Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - San Gimignanos Distinctive Tower Skyline and Medieval Charm

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting

Experience Tuscany with a full-day trip from Florence, including guided visits to Siena & San Gimignano, a 3-course lunch, and wine tasting at a Chianti winery.

Exploring Tuscany’s charming towns becomes effortless with the Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting. Priced at $114.95 per person, this 9-hour journey combines guided sightseeing, free time, and culinary delights, making it ideal for those who want a well-rounded day without the hassle of driving. The tour departs from Piazzale Montelungo in Florence at 8:00 am, with round-trip transportation on a comfortable coach equipped with Wi-Fi, USB chargers, and water.

The tour’s highlights include visits to UNESCO World Heritage Sites like Siena and San Gimignano, along with a stop at a renowned organic Chianti winery for a three-course lunch and wine tasting. The guided exploration is complemented by free time in each town, giving travelers the chance to soak in the atmosphere and discover hidden corners at their own pace. While some reviews mention the extensive walking involved, most agree that the sightseeing and food experiences make for a memorable day.

Key Points

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - Key Points

  • Full-day trip from Florence covering Siena and San Gimignano for $114.95
  • 9-hour experience includes guided tours, free time, lunch, and wine tasting
  • Round-trip transportation on a comfortable, air-conditioned coach with Wi-Fi and USB chargers
  • Expert English-speaking guides lead the visits, with Siena guided from April to October
  • Visit UNESCO sites and enjoy scenic views of Tuscany’s countryside
  • Includes a 3-course lunch with wine pairing at an organic Chianti winery

Guided Tour of Siena’s Medieval Streets and Palio Traditions

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - Guided Tour of Siena’s Medieval Streets and Palio Traditions

This tour kicks off with a bus ride from Florence to Siena, accompanied by an English-speaking tour leader who shares insights into the town’s history and famous Palio horse race. Upon arrival, a guided 1-hour walking tour takes you through Siena’s medieval core, revealing its enchanting streets and iconic main square, Piazza del Campo. The guided portion offers a window into the town’s traditions, architecture, and vibrant atmosphere.

Following the guided walk, travelers enjoy an hour of free time to wander independently. This period allows for exploring shops, grabbing a coffee, or simply absorbing the historic ambiance. The Siena visit is particularly engaging in spring through fall, when local guides provide detailed commentary, but even in quieter months, the town’s beauty remains compelling.

San Gimignano’s Distinctive Tower Skyline and Medieval Charm

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - San Gimignanos Distinctive Tower Skyline and Medieval Charm

On the way to San Gimignano, travelers pass through the Tuscan countryside, with views of rolling hills, vineyards, and olive groves. The town’s medieval tower houses, visible from afar, form a striking silhouette against the sky. Once in San Gimignano, free time allows visitors to stroll along narrow streets, browse artisan shops, and admire the well-preserved medieval architecture.

The tour leader offers suggestions on where to find the best gelato, which is a highlight for many visitors. The one hour and thirty minutes spent in San Gimignano provides ample opportunity to explore the encircling walls, climb towers, or relax in local cafes, all while soaking in the scenic views of the Tuscan landscape.

Lunch and Wine Tasting at a Chianti Organic Winery

Midday, the group visits a Chianti region winery, where a three-course lunch is served, paired with four different wines. The meal features regional ingredients, and the wine tasting highlights the area’s renowned organic wines. The winery visit also includes a guided tour of the wine cellars, offering insight into local production methods.

Guests frequently praise the quality of the lunch and wines, with many noting the fabulous farm-to-table experience. The tastings are conducted with attention to detail, allowing guests to appreciate the complexity of Chianti wines while enjoying the rustic setting of the winery.

Practical Details: Transport, Group Size, and Accessibility

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - Practical Details: Transport, Group Size, and Accessibility

Transportation is a key strength of this tour, with a private coach providing a comfortable and air-conditioned ride. The vehicle includes Wi-Fi, USB chargers, and water, ensuring a pleasant journey between stops. The tour accommodates up to 50 travelers, fostering a lively but manageable group environment.

The meeting point is at Piazzale Montelungo in Florence, which is near public transportation. The tour is suitable for most travelers, though some reviews mention that the extensive walking and uphill climbs in Siena and San Gimignano can be challenging, especially on uneven pavement. The guide is available to assist with navigation, and there are options for those with mobility restrictions, though the towns’ historic layouts involve some uphill walking.

Highlights of the Scenic Tuscan Countryside

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - Highlights of the Scenic Tuscan Countryside

Travelers enjoy scenic views of vineyards, olive groves, and cypress trees along the drive from Florence to Siena and San Gimignano. The countryside setting enhances the overall experience, offering picture-perfect landscapes that are integral to Tuscany’s charm. The guide often shares stories about the region’s history of wine production and its influence on local culture.

These vistas provide a picturesque backdrop for the day’s exploration, making the journey as rewarding as the destinations themselves.

The Role of the Tour Guides and Their Personalities

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - The Role of the Tour Guides and Their Personalities

The English-speaking guides are a notable feature, with Renata and Lucia receiving praise for their knowledgeable, enthusiastic, and engaging narration. They offer historical insights, local anecdotes, and tips for making the most of free time. Some reviews mention that guides can be difficult to hear at times or that their engagement varies, but overall, most travelers appreciate their friendly and informative approach.

Guides are also attentive to special needs and can adapt the pace accordingly, making the experience accessible to a variety of travelers.

Pacing, Timing, and Overall Experience

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - Pacing, Timing, and Overall Experience

The tour balances guided sightseeing with free time, allowing for a relaxed yet comprehensive day. The total duration is approximately 9 hours, with each stop timed to give enough exploration without feeling rushed. The lunch and wine tasting at the winery takes about 2 hours, fitting well into the overall schedule.

The last stops in San Gimignano often attract visitors eager to wander independently, while the guided parts provide context and background. Some reviews note that the uphill walks can be tiring, but this is balanced by the stunning views and delicious food.

Who Will Appreciate This Tour Most?

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting - Who Will Appreciate This Tour Most?

This tour suits those who appreciate a mix of guided cultural insights and free exploration, along with a taste of Tuscan cuisine and wines. The price point of $114.95 offers good value, considering the lunch, wine tastings, and transportation included. It is ideal for travelers wanting to see both Siena and San Gimignano in one day without the hassle of self-driving.

Participants comfortable with walking uphill and uneven pavement will enjoy the towns’ beauty, but those with mobility challenges should review the physical demands beforehand. Families, couples, and small groups will find this trip rewarding, especially with the opportunity to indulge in regional wines and authentic Italian cuisine.

Siena & San Gimignano Day Trip: An Authentic Taste of Tuscany

This tour provides a balanced experience of Tuscany’s historic towns, scenic countryside, and culinary delights. The expert guides enhance the sightseeing with engaging commentary, while the round-trip transportation ensures a stress-free day. The included lunch and wine tasting at an organic Chianti winery elevate the experience, making it more than just a sightseeing trip.

While some may find the walking involved to be strenuous, most will agree that the stunning views, rich history, and delicious food make it worthwhile. The flexible free time in each town allows for personalized exploration, whether to admire architecture, take photographs, or indulge in local treats.

This tour offers a comprehensive introduction to Tuscany’s highlights at a reasonable price, perfect for those wanting a taste of Italy’s famed landscapes and culture in one day.

Ready to Book?

Florence: Siena & San Gimignano DayTrip with Lunch & Wine Tasting



4.5

(76)

“Comfortable bus ride with nice driver & Nella, the tour guide. She explained the cities as we got there. Would have appreciated more explanation o…”

— Teri W, May 2025

Frequently Asked Questions

What is included in the tour price?
The $114.95 fee covers round-trip transportation, a guided tour of Siena, free time in Siena and San Gimignano, a 3-course lunch and wine tasting at a Chianti winery, and guidance from English-speaking guides.

How long is the total tour?
The experience lasts approximately 9 hours, starting at 8:00 am from Piazzale Montelungo in Florence and returning at the same meeting point.

Are there any physical demands to consider?
Yes, both Siena and San Gimignano involve walking uphill on uneven pavement. The tour is suitable for most travelers, but those with mobility issues should be aware of the walking aspects and the steep streets.

Is the lunch vegetarian-friendly?
Yes, dietary restrictions can be communicated during booking, and vegetarian options are available.

Can I cancel this tour?
Yes, free cancellation is available up to 24 hours before the start. Cancellations made less than 24 hours in advance are non-refundable.

This tour from City Wonders Ltd offers a well-organized, scenic, and culturally rich way to experience Tuscany’s iconic towns, with the added pleasure of regional wines and a delicious meal.