4 Private Day Trips from Florence Worth the Early Start

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

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

Travel from Florence by private luxury car or minivan with an English-speaking driver such as Marco, Simone, or Massimo. Visit Siena and San Gimignano, stop for Chianti views, and add a winery lunch for €50 to €70 per adult. This is a private driving tour, not a guided walking tour.

“Amazing day touring beautiful Tuscan region with Simon. He was always helpful with ideas for options. Highly recommended.”

Check availability →Read our full review

2.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 more. Add a private Florence guide with timed entry to the Accademia or Uffizi.

“Both Alesseo and Francesco were great hosts and went out of our way to be sure we had a great day. Ale picked us up promptly and on time and took some scenic routes to bring us to Florence. Francesco was extremely knowledgeable about all of the exhibits we visited and it is clear that he has a passion for art. Both of our guides created a wonderful experience and were able to recommend great restaurants as well! It is absolutely worth having a private tour and not getting caught in the huge crowds!!”

Check availability →Read our full review

3.Private day trip to Siena, San Gimignano, Chianti and Pisa, from Florence

★★★★★★★★★★5.0 · 104 reviews · 10 hours (approx.) · from $462

Travel from Florence by private Mercedes with an English-speaking driver such as Mario, Paolo, or Donatello. See Siena, San Gimignano, Chianti, and Pisa in one long day, with room to adjust the route, stop for a winery lunch, or swap Pisa for a Tuscan villa.

“What a great day! Giuseppe was excellent and had a great plan for the day, but with some flexibility as well. He had good information on how to maximize our time in each place we stopped and arranged for a fun stop at a winery in the afternoon as well. The A/C in the van was much appreciated as well.”

Check availability →Read our full review

4.Private Tuscany Tour: Siena, San Gimignano and Chianti Day Trip

★★★★★★★★★★5.0 · 64 reviews · 8 hours (approx.) · from $422Best value

Spend about eight hours with a private driver from Tuscany Top Drivers, visiting Siena, San Gimignano, and Chianti from Florence. Guides including Marco, Simone, Tommaso, Martino, Martin, and Paolo offer local stories, flexible stops, scenic detours, and optional winery lunches with wine tastings.

“It was a great day, our driver was very knowledgeable! In hind side, the time in the cities was a-little rushed so next time I would fore go the lunch at the winery and split the time in the two cities. But overall very special day!”

Check availability →Read our full review