Private day trip from Florence to Montepulciano, Siena and back
Florence, Italy

Private day trip from Florence to Montepulciano, Siena and back

Outty Ranking 56 3.8 · 4 traveler reviews7 hoursFrom €145
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Outty Ranking

56/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

3.8/5

Based on 4 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private day trip from Florence to Montepulciano, Siena and back worth booking?

Private day trip from Florence to Montepulciano, Siena and back is a 7-hour experience in Florence, Italy, from €145 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 3.8/5 rating across 4 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
56 / 100
Rating
3.8/5 (4)
Duration
7 hours
From
€145 per person

Embark on an enchanting private tour with your private driver, an expert long-distance driver, immersing yourself in breathtaking vistas, cultural treasures, and natural wonders. This journey promises unforgettable moments as you explore the world on your exclusive trip. This private tour is a pleasant way to spend your time. It includes transportation from Florence to a sightseeing stop in Montepulciano, Siena and back. All this in the comfort of a private car with an English-speaking local driver who knows the area and will be happy to share information with you. 1 to 3 people, we will provide a sedan or combi. 4 people, we will provide an MPV. 5 to 7/8 people, we will provide a VAN. If you prefer a larger vehicle and wish to ensure additional space during your trip, please choose a different number of travelers in the booking form according to this description. Our drivers are friendly and available at all times. If you have any requirements, just let us know.

What you get

    About this experience

    Embark on an enchanting private tour with your private driver, an expert long-distance driver, immersing yourself in breathtaking vistas, cultural treasures, and natural wonders. This journey promises unforgettable moments as you explore the world on your exclusive trip. This private tour is a pleasant way to spend your time. It includes transportation from Florence to a sightseeing stop in Montepulciano, Siena and back. All this in the comfort of a private car with an English-speaking local driver who knows the area and will be happy to share information with you. 1 to 3 people, we will provide a sedan or combi. 4 people, we will provide an MPV. 5 to 7/8 people, we will provide a VAN. If you prefer a larger vehicle and wish to ensure additional space during your trip, please choose a different number of travelers in the booking form according to this description. Our drivers are friendly and available at all times. If you have any requirements, just let us know.

    What's included

    Included

    • 24/7 Customer Care Service
    • Private two-way transfer in a clean, air-conditioned vehicle
    • Bottled water on board
    • All fees and taxes are included
    • Friendly English-speaking driver, not a licensed guide, but happy to share his knowledge

    Not included

    • Any tickets are not included (buy/check online or at the place or ask the operator)
    • Please independently verify the opening hours and ticket availability
    • Meals and refreshments

    What you'll see and do

    1. Montepulciano

      Arrive in Montepulciano, a hilltop town renowned for its stunning Renaissance architecture and excellent wine, particularly Vino Nobile. Explore the historic center, visit the Piazza Grande, and ascend the Torre di Pulcinella for panoramic views of the surrounding countryside.

      120 minutes here

    2. Siena

      Arrive in Siena and head to the famous Piazza del Campo, one of Europe's greatest medieval squares. Marvel at the Palazzo Pubblico and the Torre del Mangia, and absorb the vibrant atmosphere of this historic space. Then, explore the stunning Siena Cathedral (Duomo di Siena), a masterpiece of Italian Gothic architecture. Don't miss the chance to climb to the top for breathtaking views of the city.

      120 minutes here

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 5 minutes before departure.

    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
    Europe Journey - Private Sightseeing Transfers and Day Tours

    Know before you go

    • Infants are required to sit on an adult’s lap
    • Service animals allowed
    • Public transportation options are available nearby
    • Infants and small children can ride in a pram or stroller
    • All areas and surfaces are wheelchair accessible
    • Transportation options are wheelchair accessible
    • Wheelchair accessible
    • Suitable for all physical fitness levels

    Photos

    Private day trip from Florence to Montepulciano, Siena and back, photo 2Private day trip from Florence to Montepulciano, Siena and back, photo 3Private day trip from Florence to Montepulciano, Siena and back, photo 4Private day trip from Florence to Montepulciano, Siena and back, photo 5Private day trip from Florence to Montepulciano, Siena and back, photo 6Private day trip from Florence to Montepulciano, Siena and back, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 4 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    3 mentions

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

    Knowledge and storytelling

    2 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    2 mentions

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

    Small groups

    2 mentions

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

    Photo opportunities

    1 mention

    The views and photo stops come up again and again.

    Pace and timing

    1 mention

    Several reviewers found the schedule tight or the day long.

    Traveler reviews

    4 verified traveler reviews for Private day trip from Florence to Montepulciano, Siena and back. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    2
    4 star
    1
    3 star
    0
    2 star
    0
    1 star
    1
    Sort
    Aida_R · September 2026

    Extremely Disappointing Car Transportation Experience

    We’ve used Viator numerous times over the past 8-10 years and have normally been satisfied with their services. However, this time Viator really dropped the ball. My wife and I hired a private car service to take us for the day to a vineyard for some wine tasting and local sightseeing. This was expected to last about 7+hrs. Our driver arrived almost 30 minutes late and apologized because of the “heavy traffic”. While most of the other drivers arrived wearing jackets and ties coming into the hotel lobby looking for their passengers, ours arrived in shorts, sneakers and a white T-shirt. When we went outside, he showed us to our 7-8 passenger (Renault?) van which was very cramped and extremely uncomfortable, especially for the long day we had ahead of us. When I asked why the van and not the sedan that we had anticipated, he said that he was “only the driver” and had not received any details about our trip. Our agreement was specific about a car. He was polite and apologetic, but we had a few more issues later. As we were waiting on a long car line to enter the vineyard, the local police looked at our driver and waver us to the side of the road. They asked many questions about our origin, destination, his drivers license and other paperwork. He had to explain that he was in Italy for his guests and work, and in very broken English as he told them that he did not speak Italian. After about 10 minutes they let us go, but I honestly thought that the police were not going to allow him to continue driving. While he was polite, the driver was not very knowledgeable about the areas we were in nor the local protocol. A very disappointing experience with our day travel. We were extremely dissatisfied with this service

    Response from the operator: Dear Aida, Thank you for taking the time to share your feedback. We are sorry that the trip did not meet your expectations, and we have since carefully reviewed the circumstances with the driver. The driver arrived approximately 30 minutes late due to very heavy morning traffic around the highway toll gates. He informed you about the delay in advance and received confirmation that this was okay. Nevertheless, we regret the inconvenience caused by the delay. Your reservation was for two passengers. Unfortunately, a driver with a sedan was not available that day, so a larger vehicle was provided to ensure that your trip could operate as planned. We understand that you expected a sedan and that the van was not your preferred type of vehicle. We would also like to clarify the comment regarding the driver's attire. Our full-day sightseeing trips are different from short hotel or airport chauffeur transfers. We therefore do not require our drivers to wear a jacket and tie. Instead, we prefer clean, presentable and comfortable attire appropriate for a driver spending many hours on the road with guests, while professional conduct is always expected. The police stop mentioned in the review was a routine roadside document check. After approximately ten minutes, the driver was allowed to continue without any fine or other issue. We also reviewed the situation regarding the winery. The address provided for the visit was unfortunately incorrect, which resulted in approximately 40 additional minutes being spent locating the correct destination. The driver did not charge the guests for this additional time. We are sorry that the overall experience did not meet your expectations. We take your feedback seriously and will particularly use it to improve communication regarding vehicle type before future trips. Kind regards, Jan Europe Journey

    via Viator

    ScottAdams · November 2025

    Perfect private day trip to Tuscany

    Excellent and flexible on-the-go communication allowed us the use every moment of our time with Andrea to maximize our visits to San Gimignano, Sienna, and a winery in Chianti. Snacks and water were a welcome treat in the van.

    Response from the operator: Dear Scott. Thank you so much for your wonderful feedback! We’re happy to hear that the smooth communication helped you make the most of your time with Andrea. We’re also glad you enjoyed the stops and the little refreshments along the way. It was a pleasure to have you!

    via Viator

    Clarissa_S · February 2025

    Very friendly, excellent...

    Very friendly, excellent driving skills, gave us extra time at places, and was flexible. We would definitely recommend to anyone looking for a driver.

    Response from the operator: Hello, Clarissa! Thank you for your wonderful review! We’re delighted to hear that you had such a positive experience, with a friendly and skilled driver who provided extra time and flexibility during your journey. Your recommendation means a lot to us! We’d love to assist you again on your next trip.

    via Viator

    Vishwesh_S · August 2024

    Beauty in Tuscany

    Montepulciano is a very beautiful Tuscan town. Siena is also amazing. The walk in the town was just amazing with views to the Tuscan countryside. Beautiful Tuscany surrounds the small town of Montepulciano. We would have liked more time in the towns, so we could sit down and enjoy a nice meal with some Tuscan Chanti. Also the driver was not local. He was from Croatia so he did not know much about the towns. The description of the tour suggested a local driver with knowledge of the region. The driver was great, but just not a local with knowledge.

    Response from the operator: Hello! We’re glad to hear that you enjoyed the beautiful towns of Montepulciano and Siena, as well as the stunning Tuscan countryside. We apologize for the inconvenience regarding the driver’s local knowledge. While we strive to provide drivers who are familiar with the region, we appreciate your understanding on this exception and we will work to ensure better alignment with expectations in the future. Your suggestion about spending more time in the towns is valuable, and we hope to enhance your experience next time. Thank you for choosing us, and we hope to welcome you back to Tuscany soon!

    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
    Price range
    €145 to €750
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    1
    Verdict
    Worth a Look

    Who runs this experience

    Operated by Europe Journey - Private Sightseeing Transfers and Day Tours, who run 988 experiences we rank across 104 cities, with an average Outty Ranking of 46.1.

    See everything Europe Journey - Private Sightseeing Transfers and Day Tours runs

    Why this scores 56

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

    Traveler sentiment (30% weight)66
    Review evidence (18% weight)21
    Booking momentum (14% weight)11
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)32
    Booking flexibility (8% weight)100

    Private day trip from Florence to Montepulciano, Siena and back: questions travelers ask

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

    How much does Private day trip from Florence to Montepulciano, Siena and back cost?

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    Prices start at €145 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 Private day trip from Florence to Montepulciano, Siena and back 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 Florence is not rushed.

    Is Private day trip from Florence to Montepulciano, Siena and back worth it?

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    It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (3.8/5 across 4 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 Private day trip from Florence to Montepulciano, Siena and back?

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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 Private day trip from Florence to Montepulciano, Siena and back 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 Private day trip from Florence to Montepulciano, Siena and back?

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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 7-hour experience runs outdoors or after sunset.

    Where does Private day trip from Florence to Montepulciano, Siena and back 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?

    +

    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 Private day trip from Florence to Montepulciano, Siena and back?

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    Included: 24/7 Customer Care Service; Private two-way transfer in a clean, air-conditioned vehicle; Bottled water on board; All fees and taxes are included; and Friendly English-speaking driver, not a licensed guide, but happy to share his knowledge. Not included: Any tickets are not included (buy/check online or at the place or ask the operator); Please independently verify the opening hours and ticket availability; and Meals and refreshments. Always check the voucher for the final list before you travel.

    Does Private day trip from Florence to Montepulciano, Siena and back include hotel pickup?

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    Yes, pickup is offered for every traveler from 202 listed pickup locations in and around Florence. Be ready about 5 minutes before the start time. You can also enter a custom pickup address when booking.

    What languages is Private day trip from Florence to Montepulciano, Siena and back 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 Private day trip from Florence to Montepulciano, Siena and back?

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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 Private day trip from Florence to Montepulciano, Siena and back wheelchair or stroller accessible?

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    The operator notes: Infants are required to sit on an adult’s lap; Infants and small children can ride in a pram or stroller; All areas and surfaces are wheelchair accessible; and Transportation options are wheelchair accessible. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Private day trip from Florence to Montepulciano, Siena and back 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 Private day trip from Florence to Montepulciano, Siena and back?

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    Across 4 reviews averaging 3.8 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. One thing to know: Several reviewers found the schedule tight or the day long.

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