Tuscany Grand Tour: Siena, San Gimignano, Chianti & Pisa

Four Tuscan towns, three tastings, and a lunch that stops the day.

A full-day guided tour from Florence through Siena, San Gimignano, Chianti, and Pisa aboard a luxury minivan with an English-speaking guide. The itinerary pairs walking tours of medieval towns with a surprise local tasting in Siena, a traditional three-course Tuscan lunch in the countryside, and a winery visit with wine tasting in Chianti before reaching Pisa's Piazza dei Miracoli. An afternoon option skips Pisa and trades it for a sunset wine tasting and dinner in the hills instead.

Step-by-step itinerary

Tuscan towns and iconic landmarks

• Meet tour leader at Piazza Mentana
• Depart Florence by luxury minivan
• Guided walking tour of Siena
• Enjoy local tasting in Siena
• Travel to San Gimignano
• Free time in San Gimignano
• Traditional Tuscan lunch in Chianti
• Free time at Pisa's Piazza dei Miracoli
• Return to Florence

The experience

Eight to twelve hours on the road means you see four towns without driving yourself. Depart Florence at 8:00 AM from Piazza Mentana in a Mercedes minivan (maximum eight guests) with air conditioning and Wi-Fi. Your English-speaking driver and tour leader handles the route through rolling Chianti countryside: cypress-lined roads, olive groves, and historic villas pass the windows while you settle in.

Siena arrives first, where a licensed local guide leads a walking tour through medieval alleys, past the Basilica of San Domenico, along Via Banchi di Sopra with its noble palaces, and into Piazza del Campo: the heart of the Palio horse race and the city's Contrade traditions. Before leaving, a surprise local tasting introduces you to Tuscan flavors: cantucci with Vin Santo, ricciarelli, or seasonal specialties chosen by your guide. Then San Gimignano, the hilltop town of towers, gives you free time to wander artisan boutiques, sample Vernaccia wine, climb Torre Grossa for panoramic views, or simply sit with the landscape.

Lunch is a three-course meal at a trattoria or farmhouse in Chianti: handmade pasta, local cured meats, seasonal vegetables, dessert, and house wine. After that comes a guided winery tour with wine tasting in the hills, where the light turns golden and the pace slows. Pisa and its Piazza dei Miracoli close the day: free time to photograph the Leaning Tower, the Baptistery, and the Cathedral before the drive back to Florence by 7:30 PM. (Climbing the tower costs extra and is not included, tickets are available on-site if time allows.) The afternoon option trades Pisa for a sunset wine tasting and Tuscan dinner instead, better suited to a later start and a preference for fewer stops.

What’s included

• Round-trip transportation from Florence by luxury Mercedes minivan with air conditioning and Wi-Fi.
• English-speaking driver and tour leader.
• guided walking tour of Siena with a licensed local guide.
• surprise local tasting in Siena featuring Tuscan specialties.
• free time to explore San Gimignano's artisan shops and towers.
• three-course traditional Tuscan lunch in Chianti with house wine.
• guided winery tour with wine tasting in the Chianti hills.
• access to Pisa's Piazza dei Miracoli with the Leaning Tower, Baptistery, and Cathedral.

Options for this experience

4 options

Afternoon option, Pisa not includedGuide in English · 13:00 and 14:00Siena and San Gimignano with dinner: short on time? Join at 2 PM for an 8.5-hour tour of Siena and San Gimignano that ends with dinner in Chianti at sunset. Pisa is not included.

Grand Tour of Tuscany aboard a coachGuide in English · 08:00Essential coach tour: a full-day trip to Siena, San Gimignano and Pisa, with lunch in Chianti, covering the top sights at great value. Maximum comfort at a low cost.

Grand Tour of Tuscany by minivanGuide in English · 08:00Minivan tour in Mercedes vehicles: see Siena, San Gimignano, Pisa and Chianti with lunch, on a semi-private basis (maximum 8 guests), covering art, wine and iconic views in one day!

Private day trip from Florence to Pisa, Siena and San GimignanoGuide in English · 08:00, 08:05 and 08:10Private Tuscany tour: a private tour of Siena and San Gimignano with dinner, including sunset dining in Chianti, exclusively for your group

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesEvery day5 departure times: the first at 08:00, the last at 14:00

Book up toStart time

AgesAdult (13 and older) · Child (4 to 12 years) · Infant (under 4)

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated today

Good to know

Low physical effortInfant seats availablePublic transport nearby

Operated by Towns of Italy

Is this one for you?Book the full Grand Tour if you want to pack four distinct towns and their stories into one day without driving. Choose the afternoon option if you prefer a later start, fewer stops, and time to linger over wine and dinner as the light fades.

Traveler reviews

4.88★★★★★★★★★★

262 verified traveler reviews

5 ★243

4 ★11

3 ★5

2 ★2

1 ★1

Read all the reviews ›

Top questions

Can children come?

Yes. Ticket types: Child (4 to 12 years); Infant (under 4).

What's included in the Tuscany Grand Tour from Florence?

The tour includes round-trip transportation by luxury minivan from Florence, an English-speaking driver and tour leader, a guided walking tour of Siena with a licensed local guide, a surprise local tasting in Siena, free time in San Gimignano, a three-course Tuscan lunch in Chianti, a guided winery tour with wine tasting, and access to Pisa's Piazza dei Miracoli. Climbing the Leaning Tower is not included but tickets can be purchased on-site.

How long is the full Tuscany Grand Tour and what time does it start?

The tour runs eight to twelve hours total. You meet your guide at 7:45 AM in Piazza Mentana, just outside the Towns of Italy Office, and depart at 8:00 AM. Return to Florence by 7:30 PM.

What is the difference between the full Grand Tour and the afternoon option?

The full Grand Tour visits Siena, San Gimignano, Chianti, and Pisa in one day. The afternoon option skips Pisa and instead includes a sunset wine tasting and Tuscan dinner in the Chianti hills, offering a slower pace and fewer stops for travelers with less time or who prefer a later start.

Is the minivan air-conditioned and does it have Wi-Fi?

Yes, the luxury Mercedes minivan is equipped with air conditioning and free Wi-Fi throughout the journey. The vehicle holds a maximum of eight guests.

What happens during the wine tasting in Chianti?

A guided winery tour in Chianti includes a wine tasting where you sample regional wines. This stop comes after lunch and before Pisa on the full Grand Tour, or before dinner on the afternoon option.

Can I climb the Leaning Tower in Pisa during this tour?

Climbing the Leaning Tower is not included in the tour price. However, you have free time in Piazza dei Miracoli to admire the tower, the Baptistery, and the Cathedral, and tickets to climb the tower can be purchased on-site if time permits.