From San Gimignano: Half day Tuscany Wine Tour with 2 wineries

Travelers looking for a taste of Tuscany—literally—will find this half-day tour from San Gimignano a charming way to combine wine, scenery, and a bit of medieval magic. It’s a well-organized experience that takes you through two carefully selected wineries, offers guided tastings, and includes free time to explore the iconic town of San Gimignano. With a duration of about 5.5 hours and an average rating of 4.5 out of 5, it’s popular among those eager to sample authentic Tuscan wines without the hassle of driving themselves.

What we love most about this tour is how it balances guided wine tastings with free time in San Gimignano, giving you the best of both worlds. The included transportation, led by knowledgeable guides, takes the stress out of travel logistics—especially for those unfamiliar with the area. The chance to visit two different wineries, each with its own style and personality, adds depth to the experience. However, one point to consider is that the tour is somewhat structured and timed, which means if you’re a slow explorer or want more time in town, you’ll need to plan accordingly. This tour suits wine lovers, history enthusiasts, and anyone wanting a relaxed, authentic taste of Tuscany’s countryside.

Key Points

• All-Inclusive Experience: Wineries, tastings, snacks, and transportation included, making it a seamless half-day trip.
• Authentic Venues: Visits to two family-run wineries offer insight into Tuscan winemaking traditions.
• Expert Guides: Guides like Francesca, Valentina, and Caterina receive praise for their friendliness, knowledge, and ability to enhance the experience.
• Flexible Free Time: Bonus time in San Gimignano allows for sightseeing, shopping, or just soaking in the medieval skyline.
• Great Value: At around $115 per person, the tour provides a rich experience with multiple wine tastings and scenic stops.
• Convenient Logistics: Meeting at the Tuscany on Wheels office near San Gimignano simplifies planning; transportation is comfortable and air-conditioned.

Starting Point and Logistics

The adventure begins at the Tuscany on Wheels office, just a short drive from San Gimignano. The meeting is set for 10:30 am, with the tour kicking off at 10:45 am. Travelers can park for free at the office or request a pick-up service. This flexibility is particularly appreciated, especially after a long journey or if you’re coming from Florence or nearby. The group size can go up to 50 people, but reviews suggest that most tours feel intimate, thanks to guides like Francesca or Valentina, who make everyone feel welcome.

The Drive and Introduction

The 15-minute drive from San Gimignano to the first winery kicks off with a guide sharing fascinating tidbits about Tuscany’s history, culture, and landscapes. This part of the tour sets the scene perfectly, with rolling hills, vineyards, and olive groves blending into the foreground. It’s not just a transport segment but an opportunity to get context and build anticipation.

First Winery: Ulignano

The first stop is at a family-run estate in Ulignano, a charming village close to San Gimignano. Here, you’ll be greeted in a warm, welcoming atmosphere—nothing too formal, just friendly hosts eager to share their passion. The tasting session lasts about 1.5 hours and includes sampling 4 wines, such as Chianti, Super Tuscans, and Vernaccia di San Gimignano.

Reviewers consistently mention how fabulous the staff is, with Jeanine describing the winery as “very beautiful” and the staff at both locations as “fabulous.” Plus, you’ll enjoy tasting Balsamic vinegar, truffle oil, and extra virgin olive oil, all paired with local delicacies, which elevates the tasting experience beyond just wine.

Scenic Drive to the Second Winery

Following the first tasting, there’s a short scenic drive back through the hills toward the second winery. The guide shares more insights into Tuscany’s agricultural traditions, vineyards, and the different styles of wine produced in this region.

Second Winery: San Gimignano Area

The second stop involves a guided tour of the vineyards themselves, offering a closer look at the winemaking process. You’ll sample 3 wines, including a Vernaccia white, a rosé, and a Chianti Colli Senesi D.O.C.G.—a nice variety to taste the different expressions of Tuscan grapes.

Many reviews highlight how the second winery offers a more extensive tour of the vineyards, with visitors enjoying the opportunity to see the grape harvests and traditional methods firsthand. The staff’s professionalism and warmth are singled out as a highlight, with Valentina and Lorenzo earning praise for their informative and kind approach.

Bonus San Gimignano Stop

After the winery visits, the tour continues with a 1.5-hour free exploration of San Gimignano’s medieval skyline. Its iconic towers, built by wealthy families as symbols of power, dominate the skyline and make for an unforgettable photo op. Reviewers like Gabriele raved about the “feast and salute,” and many note how climbing the towers provides stunning views of the Tuscan countryside.

This part of the tour is especially valuable because it allows you to soak in the town’s authentic atmosphere—wandering the narrow streets, browsing local shops, and snapping photos of the skyline. It’s a perfect way to break up the wine tasting and add a cultural layer to your day.

Ending and Return

The tour wraps up back at the Tuscany on Wheels office around 4 pm, giving plenty of time to reflect on the day over a glass of wine in your mind. Many travelers leave with a camera full of photos, new friends, and a deeper appreciation for Tuscany’s wine and heritage.

Knowledgeable Guides

Reviewers consistently mention guides like Francesca, Valentina, and Caterina for their friendliness and expertise. They don’t just pour wine—they share stories about the regions, the winemaking process, and local traditions, making each tasting more meaningful.

Authentic Wineries

Visiting family-run estates means tasting wines made with care and passion, often paired with local food and condiments. The wineries’ intimate setting is a contrast to larger commercial operations, providing genuine insight into Tuscan winemaking.

Scenic and Cultural Balance

The combination of scenic drives, vineyard views, and San Gimignano’s medieval towers offers a well-rounded experience. This isn’t just about wine, but also about appreciating Tuscany’s landscapes and history.

Value for Money

At approximately $115, the tour offers multiple tastings, snacks, transportation, and free time in San Gimignano, which many reviewers see as excellent value. It’s a chance to sample a variety of wines without the hassle of organizing logistics or paying separately for each component.

Flexibility and Convenience

The meeting point is easy to find, and options for free parking or pickup add convenience. The tour’s duration fits neatly into a half-day, making it perfect for travelers with tight schedules or those doing a longer trip.

While most reviews are glowing, some travelers mention that the tour is somewhat structured, with limited time in San Gimignano—about 1 hour. If you’re a slow explorer or prefer a more leisurely pace, you might find this somewhat rushed.

Also, a negative review points out that late arrivals can be problematic, as guides may leave without waiting. It’s important to be punctual, especially given the tight schedule.

Finally, some reviews suggest that the tour might feel more tailored to international visitors, with less focus on Italian locals’ perspectives. That said, most find the experience genuine and engaging.

This tour is ideal for wine enthusiasts and casual drinkers alike, especially those wanting to explore Tuscany’s countryside without worrying about transportation. It’s perfect for history buffs interested in San Gimignano’s medieval charm, and photo enthusiasts will love the scenic vistas and town views. Families, couples, or groups of friends will find plenty to enjoy, as guides create a friendly and welcoming atmosphere. If you’re after a well-rounded, authentic day with excellent value, this tour ticks all boxes.

In essence, this tour offers a balanced experience—combining top-quality wine tastings, scenic drives, and historic town exploration—at a very reasonable price. The guides’ warmth and knowledge elevate what could be just a typical wine tour into a memorable day. While the schedule is somewhat tight for those wanting more time in San Gimignano, most travelers find it the perfect snapshot of Tuscany’s enchanting countryside and winemaking traditions.

If you love good wine, stunning scenery, and authentic local culture, this tour is a strong choice. It’s particularly suitable for those who appreciate the simplicity of guided experiences that handle all logistics, so you can just relax and enjoy the day.

How long is the tour?
The tour lasts approximately 5 hours and 30 minutes, starting around 10:45 am and ending at about 4 pm.

Are snacks included?
Yes, snacks are provided during the tastings at both wineries, pairing perfectly with the wines you sample.

Is transportation included?
Absolutely. The tour uses an air-conditioned vehicle, and you can choose to meet at the office or request a pickup.

Can I stay longer in San Gimignano?
The tour includes about 1.5 hours for exploring San Gimignano’s medieval streets. If you wish to stay longer, you’ll need to make your own arrangements afterward.

What wines will I taste?
The first winery offers 4 wines, including Chianti, Super Tuscans, and Vernaccia di San Gimignano. The second provides 3 wines—Vernaccia white, rosé, and Chianti Colli.

Is the tour suitable for children?
While the experience is geared toward adults, children are usually welcome; however, tasting is limited to those of legal drinking age.

What should I wear?
Comfortable clothes and shoes suitable for walking and outdoor vineyard touring are recommended. Sunscreen and a hat are advisable in warmer months.

Whether you’re new to Tuscany or returning for another round, this half-day tour offers a memorable, relaxed glimpse into the region’s wine and history—without the hassle.