Siena and Chianti Castle with Lunch&WineTasting from Florence

Florence, Italy

From $532.32

Price varies by group size

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 10 hours (approx.)
  • Pickup offered
  • Mobile ticket
  • Offered in: English


Delve into Tuscany’s history and culture on a full-day private tour of Siena, Montalcino and Val d’Orcia. Depart early from Florence to take your time as you visit lovely towns, see stunning architecture, savor delicious food and wine, and learn about the places you visit from your informative driver-guide. In the Val d’Orcia region, you can enjoy the ambiance of towns such Pienza or Montepulciano. Your driver-guide customizes the tour itinerary to best suit your interests.
  • Full-day tour of Siena, Montalcino and Val d’Orcia, from Florence
  • Soak up the scenic Tuscan countryside en route to charming towns including Montalcino, Pienza or Montepulciano
  • Stroll around the historic center of Siena, a UNESCO World Heritage Site
  • Taste wines and other local specialties
  • Hear about medieval and Renaissance architectural styles
  • Personalize the tour and get recommendations from the driver-guide

What's Included

  • Hotel pickup and dropoff
  • Air-conditioned, fully insured and licensed legal vehicle with professional English Speaking Driver
  • Dedicated Local licensed Expert Tour Guide (upgradable in Private option)
  • Brolio Castle in Chianti Area Wine Tasting
  • Brolio Castle Osteria Restaurant Lunch Included
  • Tipping is not included in our service fees, it is never mandatory although it is always appreciated

Meeting And Pickup

Pickup points

Select a pickup point

Start time

08:00 AM

Pickup details

Departure and Return Point: Your accommodation in Florence In Shared Tour Option only: Your Driver may make a few stops (usually 2/3 stops) along the way to pick up, or drop off, fellow passengers. This means that your Driver could arrive within 15-30 minutes of your scheduled pickup time.

What To Expect

Begin your tour with pickup from your Florence hotel by your private driver-guide.

Learn about the history and culture of sites around Siena, Montalcino and the Val d’Orcia area as your driver shares the highlights of the region. Your drive takes you where you want to go and gives you plenty of time to enjoy the sightseeing on your own.

Visit the UNESCO World Heritage-listed historic center of Siena, where you can see the city’s top attractions, including the Siena Cathedral (Il Duomo), the Battistero di San Giovanni and Palazzo Pubblico (Town Hall). Discover the famously delicious cuisine, visit art museums, or simply stroll around the scenic streets.

Located a short drive from Siena in the rolling hills of Tuscany, Montalcino is a picturesque medieval town that has become famous for its Brunello di Montalcino wine. Continue to UNESCO World Heritage-listed Pienza, known for its stunning Renaissance architecture, which came into existence in the early fifteenth century under the hand of native son Pope Pius II. More recently, the town has become known for its pecorino cheese.

Savor the delicious wines and foods of Montepulciano, another gorgeous medieval and Renaissance hill town near Siena. In addition to wine, specialties include pork, cheese, ‘pici’ pasta and honey. Connoisseurs consider its Vino Nobile among Italy's best wines.

When your full-day tour comes to an end, your driver returns you to your hotel.

Val d'Orcia (Pass By)

Castello di Brolio

2 hours Admission Ticket Free

Castello di Brolio

1 hour Admission Ticket Free


2 hours Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Air-conditioned, fully insured and licensed legal vehicle with professional English-speaking Driver
  • Option Private Tour: This is a private Tour. Only your group will participate. Private Tour can be modified and/or customized (even while on tour)
  • Option Shared Tour: Solution with a lower price dedicated to travelers sharing the vehicle with a small group (up to 8 people per vehicle). Not customizable. It is not possible to include attractions tickets purchased by your own
  • Wine Tasting: Minimum drinking age is 18 (soft drinks instead wine)
  • One Infant seat available on request
  • Not wheelchair accessible
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

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Siena and Chianti Castle with Lunch&WineTasting from Florence


10 hours
Free Cancellation