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Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided

8 days
•
From Cortona to Siena
5.0 (2 reviews)

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Plan your adventure:
Bicycle
Pedal through scenic landscapes on two wheels
Self-guided
Independent exploration, backed by expert advice and support
High Intensity
Travelers should be in very good physical condition and expect continuous demanding activities
Guided in English
All Ages Welcome

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Image of a map showing the route of the tour

Itinerary

  1. Intro

    Introduction

  2. Day 1

    Cortona

    Cortona
    Meals
    Breakfast

    Included Activities

    • Bike fitting and briefing in English by professional staff
    • Explore Cortona's Medieval streets

    Optional Activities

    • Visit Etruscan Museum
    • Visit Diocesan Museum with Fra Angelico paintings
    Landmarks
    Cortona
    Etruscan Museum (MAEC)
    Diocesan Museum of Cortona
  3. Day 2

    Lake Trasimeno

    Lake Trasimeno
    Meals
    Breakfast

    Included Activities

    • Cycle ride to Lake Trasimeno with route options

    Optional Activities

    • Boat ride on Lake Trasimeno to Isola Maggiore
    Landmarks
    Lake Trasimeno
    Isola Maggiore
  4. Day 3

    Pienza

    Pienza
    Meals
    Breakfast

    Included Activities

    • Cycle ride through Montepulciano medieval streets
    • Cycle ride to Pienza Renaissance town

    Optional Activities

    • Visit typical wine cellars in Montepulciano
    Landmarks
    Montepulciano
    Pienza
  5. Day 4

    Val d'Orcia

    Val d'Orcia
    Meals
    Breakfast

    Included Activities

    • Loop ride through Val d'Orcia landscape
    • Cycle through Monticchiello Medieval village

    Optional Activities

    • Sample local wines and cheeses in Pienza
    Landmarks
    Val d'Orcia
    Monticchiello
  6. Day 5

    Montalcino

    Montalcino
    Meals
    Breakfast

    Included Activities

    • Cycle ride from Pienza to Montalcino
    • Stop in Trequanda village
    Landmarks
    Trequanda
    Montalcino
  7. Day 6

    Montalcino

    Montalcino
    Meals
    Breakfast

    Included Activities

    • Cycle visit to Abbey of Sant Antimo

    Optional Activities

    • Visit Bagno Vignoni thermal spa village
    • Explore San Quirico d'Orcia
    Landmarks
    Abbey of Sant Antimo
    Castiglione d'Orcia
    Bagno Vignoni
    San Quirico d'Orcia
  8. Day 7

    Siena

    Siena
    Meals
    Breakfast

    Included Activities

    • Cycle ride to Siena
    • Pass by Monte Oliveto Maggiore monastery
    • Ride through Crete Senesi chalk hills
    Landmarks
    Monte Oliveto Maggiore
    Crete Senesi
    Siena
  9. Day 8

    Siena

    Siena
    Meals
    Breakfast

    Optional Activities

    • Explore Siena for additional days
    • Optional guided visit of Siena
    Landmarks
    Siena

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What's Included

Expand All
  • Accommodation
  • Meals
  • Additional Services
  • Optional Extras

What's Not Included

  • Flights
  • Insurance
  • Additional Services

Operated by

BikesPlus Travel

Rating
4.7 (49 reviews)
Response time
within 2 days
Response rate
50%
Cancellation policy
Learn more

Traveler Reviews

5.0
Overall rating based on 2 Reviews
  • Itinerary
    5.0
  • Transport
    5.0
  • Guide
    5.0
  • Accommodation
    5.0
  • Food
    5.0
  • 4.7

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  • Michael
    Michael5.0•July 2019
    From beginning to end, Cycle Europe was fantastic. The pre-planning and communication was incredible. The bikes...
    Show more
    Traveled in July 2019
  • kathysteinberger5.0•January 2019
    Although the route was very hilly, we loved everything about our self-guided tour. The itinerary kept us on...
    Show more
    Traveled in July 2018

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Good to know

Tour ID: 109997

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  • Deposit only

    Book now with just a $450 deposit. The remaining balance is due 90 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 $450 deposit
    Balance due
    90 days before departure
    Currency
    USD
    Booking fee
    None

    Book now with just a $450 deposit and pay the rest later. The remaining balance is due 90 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 24th, 2027 will need to be paid in full at checkout.

    Accepted for BikesPlus Travel tours

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

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  • 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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No departure dates available

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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