Florence day trip with a private driver: six routes, realistic timing and what it costs

The best Florence day trips with a private driver are the ones the train cannot do well: a day of tastings in the Chianti hills, Siena and San Gimignano together, the Val d'Orcia's villages and viewpoints, or a shopping day at the outlet in the Arno valley. Each of them is within about an hour to two hours of the city by road, and each works on a single booking that brings you back to your hotel door at the end.

Florence's own published price list has two bookings built for exactly this. The eight-hour Chianti wineries day costs from US$630 in a business sedan to US$1,255 in an Executive Sprinter, and the eight-hour full-day chauffeur, at the same prices, covers any other route. Below are six routes with routed drive times, sample timings and the cases where a train or a coach does the job just as well.

What is the best day trip from Florence with a driver?

All the drive times in this guide are routed estimates from the public OSRM network on a clear road, from Florence's historic centre. Summer weekends and the Florence ring roads at rush hour can add time.

See Florence prices and reserve

The prices that cover a day out

Every Florence day trip uses one of three published bookings from the Florence price list. Prices are per vehicle, never per person, and include the chauffeur, taxes and standard gratuity. Tolls and parking are billed at cost.

Capacities, from the fleet page: a Business Sedan or First Class Sedan seats three, a Business SUV or First Class SUV seats six, and an Executive Sprinter seats twelve. For a day trip, luggage space hardly matters; choose by people and comfort.

Route 1: a day in the Chianti hills

This is the signature Florence day trip, and it has its own eight-hour package for a reason. The Chianti Classico area begins a short drive south of the city, and the day follows the Chiantigiana road through Greve, Panzano and Castellina, with detours up farm tracks to estates. The Chianti Classico consortium lists producers that receive visitors.

The rule that matters: book the tastings first. Most estates take visits by reservation at set times. Send us the times and the chauffeur builds the route around them, usually two tastings and a long lunch. The chauffeur drives, so everyone else can taste, and follows local rules in the vehicle. More on the format on wine tours.

A typical day leaves Florence around 9.30, reaches the first estate by 10.30, lunches in Panzano or Castellina, takes a second tasting in the afternoon and is back in the city by 5.30.

Route 2: Siena and San Gimignano

Two of Tuscany's great towns in one day, both on the UNESCO list: the historic centre of Siena and the historic centre of San Gimignano, the hill town of medieval towers. San Gimignano is about an hour from Florence; from there to Siena is 42 km (26 mi), about 50 minutes; and Siena to Florence is about 1 hour 10 minutes back.

Do San Gimignano first, in the morning, before the coaches arrive, then give Siena the afternoon: the Campo, the cathedral and an early dinner before the drive home. Both centres are largely closed to traffic, so the chauffeur drops you at the edge of each and collects you at an agreed gate. Visit Tuscany's Siena page is a good planning start.

This is the day we would book for a first visit to Tuscany. It needs most of the eight hours, so if you want a Chianti tasting as well, add hours rather than squeezing it.

Route 3: the Val d'Orcia, Pienza and Montalcino

The Val d'Orcia is the landscape of cypress avenues and rolling fields that most people picture when they think of Tuscany, and it is on the UNESCO World Heritage list. Pienza, the Renaissance model town, is about 119 km (74 mi) and 1 hour 41 minutes from Florence; Montalcino, home of Brunello, is about 142 km (88 mi) and just over two hours.

This is the longest of the inland day trips, with three and a half to four hours of driving in total, much of it on country roads. It works in an eight-hour day with one tasting and a short walk in each town. For photography stops along the valley, a later sunset or a second tasting, book by the hour instead, at US$85 an hour in a business sedan. A ten-hour day by the hour is US$850 in a sedan, arithmetic for planning only.

Travelling between Rome and Florence? The Val d'Orcia also fits on that drive; our guide to Rome to Florence by private car shows the route.

Route 4: Volterra and San Gimignano, for a second visit

Volterra, the walled hill town on its ridge west of Siena, is about 78 km (48 mi) from Florence, roughly 1 hour 25 minutes. San Gimignano is only 32 km (20 mi), about 38 minutes, from Volterra, so the pair makes a quieter alternative to the Siena day for travellers who have already seen Siena. The road between them crosses open country with long views, one of the pleasures of having a car.

Route 5: Arezzo

Arezzo, about 79 km (49 mi) east, roughly an hour on the motorway, is a lively provincial city that sees far fewer visitors than Siena, with a sloping main square and churches worth an unhurried morning. It suits art lovers and repeat visitors. The train also serves Arezzo well, so this is a day where we would say: take the train if you are two people with no other plans, and book a car if you want to combine Arezzo with a hill town such as Cortona or with an estate lunch on the way back.

Route 6: an outlet shopping day

The Mall Firenze, the luxury outlet in the Arno valley, is about 37 km (23 mi) from the centre, around 40 minutes. A shopping day is usually shorter than a sightseeing day, so book by the hour with a three-hour minimum, add hours at the desk if you need them, and let the car hold the bags between stores and the drive back. Four hours by the hour costs US$340 in a business sedan or US$440 in a business SUV, arithmetic for comparison.

Pisa, Lucca and the Cinque Terre

The west of Tuscany has its own guides. Pisa and Lucca fit easily in one day, with the timed Leaning Tower climbs setting the schedule; see Florence to Pisa by car. The Cinque Terre is a much longer day, best done with a car to the coast line and the train between villages; see Florence to Cinque Terre by car.

When a train or a coach tour is the better choice

A private driver is not the answer to every day out, and pretending otherwise would not help you plan.

• Siena alone, for one or two people. Buses and trains reach Siena, and if you only want the city, public transport is far cheaper.
• Arezzo or Pisa alone. Both are on the rail network. The car earns its place only when you combine them with something else.
• A tight budget, travelling solo. A coach day tour from Florence shares the cost of the vehicle across many people.

The car wins when the day involves several places that rail cannot connect, wine tastings, children or older travellers, a group of four or more sharing one vehicle, or simply the wish to set your own timetable. For four people, a US$630 full day in a business sedan is not possible, because the sedan seats three; a Business SUV at US$810 carries six, which is about US$135 each for four as arithmetic for comparison.

Three sample days, by traveller

A couple on their first trip to Italy. Siena and San Gimignano in a Business Sedan on the full-day booking, from US$630. San Gimignano at ten, lunch on the road, Siena for the afternoon, back for dinner in Florence.

Four friends who came for the wine. The Chianti day in a Business SUV, from US$810, with two estate tastings booked in advance and lunch in Panzano. Nobody has to drive, and nobody has to watch the clock for a bus.

A family of six with teenagers. The Val d'Orcia by the hour in a Business SUV, with a gelato stop in Pienza, the view over the valley at the edge of town and a swim at the hotel pool at the end of the day.

Planning tips from the desk

• Book the fixed-time things first. Tastings, a restaurant lunch, a museum slot: send us the times and the route is built around them.
• Mornings first in popular towns. San Gimignano and Siena are quieter before the coaches.
• The limited traffic zone at the Florence end. Give your exact hotel address and the chauffeur picks you up at the closest legal point.
• Child seats. Fitted on request before pickup; give the ages when you book.
• Gratuity. Already included in every Elly8.net fare.
• Inside Florence. For a shorter half-day in the city and the hills above it, the private city highlights tour from US$340 covers Piazzale Michelangelo and Fiesole; see private city tours.

Planning a wedding, a corporate offsite or a family celebration in a villa? One Executive Sprinter keeps a group of twelve together for the day; see group transportation, or book on account through travel agent accounts and hotel accounts.

How to book

1. Enter your Florence hotel or villa as pickup and choose the Chianti day, the full-day chauffeur or an hourly booking.
2. Choose the vehicle class, and put your stops and fixed times in the notes.
3. Reserve and pay in US dollars, or use the web booker for any custom route. Confirmation comes by email.

Book any address

Rides in Florence are operated by licensed, commercially insured local chauffeur partners vetted through the Limousine Worldwide network; Elly8.net takes the booking, fixes the price and runs the 24/7 desk. Cancellation is free more than 72 hours before pickup, 10% at 72 hours or less, 50% at 48 hours or less and 100% at 24 hours or less or for a no-show, refunded to the original card. Elly8.net is a member of LimousineWorldwide.Directory, LimousineAssociation.International, HotelsWorldwide.Directory and VacationsWorldwide.Directory. Our travel partner for flights and hotels is BookingWorldwide.net; Elly8.net books the car only. Moving on from Tuscany? The same desk books Venice, Rome and Milan.