From Florence: Chianti afternoon tour & visit to 2 wineries

Taking a trip from Florence into the heart of Tuscany’s world-famous Chianti region promises breathtaking scenery, authentic wine experiences, and a chance to step back in time. This private afternoon tour offers a balanced mix of stunning landscapes, medieval charm, and wine tasting at two historic family-run wineries—all within a compact five-hour window.

What makes this experience stand out? First, the chance to enjoy immense views of rolling vineyards and sunflower fields that look like they’ve been plucked straight from a postcard. Second, the visit to two different wineries, each with their own story, producing Chianti Classico since 1926. And third, exploring medieval villages like Castellina in Chianti that feel like living museums.

However, a possible consideration is the short duration—five hours means everything is quite condensed. Travelers wanting a slow, in-depth exploration might find this a bit rushed. Still, if you’re after a taste of Tuscany’s best, this tour hits a sweet spot without breaking the bank. It’s perfect for those craving a scenic, wine-focused escape from Florence, especially if you’re eager to combine natural beauty with authentic regional tastes.

Good To Know

• Stunning scenery of vineyards, sunflower fields, and medieval villages.
• Two winery visits with multiple tastings, including Chianti Classico.
• Visit to Castellina in Chianti, a charming medieval village.
• Expert driver and private group ensure a personalized experience.
• Flexible booking and cancellation policies with full refunds up to 24 hours.
• Cost-effective for the quality of experiences packed into five hours.

You can check if your dates are available here:

What to Expect from the Chianti Afternoon Tour

This tour offers a well-rounded introduction to Tuscany’s famous Chianti wine country without the need for an all-day commitment. Starting from Florence, it’s designed for travelers who want a taste of Tuscany’s landscapes, wine, and history in a manageable, private setting.

The experience begins with a meet-up in front of the bar “il Curatone,” where your driver from Pek Tuscany in Limo will greet you with a sign bearing your name. Expect a comfortable, air-conditioned vehicle and personalized service—perfect for small groups or couples. The journey into Chianti’s rolling hills takes about an hour, with scenic stops along the way that showcase Tuscany’s iconic cypresses, vineyards, and golden fields.

Exploring Castellina in Chianti

Your first stop is the medieval village of Castellina in Chianti, which you’ll visit for about 30 minutes. This charming town is a well-preserved example of Tuscany’s enduring history, with stone houses, cobbled streets, and a relaxed vibe. You can wander at your own pace, soaking in the timeless atmosphere and perhaps peeking into local markets or small shops. Reviewers mention the town’s “hidden gem” quality and love that it feels like stepping into a living postcard.

The Vineyards and Wineries

Next, you’ll venture into the Chianti Hills, famous for their lush vineyards and the legendary Black Rooster (Gallo Nero), the symbol of Chianti wine. Your first winery stop is a family-run farmhouse established in 1926. Here, you’ll walk through vineyards and cellars, learning about traditional winemaking techniques passed down through generations. The owners are often described as warm and welcoming, sharing stories about their heritage and wines.

The tasting session at this farm includes five different wines, such as Vernaccia, Super Tuscan, and the iconic Chianti Gallo Nero. Reviewers like Kasey highlight the quality of these tastings, which include not just wines but also olive oils, vinegars, meats, and cheeses. Many mention the “treats treated like royalty,” with one winery even offering a free bottle to take home, adding a personal touch to the experience.

The second stop is another exceptional cellar, where you’ll enjoy five more wines, with a focus on premium Chianti and Super Tuscan options. Sampling region’s finest extra virgin olive oil alongside the wines enriches the tasting experience, giving you authentic flavors of Tuscany.

Scenic Views and Photo Opportunities

Throughout the tour, expect numerous chances to halt and snap photos of the stunning landscape—picturesque vineyards stretching into the horizon, cypress-lined avenues, and golden fields are common backdrops. One of the review highlights is the driver stopping “on the side of the road so we could take photos of the beautiful Tuscan landscape,” which adds a personal touch that many travelers appreciate.

More Great Thing To Do Nearby

Returning to Florence

As the afternoon winds down, you’ll head back to your original meeting point, arriving around 8:00 PM. The return journey offers a relaxed way to soak in the sunset over the hills, bringing your memorable Tuscan day to a close.

Why This Tour Offers Great Value

For just under $170, this private tour packs in multiple wine tastings, visits to historic villages, scenic drives, and insider knowledge. The focus on family-run wineries makes it particularly appealing for those seeking genuine, authentic experiences rather than commercialized tourist traps.

The inclusion of air-conditioned transportation, bottled water, brochures, and a knowledgeable driver ensures comfort and ease throughout the day. The private group format means you’ll have a more intimate experience, which many reviewers say “treats you like royalty.”

While some travelers might wish for a longer or more in-depth exploration, the compact itinerary means you’ll get a satisfying taste of Chianti’s highlights without feeling rushed. Plus, the flexible cancellation policy offers peace of mind, knowing you can adjust plans if needed.

Who Is This Tour Best For?

This experience suits wine lovers eager to taste authentic Chianti wines and visit historic Tuscan villages, all within a manageable timeframe. It’s ideal for couples or small groups who prefer a personalized experience with a private driver, rather than large coach tours.

Travelers who value scenic views and cultural authenticity will appreciate the stops in Castellina and the stops along the hillside. It’s perfect for those wanting a relaxed, picturesque afternoon that combines wine, history, and nature without the commitment of a full-day tour.

However, if you’re seeking a deep dive into Tuscany’s wine production or wish to visit multiple regions, this might feel a bit limited in scope. It’s best for those who want a beautiful, taste-focused escape rather than a comprehensive wine itinerary.

Frequently Asked Questions

Is transportation included?
Yes, the tour includes private, air-conditioned transportation from and back to Florence’s meeting point.

Can I cancel this tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

How long does the tour last?
It lasts approximately five hours, starting and ending at the same point in Florence.

Are the wine tastings at both wineries?
Yes, each winery offers a tasting of five different wines, making for a total of ten wines during the visit.

Is this tour suitable for people with limited mobility?
The tour is wheelchair accessible, but it’s advisable to check with the provider for specific mobility needs.

What should I bring?
Comfortable clothing is recommended; since the tour takes place rain or shine, bring an umbrella or light raincoat if necessary.

Final Thoughts

This private Chianti afternoon tour offers a well-balanced mix of scenic beauty, cultural charm, and wine tasting—all within a comfortable, manageable timeframe. It’s an excellent choice for travelers who want to sample Tuscany’s iconic landscapes and flavors without the fuss of a full-day commitment or large group tours.

You’ll love the way the rolling hills and medieval villages make you feel like you’ve stepped into a painting. The visits to family-run wineries, with their warm hospitality and delicious wines, add an authentic touch that many travelers cherish.

While it may be a quick snapshot rather than an all-encompassing deep dive, this tour delivers genuine value and memorable experiences. It’s perfect if you’re seeking a scenic, tasteful, and private escape into Tuscany’s heart. Whether you’re a wine enthusiast, history lover, or simply eager for stunning views, this trip is likely to leave you with a smile and a few bottles of Chianti to share at home.

Note: This tour is best suited for those who want a taste of Tuscany’s most beautiful sights and flavors in a short time, appreciating personalized service and authentic regional culture.

You can check if your dates are available here: