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2026

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AdultsAges 18 or above

2

ChildrenUnder 18

0

Siena & Wine

4 days
•
Start and end in Siena
5.0 (1 review)

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Plan your adventure:
Food & Wine
Savor the world's flavors and finest wines
Partially Guided
Independent travel, featuring selected guided excursions
Low Intensity
Travelers can expect some light physical activities
Guided in English
Group Size 1 - 6
Ages 18+

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Itinerary

  1. Intro

    Introduction

  2. Day 1

    Siena

    Siena
    Start point
    Siena, Siena, Italy (Hotel lobby, 12:30)
    Meals
    Wine Tasting (Wine tasting of 6 wines enhanced by a series of different sample foods)
    Accommodation
    Hotel 4* (Hotel Athena)

    Included Activities

    • Small Group Wine Tasting Class - 6 Tuscan wines with welcome glass of crisp local dry white wine
    • Learn about Vernaccia di San Gimignano wine cited by Dante in his Inferno
    • Explore Tuscan wine-making history and the Designation System introduced in the 1960s
    • Taste young and fruity red wine compared to older, bolder wine
    • Taste Classic Tuscan wines: Chianti, Nobile, Brunello, Supertuscan blend, and Vinsanto
    Landmarks
    Siena
  3. Day 2

    Chianti - Monteriggioni - San Gimignano

    Chianti - Monteriggioni - San Gimignano
    Meals
    Dinner (Full Tuscan dinner at organic farm with Vernaccia white wine and Chianti red wine, weather permitting served on a terrace overlooking cultivated fields and San Gimignano skyline)
    Accommodation
    Hotel 4* (Hotel Athena)

    Included Activities

    • Chianti wine estate visit with cellar tour and Chianti Classico wine tasting
    • Monteriggioni visit - explore the 13th-century medieval fortress with complete ring of city walls and turrets
    • San Gimignano visit at sunset - explore cathedral, civic museum, streets and shops of local artisanal objects and products
    • Organic farm dinner experience

    Optional Activities

    • Visit the Cathedral in San Gimignano
    • Visit the Civic Museum in San Gimignano
    • Browse streets and shops in San Gimignano
    • Light a candle in the local church in Monteriggioni
    • Sit in San Gimignano's main square and enjoy gelato or coffee
    Landmarks
    Chianti
    Monteriggioni
    San Gimignano
  4. Day 3

    Montalcino

    Montalcino
    Meals
    Lunch (Traditional Tuscan meal at family-run winery with farm wines)
    Accommodation
    Hotel 4* (Hotel Athena)

    Included Activities

    • First winery visit - walk vineyard rows, explore cellars, introductory Brunello wine tasting
    • Montalcino hilltop town visit - climb fortress walls, explore town squares and roads
    • Family-run winery visit with owner/winemaker meeting and farm visit
    • Traditional Tuscan meal at family-run winery with farm wines
    • Abbey of Sant'Antimo visit - mystical Benedictine monastery
    • Third winery visit - explore wine-making processes, aging barrels (oak), Brunello wine tasting

    Optional Activities

    • Browse stores in Montalcino
    • Visit town squares and roads in Montalcino for views of valleys and vineyards
    Landmarks
    Montalcino
    Abbey of Sant'Antimo
  5. Day 4

    Siena

    Siena
    End point
    Siena, Siena, Italy (Hotel lobby, 11:00)
    Meals
    Breakfast

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What's Included

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  • Accommodation
  • Guide
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights
  • Insurance
  • Optional
  • Additional Services

Where You'll Stay

All accommodations are subject to change

Operated by

Tuscan Escapes

Response time
9 hours
Response rate
100%
Cancellation policy
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What our customers ask about this tour

The content in our FAQ section is subject to change.
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  • K

    Kyle

    Asked on June 3rd, 2026

    If I booked as a solo traveller what are the chances that all other people are couples? It sounds like it would be a popular couples trip, do you get many solo travellers booking for this trip?

    Group size
    • Tuscan EscapesOperator•Written June 2026

      We offer daily shared group tours that are frequently booked also by solo travelers, as well as by couples and families.

    • K

      Kyle

      Traveler•Written June 2026

      This sounds even more interesting now, however it would be a concern if the hotel prices were to be significantly more expensive than first thought. I understand that is out of your control, but if you had to give your best estimate how much could the total cost be due to the event?

    • Tuscan EscapesOperator•Written June 2026

      The hotels that we normally use (Villa Elda and Hotel Athena in Siena) are more expensive during the 4 days of the Palio race as they would charge for min 4 full nights even if you were to stay for 2 or 3 nights only. However, there are a lot of Airbnb and other smaller hotels that do not have the limitation of 4 nights. Would you be willing to do a search and maybe book your own accommodation and then book just the tours with us? This might make more sense since you are better at evaluating your accommodation standard and how far from the city center you are willing to stay. We don't normally deal with hotels much besides for the 3 day package that you see here, but the Palio dates are problematic so we would prefer to offer just the tours which depart from Piazza San Domenico at 9:30am or 2:30pm.

    • K

      Kyle

      Traveler•Written June 2026

      Would the 26th June - 29th June tour avoid the disruption of the horse race? And is that going ahead as planned, my plans are very last minute at the moment. But I am open to options.

    • Tuscan EscapesOperator•Written June 2026

      We have full-day tours that depart daily from Siena. The Brunello Wine Tour is offered every day while the SUNSET Tour to San Gimignano and the Chianti is available on Wednesdays and Saturdays only. However, we also offer a sight-seeing and wine tour to Pienza and Montepulciano (everyday except Wednesdays), a Chianti Wine Tour (Mondays and Thursdays) and a sight-seeing tour to San Gimignano and Volterra (Tuesdays, Fridays and Sundays). A lot of visitors take the Chianti Wine Tour and the San Gimignano & Volterra Tour so the SUNSET Tour kind of combines both into a single day, but our Pienza and Montepulciano is also a fantastic itinerary combining sites with wine, so you can stay for 2 or 3 or 4 days and have a few different options daily!

    • K
      4 more answers
  • C

    Craig

    Asked on January 10th, 2025

    Do you have food tours as well as wine tours?

    Other
    Tour Details
    • Tuscan EscapesOperator•Written January 2025

      We offer a 2h Food and Wine Tour in Siena called Savor Siena, which starts at 12pm on Friday. You can join this tour instead of the 5pm Tuscan Classics wine tasting class which has srhe same cost. You can then take the Chianti and San Gimignano Sunset Tour on Saturday, which includes a farm to table dinner with wine. On Sunday, you would take our Brunello Wine Tour, which visits 3 different Brunello wineries, one for lunch with wine.

  • L

    Leah

    Asked on September 27th, 2024

    Do you have dates for 2025?

    Tour Details
    • Tuscan EscapesOperator•Written October 2024

      We are happy to confirm that the tour dates for the 2025 will be the same of this year, maybe we will add more availability for some of ours Tours, but we don't know yet so please let us know your tour date or the possible tour dates and we can provide to you of a proper quote and confirm the availability.

  • D

    Diana

    Asked on February 14th, 2023

    do you offer any tours this summer? If yes, how much would it cost for 2 people?

    Price / Availability
    Tour Details
    • Tuscan EscapesOperator•Written February 2023

      Yes, we offer full-day wine and sight-seeing tours in shared, small groups that depart daily from Siena, operated in 9 seater vans (max 8 participants) with the Chianti and Castles itinerary on Mondays and Thursdays, the Chianti and San Gimignano Sunset itinerary on Wednesdays and Saturdays and the Brunello Wine Tour itinerary available daily, so we can accommodate any tour dates according to accommodation availability.

Can’t find the answer to your question?
Reach out to the experts at Tuscan Escapes with your enquiry, they usually respond within 9 hours.

Good to know

Tour ID: 178292

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      Used in Italy

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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec