2 verified traveler reviews for Tour of San Gimignano and Private Wine Experience in Chianti. Ratings and reviews provided by Viator and Tripadvisor.

5 star
2
4 star
0
3 star
0
2 star
0
1 star
0
Sort
Resort09661931083 · January 2026

Beautiful family-owned winery in the heart of Chianti

Fantastic wines, beautiful vineyard and small, family-owned winery with a gracious and knowledgeable host. It was the nicest wine tasting we've done in either Tuscany or Umbria. Highly recommend!

via Tripadvisor

valeriegA703VW · March 2025

Winery tour and tasting

We had the best experience on this private wine tasting tour in March 2025! It is very closely located to San Gimignano and about 45 minutes from Florence. The location of the winery is scenic and quiet. We were greeted by Arianna, the sommelier. She was very knowledgeable and explained the different types of wines produced. The tasting was fantastic and we enjoyed a delicious homemade lunch of pasta with a sample of meats and cheeses as well as their family produced olive oil which all complimented the wines. The atmosphere was intimate and so quaint. We would highly recommend this tour to anyone who is looking for an authentic family owned winery tour and tasting.

Response from the operator: That's very kind of you Valarie!

via Tripadvisor

Good to know

Duration
5 hours
Free cancellation
Up to 24h before
Minimum age to book
All ages
Availability
Bookable today
Runs on
Every day
Price range
$100 to $275
Hotel pickup
Included for all travelers
Booked in 30 days
1
Verdict
Solid Choice

Why this scores 60

The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

Traveler sentiment (30% weight)80
Review evidence (18% weight)15
Booking momentum (14% weight)11
Value for money (12% weight)82
Listing quality (10% weight)100
Local standing (8% weight)54
Booking flexibility (8% weight)100

Tour of San Gimignano and Private Wine Experience in Chianti: questions travelers ask

Practical detail on this experience, plus the wider planning questions for Florence.

How much does Tour of San Gimignano and Private Wine Experience in Chianti cost?

+

Prices start at $100 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 Tour of San Gimignano and Private Wine Experience in Chianti take?

+

Plan for about 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 Tour of San Gimignano and Private Wine Experience in Chianti worth it?

+

It holds an Outty Ranking of 60 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 2 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 Tour of San Gimignano and Private Wine Experience in Chianti?

+

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 Tour of San Gimignano and Private Wine Experience in Chianti suitable for kids and families?

+

Yes, all ages are welcome. Families should still weigh the 5-hour running time, and strollers are easier on the earlier, quieter departures.

How far in advance should I book Tour of San Gimignano and Private Wine Experience in Chianti?

+

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?

+

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 5-hour experience runs outdoors or after sunset.

Where does Tour of San Gimignano and Private Wine Experience in Chianti start and how do I get there?

+

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?

+

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?

+

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?

+

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?

+

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.

Ready to lock in your spot?

Pick a date, choose your group, and see the exact price for Tour of San Gimignano and Private Wine Experience in Chianti.

Pick your date