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Who is travelling?

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From
US $1,514 per person

The Ultimate Tuscany Escape: Florence, San Gimignano, Val D'Orcia & Chianti | 5 Days

5 days
•
From Florence to San Gimignano
4.6 (392 reviews)
From
US $1,514 per person

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 5% today. The rest is due 50 days before departure. Learn more

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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 2 - 8
Ages 18+
Image of a map showing the route of the tour

Itinerary

  1. Intro

    Introduction

  2. Day 1

    Florence

    Florence
    Start point
    Florence, Italy (Check in available from 2:00 pm. Meet your guide in the afternoon to join the walking tour. Detailed information will be released 2 weeks before the tour departure, 14:00 - 17:00)
    Accommodation
    Hotel 3* (Hotel Corona or similar)

    Included Activities

    • Introductory stroll through Florence's city center
    • Visit to Duomo
    • Visit to Piazza della Signoria
    • Visit to Ponte Vecchio

    Optional Activities

    • Florentine aperitivo featuring Spritz and regional specialties
    Landmarks
    Duomo
    Piazza della Signoria
    Ponte Vecchio
  3. Day 2

    Florence

    Florence
    Accommodation
    Hotel 3* (Hotel Corona or similar)

    Optional Activities

    • Day Trip to Pisa & Cinque Terre - explore Tuscany's coastline and visit the Leaning Tower of Pisa
    • Accademia & Uffizi Museums Walking Tour - guided tour of Florence's world-renowned art collections
    • Wine Windows & Oltrarno Artisans Tour - discover hidden gems, local craftsmanship, and historic wine windows
    Landmarks
    Leaning Tower of Pisa
    Accademia Gallery
    Uffizi Gallery
  4. Day 3

    Florence - Siena - Cortona - Montepulciano - San Gimignano

    Florence - Siena - Cortona - Montepulciano - San Gimignano
    Meals
    Breakfast (Hearty breakfast before departure)
    Accommodation
    Hotel 3* (Hotel Leon Bianco or similar)

    Included Activities

    • Guided tour through Siena's medieval streets
    • Visit to Piazza del Campo
    • Visit to Siena's Gothic cathedral
    • Stop in Cortona with panoramic views and artisan shops
    • Local countryside farm visit and tasting of traditional cured meats
    • Visit to Montepulciano medieval town
    Landmarks
    Piazza del Campo
    Siena Cathedral
    Cortona
    Montepulciano
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 4

    San Gimignano - Chianti Region - San Gimignano

    San Gimignano - Chianti Region - San Gimignano
    Accommodation
    Hotel 3* (Hotel Leon Bianco or similar)

    Included Activities

    • Visit to boutique Chianti winery with behind-the-scenes tour
    • Chianti wine tasting paired with authentic regional specialties
    • Visit to family-run estate in Chianti
    • Award-winning wine sampling at family estate
    • Guided exploration of San Gimignano medieval streets and towers
    Landmarks
    San Gimignano
    Chianti Region
  6. Day 5

    Chianti - Florence

    Chianti - Florence
    End point
    Florence, Italy (Check out in Chianti before 11:00 am. Back to Florence by 5:15 pm, 17:00 - 17:30)
    Meals
    Lunch (Tuscan lunch - taste your own creations from cooking class paired with regional wine)

    Included Activities

    • Hands-on cooking class led by local chef
    • Prepare traditional Tuscan dishes with fresh, seasonal ingredients
    • Tuscan lunch - taste your own creations
    • Wine pairing with regional wine

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What's Included

Expand All
  • Accommodation
  • Additional Services
  • Transport

What's Not Included

  • Additional Services

Where You'll Stay

All accommodations are subject to change
Gold Operator
Rating
4.6 (392 reviews)
Response time
within 2 days
Response rate
96%
Cancellation policy
Learn more

Reviews from other tours by Italy on a Budget Tours

  • Joelle5.0•July 2026
    Gio was so lovely and knowledgeable, very good.

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Dates & Prices

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2026

Jan
Feb
Mar
Apr
May
Jun
Jul
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Oct
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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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  • From Friday
    16 Oct, 2026
    To Tuesday
    20 Oct, 2026
    English
    From:
    US$1,514 per person
    Price based on Private Double Room
  • From Tuesday
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    To Saturday
    24 Oct, 2026
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    From:
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    Price based on Private Double Room
  • From Friday
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    To Tuesday
    27 Oct, 2026
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    From:
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  • From Friday
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    3 Nov, 2026
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  • From Thursday
    5 Nov, 2026
    To Monday
    9 Nov, 2026
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  • Instant Confirmation
    From Thursday
    19 Nov, 2026
    To Monday
    23 Nov, 2026
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  • Instant Confirmation
    From Thursday
    11 Mar, 2027
    To Monday
    15 Mar, 2027
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    From:
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    18 Mar, 2027
    To Monday
    22 Mar, 2027
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  • Instant Confirmation
    From Thursday
    25 Mar, 2027
    To Monday
    29 Mar, 2027
    English
    From:
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    Price based on Private Double Room

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What our customers ask about this tour

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  • V

    Valerie

    Asked on August 26th, 2026

    Just inquiring about this Tour if it's available for 2027

    Price / Availability
    • Italy on a Budget ToursOperator•Written August 2026

      I'm delighted to confirm that our 2027 tour availability is already open, so you can check the availability and exact price for the Thursday, May 13th, 2027 departure directly on the booking page.

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Trip essentials

Good to know

Tour ID: 158439

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  • Pay in installments

    Spread the cost in interest-free biweekly installments of $80.

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    You’ll encounter Euro in Italy.

  • Plug type L

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

  • Currency

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    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

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From
US $1,514 per person

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 5% today. The rest is due 50 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

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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