8 Private Tours in Tuscany, Priced and Compared

1.From Florence: Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours Our pick

Spend six hours in the Chianti hills with a guide such as Anna, Chiara, or Abbie, traveling by minivan from Florence to Radda and two very different wineries. Taste six local wines with salami, cheese, and olive oil, learn how wine reaches the bottle, and shop for Tuscan products along the way.

“My trip was incredible! I was initially car sick but Anna (the host) and Mario (our driver that day) were so kind, they kept checking up on me from time to time to make sure I was okay and if I needed anything. The tour was wonderful, we visited 2 wineries and had a lovely time. Definitely recommend!!!”

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2.Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 775 reviews · 4 to 7 hours (approx.) · from $96Best value

John at E-Bikes Florence sets you up with a pedal-assist bike, helmet, phone holder, and GPS route. You ride independently from Florence to Fiesole, through hills and countryside to a boutique vineyard, then return by way of Piazzale Michelangelo. Wine, food, and roadside help are available, but the route requires confident cycling.

“The e-bikes made this journey so enjoyable, even with all of the hills! Incredible views and an excellent way to see more of the surrounding area.”

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3.Da Vinci’s Last Supper Express Semi-Private Guided Tour

★★★★★★★★★★4.8 · 427 reviews · from $123

Meet your English-speaking guide at Santa Maria delle Grazie and enter the Last Supper with a group of no more than six. Guides such as Larissa, Barbara, Roberto, and Paivi explain Leonardo’s art, the painting’s restoration, and its historical setting, then leave you quiet time to take it in.

“Our tour was amazing. Our guide Larissa was absolutely brilliant!!!”

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4.Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

★★★★★★★★★★5.0 · 405 reviews · 8 hours (approx.)

Travel from Florence by private car or minivan to Siena, San Gimignano, and the Chianti hills. Your English-speaking driver, often Marco, Simone, Massimo, or Samuele, handles the roads and shares local stories. Add a winery lunch and tasting for €50 to €70 per adult, but expect less time in the towns.

“This was our favorite highlight of the trip. We have traveled quite a lot and can hands down say Marco is the best guide anyone could have. We learned a lot of interesting facts about his country. The winery lunch and visit was so relaxing and enjoyable. Wonderful day all the way around”

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5.3h Private City Walking Tour with Optional Cathedral

★★★★★★★★★★4.7 · 392 reviews · from $164

Let a local guide lead you through Siena’s medieval center, from Basilica di San Domenico and Saint Catherine’s sanctuary to Piazza del Campo, Palazzo Pubblico, and the Duomo. Guides such as Mare, Ludovica, and Ludmila bring the Palio and contrade traditions to life. Add the cathedral visit if you want art and marble interiors.

“Great tour. Our tour guide was very knowledgeable and friendly. Would definitely recommend!”

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

★★★★★★★★★★5.0 · 238 reviews · 8 to 9 hours (approx.) · from $399

Spend 8 to 9 hours exploring Siena, Monteriggioni, San Gimignano, and the Tuscan countryside from Florence. Alessandro provides private transport for up to six people, shares local history and wine knowledge, and leaves time to wander independently. Add an organic winery lunch and tasting for an extra €55 to €65 per person.

“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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7.Livorno Shore Excursion: Pisa and Florence Private Day Trip

★★★★★★★★★★4.5 · 198 reviews · 9 hours (approx.) · from $546

Travel by private Mercedes from Livorno to Pisa and Florence with an English-speaking driver. See the Leaning Tower, Piazzale Michelangelo, the Duomo, Ponte Vecchio, and Santa Croce. Add a three-hour Florence guide with timed entry to the Accademia or Uffizi, subject to availability.

“This private tour was absolutely worth the cost! We were met at our cruise ship dock by our driver, Alex. He shared the history of the Florence/Pisa region as we drove to the Plaza del Duomo to meet up with our guide for the Uffizi Gallery (entry tickets were included in cost of tour). Our guide for this part of the tour was Francesco. He was AWESOME! Funny, personable, and an Art PhD. We had a coffee and a walk about in the Plaza del Duomo and then went into the Uffizi Gallery; so many beautiful treasures contained within those walls. Once finished with the tour, we met back up…”

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8.Semi Private Deep Wine Chianti and San Gimignano from Florence

★★★★★★★★★★5.0 · 191 reviews · 8 hours 30 minutes (approx.) · from $252

Spend 8.5 hours with a driver-guide such as Sara, Alberto, Gabriel, or Francisco, visiting San Gimignano and two Chianti estates. You’ll taste several wines and olive oil, enjoy a regional lunch, see Florence from Piazzale Michelangelo, and travel in a Mercedes van with no more than eight people.

“Excellent experience for seeing the Chianti countryside and vineyards. Top tier wine tour with a local guide eager to share Tuscan history.”

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