Multi-Day Tuscany Tours

TUSCANY

10 Best Multi-Day Tuscany Tours

Tuscany's standouts.

The 10 multi-day tuscany 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 Multi-Day Tuscany Tours

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

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

Most Popular 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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Full-Day Tuscany Castles Tour with Wine Tasting from Florence

Full-Day Tuscany Castles Tour with Wine Tasting from Florence - Castello del Trebbio: old cellars and a tasting of five wines

2.Full-Day Tuscany Castles Tour with Wine Tasting from Florence

5.0

Florence to Chianti for two winery visits with tastings, a 2-course lunch, and round-trip minivan transport in English.

“The Castles are really manor homes which have been converted to wineries or may have always been wineries. Not really castles in my opinion. They were interesting but one of my friends was really interested in the castle aspect and not so much the wine.”

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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

3.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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Active Full Day Tuscan Bike Tour With Wine Tasting and Lunch

Active Full Day Tuscan Bike Tour With Wine Tasting and Lunch - 7 hours of real riding: bikes, hills, and your e-bike choice

4.Active Full Day Tuscan Bike Tour With Wine Tasting and Lunch

5.0

Active Florence-to-Chianti bike day with wine and olive oil tastings plus a sit-down lunch, panoramic stops, and small-group guide care.

“Beautiful authentic ride through urban, suburban and countryside of Tuscany. Not the easiest ride (up) on bicycle but absolutely worth the effort. Andrea was a great host. And La Pia in Percussina was the best destination.”

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Chianti Countryside Full-Day Tour by Vintage Fiat 500

Chianti Countryside Full-Day Tour by Vintage Fiat 500 - Getting started from Siena or Badesse (and why the meeting point matters)

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional - Greve in Chianti: The Town Stop That Actually Lets You Feel the Region

7.Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

5.0

Private Mercedes ride from Florence through Chianti hill towns, with flexible stops and optional winery lunch and tastings.

“Amazing experience, Placido was a phenomenal driver and guide. We went to some amazing wineries and just had a perfect no rush day. I would book this again and again.”

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PRIVATE Full-Day Wine Experience in Chianti Classico.

PRIVATE Full-Day Wine Experience in Chianti Classico. - Greve in Chianti and Falorni: Snacks, Sights, and Local Pride

8.PRIVATE Full-Day Wine Experience in Chianti Classico.

5.0

Private full-day Chianti Classico experience from Florence with Greve and Montefioralle, organic tastings, and a farm lunch with wine.

“One of the best tour's we took while in Italy. Our driver, Alessandro was FANTASTIC! Showed up on time, was patient and always responded to any questions I had. Don't hesitate to book this tour. It was fabulous 👌.”

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Full-Day Excursion to Siena, San Gimignano & Chianti

Full-Day Excursion to Siena, San Gimignano & Chianti - Florence meet-up: the 9:00 AM start matters

9.Full-Day Excursion to Siena, San Gimignano & Chianti

4.8

Full-day Florence trip to Siena, San Gimignano, and Monteriggioni, with a guided Siena walk and time to wander the towers.

“We loved this tour but felt the time we were allocated wasn’t near enough at Monteriggiono, Siena and San Gimignano. Our guide Alberto very graciously returned to San Gimignano after a spectacular lunch so we could have a better experience. We truly appreciated this. Siena was beautiful to the point that we do want to…”

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Full-Day Tuscan Countryside Bike Tour

Full-Day Tuscan Countryside Bike Tour - The Bike Portion: Scenic, Light-Feeling, and Not a Tour for Sore Legs

10.Full-Day Tuscan Countryside Bike Tour

4.5

Full-day bike ride from Florence to Chianti country for a family winery lunch, wine tasting, and a guided cantina tour in English.

“We enjoyed this experience! It was a 5 star experience but the few notes below suggest more of 4-4.5 star experience. The people were great. The views were great. The details of the trip when booking it were a bit vague but went with the booking anyway. I got the impression that it was all…”

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