From Florence: Tuscany & San Gimignano Tour with 2 Tastings

Chianti wine, two very different wineries, and a stop in San Gimignano make a satisfying day out from Florence. You taste up to seven wines, including Chianti Classico and Vernaccia, and get a look at how wine and olive oil are made in the Tuscan countryside.

I like the contrast between the two winery visits: one is set up for a polished tasting lesson, while the other brings you closer to a family-run operation and its vineyards. I also like that San Gimignano is part of the day, not just a view from the road. The trade-off is time: with two tastings and several drives, the town visit can feel brief.

At a glance

• Two contrasting winery visits: Expect a more formal tasting at one stop and a family-run winery at the other.
• Up to seven wines: Tastings may include Chianti Classico, Super Tuscan wines, Vernaccia, and Chianti Colli Senesi.
• Olive oil and balsamic: Samples include extra-virgin olive oil and balsamic vinegar, with truffle oil offered at one tasting.
• San Gimignano on your own: Set aside time to walk the medieval streets, browse shops, or try gelato from a world-champion maker.
• A full day, not a long lunch: The trip lasts about seven hours, with transport, a guide, and tastings included. Extra food and drinks are not.

From Florence to the Chianti hills

The day starts at 9:45 AM at Piazza della Calza, in front of Porta Romana, near the Church of San Giovanni Battista della Calza. Look for a guide in a purple T-shirt by the blue parking sign. This is not a hotel pickup, so plan your route to the meeting point before the morning gets busy.

From central Florence, you can walk, take a taxi, or use the bus. Bus 11 goes to Calza Serragli; buses 36 and 37 serve Porta Romana. If you take one of the latter, be sure you are on the inner side of the gate. The meeting-point directions are unusually specific for a reason: arriving at the wrong side of Porta Romana can leave you circling the roundabout instead of meeting the group.

Once underway, the drive to the first winery takes about an hour. That travel time is part of the appeal. Florence’s close-packed streets give way to country roads and rolling Chianti hills, and your guide can use the journey to share information about the region. Guides named on different departures include Dom, Anna, Alessandro, Christina, and Marie. The guide you get depends on the day, but strong guiding is a recurring feature of this tour’s character: guests are kept informed about what comes next and how to make the most of each stop.

Transport may be by bus, coach, or van. Small-group departures are available, but the size is not guaranteed for every date. In summer, the group can reach 50 people, so don’t book assuming an intimate van unless your chosen departure confirms it.

First tasting: a polished introduction to Tuscan wine

The first winery visit lasts about an hour and a half. It is described as a luxury winery, with a guided tasting that introduces four wines, including Chianti Classico marked with the black rooster and Super Tuscan wines. You also sample 30-year-old balsamic vinegar and truffle extra-virgin olive oil.

This stop is the more structured part of the day. A wine producer leads a lesson, giving you a chance to learn how to taste rather than simply work through a row of glasses. That makes a difference if you are new to Tuscan wine or want a little context for names you may see on restaurant lists later.

The tasting is also a chance to compare styles. Chianti Classico is the best-known wine in the set, while Super Tuscan wines offer a different expression of the region. The balsamic and olive oil are not an afterthought: they bring in two other local products and give your palate something to compare with the wine.

Some departures have included food such as bread or cold meats alongside the tastings, but food is not listed as a guaranteed inclusion. Treat the wine and samples as the core experience, not as a promised lunch. If you need a substantial meal, plan to buy food during your free time in San Gimignano.

Second tasting: vineyard views and a family-run feel

A short drive, about 20 minutes, brings you to the second winery. This is described as a local, family-run operation facing the famous towers of San Gimignano. The visit includes the vineyards and cellars, with winemakers explaining the production of wine and oil.

The contrast with the first winery is one of the tour’s strengths. The first stop is the more formal lesson; the second is closer to the working side of a small producer. The setting is a major part of the visit, too. The views toward San Gimignano’s towers connect the day’s wine country with the town you will explore later.

The tasting here includes Vernaccia, the local white wine, and Chianti Colli Senesi DOCG. The producers can also offer local bottles and products for purchase, with the option to ship wine to friends or family. If you find something you like, this is a convenient place to ask about buying it rather than trying to track down the same bottle in Florence.

A practical note: the order and feel of winery visits may vary by departure. Some groups describe a small first winery and a more polished second stop, while the planned experience presents the luxury winery first and the family-run one second. Either way, expect two distinct settings rather than two copies of the same tasting.

San Gimignano: towers, narrow streets, and a quick gelato stop

After the wineries, the group reaches San Gimignano for free time. The visit is planned for about an hour and a half, though the day’s schedule and actual time on the ground can vary. Some departures have had closer to 50 minutes or an hour, so it is wise to keep your plans simple.

San Gimignano is compact enough for a rewarding walk without a guide, but it is easy to lose time browsing. Its narrow streets, shops, and famous medieval towers make it a natural change of pace after the cellar visits. You can wander, shop, take in the architecture, or make a beeline for gelato at the world-champion gelateria highlighted as part of the stop.

If you want to climb a tower, check how much time you have as soon as you arrive. A climb can be worthwhile for the views, but it competes with lunch, shopping, and a relaxed walk. The same goes for a sit-down meal. Since extra food and drinks are not included and the stop is limited, a quick lunch or snack may be the more practical choice.

The bus is scheduled to leave around 3:45 PM, with about an hour’s drive back to Florence and an expected arrival around 5 PM. That gives you an evening in the city, but leave a little flexibility in your plans in case the return runs late.

What the $84.96 price includes

At $84.96 per person, this is good value if you want to visit the countryside without arranging transport and winery appointments yourself. The price covers a return ride from Florence, a local tour leader, visits to two wineries, two tastings of up to seven wines, and samples of balsamic vinegar and extra-virgin olive oil. It also includes the free-time stop in San Gimignano.

The value is not just the number of pours. You get two different winery settings, a guided introduction to the wines, and the convenience of a driver for the country roads. For anyone without a rental car, that removes the need to coordinate buses or taxis between rural stops. And, of course, you can taste without having to be the person who drives back.

Keep the exclusions in mind. Hotel pickup and drop-off are not provided, and additional food and drinks cost extra. You may be offered food alongside a tasting, but do not count on that as a full meal. If you buy wine, olive oil, or other products, those are separate purchases as well.

Who will enjoy this day most

I would choose this tour if you want a taste of Tuscany in one day and care as much about the countryside as about the wine. It suits couples, friends, and solo visitors who like guided tastings but still want some independent time in a town. The combination of wine, oil, balsamic, and a medieval stop keeps the day varied.

It is also a sensible choice if you are curious about wine but not yet confident tasting it. The producer-led lesson offers more than a quick pour, and the two wineries make it easier to compare places and styles. If you already know your way around Tuscan wine, you may value the vineyard and cellar visits more than the introductory explanations.

This is less suited to anyone who wants a long, leisurely visit in San Gimignano or an unhurried lunch. You have to share the day among two tastings, drives, and the town stop. It is not suitable for children under 18, pregnant women, or wheelchair users. Bring a passport or ID card, as requested for the activity.

The minimum group size is three. If that number is not reached, a private option with a supplement may be offered. Free cancellation is available up to 24 hours in advance, and you can reserve now and pay later.

A useful route to Siena

If you are spending the night in Siena, ask your guide whether you can be dropped off in San Gimignano instead of riding all the way back to Florence. From San Gimignano, a local bus can take you to Siena. Arrange this with the guide rather than assuming the drop-off is automatic, and make sure the plan works for your onward connection.

That option can make the day more efficient if Siena is your next stop. It is less useful if you need to return to Florence or have luggage and transport plans that depend on the original endpoint. The tour begins and ends at Piazza della Calza unless you have confirmed another arrangement.

Should you book this Tuscany tour?

Book it if you want an easy, well-paced introduction to Chianti, with two winery styles, up to seven wines, olive oil and balsamic samples, and a look around San Gimignano. The guides are a particular asset, and the return transport makes the countryside practical to visit in a day.

Think twice if your main goal is spending several hours in San Gimignano, having a long lunch, or visiting wineries at a slow pace. The town stop is a bonus, not the whole day, and timing can feel tight. For a first Tuscan wine-country outing from Florence, though, the mix of tastings, views, and free time is a strong use of seven hours.

FAQ

How long is the tour?

The tour lasts about seven hours. It starts at 9:45 AM and is expected to return to the meeting point in Florence at about 5 PM.

Where is the meeting point?

Meet at Piazza della Calza, directly in front of Porta Romana, by the blue parking sign near the Church of San Giovanni Battista della Calza. Look for a guide wearing a purple T-shirt.

How many wines will I taste?

The tour includes two tastings of up to seven wines in total. The selections can include Chianti Classico, Super Tuscan wines, Vernaccia, and Chianti Colli Senesi DOCG.

Are food and drinks included?

The included tastings cover wine, balsamic vinegar, and extra-virgin olive oil. Additional food and drinks are not included, so plan to buy any meal or extra refreshments you need.

How much time do I get in San Gimignano?

The free visit is planned for about an hour and a half. The time available can vary, so keep your plans flexible and check the return time with your guide.

Can I join the tour if I am under 18 or use a wheelchair?

No. The activity is not suitable for children under 18 or wheelchair users. It is also listed as not suitable for pregnant women.

Can I finish the tour in San Gimignano instead of Florence?

If you are staying in Siena, ask your guide about being dropped off in San Gimignano. From there, you can take a local bus to Siena, but you should confirm the arrangement with the guide.