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2026

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2027

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2028

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Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
US $4,338 per person

Tour of Tuscany

7 days
From Radda in Chianti to Bagno Vignoni
5.0
1 traveler review
From
US $4,338 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

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2026

Jan
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Mar
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May
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2027

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Feb
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May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
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Plan your adventure:
Bicycle
Pedal-powered journeys for two-wheeled explorers
Fully Guided
An experienced guide will be with you for the entire tour
Medium Intensity
Travelers should be comfortable with somewhat-demanding activities
Guided in English
Other languages on request: Spanish
Group Size 1 - 100
Ages 18+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Chianti

    Meals
    Lunch (Light lunch upon arrival at the hotel), Dinner (Welcome evening meal hosted by the hotel's excellent chef)

    Included Activities

    • Warm-up ride in Chianti (19.3 km, 306m elevation gain)
    Landmarks
    Chianti
  2. Day 2

    Greve to Volpaia

    Meals
    Breakfast, Lunch (Lunch en route), Dinner (Evening meal in town)

    Included Activities

    • Ride to Greve and Volpaia (66.9 km, 1655m elevation gain)
    • Wine tasting in Chianti vineyard
    Landmarks
    Greve in Chianti
    Volpaia
  3. Day 3

    Gaiole in Chianti

    Meals
    Breakfast, Lunch (Lunch en route)

    Included Activities

    • Ride to Gaiole in Chianti (69.9 km, 1216m elevation gain)

    Optional Activities

    • Visit watchtowers in Gaiole
    Landmarks
    Gaiole in Chianti
  4. Day 4

    Radda to Siena

    Meals
    Breakfast, Lunch (Lunch en route), Dinner (Evening meal at the hotel)

    Included Activities

    • Ride from Radda to Siena via Castelnuovo Berardenga (74.2 km, 1671m elevation gain)
    Landmarks
    Castelnuovo Berardenga
    Siena
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Siena to Bagno Vignoni

    Meals
    Breakfast, Lunch (Lunch en route in San Quirico), Dinner (Evening meal at the hotel)

    Included Activities

    • Ride through Crete Senesi and Le Strade Bianche section (62 km, 1271m elevation gain)
    • Pass through Asciano and San Giovanni d'Asso
    Landmarks
    Crete Senesi
    Le Strade Bianche
    Asciano
    San Giovanni d'Asso
    San Quirico
    Bagno Vignoni
  6. Day 6

    Bagno Vignoni to Pienza or Montalcino

    Meals
    Breakfast, Lunch (Lunch en route), Dinner (Farewell evening meal in the village)

    Included Activities

    • Ride to Pienza or Montalcino (83.1 km, 1976m elevation gain - long route option)

    Optional Activities

    • Short ride to Pienza (UNESCO site known for Pecorino cheese)
    • Long ride to Montalcino (renowned for wine)
    Landmarks
    Pienza
    Montalcino
  7. Day 7

    Departure

    Meals
    Breakfast

    Optional Activities

    • Arrange transfers based on departure plans
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What's Included

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  • Accommodation
  • Guide
  • Meals
  • Additional Services

What's Not Included

  • Flights
  • Insurance
  • Optional
  • Additional Services
  • Transport

Operated by

Eat Sleep Cycle

5
(1 review)

Number of tours

40

Age Range

18 to 90 years old

Response time

within 2 days

Response rate

80%

At Eat Sleep Cycle it’s our pedal powered mission to share our love of...

Read more

Your Peace of Mind Options

Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Reviews from other tours by Eat Sleep Cycle

  • ALEXANDER
    October 5th, 2023
    5.0
    The route was frankly ridiculous, way to long ,the way I made it was by not doing gravel, but state roads,not what I...
    Show more

Dates & Availability

Select departure month and travellers

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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
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  • Instant Confirmation
    From Monday
    1 Jun, 2026
    To Sunday
    7 Jun, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Tuesday
    2 Jun, 2026
    To Monday
    8 Jun, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Wednesday
    3 Jun, 2026
    To Tuesday
    9 Jun, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Thursday
    4 Jun, 2026
    To Wednesday
    10 Jun, 2026
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    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Friday
    5 Jun, 2026
    To Thursday
    11 Jun, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Saturday
    6 Jun, 2026
    To Friday
    12 Jun, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Sunday
    7 Jun, 2026
    To Saturday
    13 Jun, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Monday
    5 Oct, 2026
    To Sunday
    11 Oct, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Tuesday
    6 Oct, 2026
    To Monday
    12 Oct, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
  • Instant Confirmation
    From Wednesday
    7 Oct, 2026
    To Tuesday
    13 Oct, 2026
    English, Spanish
    From:
    US $4,338 per person
    Multiple Room Types
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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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  • P

    Philip

    Asked on September 1st, 2024

    What is the level? Do you use road bikes? The review says something about gravel. Do you have availability in other tours/countries in October.

    Tour Details
    Transport
    • Eat Sleep CycleOperatorWritten September 2024

      We use road bikes. Regarding the gravel, there is an option to so some sections of gravel if you want, but it's not mandatory. We have many Tours in different destinations, like Slovenia, Portugal & Spain.

    • P

      Philip

      TravelerWritten September 2024

      Do you have availability in Tuscany tours in October? Do you have extra rooms?

    • Eat Sleep CycleOperatorWritten September 2024

      I already answer your email.

    • P
      2 more answers
Can’t find the answer to your question?
From
US $4,338 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
Save and compare this adventure

Best price guarantee Learn More

Plan your adventure:

Good to Know

Tour ID: 251015

  • 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 June 16th, 2026 a full payment is necessary. For tours departing after June 16th, 2026, a minimum payment of 50% is required to confirm your booking with Eat Sleep Cycle. 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 65 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 Eat Sleep Cycle will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Eat Sleep Cycle" 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
  • 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