Private Tours & Drivers

TUSCANY

10 Best Private Tours & Drivers Tours In Tuscany

Tuscany's standouts.

The 10 private tours & drivers tours travellers book most often across Tuscany. Each one with the price you pay, the operator behind it and the day you actually get when you turn up.

10 Best Private Tours & Drivers Tours In Tuscany

PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence - Siena in a Tight Time Window: Duomo and Piazza del Campo

2.PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

5.0

Private Florence day trip to Siena, Monteriggioni, San Gimignano, with optional organic winery lunch and wine pairing, no car needed.

“A wonderful experience! We went for our honeymoon and this was truly a sweet relaxed day! Completely customed to what we would like to do with the day and our guide was so knowledgeable.”

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Private Wine & Oil Tasting with Lunch

Private Wine & Oil Tasting with Lunch - The 1.5-Hour Timeline: From Vineyard Intro to Full Lunch

3.Private Wine & Oil Tasting with Lunch

4.5

A private 1.5-hour biodynamic tasting at Podere La Marronaia: organic wines, EVO oils, balsamic, plus a 4-course Tuscan lunch near San Gimignano.

“This experience was second to none! What a beautiful place! The wine was excellent and they catered to a non drinking friend as well with juices! Food was excellent and there was no pressure to buy! Beautiful experience!”

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Tuscany EXCLUSIVE Private Day Trip from Florence by Car with Wine

Tuscany EXCLUSIVE Private Day Trip from Florence by Car with Wine - Getting Started in Florence: Pickup That Keeps the Day Moving

4.Tuscany EXCLUSIVE Private Day Trip from Florence by Car with Wine

5.0

Private Chianti day trip from Florence with wine tasting, hilltop abbey views, and medieval Greve in Chianti, led by a local guide.

“We had a blast with Lorenzo exploring the Tuscany countryside. We saw so many beautiful villas, learned a lot about the history of Tuscany. The winery we visited was absolutely gorgeous. I would recommend this tour to anyone.”

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Private Chianti wine tour

Private Chianti Wine Tour - Panzano in Chianti: A Short Stop Built for Photos

5.Private Chianti wine tour

5.0

Private Chianti tour from Florence with winery tastings, vineyard views, lunch, and Castellina’s medieval streets. Pickup and private transport included.

“This was a wonderful experience! Our guide, Stefano was happy to explain a bit about the Chianti Wine region in Italy as we drove out to the vineyards. Our 2 stops, although very different, were both very enjoyable. We enjoyed our time at both vineyards. The wines were delicious and so was our lunch. The…”

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Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour - Greve in Chianti: where the day feels most Tuscan

6.Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

5.0

Private Chianti wine tour from Livorno with Greve village stops, winery + olive oil tastings, and guaranteed port return.

“Nicolette was an exceptional guide who shared the history and important facts of the places we were visiting. She took us to the second leaning tower at a cathedral that we did not know about and was fun, beautiful, knowledgeable and we highly recommend her! 🫶🏻”

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Private Tour in San Gimignano

Private Tour in San Gimignano - Piazza della Cisterna: the rivalry square that explains the skyline

7.Private Tour in San Gimignano

5.0

2-hour private English tour of UNESCO San Gimignano: tower stories, optional Duomo and Palazzo/Torre, panoramas, and local gelato tips.

“Barbara was absolutely a delight! She was knowledgeable and friendly and didn't rush us. It was a beautiful day spent in San Gimignano!”

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The Best of Tuscany: Private Full Day Tour From Florence

The Best of Tuscany: Private Full Day Tour From Florence - Pisa’s Piazza dei Miracoli: what to look for in your one-hour stop

8.The Best of Tuscany: Private Full Day Tour From Florence

5.0

Private day trip from Florence to Pisa, San Gimignano, Siena, and Chianti. Hotel pickup, English driver-guide, and big scenery in one day.

“Massimo was wonderful! He was so knowledgeable and was the perfect driver for our day in Tuscany. He got us right from our hotel. Easy to communicate with. It was great because we could customize our day to fit exactly what we wanted. It was a day that my wife and I will never forget.…”

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Florence: Private Half-Day Chianti Tour and Wine Tasting Optional

Florence: Private Half-Day Chianti Tour and Wine Tasting Optional - Greve in Chianti: Town Time That Works for Real People

9.Florence: Private Half-Day Chianti Tour and Wine Tasting Optional

4.5

Private Chianti half-day tour from Florence with Mercedes pickup, scenic photo stops, free time in Greve, and optional winery tastings.

“Placedo is an excellent guide! He greeted us promptly at our hotel at our designated pick up time and from that moment on our experience was 5 stars. Placedo is very friendly and his intimate and extensive knowledge of the area were amazing. We have never been to Florence or Chianti so he explained things…”

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Private Day Tour from Florence to Pisa, Chianti and San Gimignano

Private Day Tour from Florence to Pisa, Chianti and San Gimignano - Piazzale Michelangelo at Sunset: Short Stop, Big Payoff

10.Private Day Tour from Florence to Pisa, Chianti and San Gimignano

5.0

AC private Florence day trip to Pisa, Chianti wine road and San Gimignano, ending with sunset views at Piazzale Michelangelo.

“This was the perfect tour to experience Pisa and the Tuscany landscape. Comfortable van and perfect tour. We totally enjoyed the lunch and wine tasting option. The sunset at Piazzale Michelangelo was the perfect ending to an amazing day.”

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