Day Trips From Florence: Siena, San Gimignano, Pisa and Chianti

As of October 2026, all six day trips on this page had dates on 7 or 8 October when we checked. Four are coach days to Siena, San Gimignano, Pisa or the Chianti wineries, one goes to the Cinque Terre, and one rides vintage Vespas into the hills. Whether you need a tour at all depends on where you are going.

By train: Pisa, Lucca and Siena

Pisa is the easy one. From Santa Maria Novella the timetable lists 78 direct trains to Pisa Centrale, and the Regionale Veloce takes 51 to 66 minutes. Lucca has 32 direct regional trains, taking 71 to 106 minutes. Siena is slower by rail: its 17 direct regional trains take 87 to 98 minutes. Autolinee Toscane also runs a coach to Siena from Florence’s bus station, line 131R, though its page gives no journey time.

The Cinque Terre are further. The 13 direct trains to La Spezia Centrale, the gateway to the five villages, take 147 to 171 minutes; Trainline lists a fastest itinerary of 1 hour 57 minutes and an average of 2 hours 32 minutes. From La Spezia, the Cinque Terre Treno MS Card gives unlimited second-class travel on regional trains as far as Levanto.

Where a tour or a car does the work

San Gimignano has no station. Trenitalia sells the trip as a regional train to Poggibonsi-San Gimignano and a bus to the old town, which costs €2.90 (2026) on top of the train fare, and the Comune of San Gimignano says buses 130 and 133 meet the trains from Florence via Empoli. Greve in Chianti has a regional bus from Florence, Autolinee Toscane’s line 365, but the timetable we read gives no journey time.

That is where the tours come in. Siena, San Gimignano and Pisa in one day, with a winery lunch between, is a long chain of connections by public transport and a single seat on a coach tour. The same goes for a tasting at a Chianti winery, where the tour also does the driving after the wine. If you hire a car instead, keep it out of the historic centre: the whole centre of Florence is a limited traffic zone (ZTL), watched by cameras that read every number plate, and the fines are steep.

The day on this page

Walkabout Tours’ day to Siena, San Gimignano and Pisa costs from $152 as of October 2026, and it is rated 4.9 from 5,342 reviews. You meet the guide in front of Santa Maria Novella station, by the description (the itinerary lists two starting points, depending on the option), and board an air-conditioned coach; there is no hotel pickup. In Siena a local guide walks you through the streets to Piazza del Campo, home of the Palio horse race, and into the cathedral, whose entry ticket is included. If the cathedral is closed for religious services, you see the Palazzo delle Papesse instead. Free time follows.

With the lunch option, the next stop is a family-owned organic winery in Chianti, for a farmhouse lunch of homemade pasta, cured meats, local cheeses, salad and biscotti and a tasting of 4 regional wines, Chianti, Vernaccia and Vin Santo among them. Without it, you get longer in San Gimignano, the next stop, for free time among its squares and towers. The coach then drives to Pisa for the Leaning Tower, the Cathedral and the Baptistery, a short guided walk and free time. Climbing the tower needs the option that includes its ticket.

The itinerary allows about 1.5 hours at each stop, and the coach is back in Florence around 8:30 pm. The operator suggests booking any onward train from Florence after 9:00 pm; if you are flying or taking a train from Pisa, you can bring your luggage and leave the tour there. The day is not suitable for people with mobility impairments, and it has a vegetarian option but no gluten-free meals. Cancellation is free up to 24 hours before.

If you want all three towns in one day, with a guided walk in Siena, and would rather not chain trains and buses, this is the day to book.

See dates for the three-town day →

The other five

My Tour in Italy’s three-town day (from $55, 4.6 from 11,857 reviews) covers Siena, a Chianti winery, San Gimignano and Piazza dei Miracoli in Pisa in about 12 hours, but it sells four levels. The “Low Cost Tour” is transport only; lunch comes from the “Basic Tour” up, the guided walk in Siena from the “Traditional Tour”, and the cathedral ticket only with the “Full Options Tour”, so check what your option includes before you compare prices. It meets at the Villa Costanza tram and bus terminal, or in Via dell’Oriuolo for the small-group option. The Siena guiding is in English only, some languages need 4 participants, and tips are extra.

Ciaoflorence Tours & Travel’s Chianti wineries tour (from $56, 4.5 from 11,741) is a half day. A coach with air conditioning and Wi-Fi leaves from the Piazzale Montelungo bus stop, a 5 to 10-minute walk from Santa Maria Novella, for two wineries, each with a guided visit and a tasting of 3 to 4 wines with bread, olive oil, balsamic vinegar and salami. Lunch is not included, friends who book separately may end up on different buses, and luggage and large bags are not allowed.

CAF Tour & Travel - Gray Line Florence’s San Gimignano, Siena and Chianti day (from $89, 4.6 from 4,209) gives about two hours in San Gimignano, then a winery visit with a 3-course lunch and a guided tasting of 3 Chianti wines, then Siena, where the guided walk and the cathedral visit come with an option. In season it adds the walled village of Monteriggioni; from November to March it does not, and it gets back about 30 minutes earlier. The listing does not name the meeting point, which depends on the option, and a lost audio guide costs €80.

Walkabout Tours’ Cinque Terre day (from $62, 4.9 from 6,221) meets in central Florence and goes by coach to La Spezia, about 2 hours by its estimate, then by train between the villages: Manarola, Corniglia with an optional guided hike to Vernazza, Monterosso and Riomaggiore, or three villages and Pisa on the Pisa option. The national park entry and the trains are included, except on the transport-only option. Food is not, and the boat along the coast is paid on the day, weather permitting, from late March to October, with a train in its place from November to March. It is not suitable for children under 8, and open-toed shoes, sandals and high heels are not allowed.

Walkabout Tours’ Vespa tour (from $169, 4.8 from 825) starts at a garage in the city, where you are fitted with a helmet and briefed on a vintage automatic Vespa. Then it rides out into the hills, with photo stops looking back over Florence, lanes between villas, olive groves and vineyards, and a tasting of pasta, cheese and prosciutto with a glass of Chianti on a private terrace. Drivers must be 18 or over, know how to ride a scooter and bring a valid driving licence; two people can share a Vespa. It is not suitable for pregnant women or people with mobility impairments, and there is no hotel pickup.

Who each day suits, and how long to allow

The coach days take the whole day: back around 8:30 pm on Walkabout Tours’ three-town day, after about 12 hours on My Tour in Italy’s. They suit a stay of three days or more, and the Florence itinerary shows where one fits. The half-day Chianti trip leaves the rest of the day for the city.

If you are happy on trains, Pisa, Lucca and Siena are easy on your own; a tour earns its price on San Gimignano, the wineries and the three-towns-in-one day. The Cinque Terre day needs closed shoes and suits walkers aged 8 and over, and the Vespa suits confident riders with a licence. Two of the cooking classes also go out to Tuscan farms, where you cook the meal you eat.