From Rome : Siena and San Gimignano Private Excursion with Wine in Rome
Rome, Italy

From Rome : Siena and San Gimignano Private Excursion with Wine

Outty Ranking 61 5.0 · 2 traveler reviews12 hoursFrom $58

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September 2026

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Adults

Age 13 and over

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Age 12 and under

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From, per person$58
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Outty Ranking

61/100

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 From Rome : Siena and San Gimignano Private Excursion with Wine worth booking?

From Rome : Siena and San Gimignano Private Excursion with Wine is a 12-hour experience in Rome, Italy, from $58 per person. It scores 61 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
61 / 100
Rating
5/5 (2)
Duration
12 hours
From
$58 per person

Embark on a fascinating private excursion into the Tuscan hills, visiting the historic cities of Siena and San Gimignano. We will pick you up from your hotel or apartment in Rome. The tour will start with the exploration

What you get

  • Tickets of the Cathedral of Siena
  • Private transportation
  • Pick up and drop off
  • On-board WiFi
  • Driver
  • In-vehicle air conditioning

About this experience

Embark on a fascinating private excursion into the Tuscan hills, visiting the historic cities of Siena and San Gimignano. We will pick you up from your hotel or apartment in Rome. The tour will start with the exploration of Siena, its magnificent Piazza del Campo and its majestic Duomo. Admire the medieval architecture and immerse yourself in the history and culture of this beautiful city. The tour continues to San Gimignano, known as the "Manhattan of the Middle Ages" for its imposing towers. Stroll through the cobbled streets and enjoy the panoramic views of the surrounding hills. After enjoying free time in San Gimignano we will head to a charming wine estate in the countryside where you will have the opportunity to participate in a tasting of local wines accompanied by typical products, tasting the fine Tuscan wines and discovering the secrets of their production. Return to Rome is scheduled for the afternoon.

What's included

Included

  • Tickets of the Cathedral of Siena
  • Private transportation
  • Pick up and drop off
  • On-board WiFi
  • Driver
  • In-vehicle air conditioning
  • Tour assistant for the entire duration of the tour
  • Wine and local products tasting on a country estate

Not included

  • Gratuities

What you'll see and do

  1. Siena

    Siena, located in the heart of Tuscany, is a medieval city famous for its beauty and its historical heritage. The historic center of Siena, recognized as a World Heritage Site by UNESCO, is characterized by narrow and winding streets, historic buildings and charming squares. Piazza del Campo is the hub of city life and hosts the famous Palio, a horse race that takes place twice a year. Siena Cathedral, with its extraordinary black and white marble facade, is a masterpiece of Italian Gothic architecture. Inside, visitors can admire works of art by famous artists such as Donatello, Michelangelo and Pinturicchio. Siena is also renowned for its traditional Tuscan cuisine and fine wines, such as Chianti and Brunello di Montalcino.

    120 minutes here

  2. San Gimignano

    San Gimignano, located in the heart of Tuscany, is famous for its many medieval towers, which have earned it the nickname "Manhattan of the Middle Ages". This charming city is a UNESCO World Heritage Site and offers visitors a fascinating immersion in medieval history and art. Walking through its cobbled streets, you can admire the ancient towers that stand out over the landscape. San Gimignano is also renowned for its white wine, Vernaccia di San Gimignano, one of the finest in Tuscany.

    60 minutes here

Where it starts and ends

Hotel pickup

Pickup is included for all travelers. Pickup begins about 10 minutes before departure.

Options you can book

  • PRIVATE TOUR

    Private tour: The private tour is wheelchair accessible. Pickup included

  • SMALL GROUP TOUR

    Tour for small groups: Small Group Tour: Accommodates a maximum of 6 people per minivan and up to 12 people per assistant Pickup included

Before you book

Cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Languages
pt, en, fr, es
Ticket
Mobile Only
Runs on
Every day
Group size
Up to 12 travelers per booking
Operated by
Mamma Mia Italia

Know before you go

  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Specialized infant seats are available
  • Transportation options are wheelchair accessible
  • All areas and surfaces are wheelchair accessible
  • Suitable for all physical fitness levels
  • During the tasting the wines will be served to those over 18 years old, according to the Italian standard.

Photos

From Rome : Siena and San Gimignano Private Excursion with Wine in Rome, photo 2From Rome : Siena and San Gimignano Private Excursion with Wine in Rome, photo 3From Rome : Siena and San Gimignano Private Excursion with Wine in Rome, photo 4From Rome : Siena and San Gimignano Private Excursion with Wine in Rome, photo 5From Rome : Siena and San Gimignano Private Excursion with Wine in Rome, photo 6From Rome : Siena and San Gimignano Private Excursion with Wine in Rome, photo 7

Traveler reviews

2 verified traveler reviews for From Rome : Siena and San Gimignano Private Excursion with Wine. Ratings and reviews provided by Viator and Tripadvisor.

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Michelle_M · October 2025

Dina & Max Mamma Mia!

Sienna was an absolutely beautiful and unique city less touched by tourism. Dina and Max were an excellent pair enhancing the entire dsy with delightful historical information and conversation.

Response from the operator: Thank you so much for your wonderful review! We are glad that you enjoyed Siena so much and that Dina and Max helped make the day special and memorable. We hope to accompany you again soon to discover more Italian wonders together with Mamma Mia Italia!

via Viator

Rachel_M · May 2025

Perfect glimpse into the heart of Tuscany: must do!!!

Yesterday May 30th, 2025 we did the semi-private (which ended up being private) tour to Tuscany from Rome, visiting both the towns of Siena and San Gimignano. We had the most fabulous tour guide- Irene Maniscalco. She was very knowledgable of these most beautiful towns- our whole experience was PERFECTO!!! We had great conversation and learned much about these ancient and Medieval towns and also our names, which are the same, such a neat coincidence. We highly recommend this tour and Irene! We booked this specific tour less than 12 hours out, as we had one free day left in Rome, and we wanted to see Tuscany, specifically these towns, and they were most accommodating! While our visits to these town were most memorable we thoroughly enjoyed the winery and wine tasting at: Tenuta Torciano a true hidden gem off the beaten path that was perfection of what I imagined Tuscany to be! The wine and food were amazing and we ended up shipping some wine home! Loved that they picked us up and dropped us off in front of our hotel. Great experience and value for the price, couldn’t have done any better. Thank you Irene and Mamma Mia Tour Operator via Trip Advisor for this most memorable experience.

Response from the operator: Thank you so much for your wonderful review! We are so happy that the semi-private tour in Tuscany exceeded your expectations and that Irene made the visit to Siena and San Gimignano a perfect experience! We are so happy to hear that Tenuta Torciano gave you an authentic moment of Tuscany, with excellent wine and food. We are happy that the pick-up and drop-off service made the tour convenient and that you appreciated our flexibility, even with a last minute booking. A warm hug and we hope to see you again soon for another wonderful adventure among the beauties of Italy! Martina per Mamma Mia Italia

via Viator

Good to know

Duration
12 hours
Free cancellation
Up to 24h before
Minimum age to book
All ages
Availability
Bookable today
Runs on
Every day
Price range
$58 to $1104
Hotel pickup
Included for all travelers
Booked in 30 days
1
Verdict
Solid Choice

Why this scores 61

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

Traveler sentiment (30% weight)76
Review evidence (18% weight)15
Booking momentum (14% weight)11
Value for money (12% weight)100
Listing quality (10% weight)100
Local standing (8% weight)54
Booking flexibility (8% weight)100

From Rome : Siena and San Gimignano Private Excursion with Wine: questions travelers ask

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

How much does From Rome : Siena and San Gimignano Private Excursion with Wine cost?

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Prices start at $58 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Rome usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

How long does From Rome : Siena and San Gimignano Private Excursion with Wine take?

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Plan for about 12 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 Rome is not rushed.

Is From Rome : Siena and San Gimignano Private Excursion with Wine worth it?

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It holds an Outty Ranking of 61 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 Rome, and how flexible the cancellation terms are.

Can I cancel or reschedule From Rome : Siena and San Gimignano Private Excursion with Wine?

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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 Rome : Siena and San Gimignano Private Excursion with Wine suitable for kids and families?

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Yes, all ages are welcome. Families should still weigh the 12-hour running time, and strollers are easier on the earlier, quieter departures.

How far in advance should I book From Rome : Siena and San Gimignano Private Excursion with Wine?

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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 Rome 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 Rome and add a light layer if any part of the 12-hour experience runs outdoors or after sunset.

Where does From Rome : Siena and San Gimignano Private Excursion with Wine 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 Rome 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 Rome?

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Rome runs on skip-the-line access. The Colosseum underground, the Vatican before opening, and the catacombs south of the walls all require a licensed operator, and the price gap between the good ones and the rest is smaller than you would expect. We rank by guide credentials, group size and how reliably the promised access actually materialises. On Outty we rank every Rome experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Rome Pasta and Tiramisu Class: Ravioli, Fettuccine & Fine Wine 5*, Pasta Making & Wine Tasting with Dinner in Frascati from Rome, Rome: Pizza & Tiramisu or Gelato Class with Flowing Fine Wine 5*. 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 Rome?

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April, May, September and October. August is hot and half the city is shut. 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 Rome?

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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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