Tours/Florence/Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - Small Group
Viator · group up to 8 pax

Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - Small Group

4.8(100)Florence1 hour
VIATOR4.7(11)TRIPADVISOR4.9(89)

Description

This trip is perfectly designed for those short on time, or simply want to see more of the region in a single day by 8-seat minivan. Lead by a seasoned team of passionate, local experts, this day tour perfectly balances fun and authenticity. Travellers will get a chance to discover some hidden treasures of Tuscany through a combination of activities and free time. So discover the best of Tuscany, and visit SIENA, MONTERIGGIONI, SAN GIMIGNANO and the CHIANTI REGION!

Tour Options

From Florence : Private Tour
  • Minivan: Travel in your own private minivan with a dedicated guide — just for your group of 2 to 8 people Starting point: Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy
From Florence: Classic Tour
  • Minivan : Intimate small group experience – never more than 8 guests Starting point: Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy
From Rome: Classic Tour
  • Combo: Return fast speed train from Rome to Florence & Tour in a 8 seat van from Florence to Tuscany included Starting point: Rome Termini station, Via Giovanni Giolitti, 40, 00185 Roma RM, Italy

Itinerary

10 min

08:45am - Meet and greet your guide and the other travellers near Porta Romana to travel by minivan to discover the best of Tuscany.

40 min

the first stop will be Monteriggioni, the most well preserved medieval village in Tuscany. This fortress city is also where “The Gladiator” was filmed, and is one of the locations for “Assassin’s Creed”. Along the journey get ready to immerse yourself in the Italian vibes and learn from your tour leader interesting facts about Tuscany & its famous cuisine.

120 min

your second stop, the dreamy town of Siena. During the orientation walk you will discover its unique architecture passing by the numerous artisan shops and finally stop at one of the most remarkable Piazzas of Italy, Piazza del Campo, site of the famous Palio race every July and August. Get some downtime to relax and explore the city at your leisure; do not miss a visit of the impressive Cathedral.

60 min

The tour will definitely pass through the Chianti Region, the heaven of Tuscan wine. A local winery will be visited and you will have a chance to merge with the Tuscan goodness: 7 different wines, extra virgin olive oils and balsamic vinegar will make your taste buds happy together with an amazing traditional Tuscan meal.

60 min

Your next destination is San Gimignano. On the way to the village, the guide will provide each traveller with a map and tips for the best places in town. Take a stroll through the cobblestone pathways, piazzas and palaces of this other UNESCO World Heritage Site known as the ‘Manhattan of Tuscany’ and explore this magical and timeless town in complete freedom.

60 min

After 1h drive, we will be back to Porta Romana at 6:00pm

Highlights

Scenic drive of the Chianti region
Wine and Extra Virgin olive oil tasting in a local winery
A short visit of Monteriggioni
Transport on a 8 seat minivan
Authentic Tuscan meal: Antipasti Toscani (bruschetta, pecorino cheese, Tuscan cured meat), Lasagna with truffle oil, traditional Ribollita Soup & Cantuccini. Veg,vegan and gluten free menu on request.
Orientation walk of Siena with our tour leader, then free time to explore independently the city
1h stop in San Gimignano and free time to discover the village at your own leisure

What's included

Included
Scenic drive of the Chianti region
Wine and Extra Virgin olive oil tasting in a local winery
A short visit of Monteriggioni
Transport on a 8 seat minivan
Authentic Tuscan meal: Antipasti Toscani (bruschetta, pecorino cheese, Tuscan cured meat), Lasagna with truffle oil, traditional Ribollita Soup & Cantuccini. Veg,vegan and gluten free menu on request.
Orientation walk of Siena with our tour leader, then free time to explore independently the city
1h stop in San Gimignano and free time to discover the village at your own leisure
Not included
Gratuities
Guided walking tours on the villages

Traveller Ratings

4.8
100 reviews
5
89
4
8
3
2
2
1
1
0

Important Information

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • The best of Tuscany in 1 day
  • Small groups, no bus tours, no families with crying kids and mainly only 1 language to listen to.
  • Please note, the tour requires a minimum of 3 participants. If not reached, a private option with a supplement will be offered.
  • Not recommended for travelers with walking disability

Reviews(100)

L
L9917MRbrianm
June 22, 2026
First trip to Tuscany

Great experience and enjoyed every bit of it. Tony was great! Just a fabulous time on first trip to Tuscany

X
X580FTjosephl
June 22, 2026
Chianti region, in a day.

Tony, our guide, was friendly and knowledgeable. We saw so many wonderful sights— Sienna, Monteriggioni, San Gimignano. The winery was excellent.

G
G7882IUkellyl
June 16, 2026
Don’t miss experience!

What an amazing day! This tour was the perfect combination of guided and self directed exploration. All the towns are different and worth seeing, and the lunch at the winery was 10/10! Antonello was a wonderful guide.

B
bellacX3418MM
June 15, 2026
Awesome experience

Alberto was a great guide, we learned so much, explored new locations and we had a great time!! Definitely recommend!

R
Renee F
June 15, 2026
Tony was a wonderful guide

Tony provided a wonderl tour! He was on time, informative and very nice. It was a great way to see a bit of Tuscany.

4
472rosemaryf
June 15, 2026
Toni is an awesome guide!

Toni was wonderful! The day trip was absolutely beautiful, we had no issues at all, and he was very knowledgeable!

D
davehO848OZ
June 11, 2026
Great Tour

Ned did a fabulous job! Would go again.

C
Companion64435518892
June 8, 2026
An enjoyable trip to Tuscany

It was a wonderful and pleasant experience. We joined the group from Rome with the meeting point at Florence. So we needed to travel by an early train by ourselves from Rome to Florence. We have never taken any train by ourselves in Italy before. However, the company has been very supportive giving us detailed instructions and advices.They also checked in with us that morning. It was a smooth experience from Rome to the meeting point in Florence. We had a wonderful experience on the day. Our guide Antonelle provided us good service, knowledgable and customer centric. We enjoyed the wine tasting and lunch, which was held in a beautiful vineyard. The few stops on the itinerary offered beautiful scenery or unique medieval vibes. We were glad that we have taken this trip.

K
K8907IPcharlesc
June 8, 2026
Tony is the man!!!

Tony our guide was amazing. Full day of touring the Tuscany region. Great wine tasting, gelato, and scenery. Highly recommend this tour and especially Tony!!!

A
abbybH2537XN
June 6, 2026
Would definitely recommend this tour!

Valentina was such a wonderful tour guide! Very knowledgeable, and super friendly! The tour itself was amazing, very glad to stop at so many locations within Tuscany, all within one day!

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