Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno
Livorno, Italy

Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno

Outty Ranking 65 5.0 · 8 traveler reviews7 hoursFrom $450
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Outty Ranking

65/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 8 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno worth booking?

Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno is a 7-hour experience in Livorno, Italy, from $450 per person. It scores 65 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 8 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
65 / 100
Rating
5/5 (8)
Duration
7 hours
From
$450 per person

The best unforgetable tour in Tuscany in order to discover the real life in Tuscany. You will visit the great countryside, you will discover the old wineries so you can understand the old and news wine-making process. Vineyards, olive trees, old houses, this is just something you will find in your tour. San Gimignano, the ancient medieval village, considered one of the most beautiful village in Italy.

What you get

    About this experience

    The best unforgetable tour in Tuscany in order to discover the real life in Tuscany. You will visit the great countryside, you will discover the old wineries so you can understand the old and news wine-making process. Vineyards, olive trees, old houses, this is just something you will find in your tour. San Gimignano, the ancient medieval village, considered one of the most beautiful village in Italy.

    What's included

    Included

    • Private tour
    • Visit San Gimignano
    • Visit 2 wineries
    • Driver/guide
    • Port pickup and drop-off

    Not included

    • Gratuities
    • Wine Tasting in both wineries and one Light Lunch 75 Euro/person 35 Euro/perosn Children 3-17

    What you'll see and do

    1. Strada Statale 222 Chiantigiana

      Visit and wine tasting in 2 wineries

      300 minutes here · Admission included

    2. San Gimignano

      visit San Giignano

      120 minutes here

    Where it starts and ends

    Meeting point

    Livorno

    We will wait for you just outside your cruise with a your name's sign at the meeting time (YOU DON'T NEED TO USE ANY SHUTTLE)

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    We will wait for you just outside your cruise with a your name's sign at the meeting time (YOU DON'T NEED TO USE ANY SHUTTLE)

    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 8 travelers per booking
    Operated by
    Bellaitalia Tour

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Public transportation options are available nearby
    • Infants are required to sit on an adult’s lap
    • Specialized infant seats are available
    • Suitable for all physical fitness levels
    • Children must be accompanied by an adult
    • Children <18 years old are not allowed to drink wine
    • Please specific food restrictions

    Photos

    san gimignano, Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From LivornoBella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno, photo 3Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno, photo 4Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno, photo 5Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno, photo 6Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 8 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    7 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    7 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    6 mentions

    The tastings and food stops are a highlight for most reviewers.

    Good for families

    5 mentions

    Reviewers traveling with kids report it landed well with their group.

    Photo opportunities

    4 mentions

    The views and photo stops come up again and again.

    Small groups

    4 mentions

    The group size is repeatedly described as intimate rather than packed.

    Traveler reviews

    8 verified traveler reviews for Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    8
    4 star
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    3 star
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    Sort
    jessiep793 · May 2026

    10/10 Would Do It Again

    The tour was fantastic. The wineries were amazing, and our driver, Massimo, was so knowledgeable and a great guide throughout Tuscany. He curated the day perfectly—each stop felt unique, from intimate family‑run vineyards to stunning estates with unforgettable views. We also loved having time to explore San Gimignano, which was such a fun addition to the day. Wandering through the medieval streets, grabbing gelato, and popping into the little shops made the experience feel even more special. We never felt rushed, and Massimo’s insights into the region’s history, wine production, and local culture made everything come alive. The tastings were generous, the wines exceptional, and the entire day felt effortless and beautifully organized. It was truly the highlight of our trip.

    via Tripadvisor

    Carleen_P · April 2026

    A perfect Tuscan day!

    Massimo was the best! He was so knowledgeable and so accommodating. And the wineries we visited were awesome. Beautiful views, delicious food, and great local wines, olive oils, etc. Just a wonderful day.

    via Viator

    Alex_W · October 2025

    Massimo Made Tuscany Unforgettable

    Our guide, Massimo, warned us not to fall in love with Tuscany. We laughed—how could seven hours make us fall in love? Well, he was right. We stopped in Livorno on our cruise and wanted to go wine tasting in Tuscany. After lots of research, we booked this tour, and while it was expensive, it was worth every penny. It ended up being our favorite experience from our two-week trip. Massimo met us right at the cruise terminal (super easy!) and was incredibly knowledgeable and proud of his country. The drive itself was stunning—we stopped several times for photos—and our visit to San Gimignano was a highlight. The wineries were authentic, family-run gems with amazing hosts, generous tastings, and what was supposed to be a “light lunch” that turned out to be the best meal we had in all of Europe. We can’t recommend Massimo enough. He made the day unforgettable, and we’re already planning our return.

    via Viator

    Kevin_U · November 2024

    DO THIS TOUR!!!

    We were in Livorno on a cruise ship stop. We have done numerous cruise booked excursions, but this was by far the highlight of the entire trip. If you want a unique, private experience, and want to avoid the large canned cruise excursions, this is for you. My party of 4 were met promptly at the time scheduled by our Drive and Guide, Massimo. He was extremely funny and friendly. He knew the area intimately and is also a sommelier, which was a huge benefit for any winery tour. After an hour long scenic drive through the Tuscan countryside, we came to our first stop, the beautiful medieval town of San Gimignano. One of the highlights of this was the fact that we beat the large cruise ship tours and were able to experience the town with out the large crowds. They did show up about halfway during our free time in the village, but it was no fault as we had plenty of time to explore and appreciate prior to the larger tours. We then left for about a 30 minute drive through Tuscany heading towards our first stop. During each drive, our guide Mossimo kept us entertained through his knowledge of the area and simply his banter and comedy. We connected so well with him. On this short drive he even found time to stop at a scenic overlook and being that is was olive harvest season, we was even able to show us an olive tree and explain the harvesting processing and we tasted some olives right off the branch. Beware, olives themselves are bitter, but it was till such a great experience. Our first winery, was a "small" family estate and winery. I say small only since compared to larger vineyards their production is small, but their home winery was beautiful. After a tour through their production process and property, we sat in their beautiful dinning room and tasting area where they provide a traditionally Tuscan Italian lunch which was cooked in home by their Nona. It was so much food with delicious pasta, meats, cheeses, local honey, freshly pressed (I mean that morning) olive oil, and of course their delicious wines. They do offer you options to purchase but there was no pressure. The family treated us like family friends and guests. We then had another 30 minute drive to a second winery. This winery was larger in production and definitely went back much further as evident by their amazing wine cellar which had bottles from over 50 years prior. The grounds were just as beautiful and the winery guide was so friendly. They let us try 6 wines here and also provides us some amazing food pairings. They also provided options to buy and ship which were so good, we couldn't help ourselves and place some orders. When the entire day was complete, we were all sad the day had ended. I want to go back and explore the region more, Massimo lives locally in a city called Lucca and he gave such great details of the area, I think I can go back and spend a week there or more. If I have any regrets it is that I wish we bought more of the wines and olive oil and that I wish I had more time to enjoy such a wonderful and amazing area. Please make sure you bring enough cash to tip if you chose and also to pay for the tastings. It is noted in the tour description that the winery tastings are separate, but they are reasonable for the experience you get. It was about $75 Euro per person total. Honestly the experience you get $75 Euro felt like a steal.

    via Viator

    Jacqueline_W · September 2024

    Cruise excursion to Tuscany

    This was the highlight of our whole trip. Massimo was the best guide we could have asked for. He was friendly, engaging, & very knowledgeable about wines & all things Tuscany! He helped us fall in love with Tuscany & we will definitely be back. The wineries he took us to were family owned & gave us the most amazing personal attention. The wines spoke for themselves as they were some of the best I’ve ever tasted. Would highly recommend this tour!

    via Viator

    Good to know

    Duration
    7 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    3
    Verdict
    Solid Choice

    Who runs this experience

    Operated by Bellaitalia Tour, who run 44 experiences we rank across 4 cities, with an average Outty Ranking of 56.8.

    See everything Bellaitalia Tour runs

    Why this scores 65

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

    Traveler sentiment (30% weight)85
    Review evidence (18% weight)37
    Booking momentum (14% weight)29
    Value for money (12% weight)74
    Listing quality (10% weight)70
    Local standing (8% weight)60
    Booking flexibility (8% weight)100

    Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno: questions travelers ask

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

    How much does Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno cost?

    +

    Prices start at $450 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Livorno usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno take?

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    Plan for about 7 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 Livorno is not rushed.

    Is Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno worth it?

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    It holds an Outty Ranking of 65 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 8 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Livorno, and how flexible the cancellation terms are.

    Can I cancel or reschedule Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno?

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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 Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 7-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno?

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    Around 3 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 Livorno 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 Livorno and add a light layer if any part of the 7-hour experience runs outdoors or after sunset.

    Where does Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno 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 Livorno 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 Livorno?

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    On Outty we rank every Livorno experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Full day Shore Excursion to Florence from Livorno with tasting, Full day shore excursion to Florence and Pisa from Livorno with tasting, Bolgheri: Classic Wine Tasting with Winery Tour. 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 Livorno?

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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 Livorno?

    +

    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 Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno?

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    Included: Private tour; Visit San Gimignano; Visit 2 wineries; Driver/guide; and Port pickup and drop-off. Not included: Gratuities; and Wine Tasting in both wineries and one Light Lunch 75 Euro/person 35 Euro/perosn Children 3. Always check the voucher for the final list before you travel.

    Where is the meeting point for Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno?

    +

    We will wait for you just outside your cruise with a your name's sign at the meeting time (YOU DON'T NEED TO USE ANY SHUTTLE) Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno offered in?

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    It runs in English. 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 Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno?

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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 Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno wheelchair or stroller accessible?

    +

    The operator notes: Infants and small children can ride in a pram or stroller; Infants are required to sit on an adult’s lap; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno if the weather is bad?

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    It generally runs rain or shine, so dress for the forecast in Livorno. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno?

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    Across 8 reviews averaging 5.0 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works.

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