Private Day Trips from Florence: Siena, San Gimignano and the Cinque Terre

Side by side

Read the price unit before anything else. Two tours charge per person, so the total grows with every seat. The Cinque Terre day charges per group, so one price covers everyone in the party.

A private day to Siena, San Gimignano and Chianti can take up to seven people, which is why travel guides call it a cost-effective pick for families and friends.

Siena

Siena is the larger of the two towns and the busier one at peak hours. Travellers warn that Siena and San Gimignano get packed when many tour buses arrive at the same time. A private day lets you shift the order of stops so you reach each town outside that wave.

San Gimignano

San Gimignano is called the Manhattan of the Middle Ages for its 14 stone towers. It is small, so an hour or two covers the main streets.

The Chianti stop

Chianti sits between Florence and Siena, so the wine stop fits on the way out or on the way back. Travellers who took smaller private tours to lesser-known wineries said those days felt calmer and better than tours with fixed stops. That is the main thing a private day gives you over a coach: you can ask for a quieter estate.

What fits into the day

A Cinque Terre day trip that covers all five villages takes about 14 hours from Florence, according to travel guides. The Full-Day Private Cinque Terre Tour with Pisa runs 11 hours and adds Pisa to the route, so expect to choose which villages get the most time. Some Cinque Terre day tours combine a ferry-boat with a minivan, which gives you the cliffs from the water and the road between villages.

If you want to hike

The paths between the villages are managed by the Cinque Terre National Park. Walkers need a Cinque Terre Trekking Card, sold as a 1-day adult card, and the park charges more for it in high-demand periods. Check the park's page before you go and ask your driver which village to start from.

Per person or per group

The Private Day Trip Siena, San Gimignano and Chianti from Florence costs $383.81 per person and the From Florence: Tuscany Day Trip with a Private Chauffeur costs $438 per person. With these, each extra traveller adds a seat to the bill. The Full-Day Private Cinque Terre Tour with Pisa costs $893 per group, so the price stays the same whether two or more of you travel.

Why groups look at private days

Travel guides note that a private Siena, San Gimignano and Chianti day takes up to seven people, which makes it a cost-effective option for groups. For a family or friends, compare the per-person totals with the single group price.

What the three share

Every tour here are private, start from Florence and offer free cancellation up to 24 hours before the start. The From Florence: Tuscany Day Trip with a Private Chauffeur is built around a private chauffeur for 8 hours. The other two follow a set route: Siena, San Gimignano and Chianti, or the Cinque Terre and Pisa.

What to check before you pay

Look on the listing for wine tastings, lunch and entry tickets, since these vary from one operator to the next. On the coast, a Cinque Terre Trekking Card from the national park is a separate purchase if you plan to walk between villages. Operators also say private trips can be customised, so ask before you book if you want an extra stop.

Book it if

You want Siena, San Gimignano and a winery in one day, which public transport cannot link easily. You are a family or a group of friends who can share a per-group price. You want to avoid the hours when tour buses fill San Gimignano and Siena.

You prefer a calmer, smaller winery to a fixed coach stop.

Skip it if

You only want to see one city. Trains from Florence reach Pisa in 1 hour and Siena in 1.5 hours, so a single-town day works without a driver. If you would rather stay in the city, look at private tours in florence italy for walking and museum days.

Harvest season

Travellers report that October brings harvest and festivals, so the towns and roads are busier. If you want the vineyards at work, go then and start early. If you want quiet streets, choose a month outside the harvest.

Beating the bus wave

San Gimignano and Siena get crowded when tour buses drop groups at the same time. On a private day, ask your driver to reverse the usual order of stops, or to reach San Gimignano first thing. Use the busiest hours for the winery, where the crowds do not follow.

Train times from Florence

Travel guides list these journey times from Florence. They suit a self-guided day in one place.

Train or car

The hill towns and the Chianti estates sit away from the rail line. That is why the Tuscany days on this page run 8 hours or more by road. Take the train for Pisa or Lucca on their own, and book a private day when the route has three stops or more.

Beyond Siena and the coast

Private day trips with a driver from Florence reach Siena, San Gimignano, Pisa, Lucca, Chianti, the Cinque Terre and even Venice, Rome and Verona. Other routes include Assisi and Perugia with wine tasting, Montalcino and Montepulciano for wine, and San Gimignano with Volterra. Private trips in Tuscany can be customised, and operators also depart from Pisa, Lucca, Livorno and La Spezia.

Three quick rules

For a first Tuscany day, the Private Day Trip Siena, San Gimignano and Chianti from Florence at $383.81 per person has the most reviews, 271, with a rating of 5. For a day built around a private chauffeur, the From Florence: Tuscany Day Trip with a Private Chauffeur at $438 per person runs 8 hours and holds a rating of 5 from 22 reviews. For the coast, the Full-Day Private Cinque Terre Tour with Pisa at $893 per group runs 11 hours and holds 4.9 from 186 reviews.

All three offer free cancellation up to 24 hours before the start.