Small group tour: San Gimignano, Siena & Chianti

Traveling through Tuscany, especially on a day trip, can often feel like trying to cram in too many sights. But this particular experience, offered by My Tour in Italy, takes you on a well-paced journey through some of the most iconic and picturesque spots in the region—San Gimignano, Siena, and Monteriggioni—with a delightful stop for wine tasting in the Chianti hills. Priced at $146.14 per person and limited to just 8 participants, it promises a small-group vibe, personalized attention, and a balance of guided sightseeing with free time to explore on your own.

Two things I particularly like about this tour are the enchanting views of Tuscan landscapes and the opportunity to stroll through towns that seem frozen in time. The itinerary is thoughtfully structured, offering engaging stops, scenic drives, and the chance to sample some of Italy’s best wines—an added bonus for wine lovers. A potential consideration is the long day—at 11 hours, it’s quite full, so travelers with limited mobility or those seeking a more relaxed pace might want to prepare accordingly.

This tour strikes a good balance between guided insight and free exploration. While it’s a busy schedule, the variety of towns and experiences packed into one day delivers real value for those wanting an authentic taste of Tuscany without the hassle of self-driving.

Key Points / Takeaways

• Authentic small-group experience offers more personalized attention and fewer crowds.
• Stunning views of rolling hills and medieval skyline make every photo a keeper.
• Expert guidance from a professional driver who shares local insights.
• Balanced itinerary includes guided visits, tastings, and ample free time.
• Convenient pickup at Villa Costanza simplifies logistics from Florence.
• Ideal for travelers wanting a comprehensive Tuscany day trip with a focus on authenticity and scenic beauty.

Entering Tuscany’s Medieval Heart: San Gimignano

The first stop, San Gimignano, is often called the “medieval Manhattan” thanks to its skyline of ancient towers. Built during the 14th century by wealthy families to demonstrate their status, these towers are still visible today and create a fairy-tale atmosphere. Expect to wander through narrow cobbled streets, peek inside small artisan shops, and admire panoramic views over the Val d’Elsa valley.

One reviewer mentioned that San Gimignano’s towers are “like something out of a storybook,” and you’ll find many spots perfect for photos. The town is compact enough that you can enjoy a relaxed walk, and the free time here (~1 hour and 45 minutes) is plenty to soak in the sights and grab a coffee or gelato. The town’s medieval charm is palpable, and it’s a good place to get a feel for Tuscany’s storied past.

Siena: The Heartbeat of Tuscany’s Palio

Next, the journey takes you to Siena, a city famed for its Palio horse race and distinctive shell-shaped Piazza del Campo. The tour includes a photo stop, some sightseeing, and free time, giving you a chance to explore at your own pace. I love that the guide provides historical context—Siena’s cathedral, the Duomo of Santa Maria Assunta, is a particularly striking feature. Its black-and-white striped façade and intricate interior are stunning, and if you’re a fan of architecture, it’s worth a quick visit.

You’ll have about 2.5 hours here—more than enough to stroll through the historic center, shop for local products, or just relax at a café watching life unfold in the piazza. Many reviews praise the “vibrant, lively” atmosphere, and the guide’s commentary helps you understand what makes Siena so unique among Tuscan towns.

Scenic Drive through Chianti’s Hills

The drive between Siena and the Chianti area is a highlight itself. The rolling hills, dotted with vineyards and olive groves, make for an inspiring backdrop. While this part of the tour is mainly scenic (about 30 minutes), it sets the tone for the wine tasting experience ahead.

Tasting the Finest of Chianti

The visit to a local winery is a true treat. Here, you’ll enjoy a guided tour of the winery, learning about the long-standing history of wine-making in the region, which is famous worldwide. You’ll sample fine wines, paired with locally produced appetizers—a delicious way to understand what makes Chianti wines so special.

Most reviews describe this as a highlight, with many saying the wine tasting was “informative and enjoyable,” and that the guides provided clear explanations about the process. You get about one hour here, which allows for a leisurely tasting and some shopping if you want to bring home a bottle.

Monteriggioni: A Medieval Fortress

After the wine, you’ll stop in Monteriggioni, a tiny fortified village built in the 13th century. It’s a perfect example of a well-preserved medieval fortress, with circular walls and towers that you can walk around. You’ll have a free hour to explore, take photos, and enjoy the tranquil atmosphere. Many visitors find Monteriggioni to be a hidden gem—less crowded, more authentic, and full of character.

San Gimignano Revisited: Sunset Views

The last stop is San Gimignano again, but this time in the late afternoon, when the setting sun casts a warm glow on its towers. You’ll have around 1 hour and 45 minutes to wander, shop, or just sit and admire the view. Many reviews mention that the scenic views from here are “breathtaking” and worth staying for at least a little longer.

Practical Details and Logistics

The tour departs from Villa Costanza, a convenient meeting point outside Florence, making it easy to reach without hassle. The minivan transportation ensures comfort on the long day, and the small group size means you won’t be lost in a crowd. The driver, who speaks English, also acts as a guide, sharing tidbits about each location.

Start times vary, so check availability. The entire day lasts about 11 hours, including travel, sightseeing, and free time. This makes it a full but rewarding experience, especially if you’re eager to see many sights without the stress of planning logistics yourself.

The tour is cost-effective considering the included activities—transport, wine tasting, and guided insights—making it a good value for travelers wanting a comprehensive taste of Tuscany’s highlights.

Who Will Love This Tour?

This trip is perfect for history and architecture enthusiasts, wine lovers, and travelers who want a structured day with minimal planning. It’s also excellent for those who prefer small groups for a more intimate experience. If you enjoy stunning vistas, medieval towns, and tasting local wines, this tour hits all those marks.

However, keep in mind the full-day schedule if you’re not used to long excursions. It’s best suited for active travelers comfortable with walking and spending hours on the move.

Final Thoughts: Is This Experience Worth It?

If you’re after a well-rounded, authentic glimpse of Tuscany’s most iconic spots without the hassle of self-driving, this tour offers remarkable value. The combination of guided visits, scenic drives, and free exploration time makes it suitable for a variety of travelers—from history buffs to casual sightseers. The small group size ensures a more personal experience, and the included wine tasting adds a memorable flavor to the day.

The stunning views of the Tuscan landscape are a recurring highlight, and the chance to wander through medieval towns like Siena, Monteriggioni, and San Gimignano is a real privilege. The only caveat is the long hours involved—if that’s a concern, consider whether you’re prepared for a full day on your feet.

This excursion offers a taste of Tuscany’s best in a convenient, manageable package—perfect for travelers wanting a comprehensive, enjoyable day out.

FAQ

Is this tour suitable for children or families?
While it’s a full day with walking and sightseeing, the small-group setting and scenic stops can appeal to families. However, check if your children enjoy long days and walking before booking.

What should I bring?
Comfortable shoes are a must for walking on cobbled streets, and a camera is recommended to capture the scenic vistas. Don’t forget water to stay hydrated.

Is lunch included?
No, lunch is not included, so you might want to bring snacks or plan to purchase something during free time.

Can I buy souvenirs during the stops?
Yes, most towns have shops selling local products, crafts, and wines. The winery also offers shopping opportunities.

What is the group size?
Limited to 8 participants, ensuring more personalized attention and a relaxed atmosphere.

How long is the scenic drive?
The drive through Chianti hills is about 30 minutes, mainly for sightseeing and enjoying the landscape.

What are the start and end times?
Check availability for specific start times. The tour lasts 11 hours, starting from Villa Costanza and returning there.

Are there any special considerations for mobility?
The tour involves walking through towns and some uneven streets, so travelers with mobility issues should assess whether they can manage the pace.

Is the guide informative?
Yes, the driver acts as a guide, providing insights about each location, especially during the winery visit and sightseeing stops.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility if your plans shift.

This small-group day trip is an excellent way to see some of Tuscany’s most famous sights without feeling rushed. With scenic drives, medieval towns, and a wine tasting, it offers a well-balanced, authentic experience that many travelers find worthwhile. Just be prepared for a busy, full day—your reward will be unforgettable views and a deeper appreciation for Tuscany’s timeless charm.