Semi Private Deep Wine Chianti and San Gimignano from Florence

Explore the Charm of Florence’s Surroundings with a Deep Wine and Cultural Tour

The Semi Private Deep Wine Chianti and San Gimignano tour offers an engaging way to experience some of Italy’s most iconic sights and flavors. Priced at $242.67 per person and lasting approximately 8 hours and 30 minutes, this tour is perfect for those seeking an intimate, personalized experience of Tuscany’s legendary landscapes and wines. With a maximum group size of 8 travelers, the small-group setting ensures attentive guide service and a relaxed pace, making it ideal for visitors who prefer a more tailored outing over bus crowds.

Starting from Florence, the tour includes hotel pickup and drop-off, lunch paired with regional wines, and visits to renowned wineries and historic towns. The $242.67 price covers tastings, a delicious Tuscan meal, WiFi on board, and a free Prosecco bottle per group. Its popularity is clear—bookings are typically made around 60 days in advance, reflecting strong demand among those eager to explore Tuscany’s rich viticulture and medieval charm.

Key Points

• Small-group experience with a maximum of 8 travelers ensures personal attention
• Includes hotel pickup and drop-off in Florence for convenience
• Tastings of Chianti wines at two local wineries, plus a Tuscan lunch with regional specialties
• Visits to San Gimignano, famed for its towers and gelato, with ample free time
• Stops at scenic viewpoints, including a panoramic overlook of Florence
• WiFi hotspot provided for staying connected throughout the day

Starting the Day with Florence’s Best Viewpoints

The tour begins at 8:00 am with hotel pickup from Florence, including options for private hotel collection in the city center. Once aboard a luxury Mercedes van, the journey kicks off with a 15-minute drive to Piazzale Michelangelo. This spot offers a breathtaking panoramic view of Florence’s skyline, perfect for photos and taking in the city’s beauty from above. A bronze replica of Michelangelo’s David also graces the square, adding to the cultural flavor of this early stop.

This scenic overlook is a favored starting point because it combines stunning views with a chance to appreciate Florence’s architecture and history early in the day, setting the tone for the Tuscan adventure ahead.

Discovering Medieval San Gimignano’s Towers and Town Charm

At 8:30 am, the tour continues with a one-hour drive to San Gimignano, a UNESCO World Heritage site famous for its medieval towers and well-preserved walls. The town’s distinctive skyline, filled with imposing stone towers, dates back to the Middle Ages, offering a glimpse into Italy’s historic past.

In 1 hour and 25 minutes of free time, visitors can explore the narrow streets, visit the local shops, or enjoy gelato at one of the town’s renowned gelaterias. The walkable town provides plenty of photo opportunities, and the guide offers helpful pointers on local sights and best spots for tasting its famous gelato.

Visiting a Tuscan Farmhouse in Chianti’s Heartland

At 10:55 am, the group departs for San Casciano in Val di Pesa, a scenic 50-minute drive into the heart of Chianti wine country. The highlight here is a visit to a traditional Tuscan farmhouse with a cellar tour. The estate’s stunning views of rolling vineyards and olive groves form a perfect backdrop for the day’s tastings.

Here, the tour features a delicious Tuscan lunch with regional dishes, paired with local wines, including Chianti varietals. The 2 hours and 30 minutes allocated to this stop allow enough time to relax, enjoy the food, and learn about local wine production from knowledgeable staff. The lunch emphasizes regional flavors and local products like cheese, salami, and olive oil.

Tasting Chianti Wines at a Family-Run Estate

At 2:30 pm, the journey continues with a 25-minute drive to San Michele a Torri, where a family-run wine estate awaits. This stop offers a chance to sample multiple Chianti wines, including at least 5 or 6 different types, ensuring a comprehensive tasting experience. The estate’s stunning setting and friendly staff make for a memorable visit.

The 45-minute tasting session enables guests to appreciate the diversity within Chianti wines, learning the differences between labels and styles in a relaxed environment. This stop accentuates the tour’s focus on local wine craftsmanship and authentic experiences.

Scenic Return and Final Highlights

After the wine estate, the group boards the van for a 40-minute drive back toward Florence, arriving around 4:30 pm. This timing allows for some additional free time in Florence or to enjoy the city’s early evening ambiance.

Throughout the day, the tour offers WiFi via a hotspot to stay connected, and passengers enjoy bottled water and a bottle of Prosecco to toast the day’s experiences. The air-conditioned vehicle ensures comfort during the drives, which traverse some winding roads characteristic of Tuscany’s scenic landscape.

Logistics and Practical Details

The tour departs from Hotel Boccaccio at Via della Scala, 59, in Florence, with an early 8:00 am start. If staying outside the city center, private pick-up is available, including in front of Hotel Boccaccio or nearby locations like the Santa Maria Novella train station. For convenience, guests are encouraged to arrive 15 minutes early to settle in and possibly enjoy a breakfast or coffee at the meeting point, where a 10% discount is offered to those who choose Tino Caffè.

The group size is limited to 8 travelers, ensuring a personalized experience and attentive service. The tour operates rain or shine, with a full refund available if canceled more than 24 hours in advance.

What Sets This Tour Apart from Similar Experiences

What makes this tour stand out is its semi-private format, which offers a more intimate alternative to large bus excursions. Guests consistently praise knowledgeable guides like Claudius, Alberto, Sara, and Andrea, who combine professionalism with warmth and local expertise.

The combination of scenic viewpoints, historic San Gimignano, authentic Tuscan lunch, and multiple wine tastings creates a well-balanced day that satisfies both cultural interests and palate pleasures. The small group size makes it easy to ask questions, take photos, and enjoy a relaxed pace.

Who Will Appreciate This Tour Most

This experience best suits those who prefer personalized attention and off-the-beaten-path visits. It is ideal for wine enthusiasts, fans of medieval towns, or visitors seeking a comprehensive, relaxed day in Tuscany without the crowds. The inclusion of lunch and tastings makes it especially appealing for food and wine lovers.

While the winding roads may be challenging for those prone to motion sickness, the scenic drives are a highlight for many. The small group size also ensures a more connected and engaging atmosphere, making it suitable for couples, friends, or small families.

The Sum Up: A Personal and Flavorful Journey Through Tuscany

This semi-private tour offers a balanced mix of scenic views, historic towns, and top-quality wines, all within a comfortable and intimate setting. Priced at $242.67, it provides excellent value for the comprehensive experience, including lunch, tastings, and transport.

The knowledgeable guides, such as Claudius and Sara, bring the region’s stories and flavors to life, making each stop engaging and meaningful. The small-group format ensures a relaxed atmosphere, ideal for those who want to avoid crowded tours and enjoy a more personal connection with their guides and fellow travelers.

This tour is perfect for avid wine lovers, history enthusiasts, or anyone wanting to see the best of Chianti and San Gimignano with an authentic local touch. It offers a full day of exploring, tasting, and absorbing the beautiful Tuscan countryside.

Frequently Asked Questions

How long is this tour?
The entire experience lasts approximately 8 hours and 30 minutes from pickup to return.

What is included in the price?
The tour fee covers hotel pickup and drop-off, wine and olive oil tastings, a Tuscan lunch, WiFi hotspot, bottled water, and a bottle of Prosecco for the group.

Is this tour suitable for vegetarians or those with dietary restrictions?
The provided information does not specify dietary accommodations, but guests can likely discuss options with the guides beforehand.

What stops are part of the itinerary?
Stops include Piazzale Michelangelo, San Gimignano, a Tuscan farmhouse in Chianti, and a family-run winery in San Michele a Torri.

How large are the groups?
Groups are limited to 8 travelers to maintain a semi-private, personalized experience.

Do I need to book in advance?
Yes, bookings are typically made around 60 days in advance due to high demand.

What should I bring?
Comfortable walking shoes are recommended for exploring towns and wineries; WiFi and bottled water are provided on the vehicle.

Are there any age restrictions?
Most travelers can participate; specific age restrictions are not detailed, but alcohol tastings are part of the experience.

Can I cancel if my plans change?
Yes, cancellations made more than 24 hours in advance receive a full refund. Cancellations within 24 hours are non-refundable.

Is there a dress code?
No specific dress code is listed, but casual, comfortable clothing suitable for walking and warm weather is advised.