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Who is travelling?

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ChildrenUnder 18

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From
US $464 per person

The Heart of Tuscany (Florence, Siena and Montalcino) - Medieval Towns, Wines and Landscapes

6 days
From Florence to Monteriggioni
4.3 (23 reviews)
From
US $464 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

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
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Best price guarantee Learn More

Plan your adventure:
City & Culture
Immerse yourself in rich history and local traditions
Self-guided
Independent exploration, backed by expert advice and support
Low Intensity
Travelers can expect some light physical activities
Guided in English
All Ages Welcome
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Florence

    Florence
    Accommodation
    Hotel (Hotel Dali)

    Optional Activities

    • View the city skyline from Piazzale Michelangelo
    • Walk across Ponte Vecchio, the historic bridge of goldsmiths
    • Ascend Brunelleschi's dome at the Cathedral for panoramic views
    • Explore the Uffizi Gallery and masterpieces by Botticelli and da Vinci
    • Enjoy lunch at Mercato Centrale food court
    Landmarks
    Duomo (Santa Maria del Fiore Cathedral)
    Ponte Vecchio
    Piazzale Michelangelo
    Uffizi Gallery
    Piazza della Signoria
    Mercato Centrale
    Itinerary Image 1Itinerary Image 2
  2. Day 2

    Siena

    Siena
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

    • Admire the black-and-white marble facade of Siena Cathedral
    • Visit Piazza del Campo, the shell-shaped square famous for the Palio horse race
    • Climb Torre del Mangia for panoramic city views
    • Explore winding medieval alleys surrounding the main square
    • Stop at a local trattoria for authentic Tuscan cuisine
    Landmarks
    Siena Cathedral (Cattedrale di Santa Maria Assunta)
    Piazza del Campo
    Torre del Mangia
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 3

    Montepulciano

    Montepulciano
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

    • Tour the historic Contucci wine cellars located on the main square
    • Walk through charming, winding streets to discover hidden viewpoints
    • Visit the beautiful, isolated San Biagio Renaissance church
    • Taste the prestigious Vino Nobile di Montepulciano at a local enoteca
    • Relax with an aperitivo on a terrace overlooking the rolling countryside
    Landmarks
    San Biagio Church
    Contucci Wine Cellars
  4. Day 4

    Val d'Orcia - Pienza - Montalcino

    Val d'Orcia - Pienza - Montalcino
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

    • Explore Renaissance architecture of Pienza, including Palazzo Piccolomini
    • Admire panoramic views of the Val d'Orcia valley from town walls
    • Bathe in the natural, mineral-rich waters of Bagno Vignoni thermal springs
    • Sip local Brunello di Montalcino wine in Montalcino
    • Visit the historical fort in Montalcino for a unique tasting experience
    Landmarks
    Val d'Orcia
    Pienza
    Palazzo Piccolomini
    Bagno Vignoni
    Montalcino
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Bagni San Filippo

    Bagni San Filippo
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

    • Soak in the natural, white travertine pools at Bagni San Filippo
    • Marvel at the 'White Whale,' a massive natural rock formation
    • Take a gentle walk through scenic olive groves of Monticchiello
    • Explore quiet village streets of Monticchiello
    • Enjoy wine tasting at Fattoria Pulcino winery near the Pulcinella tower
    Landmarks
    Bagni San Filippo
    White Whale (Balena Bianca)
    Monticchiello
    Fattoria Pulcino
    Itinerary Image 1
  6. Day 6

    Monteriggioni - Departure

    Monteriggioni - Departure

    Optional Activities

    • Walk the historic defensive walls of Monteriggioni
    • Enjoy a final authentic Italian coffee in a local piazza
    • Sample traditional ricciarelli almond biscuits
    • Capture last-minute photos of rolling Tuscan hills
    • Reflect on your unforgettable journey while heading to the airport
    Landmarks
    Monteriggioni

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What's Included

Expand All
  • Accommodation
  • Guide
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights

Where You'll Stay

All accommodations are subject to change

Operated by

Worldee

Rating
4.3 (23 reviews)
Response time
within 1 day
Response rate
96%
Cancellation policy
Learn more

Reviews from other tours by Worldee

  • Ena5.0August 2026
    Had a Great time on Sicily! Thanks Worldee for organizing everything! :)))
  • Mark5.0August 2026
    Overall excellent. However with it being a driving tour more direction regarding ztl zones would have been helpful
  • Nikola5.0August 2026
    We had a great time in Crete! Everything went really well and the trip was very well organized. Every day was full of...
    Show more

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Dates & Availability

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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
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Upcoming departures
Hurry, deals only available for a limited time!
Ends on 9 Sep, 2026
  • Instant Confirmation
    From Sunday
    13 Sep, 2026
    To Friday
    18 Sep, 2026
    English
    From:
    US$1,003 per person
    Price based on Shared Room
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    From Monday
    14 Sep, 2026
    To Saturday
    19 Sep, 2026
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    From:
    US$787 per person
    Price based on Shared Room
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    15 Sep, 2026
    To Sunday
    20 Sep, 2026
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    From:
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    16 Sep, 2026
    To Monday
    21 Sep, 2026
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    From:
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    Price based on Shared Room
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    17 Sep, 2026
    To Tuesday
    22 Sep, 2026
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    Price based on Shared Room
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    From Friday
    18 Sep, 2026
    To Wednesday
    23 Sep, 2026
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    US$734 per person
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  • Instant Confirmation
    From Sunday
    20 Sep, 2026
    To Friday
    25 Sep, 2026
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    From:
    US$816 per person
    Price based on Shared Room
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    From Monday
    21 Sep, 2026
    To Saturday
    26 Sep, 2026
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    From:
    US$634 per person
    Price based on Shared Room
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    From Tuesday
    22 Sep, 2026
    To Sunday
    27 Sep, 2026
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    From:
    US$645 per person
    Price based on Shared Room
  • Instant Confirmation
    From Wednesday
    23 Sep, 2026
    To Monday
    28 Sep, 2026
    English
    From:
    US$643 per person
    Price based on Shared Room

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From
US $464 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

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
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Best price guarantee Learn More

Plan your adventure:

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Good to Know

Tour ID: 366643

  • Currency
    Euro
    Italy
  • Plugs & Adapters

    As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for type L.

    Type L
    Italy
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before December 9th, 2026 a full payment is necessary. For tours departing after December 9th, 2026, a minimum payment of 40% is required to confirm your booking with Worldee. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 95 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Worldee will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Worldee" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
    • Flexible options if your plans change. We hope you won't need to, but if you have to cancel, here's exactly what you get back, no surprises. Your refund depends on how close to departure you cancel. You can find the full cancellation policy here.
    • Your money is protected.
      TourRadar is an authorized agent of Worldee, and we handle payments so you don't have to. Payment is securely transferred to the Operator based on your departure date.
  • Insurance

    Our travel protection from our award-winning partner, XCover, means you and your travel companions can book with peace of mind knowing there’s protection available in case your trip doesn’t go to plan. At checkout you will be able to select between different options in case you or the tour are eligible for insurance. In case no option is available, you are always able to purchase travel insurance outside of TourRadar.

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  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

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