Chianti, San Gimignano and Siena Full Day Trip with Wine Tastings

Exploring Tuscany: A Look at the Chianti, San Gimignano, and Siena Full Day Trip

Our review of this full-day adventure from Florence covers all the essentials—what’s included, the highlights, and the real-world experiences you can expect. Designed for those eager to soak up Tuscany’s timeless beauty, indulge in local wines, and stroll through enchanting medieval towns, this tour offers a practical way to see some of Italy’s most iconic sights.

What draws many travelers is the chance to visit Siena, famed for its Gothic architecture and the spirited Palio horse race, as well as San Gimignano, known for its distinctive towers and Vernaccia wine. Plus, the scenic Chianti region promises rolling hills and authentic wine tastings.

However, it’s worth noting that this isn’t a private experience, and some reviews suggest that the value may vary depending on expectations—particularly regarding guides and meal inclusions. That said, this tour is well suited for those wanting a guided overview of Tuscany in a single day, especially if they love history, scenic landscapes, and wine.

Key Points

• Balanced itinerary covering major Tuscan highlights in one day
• Comfortable transportation in air-conditioned mini vans
• Expert guides providing context and local insights
• Wine tastings and local food offered at a Chianti vineyard
• Flexible free time to explore towns at your own pace
• Mixed reviews on value—be aware of optional upgrades and extra costs

The Itinerary Breakdown: What to Expect

This tour is structured to hit several of Tuscany’s most picturesque spots, with a mix of guided tours and free time. It starts early, with a pickup at Piazzale Montelungo in Florence at 8:45 am, and runs approximately 11.5 hours. The schedule is tight but designed to maximize your exposure to Tuscany’s art, history, and flavors.

Stop 1: Monteriggioni – The Medieval Jewel

Your journey begins with a scenic drive through the Chianti Hills, setting the tone for the day. The first stop is Monteriggioni, a small hill town famous for its intact medieval walls. We loved the way this town feels like stepping back in time—imagine narrow cobbled streets and fortress walls that seem untouched by centuries.

Here, you get about 2 hours, which is usually enough to enjoy a cappuccino or espresso at a local cafe before exploring. As one reviewer noted, it’s an “impressive little town,” perfect for a quick stroll and some photos, but no entrance fees are required.

Stop 2 & 3: Siena – Gothic Grandeur and the Piazza del Campo

Next, the tour heads to Siena, a city renowned for its Gothic architecture and vibrant history. The guided portion begins at Piazza del Campo, the heart of Siena and host of the famous Palio horse race. Expect around 30 minutes here with an included guided tour—an ideal chance to learn about Siena’s past and its stunning architecture.

Following that, you’ll visit Piazza del Duomo to admire its Gothic cathedral, a highlight that many travelers find breathtaking. As one reviewer shared, the Siena portion was “informative,” although some found the guided time a bit short. Still, the town’s atmosphere shines through, and you’ll get plenty of time afterward to wander independently, soak in the views, and take photos.

Stop 4 & 5: San Gimignano – Towers, Wine, and Views

The next stop is San Gimignano, a UNESCO World Heritage site famous for its medieval towers. We loved the freedom to explore this charming town at our own pace—meandering through narrow streets, browsing artisan shops, or simply soaking in the panoramic vistas from above.

A reviewer highlighted that, even if many shops close on winter Mondays, the lack of crowds actually made wandering more enjoyable. You get around 2 hours here, which should be enough to enjoy some Vernaccia wine or a gelato, and soak up the authentic Tuscan vibe.

Stop 6: Castellina In Chianti – Wine and Olive Oil Tasting

The afternoon is dedicated to the Chianti wine region, with about 3 hours allocated for a visit to a local vineyard. Here, the real highlight is the tasting experience, where you’ll sample top-notch wines, fresh olive oils, and regional delicacies.

We appreciated the opportunity to meet the wine owner, whose insights made the tasting more meaningful. The reviews also praised the knowledgeable guides who enhanced the experience with their expertise. This part of the tour is a genuine highlight for wine lovers and those eager to get a taste of rural Tuscany.

Return to Florence

After a full day of exploring, your group will return to Florence, usually around 7 or 8 pm. The comfortable, air-conditioned minivans or coaches make the long drive more pleasant, and most travelers find the value well worth the effort.

What’s Included and What’s Not?

The tour includes visits to rustic vineyards in Chianti, with tastings of wines, extra-virgin olive oils, and regional products. Guided tours are led by experienced multilingual escorts, and there’s some free time built into the schedule for personal exploration. Lunch at Piazza del Campo is available as an optional extra, with vegetarian options upon request—important for those with dietary restrictions.

On the downside, tips and gratuities are not included, and certain entrance fees to attractions not part of the tour are at your expense. It’s also worth noting that the tour operates as a group experience, and the mode of transportation depends on the number of participants—though all vehicles are air-conditioned.

The Value and The Caveats: What Travelers Should Know

While the tour offers a comprehensive look at Tuscany’s highlights, reviews indicate that some aspects could be improved. For instance, one traveler criticized the cost, noting that the itinerary did not include guided tours or lunch as initially described, and these were considered optional upgrades costing extra on arrival. They pointed out that the total expense felt steep for just transportation and sightseeing.

Another reviewer praised the knowledgeable guides and stunning scenery, emphasizing that the guided Siena tour was particularly memorable. They also appreciated the flexibility at San Gimignano to explore on their own, which allowed for a more relaxed experience.

A key consideration is the group size—with a maximum of 20 travelers, the tour aims for a more intimate experience, but some may find it crowded or rushed, especially if their interest is solely in exploring towns at leisure.

Transportation and Timing

Travel is in air-conditioned mini vans or coaches, which is important in the warmer months. The itinerary’s timing—starting early and returning late—means you’ll spend a significant part of the day on the road, but the scenic drive itself is part of the experience.

The tour’s duration of roughly 11.5 hours is long but structured to include enough time in each location. The early start and late finish are typical for day trips from Florence, but travelers should be prepared for a full day.

Who Is This Tour Best For?

This trip caters well to travelers who want a thorough overview of Tuscany without the hassle of planning multiple separate visits. It’s ideal for those who enjoy guided experiences, appreciate local wine and food, and are happy to share the journey with a small group.

If you’re seeking more in-depth guided tours or private experiences, you might find this tour a bit rushed or lacking in some details. However, if you’re after scenic views, cultural highlights, and a taste of wine country, this package offers a lot of value.

It’s especially suited for first-time visitors to Florence who want a comprehensive day out that hits the major spots while providing some local flavor in the form of tastings.

Frequently Asked Questions

Is this tour suitable for all ages? Yes, most travelers can participate, as it’s designed for a broad audience. However, keep in mind the long day and walking involved.

Are meals included? Lunch at Piazza del Campo is optional and available for an extra fee. Vegetarian options can be requested in advance.

How much flexibility is there during free time? You have some free time at San Gimignano to explore on your own, but the rest of the day is scheduled.

What language are the guides? Guides are multilingual, so expect at least English guidance, along with other languages depending on the day.

What should I wear? Comfortable shoes are recommended for walking through towns and cobbled streets. Dress appropriately for the weather.

Are entrance fees included? No, entrance fees to attractions outside the included tours are at your own expense.

Can I book last-minute? Reservations made less than 12 hours before departure can’t be guaranteed, so plan ahead if possible.

What’s the price for this tour? It costs around $177.47 per person, which includes transportation, guided tours, and tastings—but be aware of optional upgrades and extras.

Is tips or gratuity included? No, tips are not included and are at your discretion.

Final Thoughts

This full-day tour from Florence offers a practical way to experience Tuscany’s most beloved towns, anchored by scenic drives, guided insights, and tastings of regional wines and oils. The stops at Monteriggioni, Siena, San Gimignano, and Chianti showcase the diversity of Tuscan scenery and culture, making it a satisfying choice for first-time visitors or those wanting a rundown.

While some travelers found the value a bit lacking—especially if expecting guided tours and included meals—many appreciated the knowledgeable guides, beautiful landscapes, and authentic wine experiences. It’s a balanced option if you’re comfortable with a group setting and want to see as much as possible in one day.

For those who prefer a more personalized or in-depth experience, consider exploring options for private tours or smaller groups. But if your goal is to tick off key Tuscan highlights with some excellent wine tastings along the way, this trip can definitely deliver a memorable day out.

Whether you’re a history buff, a wine lover, or simply after breathtaking scenery, this tour promises a well-rounded taste of Tuscany’s enduring charm.