From Florence: Siena & San Gimignano Private Day Trip in Florence
Florence, Italy

From Florence: Siena & San Gimignano Private Day Trip

Outty Ranking 558 hoursFrom $159

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

0

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From, per person$159
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Outty Ranking

55/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

Not yet rated

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Quick answer

Is From Florence: Siena & San Gimignano Private Day Trip worth booking?

From Florence: Siena & San Gimignano Private Day Trip is a 8-hour experience in Florence, Italy, from $159 per person. It scores 55 out of 100 on the Outty Ranking, which we label “Worth a Look. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
55 / 100
Rating
Not yet rated
Duration
8 hours
From
$159 per person

Begin your private day trip with hotel pickup in Florence by a friendly, English-speaking driver in a comfortable, air-conditioned vehicle. Travel through Tuscany’s scenic hills to explore two iconic destinations. First,

What you get

  • Hotel pickup and drop-off
  • Fuel and Tolls
  • Water
  • On-board WiFi
  • Hotel or custom pickup and drop-off
  • Professional English-speaking local driver/informal guide

About this experience

Begin your private day trip with hotel pickup in Florence by a friendly, English-speaking driver in a comfortable, air-conditioned vehicle. Travel through Tuscany’s scenic hills to explore two iconic destinations. First, visit Siena, known for its medieval streets, Piazza del Campo, and Gothic cathedral. Then, enjoy an optional lunch and wine tasting at a local vineyard nestled among the rolling countryside. Continue to San Gimignano, a UNESCO-listed hilltop town famed for its medieval towers, charming streets, and stunning views. This fully customizable tour lets you adjust stops and timing. End the day with a relaxing ride back to Florence, filled with memories of Tuscany’s beauty and flavor.

What's included

Included

  • Hotel pickup and drop-off
  • Fuel and Tolls
  • Water
  • On-board WiFi
  • Hotel or custom pickup and drop-off
  • Professional English-speaking local driver/informal guide
  • All taxes and handling charges

Not included

  • Meals and beverages
  • Tips and Gratuities
  • Licensed guides available to accompany you inside the attractions

What you'll see and do

  1. Florence

    Your Welcome driver will pick you up from your accommodation in Florence, at a convenient time of your choice.

    120 minutes here

  2. Siena

    Siena is a charming Tuscan city known for its medieval architecture and the lively Piazza del Campo.

    120 minutes here

  3. Local Winery. A delightful lunch at a charming winery (costs not included in tour price).

    120 minutes here

  4. San Gimignano

    San Gimignano is a hilltop town famed for its medieval towers and well-preserved historic center.

    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, it
Ticket
Mobile Only
Runs on
Every day
Group size
Up to 7 travelers per booking
Operated by
Welcome Pickups

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
  • For 1-3 people: A comfortable sedan will be assigned to your group.
  • For 4-7 people: A spacious minivan will be assigned to your group.
  • Throughout your ride, our drivers serve as informal local guides—sharing stories, history, and local tips at every stop. Please note that drivers are not permitted to enter museums or archaeological areas, but they’ll ensure you make the most of your visit with suggestions and background information before you explore on your own.
  • Some stops on your itinerary may be closed on the date of travel due to public holidays, maintenance or special events. We recommend verifying opening hours on the attraction’s official website or contacting us before your tour. If a stop is unexpectedly closed, we will try to offer a suitable alternative.

Photos

From Florence: Siena & San Gimignano Private Day Trip in Florence, photo 2From Florence: Siena & San Gimignano Private Day Trip in Florence, photo 3From Florence: Siena & San Gimignano Private Day Trip in Florence, photo 4From Florence: Siena & San Gimignano Private Day Trip in Florence, photo 5From Florence: Siena & San Gimignano Private Day Trip in Florence, photo 6From Florence: Siena & San Gimignano Private Day Trip in Florence, photo 7

Good to know

Duration
8 hours
Free cancellation
Up to 24h before
Minimum age to book
All ages
Availability
Bookable today
Runs on
Every day
Price range
$159 to $988
Hotel pickup
Included for all travelers
Booked in 30 days
0
Verdict
Worth a Look

Why this scores 55

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

Traveler sentiment (30% weight)78
Review evidence (18% weight)0
Booking momentum (14% weight)0
Value for money (12% weight)82
Listing quality (10% weight)96
Local standing (8% weight)50
Booking flexibility (8% weight)100

From Florence: Siena & San Gimignano Private Day Trip: questions travelers ask

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

How much does From Florence: Siena & San Gimignano Private Day Trip cost?

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Prices start at $159 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 From Florence: Siena & San Gimignano Private Day Trip take?

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Plan for about 8 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 From Florence: Siena & San Gimignano Private Day Trip worth it?

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It holds an Outty Ranking of 55 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 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 From Florence: Siena & San Gimignano Private Day Trip?

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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 From Florence: Siena & San Gimignano Private Day Trip suitable for kids and families?

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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.

How far in advance should I book From Florence: Siena & San Gimignano Private Day Trip?

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Around 0 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 8-hour experience runs outdoors or after sunset.

Where does From Florence: Siena & San Gimignano Private Day Trip 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 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?

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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.

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