Florence to Tuscany: Chianti, Siena, San Gimignano & Wine + Lunch

Exploring Tuscany from Florence becomes effortless and enjoyable with this 9-hour small-group tour, limited to 14 participants or fewer. For $219.44 per person, you get comprehensive visits to Siena, San Gimignano, and a scenic drive through the rolling hills of Chianti, with several highlights along the way. The tour is especially suited for those who appreciate local cuisine, wine, and compact, well-organized trips. It includes round-trip transportation, a gourmet lunch paired with Chianti wines, and expert guides who bring each town’s story to life.

While it promises a fulfilling day in Tuscany, the tour’s pace can be quite brisk, especially in towns like Siena and San Gimignano. The limited time in each location means visitors should be prepared for quick visits rather than deep exploration. Nonetheless, this tour offers a balanced experience of sightseeing, tasting, and scenic drives, making it ideal for those wanting a curated taste of Tuscany’s best.

Key Points

• Small-group experience limited to 14 people or fewer ensures a more personal atmosphere
• Includes round-trip transport from Florence in air-conditioned vehicles
• Visit Siena, with its medieval architecture and famous Palio horse race
• Explore San Gimignano, a UNESCO World Heritage Site known for its medieval towers
• Enjoy a seasonal Tuscan lunch with Chianti wine tasting at a family-run vineyard
• Paced for efficiency with brief stops, suitable for those who prefer a curated overview

Starting from Florence to Discover the Tuscan Countryside

This tour departs from Piazza della Repubblica in Florence at 8:30 am, and the group is transported in air-conditioned minivans. The vehicle choice allows the group to avoid parking hassles and move smoothly between towns. The driver and guide work seamlessly together, making sure the experience stays on schedule and comfortable.

Once on the road, the driver takes you through the hills of Tuscany, with a photo stop at the best panoramic viewpoint of Florence. The scenic drive offers a glimpse of Tuscany’s lush landscapes, setting the perfect tone for the day ahead.

Siena: A Well-Preserved Medieval Treasure

The first major stop is Siena, a city famous for its medieval architecture and the Palio horse race held twice each summer. This UNESCO-listed city escaped destruction during WWII, preserving its ancient buildings, narrow cobbled streets, and impressive medieval facades.

The 1 hour and 30 minutes spent here allows visitors to appreciate Siena’s historic atmosphere and take photos of its picturesque scenery. The highlight is the exterior visit to Siena’s Cathedral, a Tuscan gem, although entry tickets are not included. The tour includes a guided walk through the city, explaining its history, culture, and local traditions.

Exploring Siena’s Iconic Piazza del Campo

Next, the tour stops at Piazza del Campo, the heart of Siena’s social life and the site of the Palio. This famous shell-shaped square is lined with medieval buildings and offers a lively atmosphere. Visitors have about 15 minutes to take in the view, snap photos, and imagine the energy during Palio race days.

The silk banners awarded to winning horses hang in the square, adding to its charm. While quick, this stop captures the spirit of Siena and its medieval charm.

Chianti: Vineyard Tour and Gourmet Lunch

One of the tour’s highlights is the 3-hour visit to a family-run vineyard in Chianti, which includes a behind-the-scenes tour of vineyards, wine cellars, and growing areas. The hosts share insights into wine production, making it more than just a tasting.

Following the tour, guests sit down for a sumptuous, all-inclusive Tuscan lunch featuring local, seasonal ingredients. The meal is paired with Chianti wines, carefully selected to enhance each dish. The lunch and tasting are praised for their quality and authenticity, offering a true taste of Tuscany’s wine culture.

San Gimignano: The Towered Village

The final stop is San Gimignano, a UNESCO World Heritage Site renowned for its medieval towers that create a striking skyline. The 1 hour and 30 minutes allocated here provides enough time for sightseeing and photo opportunities. Visitors can explore the narrow streets and appreciate the unique architecture, making it a highlight of the trip.

While the visit is brief, the architecture and unique skyline leave a lasting impression. This town’s medieval history and picturesque views make it a favorite for many.

Return Journey and Comfort in the Group Transportation

After a full day of sightseeing, the tour concludes with a 1-hour drive back to Florence. The private coach bus provides a comfortable ride, allowing travelers to relax and reflect on the day’s sights and tastes. The small-group setup ensures a personalized experience, with some reviews noting the guides’ enthusiasm and knowledge.

The Experience of the Guides and Logistics

The guides on this tour are described as friendly, knowledgeable, and capable of enhancing the experience with their explanations of local history and culture. The driver ensures smooth transport, and the small group size enhances interaction and comfort.

Guests should note that tickets for Siena Cathedral are not included, but guides assist with purchasing if desired. The pickup point is convenient, and the tour is designed for most travelers capable of walking at a moderate pace.

Food, Wine, and Local Flavors

The lunch at the vineyard is frequently praised for its quality, delicious regional ingredients, and excellent wine pairings. The Chianti wines are a highlight, with many reviews noting the variety and flavorful profiles. The wine tasting is described as a fun and worthwhile part of the trip, even for those who are not avid wine drinkers.

The lunch provides a great opportunity to relax and enjoy authentic Tuscan flavors after a morning of sightseeing.

Practical Tips and Considerations

This tour is ideal for those who appreciate a well-organized, curated experience. The pace is brisk, with limited time in each town, so visitors should be prepared for short visits rather than extended explorations. The walking involved is moderate, and the small group size makes navigating towns easy.

Guests interested in visiting Siena Cathedral’s interior should plan to purchase tickets separately. The tour does not include hotel pickup or drop-off, so travelers should meet at the designated starting point in Florence.

Who Will Enjoy This Tour Most?

This tour appeals most to travelers seeking a rundown of Tuscany’s highlights in a single day, with emphasis on food and wine. It suits those who prefer small-group intimacy, comfortable transport, and structured visits. It’s less ideal for those wanting deep exploration of each town or longer visits.

The Sum Up: A Well-Rounded Day in Tuscany

The Florence to Tuscany tour offers a balanced experience of scenic drives, historic towns, delicious food, and wine tasting. Many praises focus on the knowledge of guides, the quality of the vineyard lunch, and the stunning views of San Gimignano.

While the limited time at each location can feel rushed for those wanting to explore more deeply, the curated nature ensures you hit many of Tuscany’s highlights efficiently. This tour is perfect for first-time visitors or those short on time but eager to sample Tuscany’s culture, cuisine, and scenery in one day.

Frequently Asked Questions

Is hotel pickup included?
No, the tour does not include hotel pickup or drop-off. The starting point is Piazza della Repubblica in Florence.

How long is the tour?
The tour lasts approximately 9 hours, starting at 8:30 am and returning around 5:30 pm.

What is included in the price?
The price covers round-trip transportation, an expert-guided tour of Siena and San Gimignano, a vineyard tour, a gourmet lunch, and Chianti wine tasting.

Are tickets for Siena Cathedral included?
No, tickets for the Siena Cathedral are not included, but guides assist with purchasing them if you wish to visit inside.

Is the tour suitable for all fitness levels?
Yes, but guests should be able to walk at a moderate pace on uneven surfaces. The tour involves some walking in towns, but no strenuous activity.

How many people are in the group?
The tour is limited to 14 guests or fewer, ensuring a more personalized experience.

Can dietary restrictions be accommodated?
Guests with special dietary needs should contact the tour provider after booking. However, vegans and those with celiac disease cannot be accommodated for the included lunch.

What makes this tour stand out?
Its small-group format, quality vineyard lunch, expert guides, and timed visits to Siena and San Gimignano make this a well-organized way to experience Tuscany’s essence in a day.

What should I bring?
Comfortable walking shoes, a camera for the panoramic views, and any personal items needed for the day. It’s also wise to bring water, especially in hot weather.

Can I visit Siena Cathedral?
Yes, guides will assist with purchasing tickets, but entrance is not included in the tour price. Be aware that the cathedral is closed on Sundays and certain holy days.