Siena, Cortona & Montepulciano Small Group Minivan Tour

Four Tuscan towns in one day without renting a car or navigating alone

A guided minivan tour from Florence through Cortona, Montepulciano, Val d'Orcia and Siena, with stops at a local farm for cured meats and wine, a 14th-century cellar tasting, and free time to walk each town. The group stays under eight travelers, and a local English-speaking guide drives and narrates the route. The tour runs 12 hours, departing at 8am from Porta Romana in central Florence and returning around 8pm.

Step-by-step itinerary

Stops and time spent at each

1. Val d'Orcia1h 30m
2. Pubblico Palace1h 50m

Tuscan towns and wine tasting tour

• Meet tour leader in Florence at 7:45am
• Travel 1.5 hours through Tuscan countryside
• Explore hilltop town of Cortona independently
• Visit local farm for tasting and stroll
• Travel to Montepulciano and explore town
• Enjoy wine tasting in 14th-century cellar
• Drive through Val d'Orcia and admire landscapes
• Visit medieval Siena and explore main piazza
• Return to Florence by 8:00pm

The experience

You meet your guide at Porta Romana in central Florence at 7:45am, and the minivan leaves at 8am. The drive to Cortona takes about 90 minutes through open Tuscan countryside: the guide fills the time with stories about the region and the films shot here. Cortona itself sits on a hilltop with narrow streets and olive groves. You have free time to walk it at your own pace, and the town is the one Diane Lane explored in "Under the Tuscan Sun."

From Cortona, a 40-minute drive brings you to a working farm where Cinta Senese pigs roam semi-wild among olive trees and vineyards. The operator has arranged a tasting board of cured meats and bruschetta made from garden vegetables, paired with the farm's own wine. You eat and drink here without a separate stop to find lunch. After the farm, you head to Montepulciano, a walled medieval town famous for the Twilight films and for its DOCG wine. The guide gives you free time to explore the town, and near the entrance sits a 14th-century underground cellar where you get a complimentary tasting of local wines and cheeses. The cellar is included. You do not pay extra.

The drive from Montepulciano takes you through Val d'Orcia, the rolling-hills landscape that appears in "Letters to Juliet" and other films. You stay in the van for this stretch and have time to watch the countryside pass. Your last stop is Siena, a medieval town with narrow streets and the Palazzo Pubblico overlooking the main piazza. The guide walks you from the parking area to the center, then you have about an hour of free time to wander. The return drive to Florence takes roughly an hour, and you arrive back at Porta Romana around 8pm.

What’s included

• Transport in an eight-seat minivan with a local English-speaking guide.
• tastings of cured meats, bruschetta and wine at a working farm.
• complimentary wine and cheese tasting in a 14th-century cellar in Montepulciano.
• free time to explore Cortona, Montepulciano and Siena on your own.
• narration and stories about the towns and the films shot in them during the drive.

Options for this experience

3 options

Classic tour from ChiantiGuide in English · 08:45Departure from the Tuscany on Wheels office at Strada di Sant'Appiano 9/I, Barberino Tavarnelle (FI). Small group tour (maximum 8 people). Starting point: Tuscany on Wheels - Tours in & from San Gimignano, Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI, Italy

Classic tour from FlorenceGuide in English · 08:00Departure from central Florence at 8:00 am, at Piazza della Calza 1, next to the "P" parking sign. Small group tour (maximum 8 people). Starting point: Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy

Private TourGuide in English · 08:00Private minivan for 8 passengers. Starting point: Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy

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

Before you book

Days and timesMonday, Thursday and SaturdayDepartures at 08:00 and 08:45

Book up to4h before

AgesAdult (18 to 79 years) · Under 18: can't be booked

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.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Moderate physical effortNot recommended during pregnancyNot recommended with heart problems

Operated by Italy on a Budget tours

Is this one for you?Book the classic tour if you are comfortable sharing the minivan with other travelers and want a set departure time. Choose the private option if your group prefers to travel alone. The 12-hour day and the amount of driving suit travelers who want to see multiple towns without renting a car or navigating themselves, though the hilltop towns involve walking on steep streets.

Traveler reviews

4.85★★★★★★★★★★

144 verified traveler reviews

5 ★133

4 ★5

3 ★3

2 ★1

1 ★2

Read all the reviews ›

Top questions

What's the difference between the classic and private tour options from Florence?

The classic tour runs on a set schedule with other travelers (minimum four participants required to depart). The private tour is just your group in the same minivan with the same stops and tastings, at a higher price. Both include the guide, the farm tasting, the wine cellar visit and free time in each town.

Do I have to walk much in each town, or can I stay in the van?

Each town (Cortona, Montepulciano and Siena) gives you free time to explore on your own. The guide walks you from the parking area to the center of Siena and points out the main piazza, but the rest is your choice. Cortona and Montepulciano are hilltop towns with steep streets, so walking is involved if you want to see them.

Is lunch included, or do I need to bring food?

Lunch is included as a tasting at a local farm: cured meats, bruschetta and wine paired together. If you want a full meal or something different, you can buy food in any of the towns during your free time.

How much driving is there, and will I get carsick?

The tour involves about five hours of driving across the 12-hour day, broken into segments between stops. You travel in an eight-seat minivan, not a coach, so the ride is smoother on winding roads than a larger bus would be. The longest single drive is 90 minutes to Cortona at the start.

What is Val d'Orcia, and why do we pass through it?

Val d'Orcia is a UNESCO-listed valley in southern Tuscany famous for its rolling hills, cypress trees and the light that appears in films like "Letters to Juliet." You drive through it between Montepulciano and Siena so you see the landscape, but it is not a stop where you get out. You relax in the van and watch it pass.

Can I book this tour if I'm visiting from somewhere other than Florence?

The tour departs from Porta Romana in central Florence. If you are staying in the Chianti region, a separate classic tour option departs from there instead. Check which option matches your location when you book.