14 tours · €44–€195 per person · ★ 4.8
A Siena day trip from Florence almost always brings San Gimignano along, and the 14 tours here were picked by hand from every listing rated 4.5★ or higher. Prices run from €44 per person for a coach day that stops in both towns with a winery tasting on the way to €195 for a private car with your own driver, priced per group. Between them sit the small group days by minivan with a guided walk in Siena, free time in San Gimignano and lunch at a Chianti estate, and a Tuscany wine tour from Florence that pairs two cellars with the towers of San Gimignano.
A quick way to choose: read the option tier, because on the coach tours the guided walk in Siena, the winery lunch and the Monteriggioni stop belong to the upper tiers, and the low cost version is little more than transport. Siena Cathedral tickets are usually an extra paid on the day, and the cathedral is closed on Sundays. Hotel pickup is rare. The best reviewed San Gimignano and Siena tours from Florence come first below.
Siena & San Gimignano Day Trips in Florence: 14 tours, drawn from the 96 Guidekin lists out of 3,254 on Viator, chosen by rating (4.5★ or higher, 30+ reviews), each one read and summarised.
Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable...
Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards...
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to ...
A day trip exploring Tuscany with visits to 2 wineries. Taste 8 different types of wine, three extra virgin olive oils, balsamic vinegar and Tuscan sn...
Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will ...
*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tusc...
When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, wander the storyboo...
Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine. ...
Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a g...
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countrysid...
You leave in the morning to Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous...
Discover the best of Tuscany in just one day on this expertly planned tour from Florence. Skip the stress of organizing transport and enjoy a seamless...
There’s more to Tuscany than Florence. Leave the city behind and discover three other enchanting Tuscan destinations on this day trip to Siena, San Gi...
Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes,...
Tours and prices on this page last updated November 2, 2026
Editorial picks checked: September 18, 2026 · Ranked by Rating weighted by review volume, then what the price covers and the conditions. Prices and ratings on tour cards are live. Commissions never affect the order.
We compared 14 Siena and San Gimignano day trips from Florence by winery lunch, Monteriggioni, guided Siena or free time, and private cars.
Guided Siena, winery lunch and wine at €149 per person; minibus passes Monteriggioni without stopping, cathedral extra. 4.92 from 1,886 reviews.
Semi Independent at €86 per person: coach, guided Siena and free time in San Gimignano and Pisa; no winery, lunch or cathedral. 4.86 from 24,384 reviews.
Hotel pickup and a private car or minivan for three to seven at €710 per group/vehicle per group; the driver is not a guide inside Siena. 4.85 from 436 reviews.
| Tour | Best for | Price | Rating | Duration | Trade-off |
|---|---|---|---|---|---|
| Siena and San Gimignano with Winery Lunch | Small group with lunch | €149 per person | 4.92★ (1,886) | 10h | Cathedral extra; group pace |
| Siena, San Gimignano, Pisa and Winery Lunch | Adds Pisa, coach | €86 per person | 4.86★ (24,384) | 12h | Base skips winery, lunch and Siena Cathedral |
| Private Siena, San Gimignano and Chianti Day | Private, three to seven | €710 per group/vehicle | 4.85★ (436) | 8h | Per group; no guide in Siena |
| Small Group Wine Tour and San Gimignano | Two wineries, no Siena | €190 per person | 4.92★ (823) | 8h | Skips Siena; pickup on request |
| San Gimignano, Siena and Monteriggioni Lunch | Farm lunch and Monteriggioni | €79 per person | 4.52★ (5,334) | 11h | Monteriggioni skipped November to March |
| Siena, San Gimignano and Chianti Wines | Coach, Siena guide option | €65 per person | 4.66★ (3,549) | 10h 30m | No lunch; Free Time tier has no Siena guide |
| Siena and San Gimignano with Winery Dinner | Afternoon start, dinner | €106 per person | 4.72★ (356) | 9h–12h | Grand Tour tier swaps dinner for lunch |
| Tuscany in One Day with Chianti Lunch | Cathedral on selected tier | €59 per person | 4.77★ (3,191) | 12h | Base excludes lunch, Siena guide and cathedral |
Our editorial picks require a rating of 4.5★ or higher and at least 50 traveler reviews. Read our methodology.
The highest-rated experiences here, chosen by thousands of real reviews.
Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable...
Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards...
Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will ...
A day trip exploring Tuscany with visits to 2 wineries. Taste 8 different types of wine, three extra virgin olive oils, balsamic vinegar and Tuscan sn...
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to ...
*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tusc...
When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, wander the storyboo...
Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine. ...
Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a g...
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countrysid...