Siena Cathedral facade with visitors in Piazza del Duomo, Italy.
Santa Maria della Scala museum facade in Siena, Italy, with visitors in the courtyard.
Winding road through vineyards on Via Chiantigiana, Tuscany.
Vineyards in Chianti landscape during wine tasting tour.
Chianti winery tasting room with tables set for wine sampling.
Group toasting with wine at a winery table surrounded by barrels.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.

From Florence: Siena and Chianti Day Trip with Dinner & Regional Pairings

Florence
Day Trips
Google Verified Seller

Duration: 7 hours (approx.)

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Transfers included

Comfortable roundtrip transfers in a A/C Bus

Meals included

Dinner and Wine Tasting

Guided tour

Expert local tour guide

Get your booking confirmed instantly

Start an memorable journey with our Siena and Chianti Day Trip departing from Florence, Italy. Explore Tuscany's rich heritage as you visit historical sites in Siena and savor the renowned wines of the picturesque Chianti region. Your ticket will be emailed to you; upon arrival at Piazzale Montelungo Bus Terminal near your departure point, proceed directly to the TOURS & NEWS KIOSK for further instructions.

From Florence's Piazzale Montelungo Bus Terminal, start an adventure along Via Chiantigiana in a spacious AC bus. Enjoy expert commentary provided live in English or Spanish.

At the heart of Siena lies the central Plaza del Campo where you'll have ample free time to explore and soak up local culture at your leisure.

Visit a rustic vineyard located in the core of the Chianti region, offering traditional pasta dishes paired with locally crafted wines that complement every bite perfectly.

Indulge in an exquisite Tuscan dinner featuring top-quality regional ingredients during this half-day excursion from Florence to Siena and Chianti.

Half-day exploration of Siena and the Chianti region

English or Spanish-speaking expert local guide to accompany you

Pick-up service at Florence's Piazzale Montelungo Bus Terminal

Round-trip AC bus transfer for convenience (based on option selected)

Visit a vineyard in Chianti, enjoy wine tasting and dine with regional pairings

Individual shopping expenses

Accommodation shuttles

Siena Cathedral facade with visitors in Piazza del Duomo, Italy.

Siena Cathedral facade with visitors in Piazza del Duomo, Italy.

Tuscany, one of the birthplaces of the Italian Renaissance, has been home to numerous influential figures across art and science. Renowned for its wines like Brunello di Montalcino, Morellino di Scansano, and Chianti from the scenic Chianti region, Tuscan cuisine is celebrated for its simplicity—featuring a variety of breads, cheeses, meats, and legumes.

Starting Your Adventure

Your ticket will be emailed to you. Upon arrival at Piazzale Montelungo Bus Terminal—a 5-10 minute walk from Santa Maria Novella Train Station—look for staff in bright fuchsia Ciaoflorence jackets with clipboards.

What's on the Itinerary

The journey begins as you depart Florence, heading to Siena. Here, explore its medieval allure by visiting its Gothic cathedral and hidden gems like Santa Maria della Scala museum. A scenic drive along Via Chiantigiana awaits aboard a comfortable air-conditioned bus with live commentary available in English or Spanish.

As the day concludes at a charming Chianti winery, indulge in an exquisite dinner of traditional pasta and seasonal dishes paired perfectly with exceptional local wines. This excursion offers a rich blend of sights, tastes, and experiences that epitomize Tuscany's essence.

Tour Highlights

  • Visit Siena: Explore the medieval city and its Gothic cathedral.
  • Discover Santa Maria della Scala museum among other hidden gems.
  • Savor a scenic drive on Via Chiantigiana through picturesque countryside views.
  • Experience an authentic Tuscan evening at a Chianti winery with dinner and regional pairings.
Santa Maria della Scala museum facade in Siena, Italy, with visitors in the courtyard.

Santa Maria della Scala museum facade in Siena, Italy, with visitors in the courtyard.

Winding road through vineyards on Via Chiantigiana, Tuscany.

Winding road through vineyards on Via Chiantigiana, Tuscany.

Vineyards in Chianti landscape during wine tasting tour.

Vineyards in Chianti landscape during wine tasting tour.

What to bring

    Comfortable walking shoes are recommended, as vineyards often sit atop hills with a short inclined walk at the start of your visit.

    Accessibility

      This tour is not wheelchair or pram/stroller accessible.

      Additional information

      • Please inform us in advance about any food intolerances or allergies you have.
      • Tours are available in English and Spanish. For tours in Italian, Portuguese, or French, a minimum of 4 participants is required to confirm the excursion.

      No alcoholic beverages will be served to individuals under 18 years old.

      Chianti winery tasting room with tables set for wine sampling.

      Chianti winery tasting room with tables set for wine sampling.

      Group toasting with wine at a winery table surrounded by barrels.

      Group toasting with wine at a winery table surrounded by barrels.

      Book your tour in advance, especially during peak season, to ensure availability and avoid disappointment.

      Wear comfortable walking shoes as you'll be visiting vineyards located on hills with short inclined walks.

      If you have any food intolerances or allergies, please inform the organizers ahead of time so they can accommodate your needs during dinner.

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      FAQs

      The ideal time for dinner pairings in Florence, Siena, and Chianti is during spring (April-June) or autumn (September-November). These seasons offer pleasant weather with fewer tourists. Summer can be crowded but offers more dining options. Winter has smaller crowds but may be chilly.
      Transportation options vary based on your starting point. Many tours offer pickup from central Florence hotels or train stations, with transfers by bus or minivan to multiple vineyards and towns like Siena and Greve in Chianti. Private car services are also available for more flexibility.
      Photography is generally allowed throughout your dinner pairing experience in Florence, Siena, and Chianti regions, including during tastings and meals. However, some wineries may have restrictions on flash photography or specific areas off-limits to cameras due to privacy concerns.
      A typical dinner pairing tour in Florence, Siena, and Chianti lasts around 6-8 hours including transportation between locations, wine tastings, and a gourmet meal. Plan for an early evening start to ensure you make the most of your experience.
      Bring comfortable walking shoes as there will be some walking involved in vineyards and historic towns. Dress casually but comfortably, with layers if visiting during cooler months. Don't forget a camera for capturing the beautiful landscapes and memorable moments.
      Your dinner pairing experience includes transportation between locations, guided tours of selected wineries, tastings of local wines, a multi-course gourmet meal at a traditional Tuscan restaurant, and sometimes olive oil tasting. Some packages may also include cheese tastings or cooking demonstrations.
      While children are welcome on dinner pairing tours, some venues may have age restrictions or be more suitable for adults due to tasting experiences. It's recommended to check specific venue policies beforehand and plan activities that cater to the whole family.
      It's highly recommended to book your dinner pairing experience well ahead of time, especially during peak travel seasons such as April through June and September through November. Booking early ensures availability at popular venues and helps secure the best deals.

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