Key Points

Visit Siena and San Gimignano with ample free time to explore their iconic sights and streets
Tour a family-run Chianti winery, walk through vineyards, cellar, and sample six wines
Enjoy a 3-course Tuscan lunch, paired with wines like Super Tuscan Riserva and Vernaccia di San Gimignano DOCG
Travel comfortably in an air-conditioned vehicle with pickup from Florence included
Rated 4.7/5 based on 184 reviews, highlighting knowledgeable guides and delicious food and wine

This full-day tour from Florence offers an immersive taste of Tuscany’s best-loved towns, scenic landscapes, and wine experiences. For 7 to 9 hours, travelers explore Siena, famous for its stunning Gothic cathedral and lively Piazza del Campo, then wander through San Gimignano’s medieval streets and towers. Along the way, the tour includes a visit to a family-owned Chianti winery where you walk through vineyards and cellars, culminating in a wine tasting of 6 exceptional wines. The day ends with a traditional Tuscan lunch, featuring local cheeses, cured meats, and signature dishes like Lasagna al Tartufo, all enjoyed with accompanying wines.

While this tour offers a comprehensive experience, it’s worth noting that time in each town is limited—around 1 to 1.5 hours—so visitors should plan to prioritize their favorite sights. The air-conditioned coach and hotel pickup make it easy to relax during the scenic drive through Tuscany’s rolling hills. Thanks to the positive reviews, it’s clear that knowledgeable guides, delicious food and wine, and well-organized logistics make this tour a favorite for many travelers.

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From Florence to Tuscany’s Sights in One Day

This guided tour departs from Florence with a pickup at Piazzale Montelungo, next to the Piccolo Ristoro kiosk. The group travels in a comfortable, air-conditioned coach for approximately 1.5 hours through Tuscany’s lush landscapes. The efficient schedule balances city visits, winery experiences, and free time, aiming to give a fulfilling taste of the region without feeling rushed.

The tour is designed to suit those who want a structured day of sightseeing, tasting, and cultural exploration. It’s especially appealing for travelers who prefer organized transportation, engaging guides, and a mix of towns and countryside. The small group size options provide a more personalized experience, and the easy pick-up and drop-off make it accessible for most visitors staying in Florence.

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Exploring Siena’s Architectural Marvels

The first stop is Siena, a city celebrated for its medieval architecture and lively Piazza del Campo. The guide leads you past the square’s iconic shell shape, where the famous Palio horse race takes place. Afterward, there’s a photo stop at Siena Cathedral, a Gothic masterpiece renowned for its intricate façade and stunning interior (ticket not included).

Travelers are given about 1.5 hours of free time to wander through Siena’s narrow streets, browse local shops, or visit the cathedral at their own pace. The guide shares stories about Siena’s history, making the short visit both informative and enjoyable. Some reviews suggest that more time in Siena to explore the cathedral or walk around the city would enhance the experience, but the schedule strikes a good balance for most.

The Charm of San Gimignano’s Towers

The final stop is San Gimignano, famous for its medieval towers that create a skyline unlike any other Tuscan town. Visitors have about 1 hour and 15 minutes free time to stroll its cobbled streets, visit Piazza della Cisterna, or enjoy a scoop of the town’s famous gelato.

Many appreciate the breathtaking views from the city walls and the chance to climb a tower for panoramic vistas. Some reviews mention that with only an hour, it’s difficult to fully explore, but the visit offers plenty of Instagram-worthy scenery and charming shops. This town provides a perfect blend of history, views, and relaxed wandering.

The Chianti Winery Visit and Tasting Experience

One of the tour’s highlights is the visit to a family-run Chianti winery. Here, guides lead you through the vineyards and cellar, explaining the winemaking process. The winery visit includes a tasting of six wines, such as Super Tuscan Riserva and Vernaccia di San Gimignano DOCG.

Following the tour, guests enjoy a delicious 3-course Tuscan lunch, featuring local cheeses, cured meats, Lasagna al Tartufo, and Ribollita. Throughout the meal, wines are sampled, complementing each dish. Many reviews praise the quality of wines and the engaging, friendly hosts. Some mention that the lunch and tastings are the best part of the day, offering genuine value for money.

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Lunch at the Heart of Tuscany’s Vineyards

The 3-course lunch is served at the vineyard estate, offering a chance to savor authentic Tuscan flavors. The menu includes Lasagna al Tartufo, Ribollita, and a selection of local cheeses and cured meats. The meal is enjoyed with multiple wine tastings, including some of the estate’s best wines.

Guests often find the lunch to be plentiful and flavorful, with reviews highlighting the excellent wine pairing and the friendly, engaging hosts. The setting provides spectacular views of the vineyards and hills, making it a memorable part of the day.

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Discovering San Gimignano’s Medieval Streets

The free time in San Gimignano allows for spontaneous exploration. Visitors often browse the local shops, admire the medieval towers, or climb one for a panoramic view. The pictorial square and local gelato shops add to the charming atmosphere.

Although one review suggests that more than an hour would make the visit more satisfying, most agree that it perfectly caps the day’s sightseeing. Its timeless appeal makes it an ideal spot for photos, strolling, or relaxing before heading back to Florence.

Comfortable Return Trip to Florence

After a full day of sightseeing, wine tasting, and exploring, the coach departs San Gimignano for Florence. The return journey takes approximately 1 hour. Travelers can reflect on the day’s highlights, from Siena’s historic streets to the stunning towers of San Gimignano, and the delicious wines enjoyed at the vineyard.

Many reviews mention the spacious, comfortable bus and a professional driver as part of the enjoyable experience. The hotel drop-off option makes it convenient for those staying in Florence city center.

Who Should Consider This Tuscany Day Trip

This tour appeals most to those seeking a balanced experience of culture, scenery, food, and wine. It suits travelers who appreciate guided visits, ample free time to explore towns at their own pace, and delicious Tuscan cuisine.

With positive reviews praising the guides’ knowledge, the quality of wine tastings, and the authenticity of the lunch, many find it offers good value. However, those who prefer more time in each location or full access to museums and cathedral interiors might find the schedule a bit tight.

The tour is not suitable for wheelchair users due to the walking involved in Siena and San Gimignano, and dress code restrictions apply for religious sites like Siena’s Cathedral.

Final Thoughts on the Tuscany, Siena, San Gimignano & Winery Lunch Tour

This 7 to 9-hour journey from Florence delivers a well-organized introduction to Tuscany’s iconic towns, scenic landscapes, and wine culture. It’s an excellent choice for visitors wanting a comprehensive day with expert guides, authentic food, and top-quality wines.

The small group options and hotel pickup add convenience, while the limited time in each town encourages focused exploration. The highlighted winery experience and delicious Tuscan lunch provide memorable flavors, making this tour a favorable pick for anyone eager to experience Tuscany’s charm beyond Florence.

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From Florence: Tuscany, Siena, San Gimignano & Winery Lunch

4.7

(184)

Frequently Asked Questions

Is hotel pickup included?
Yes, hotel pickup from within Florence city limits is included—just provide your accommodation details when booking.

How long is the total tour?
The tour lasts between 7 and 9 hours, depending on the day and traffic conditions.

What are the main stops?
Stops include Siena, San Gimignano, and a Chianti winery with tastings and lunch.

Is there free time in each town?
Yes, approximately 1 to 1.5 hours in Siena and San Gimignano for independent exploration.

Are tickets to Siena Cathedral included?
No, the ticket for Siena Cathedral is not included, but there’s a photo stop and plenty of time to see the exterior and explore.

What does the winery visit involve?
Guides lead guests through the vineyards and cellar, ending with 6 wine tastings of local wines.

What food is served at lunch?
The 3-course Tuscan meal features Lasagna al Tartufo, Ribollita, and local cheeses and cured meats.

Is the tour suitable for children?
The tour is not suitable for wheelchair users and requires comfortable walking; minors under 18 cannot drink alcohol.

What should I bring?
Bring passport or ID, sun protection, comfortable shoes, and an empty stomach for the wine tastings.

Can I cancel if my plans change?
Yes, full cancellation is possible up to 24 hours in advance for a full refund.