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2026

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Who is travelling?

Who is travelling?

AdultsAges 18 or above

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ChildrenUnder 18

0
From
US $510 per person

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

6 days
•
From Florence to Monteriggioni
4.2 (28 reviews)
From
US $510 per person
+ $707 Double room with a double bed

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select departure month

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
Pay only 40% today. The rest is due 95 days before departure. Learn more

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. Intro

    Introduction

  2. Day 1

    Florence

    Florence
    Accommodation
    Hotel (Hotel Dali)

    Optional Activities

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

    Florence to Siena

    Florence to Siena
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

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

    Montepulciano

    Montepulciano
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

    • Tour historic Contucci wine cellars located on the main square
    • Walk through charming, winding streets to discover hidden viewpoints
    • Visit beautiful, isolated San Biagio Renaissance church
    • Taste prestigious Vino Nobile di Montepulciano at a local enoteca
    • Relax with an aperitivo on a terrace overlooking rolling countryside
    Landmarks
    Contucci Wine Cellars
    San Biagio Church
  5. 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 Val d'Orcia valley from town walls
    • Bathe in natural, mineral-rich waters of Bagno Vignoni thermal springs
    • Sip local Brunello di Montalcino wine in hilltop town of Montalcino
    • Visit historical fort in Montalcino for unique tasting experience
    Landmarks
    Val d'Orcia
    Pienza
    Palazzo Piccolomini
    Bagno Vignoni
    Montalcino
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  6. Day 5

    Bagni San Filippo

    Bagni San Filippo
    Accommodation
    Hotel (La casina di Iole)

    Optional Activities

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

    Monteriggioni to Airport

    Monteriggioni to Airport

    Optional Activities

    • Walk historic defensive walls of medieval village Monteriggioni
    • Enjoy final authentic Italian coffee in local piazza
    • Sample traditional ricciarelli almond biscuits
    • Capture last-minute photos of rolling Tuscan hills
    • Reflect on unforgettable journey while heading to 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
4.2 (28 reviews)
Response time
within 2 days
Response rate
100%
Cancellation policy
Learn more

Reviews from other tours by Worldee

  • Ena5.0•August 2026
    Had a Great time on Sicily! Thanks Worldee for organizing everything! :)))
  • Mark5.0•August 2026
    Overall excellent. However with it being a driving tour more direction regarding ztl zones would have been helpful
  • Bernard5.0•October 2026
    Great experience! A really well organized trip. Super recommended.

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Dates & Prices

Select departure month

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
Upcoming departures
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  • Instant Confirmation
    From Wednesday
    28 Oct, 2026
    To Monday
    2 Nov, 2026
    English
    From:
    US$709 per person
    Price based on Private Double Room
    Double room with a double bed
    $707
  • Instant Confirmation
    From Thursday
    29 Oct, 2026
    To Tuesday
    3 Nov, 2026
    English
    From:
    US$669 per person
    Price based on Private Double Room
    Double room with a double bed
    $668
  • Instant Confirmation
    From Friday
    30 Oct, 2026
    To Wednesday
    4 Nov, 2026
    English
    From:
    US$657 per person
    Price based on Private Double Room
    Double room with a queen-size bed and shared bathroom
    $656
  • Instant Confirmation
    From Saturday
    31 Oct, 2026
    To Thursday
    5 Nov, 2026
    English
    From:
    US$656 per person
    Price based on Private Double Room
    Superior Apartment
    $654
  • Instant Confirmation
    From Sunday
    1 Nov, 2026
    To Friday
    6 Nov, 2026
    English
    From:
    US$523 per person
    Price based on Private Double Room
    Double room with a double bed and shared bathroom
    $522
  • Instant Confirmation
    From Monday
    2 Nov, 2026
    To Saturday
    7 Nov, 2026
    English
    From:
    US$536 per person
    Price based on Private Double Room
    Deluxe Double Room with Queen Bed
    $534
  • Instant Confirmation
    From Tuesday
    3 Nov, 2026
    To Sunday
    8 Nov, 2026
    English
    From:
    US$531 per person
    Price based on Private Double Room
    Double room with a double bed and shared bathroom
    $530
  • Instant Confirmation
    From Wednesday
    4 Nov, 2026
    To Monday
    9 Nov, 2026
    English
    From:
    US$530 per person
    Price based on Private Double Room
    Double room with a double bed and shared bathroom
    $529
  • Instant Confirmation
    From Thursday
    5 Nov, 2026
    To Tuesday
    10 Nov, 2026
    English
    From:
    US$533 per person
    Price based on Private Double Room
    Double room with a double bed and shared bathroom
    $532
  • Instant Confirmation
    From Friday
    6 Nov, 2026
    To Wednesday
    11 Nov, 2026
    English
    From:
    US$533 per person
    Price based on Private Double Room
    Double room with a double bed and shared bathroom
    $532

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Trip essentials

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Tour ID: 366643

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  • Deposit only

    Book now with just a 40% deposit. The remaining balance is due 95 days before departure.

  • € - Euro

    You’ll encounter Euro in Italy.

  • Plug type L

    You’ll need an adapter for these sockets in Italy.

  • 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

      Used in Italy

  • Visa

    Whether you need a visa depends on your nationality and how long you stay. We can’t process visas for you, but here’s a quick indication for this trip.

    This is only an indication. Visa rules depend on your passport, trip length and purpose. Always confirm with the official embassy or consulate before you travel.

  • Payment information

    Pay now
    A 40% deposit
    Balance due
    95 days before departure
    Currency
    USD
    Booking fee
    None

    Book now with just a 40% deposit and pay the rest later. The remaining balance is due 95 days before departure, charged automatically to your card. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before January 23rd, 2027 will need to be paid in full at checkout.

    Accepted for Worldee tours

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    • PayPal

    TourRadar does NOT charge you an extra fee for using any of these payment methods.

  • Cancellation Policy

    Cancellation terms may vary per tour. Please check for the full cancellation policy here.

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From
US $510 per person
+ $707 Double room with a double bed

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select departure month

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
Pay only 40% today. The rest is due 95 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

Earn while you share

With TourRadar RISE, you can earn commission when someone books a tour through a link you share — like this one.

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