Italy · Wine & Beer

Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch

9 Hours Round trip from Florence Moderate pace

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The journey

Trip highlights

01 Full-day Tuscany trip from Florence
02 Explore historic Siena and Piazza del Campo
03 Free time to discover San Gimignano
04 Guided visit to a family-run Chianti winery
05 Tour the cellars and vineyard
06 Enjoy a traditional 3-course Tuscan lunch
07 Taste 5 locally produced wines
08 Travel in a climate-controlled vehicle with an English-speaking tour leader

Discover the beauty, flavours, and history of Tuscany on a full-day trip from Florence. Travel through rolling countryside to Siena and San Gimignano, two of the region’s most iconic historic towns, with time to explore their streets, landmarks, and atmosphere at a relaxed pace.

Along the way, visit a traditional family-run winery in Chianti for a guided tour of the cellars and vineyard, followed by a 3-course Tuscan lunch and a tasting of locally produced wines. With round-trip transport included and an English-speaking tour leader throughout the day, this experience offers an easy and enjoyable way to experience some of Tuscany’s most memorable highlights.

Along the way, visit a traditional family-run winery in Chianti for a guided tour of the cellars and vineyard, followed by a 3-course Tuscan lunch and a tasting of locally produced wines.

From the itinerary

At a glance

What this trip includes

Duration 9 Hours

Tour type Shared

Activity level Moderate

Accommodation Not included

Transport Included

Wheelchair access Not applicable

Cities Florence, Siena, Chianti, Tuscany, San Gimignano

Languages English

Day by day

The itinerary

Day 01

Meet your guide

Marvel at the Hills of Tuscany

Explore Piazza del Campo

Free time in Siena

Guided Tour of a Chianti Winery

Visit the Cellars & Vineyard

Enjoy a 3-Course Tuscan Lunch

Sample 5 locally produced wines

Explore San Gimignano

Return to Florence

The route

Where you'll travel

Tour route map — Round trip from Florence 5 cities · 9 Hours

The fine print

Trip details

What's Included

Round-trip transportation from Florence in a climate-controlled vehicle
Visit beautiful Siena with free time to visit the cathedral (on your own)
Wine tour and tasting at a traditional, family-run winery in Chianti
Taste 5 different wines
Traditional 3-course Tuscan lunch
Visit the picturesque medieval town of San Gimignano
An English-speaking tour leader for the day
Maximum group size of 29

What's Not Included

Entrance fees to ticketed places in San Gimignano
Entrance fees to the Siena Cathedral
Hotel drop-off / pick-up
Gratuities (optional)

Know before you go

Please read our meeting point directions thoroughly in advance. It is the responsibility of all visitors to be at the meeting point 10 - 15 minutes before departure. Guests arriving after departure cannot be accommodated, & missed tours or tickets cannot be refunded.
Mandatory: Everyone is required to carry a copy of the identification page of their passports on all tours. A photo of the first page of your passport saved on your smartphone works as well.
We regret that we are unable to accommodate guests with wheelchairs or any walking impairments that require special assistance on our group tours. We are also unable to accommodate strollers or baby carriages.
TTG reserves the right to alter itineraries for reasons of safety, restoration, maintenance, adverse weather conditions or occasional events.
TTG runs tours rain or shine and no refunds will be issued due to inclement weather. In extreme weather conditions (i.e., flooding, hail storms, lightning storms, etc.) some areas may close down for safety purposes.
We will do everything within our power to ensure timings and itineraries are respected, however, due to issues beyond our control, timings and sites are subject to last minute changes on rare occasions.
If you have any food allergies or intolerances, please contact us immediately to let us know. We work with our local vendors to plan menus ahead of time so having this information before your tour is important. Please note that there are some occasions where certain allergies cannot be accommodated.
Please note that the legal drinking age in Italy is 18, we are unable to serve alcoholic beverages to minors.
DRESS CODE: Entrance into any religious site requires a strict dress code (such as Siena's Cathedral). Knees and shoulders MUST be covered for both men and women.
For any questions on the day of your tour, please reach out to The Tour Guy directly at:

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