Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena
Florence, Italy

Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena

Outty Ranking 57 4.3 · 3 traveler reviews10 hoursFrom $331
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Outty Ranking

57/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

4.3/5

Based on 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena worth booking?

Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena is a 10-hour experience in Florence, Italy, from $331 per person. It scores 57 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.3/5 rating across 3 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
57 / 100
Rating
4.3/5 (3)
Duration
10 hours
From
$331 per person

Enjiy a full day filled with unforgettable memories and photos of Tuscany's most iconic destinations! Depart from Florence and enjoy a scenic drive to Pisa. Enjoy some free time exploring the Piazza dei Miracoli, Duomo, Battistero and the iconic Leaning Tower of Pisa. Next, visit a Chianti Classico estate where a sommelier will reveal the wine-making process, followed by a wine tasting and lunch with homemade local products. Continue to Siena for a guided walking tour of the Duomo, Piazza del Campo, and more. Before returning to Florence, stop for a photo at Monteriggioni Castle.

What you get

    About this experience

    Enjiy a full day filled with unforgettable memories and photos of Tuscany's most iconic destinations! Depart from Florence and enjoy a scenic drive to Pisa. Enjoy some free time exploring the Piazza dei Miracoli, Duomo, Battistero and the iconic Leaning Tower of Pisa. Next, visit a Chianti Classico estate where a sommelier will reveal the wine-making process, followed by a wine tasting and lunch with homemade local products. Continue to Siena for a guided walking tour of the Duomo, Piazza del Campo, and more. Before returning to Florence, stop for a photo at Monteriggioni Castle.

    What's included

    Included

    • Wine estate tour in Chianti with a sommelier or wine producer
    • We can accommodate dietary restrictions such as vegetarian, vegan, gluten-free, etc.
    • Lunch with homemade local products
    • Wine tasting session
    • Free time at Piazza dei Miracoli, Duomo, Battistero in Pisa and the Leaning Tower of Pisa
    • English speaking driver (driver it is not a guide)
    • Mineral water for each passenger
    • Guided walking tour of Siena, including Duomo square and Piazza del Campo
    • Photo stop at Monteriggioni Castle
    • Round-trip transportation from Florence to Pisa, Chianti, and Siena

    Not included

    • Gratitues

    What you'll see and do

    1. Piazza dei Miracoli

      Start your day with an early morning departure from Florence at 8:00 AM and enjoy a scenic drive through the picturesque Tuscan countryside. Our first stop is the historic city of Pisa, where you’ll enjoy 1 hour and 15 minutes of free time exploring the Piazza dei Miracoli, Marvel at the grandeur of the Duomo, admiring the intricate designs of the Battistero, and capturing the quintessential photo with the iconic Leaning Tower of Pisa.

      75 minutes here

    2. Castellina In Chianti

      After exploring Pisa, we'll continue our journey to the heart of the Chianti Classico region. Here, you’ll be welcomed by a sommelier or a local wine producer who will guide you through their beautiful estate. Learn about the fascinating process of wine production, from vine to bottle, and discover the secrets behind Chianti’s renowned wines. Following the tour, indulge in a wine tasting session featuring a selection of the estate’s finest wines, perfectly paired with a delicious lunch of homemade local products. Savor the rich flavors of Tuscany with freshly made pasta, artisanal cheeses, cured meats, and more, all while enjoying the serene vineyard views.

      120 minutes here

    3. Siena

      Next, we head to the charming city of Siena. Upon arrival, a local guide will lead you on a 1 hour and 15 minute walking tour, revealing the secrets of this medieval gem. Stroll through the stunning Duomo, the majestic Piazza del Campo, and other fascinating landmarks, while learning about the rich history and culture of Siena.

      75 minutes here

    4. Monteriggioni

      Before returning to Florence, we’ll make one last stop for a photo opportunity at the magnificent Monteriggioni Castle, capturing the beauty of this historic fortress.

      20 minutes here

    Where it starts and ends

    Meeting point

    Florence

    Our driver will wait for you on the corner with via del Trebbio

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Our driver will wait for you on the corner with via del Trebbio

    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
    Keys Of Italy / Florence

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Public transportation options are available nearby
    • Specialized infant seats are available
    • Suitable for all physical fitness levels
    • The rest of time is driving time

    Photos

    Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena, photo 2Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena, photo 3Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena, photo 4Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena, photo 5Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena, photo 6Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 3 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    2 mentions

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

    Photo opportunities

    1 mention

    The views and photo stops come up again and again.

    Food and drink

    1 mention

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

    Pace and timing

    1 mention

    Several reviewers found the schedule tight or the day long.

    Traveler reviews

    3 verified traveler reviews for Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    2
    4 star
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    3 star
    1
    2 star
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    1 star
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    Sort
    Patricia_D · October 2025

    Fantastic.

    That is a unique and incredible experience! It is very worth taking this tour. All the details are very well cared for, especially in the vineyard.

    Response from the operator: ¡Muchas gracias por tu maravilloso comentario! Nos alegra saber que tuviste una experiencia tan única e increíble. Significa mucho para nosotros saber que apreciaste cada detalle, especialmente en la bodega. ¡Esperamos darte la bienvenida nuevamente en otro tour muy pronto!

    via Viator (translated)

    John_B · April 2025

    Recommended event

    The tour was great. The driver, Sal, was engaging and flexible to our request. We stopped few times along the way for a photo moment.

    Response from the operator: Thank you very much for you feedback, hearing your appreciation makes us very happy and proud of what we're doing, sharing the love for our beautiful country! Hope to see you in the future in any of our Italian destination! Regards

    via Viator

    julie_m · August 2024

    Winery was fantastic !!

    The wine tasting was excellent wonderful people, wine and food! The driver rushed us so we didn’t finish our tasting. The tour of sienna was awful. Pisa is a 2 hour drive from Chianti so I don’t know why it was part of the package too much time in the car

    via Viator

    Good to know

    Duration
    10 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
    1
    Verdict
    Worth a Look

    Who runs this experience

    Operated by Keys Of Italy / Florence, who run 50 experiences we rank across 11 cities, with an average Outty Ranking of 51.0.

    See everything Keys Of Italy / Florence runs

    Why this scores 57

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

    Traveler sentiment (30% weight)73
    Review evidence (18% weight)18
    Booking momentum (14% weight)11
    Value for money (12% weight)87
    Listing quality (10% weight)78
    Local standing (8% weight)44
    Booking flexibility (8% weight)100

    Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena: questions travelers ask

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

    How much does Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena cost?

    +

    Prices start at $331 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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena take?

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    Plan for about 10 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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena worth it?

    +

    It holds an Outty Ranking of 57 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.3/5 across 3 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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena?

    +

    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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena?

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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?

    +

    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 10-hour experience runs outdoors or after sunset.

    Where does Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena 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?

    +

    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?

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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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena?

    +

    Included: Wine estate tour in Chianti with a sommelier or wine producer; We can accommodate dietary restrictions such as vegetarian, vegan, gluten-free, etc; Lunch with homemade local products; Wine tasting session; and Free time at Piazza dei Miracoli, Duomo, Battistero in Pisa and the Leaning Tower of Pisa. Not included: Gratitues. Always check the voucher for the final list before you travel.

    Where is the meeting point for Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena?

    +

    Our driver will wait for you on the corner with via del Trebbio Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena 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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena?

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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 Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena wheelchair or stroller accessible?

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

    What happens to Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena 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: free cancellation up to 24 hours before the start.

    What do travelers say about Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena?

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    Across 3 reviews averaging 4.3 out of 5, recurring themes include the guide, photo opportunities, food and drink. Travelers single out the guide as the reason the experience works. One thing to know: Several reviewers found the schedule tight or the day long.

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