Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Two wineries and a medieval hill town make this a satisfying way to spend a day beyond Florence. You’ll taste wines from the Chianti area and the Vernaccia region, try local olive oil and balsamic, and have time to wander San Gimignano on your own.

I like the contrast between the two winery visits, which can offer different styles of tasting and hospitality, and the free time in San Gimignano, where you set your own pace. The air-conditioned ride also saves you the trouble of planning country roads and winery transport.

The main trade-off is time: you get about 90 minutes in town, enough for a walk and a landmark or two, but not a leisurely visit to everything. The two tastings are not identical in style, and the depth of the cellar visit may vary, particularly during harvest.

At a glance: wine, countryside, and a hill town

• Two winery visits bring together tastings in Chianti and near San Gimignano, including Vernaccia, rosé, and Colli Senesi wines.
• Local foods come with the wine, including extra virgin olive oil, balsamic vinegar, truffle oil, and bruschetta with tomatoes.
• San Gimignano gets about 1.5 hours of free time for its lanes, towers, shops, and town center.
• The day runs roughly 10:00 am to 5:00 pm, with pickup and return at Piazza della Calza in Florence.
• The group can reach 24 people, and at least four participants are required for the regular tour.
• Lunch is not included, so plan to eat before or after the tour rather than count the tastings as a full meal.

Leaving Florence for the Chianti countryside

Meet at the parking sign in Piazza della Calza, near Porta Romana and the church of San Giovanni Battista della Calza. Arrive by 9:45 am for the 10:00 am departure. The meeting point is not a hotel pickup, so allow time to reach it and look for the guide in a purple T-shirt.

The drive out takes about an hour. You’ll follow the Chianti Road through hills, vineyards, olive groves, and cypress-lined stretches. This is not just transfer time: the tour leader uses the ride to talk about Tuscan history, local culture, and the places you’re passing. Guides named in past tours include Emanuele, Valentina, Giovanni, Ned, and Ottavio, though the guide for your date may be someone else.

Travel is by air-conditioned minivan or coach, described as private transport for the group. With a maximum of 24 people, it’s larger than a private tasting but still small enough to share the day with a manageable group. The social side is part of the appeal: you spend several hours together, and the drive gives you time to get acquainted.

First winery: tasting and Tuscan pantry staples

The first winery is in the Chianti area, with the itinerary placing it near Ulignano. Expect about 90 minutes at the estate. The visit is described as a guided tasting with a wine producer, alongside an introduction to traditional winemaking and help identifying the wines’ flavors.

The tasting is a good fit if you want more than a quick pour at a bar. The listed selection includes Chianti, Super Tuscans, and Vernaccia di San Gimignano, with four wines described in the stop details. The tour’s included tasting allowance is listed as eight different wines across both wineries, though the exact selections may vary.

Food pairings add a useful local angle. You may sample balsamic vinegar, truffle oil, extra virgin olive oil, and bruschetta with tomatoes, along with other Tuscan products. These are tastings, not a promised lunch. Some past visits have included a generous selection of bread, spreads, oils, and vinegars, but the amount and assortment can differ.

The first winery is often the livelier of the two stops, with an engaging tasting format and plenty of food to try. That can make for a fun start, but remember that wine styles and hosting approaches differ from estate to estate. If you prefer a quiet, technical cellar visit, this stop may feel more social than formal.

Second winery: Vernaccia and a cellar visit

The second estate is about five kilometers from San Gimignano, in the area associated with Vernaccia, Tuscany’s notable white wine. You’ll have another 90 minutes here. The planned visit includes time with winemakers in the vineyard and cellar, followed by a tasting of Vernaccia, a rosé, and a Colli Senesi wine.

This stop can help you understand how much the experience changes between producers. One winery may focus on lively explanation and food pairings; another may be more relaxed, with its setting and views doing much of the talking. In some cases, the cellar tour gives a close look at the winemaking process. In others, the tasting may offer less explanation than you hoped.

That variation is worth keeping in mind. The two wineries are not presented as identical experiences, and the amount of detail can depend on the estate, the guide, and the conditions on the day. Harvest is a particularly practical consideration: vineyard or production activity can affect how much of the usual process you see. If learning the technical steps is central to your plans, ask about the visit format when booking.

The countryside setting is part of the second stop’s appeal. You may find the views as memorable as the wines, and the estate’s rural location gives you a break from Florence’s streets. Just don’t expect every tasting to have the same pace or level of explanation.

San Gimignano: towers, lanes, and a short independent visit

The final major stop is San Gimignano, often nicknamed Medieval Manhattan for its skyline of stone towers. You’ll have about 90 minutes of free time in the town center. That is enough for a purposeful wander, a look at the main squares, and perhaps a stop for a local treat, but you’ll need to choose what matters most.

The town’s landmarks include Piazza del Duomo, the Romanesque Collegiata, and Torre Grossa, the tallest tower, which offers panoramic views. The narrow cobbled lanes and artisan shops are part of the pleasure, as are local specialties such as saffron. You can spend your time exploring the streets, taking photographs, or pausing for a gelato, but the clock will be running.

I’d make a simple plan before you step off the minibus. Pick one main sight, then leave time to wander rather than trying to cover every landmark. If you want to climb Torre Grossa or linger over a meal, 90 minutes may feel tight. There is no included lunch, and the town visit is free time rather than a guided walking tour.

San Gimignano is a strong addition to the wine day because it gives the outing a different focus. You’ve spent the morning tasting and hearing about wine; the town lets you stretch your legs and see a historic center at your own pace. The short visit is a sampler, not a deep exploration.

What $229.77 buys you

At $229.77 per person, this is not the cheapest way to taste wine in Tuscany. You are paying for round-trip transport from Florence, a tour leader, two winery visits, tastings of eight wines as listed, samples of local foods, and the San Gimignano stop. For anyone without a car, the transport alone removes the work of coordinating rural appointments and getting back to Florence.

The value is strongest if you want several parts of a Tuscan day bundled together. You get a scenic drive, two contrasting estates, a guided introduction to regional wines, and time in one of the area’s best-known medieval towns. It also makes practical sense if you are based in Florence and don’t want to spend a day arranging separate transport and tastings.

The price is less compelling if your priority is a long, specialist wine visit at one estate. The day is shared across multiple stops, and the town visit takes time from the wineries. You may also want to budget separately for lunch, any purchases, and tips for the guide and driver. Tips are not included.

Timing, group size, and practical details

The outing lasts about seven hours, with a 10:00 am start and an expected return to the meeting point in Florence around 5:00 pm. That leaves your evening free for dinner, though delays on the road or at a stop can affect the schedule. The later start is helpful if you don’t want an early morning, while still giving you a full day outside the city.

The regular tour requires at least four participants and allows up to 24. If the minimum is not reached, a private option with a supplement may be offered. Confirm the terms for your date before you rely on a particular format.

The tour is for adults aged 18 and over. Most people can participate, and the meeting point is near public transportation. There is no hotel or hostel pickup, so plan your own journey to Piazza della Calza. If you have dietary requirements, advise the operator when booking. The tour includes food samples, but it does not promise a full meal or a specific menu.

Free cancellation is available up to 24 hours before the start time for a full refund. Changes made less than 24 hours before departure are not accepted, and cancellations inside that window are not refundable. If the operator cancels because the minimum group size is not met, you’ll be offered another date or experience, or a full refund.

Who should book this Tuscany day trip?

This tour suits you if you want a ready-made day in the countryside without renting a car, and you enjoy tasting wine in a friendly group. It’s also a good match if you want to see San Gimignano but don’t need a full day there. The mix of wine, local foods, scenic driving, and independent town time gives you several different experiences in one outing.

It is less suited to someone seeking a detailed wine course, a long visit at one winery, or an unhurried day in San Gimignano. The wineries can differ in how much they explain, and the town stop is brief. If those limits sound acceptable, the combination is appealing: two estates, a Tuscan tasting, and a medieval town, all with transport back to Florence arranged.

FAQ

Where does the tour start?

Meet at Parcheggio Oltrarno, Piazza della Calza, 1, near Porta Romana and San Giovanni Battista della Calza. The meeting time is 9:45 am for a 10:00 am departure.

How long is the tour?

The tour lasts about seven hours. It is scheduled to return to the Florence meeting point around 5:00 pm.

Is hotel pickup included?

No. You need to make your own way to the meeting point in Piazza della Calza. The tour ends back there.

How many wineries are included?

The tour visits two wineries. The tasting is listed as including eight different wines across the two stops.

What wines might I taste?

The wines described include Chianti, Super Tuscans, Vernaccia di San Gimignano, rosé, and Colli Senesi. The specific selection may vary.

Is lunch included?

No, lunch is not included. The tour does include tastings of regional foods such as bruschetta with tomatoes, extra virgin olive oil, and other Tuscan products.

How much free time is there in San Gimignano?

You’ll have about 1.5 hours to explore the town center on your own.

Can children join the tour?

No. The minimum age is 18 years.

What happens if the minimum group size is not reached?

The tour requires at least four participants. If that minimum is not met, a private option with a supplement may be offered.