Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Two wineries, eight wines, and a medieval hill town make this a smart way to see Tuscany without renting a car. You’ll ride the scenic Chianti Road, learn how local wine is made, and taste olive oil, balsamic vinegar, bruschetta, and other regional foods along the way.

I especially like the family-run winery setting and the contrast between the two stops. One tasting can be lively and generous, while the other offers a quieter look at Vernaccia and cellar work. I also like the 1.5 hours in San Gimignano, enough for a walk, gelato, and a look at the towers without turning the day into a rushed race.

The main caution is that the two winery visits may not feel equally polished. The first stop often includes more food, explanation, and interaction, while the second can be more basic, especially during harvest season. Lunch is not included, and San Gimignano time is pleasant but limited.

Key points at a glance

• Eight wines across two estates: Taste Chianti, Super Tuscan selections, Vernaccia, rosé, and Colli Senesi wines.
• Food pairings included: Try bruschetta with tomatoes, extra virgin olive oil, aged balsamic vinegar, truffle oil, bread, and other local products.
• Scenic Tuscan drive: The route from Florence passes vineyards, olive groves, cypress trees, hill towns, and wide views across the countryside.
• San Gimignano in a single afternoon: Explore the medieval center, towers, shops, cathedral area, and local saffron specialties during 1.5 hours of free time.
• Small-group format: The minibus or coach holds no more than 24 people, with a minimum of four required for the tour to run.
• Adult wine outing: The minimum age is 18, and children are not allowed.

Two wineries and San Gimignano in one well-planned day

At $229.77 per person, this is not the cheapest way to see Tuscany, but it includes round-trip transport from Florence, a local guide, two winery visits, eight wine samples, and tastings of regional foods. That package matters because independent visits to two estates can be awkward without a car, especially when you want to drink wine and still get back safely.

The tour lasts about seven hours, from a 10:00 a.m. departure to a return around 5:00 p.m. That schedule gives you a full Tuscan outing while leaving your evening free for dinner in Florence. I see this as a good fit if you want countryside, wine, and a famous hill town in one day rather than spending the whole day at a single estate.

The tour is social rather than private. You share the air-conditioned minibus or coach with up to 23 other people, so the feel depends partly on the group and the guide. The upside is the chance to meet people over a shared table of wine and food. The tradeoff is less control over how long you stay at each stop.

Meeting at Piazza della Calza

The morning begins at the P parking sign in Piazza della Calza, near Porta Romana and the Church of San Giovanni Battista della Calza. You should arrive by 9:45 a.m. for the 10:00 a.m. departure.

This is not a hotel pickup, so plan your route to the meeting point before breakfast. The departure area is near public transportation, but the pickup instructions deserve care. One person had trouble identifying the vehicle, although the guide eventually found the group. Look for the guide in a purple T-shirt and allow extra time to get your bearings.

Once aboard, you leave Florence and head toward the Chianti countryside. The drive takes about an hour. This is useful travel time, not dead time, since the guide explains the schedule and points out details about Tuscany’s culture, wine, and past.

The road offers the kind of scenery most people picture when they think of Tuscany: rolling hills, rows of vines, olive groves, cypress trees, and small settlements. The ride is also one reason the minibus format earns its keep. You can look out the window instead of concentrating on narrow country roads.

Guides have included Emanuele, Valentina, Giovanni, Ned, Ottavio, Francesca, Alessandro, Domenico, Luigi, Tony, and others. The strongest guides add local stories and explain the wines in a way that helps you understand what is in your glass. Ottavio, for example, was praised for mixing personal stories about growing up in Tuscany with regional history, while Valentina was also noted for offering useful advice about the rest of a Florence trip.

First winery: the most generous tasting stop

The first winery is in Ulignano, near San Gimignano, in the Chianti area. It is described as a family-run estate with a welcoming tasting room and a broad selection that can include Chianti, Super Tuscans, and Vernaccia di San Gimignano.

This stop lasts about 1.5 hours. You can expect a guided tasting of four wines, although some sessions have included six or more pours. The wines are paired with Tuscan foods, which may include bruschetta with tomatoes, bread, extra virgin olive oil, aged balsamic vinegar, truffle oil, spreads, meat, and cheese.

That food is more than a snack. Olive oil, vinegar, and wine all taste different when sampled alone and alongside bread or other foods. The guide or producer can show you how acidity, sweetness, fruit, and texture change from one pairing to the next. Even if you know little about wine, you leave with a better sense of what you like.

Tenuta Torciano was singled out as an especially strong first stop, with an extensive tasting and generous food pairings. The atmosphere here can be lively and social. It is the kind of place where the table encourages conversation, and the tasting feels like part of a Tuscan meal rather than a formal lecture.

The first winery may be the high point for people who want a festive tasting. If your main goal is a quiet, technical look at production, you may find the sociable approach less focused. Still, the mix of wine, oils, vinegars, and local food gives this stop a clear sense of place.

Second winery: Vernaccia, cellars, and wide views

After the first tasting, the minibus continues to a second estate about 5 kilometers from San Gimignano. This area is closely linked with Vernaccia, the local white grape that gives the region one of its best-known wines.

Here, you follow the winemakers through the vineyard and wine cellar before tasting three wines. The planned selection includes Vernaccia, a rosé, and Chianti Colli Senesi. This variety helps you compare a local white with a rosé and a red from the surrounding hills.

The setting is one of the rewards. The estate offers broad views over the Tuscan countryside, and there may be animals on the property. For many people, the combination of vines, cellar, and open views feels more grounded than a tasting room in the city.

The level of explanation can vary. Some guides and winery hosts provide a detailed look at the winemaking process, while another session may offer little information beyond naming each wine. Harvest season can also change the experience. When grapes are being picked and processed, parts of the normal tour may not be available.

That is worth keeping in mind when you book. The second winery is not guaranteed to match the first in service or energy. One person found the view excellent but the tasting less informative, while another especially liked the detailed explanation of production at the second estate. Your experience may depend on the day, the harvest schedule, and the host available.

San Gimignano: 1.5 hours among medieval towers

The final major stop is San Gimignano, about 5 kilometers from the second winery. You get roughly 1.5 hours to explore on your own.

San Gimignano is often called the Medieval Manhattan because of its tall stone towers. The nickname is playful, but the skyline really is unusual. Families built the towers in the Middle Ages as signs of wealth and power, and several still rise above the compact center.

Use your free time for a simple walking loop. Head through the narrow streets toward Piazza del Duomo, look into the Collegiata if it is open, and consider the Torre Grossa if you want a high view over the town and surrounding hills. You can also browse artisan shops and look for local saffron products.

Gelato is an obvious choice here, and one tasting experience specifically praised the town’s gelato. You might also use the time for a quick lunch, but remember that food in San Gimignano is not included in the tour price. With only 1.5 hours, choose one main sight rather than trying to see everything.

The town is compact, but its streets are cobbled and often uneven. Comfortable shoes will help. The free-time format is a good compromise for people who want independence after two guided tastings, though anyone hoping for a long cultural tour of San Gimignano may want a separate visit.

The return to Florence and the value of the schedule

The ride back takes about an hour, bringing you to the original meeting point around 5:00 p.m. You are not dropped at your hotel, so leave some energy for the final walk or local transport connection.

The timing is one of the tour’s practical strengths. A 10:00 a.m. start lets you sleep later than on many countryside excursions, yet the day still covers three distinct experiences. You see the countryside from the road, spend meaningful time at two wineries, and walk through one of Tuscany’s most recognizable towns.

The pace is active without being packed minute by minute. You have about three hours total at the wineries and 1.5 hours in town, with the remaining time spent on the road. Some people may wish for more time in San Gimignano, but adding another hour there would likely require cutting a tasting or returning to Florence later.

What the $229.77 price really covers

The price makes the most sense if you value convenience and want to taste wine without arranging transportation. Included are the air-conditioned vehicle, local tour leader, two winery visits, eight wine tastings, and Tuscan food samples.

It does not include lunch, hotel or hostel pickup, or tips for the guide and driver. You should budget separately for a meal or snack in San Gimignano, plus any bottles or specialty foods you decide to buy.

The package is less compelling if you only want to see San Gimignano. In that case, a simple transport option could cost less. It becomes better value if you want two winery visits, several wine styles, food pairings, and an informed guide handling the driving and route.

Wine shipping may be available at some estates for bottles you purchase, but this is not guaranteed as part of every stop. Ask at the winery if you find something you want to send home.

Who should book this Tuscany wine tour?

I would choose this tour if you are staying in Florence and want an easy introduction to Tuscan wine country without hiring a car. It suits adults who enjoy shared tastings, scenic drives, local food, and a little free time to wander.

It is especially good for first-time visitors who want variety. You are not limited to one winery, and you get both red and white wines, plus rosé and local food products. The San Gimignano stop adds architecture and town life, so the day does not become six hours of sitting at tasting tables.

You may want another option if you dislike group tours, need a long lunch, or want a highly technical wine lesson at every stop. The two wineries can differ in hospitality and explanation, and the tour cannot promise the same tasting format each day.

The tour requires at least four participants. If that minimum is not reached, a private option with an added charge may be offered. The maximum group size is 24, which keeps the outing more manageable than a large coach tour but does not make it intimate in the private-guide sense.

Dietary requirements should be given when booking. Most people can participate, but the tour is for adults aged 18 and older, with no children allowed.

Final verdict: a strong day out, with realistic expectations

I would book this tour for the mix of wine, food, views, and San Gimignano. The strongest parts are the first winery’s generous tasting, the chance to compare eight wines across two estates, and the guides who bring the drive to life with stories about Tuscany.

Go in expecting a social day, not a private wine seminar. Bring comfortable shoes, plan for your own lunch, use insect repellent if you will spend time outdoors, and arrive early at Piazza della Calza. If you are comfortable with those limits, $229.77 buys a convenient and varied day in the Tuscan countryside, with your Florence evening still intact.

Free cancellation is available up to 24 hours before the 10:00 a.m. start. Cancellations or changes made later are not refunded or accepted.

FAQ

Where does the Tuscany wine tour depart from?

The tour departs from the P parking sign at Piazza della Calza, 1, near Porta Romana and San Giovanni Battista della Calza in Florence.

What time does the tour start and end?

Meet at 9:45 a.m. for a 10:00 a.m. departure. The tour returns to the same meeting point at about 5:00 p.m.

How many wineries are included?

The experience includes visits to two wineries near San Gimignano.

How many wines will I taste?

The included tasting program features eight different wines across the two wineries. The selection can include Chianti, Super Tuscans, Vernaccia, rosé, and Chianti Colli Senesi.

Is lunch included?

No. Food pairings such as bruschetta, bread, olive oil, balsamic vinegar, and other local products are included, but lunch is not.

Are children allowed on the tour?

No. The minimum age is 18, and children are not allowed.

What happens if the tour does not reach the minimum group size?

The tour requires at least four participants. If that minimum is not reached, you will be offered a different date or experience, or a full refund.