From

US $1,176 per person

Picture Book Tuscany - Rolling Hills, picturesque Villages, Excellent Wines 8 Days

8 days

•

Start and end in Florence

4.1 (31 reviews)

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From

US $

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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1 Adult2 Adults, 1 Child2 Children

Pay only 20% today. The rest is due 65 days before departure. Learn more

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Plan your adventure:

Operator: ASI Reisen
Bicycle: Pedal through scenic landscapes on two wheels
Private Tour: Travel exclusively with your friends and family
Self-guided: Independent exploration, backed by expert advice and support
Medium Intensity: Travelers should be comfortable with somewhat-demanding activities
Guided in German
Ages 16+

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Image of a map showing the route of the tour

Itinerary

Intro
Introduction
Day 1
Florence
Florence
Landmarks
Florence
Day 2
Florence - Arezzo - Passignano sul Trasimeno
Florence - Arezzo - Passignano sul Trasimeno
Meals
Breakfast
Included Activities
- Train journey Florence to Arezzo with bike
- Walk through Arezzo old town
- Cycle through Val di Chiana valley
- Cycle through olive groves and hills to Lake Trasimeno
- Cycle along lakeshore to Passignano sul Trasimeno
Landmarks
Arezzo
Val di Chiana
Cortona
Lake Trasimeno
Passignano sul Trasimeno
Day 3
Passignano sul Trasimeno - Montepulciano
Passignano sul Trasimeno - Montepulciano
Meals
Breakfast
Included Activities
- Cycle along Lake Trasimeno lakeshore to Castiglione
- Cycle through vineyards of Vino Nobile de Montepulciano
- Explore medieval alleyways of Montepulciano
Landmarks
Castiglione del Lago
Lake Trasimeno
Montepulciano
Day 4
Montepulciano - Montalcino
Montepulciano - Montalcino
Meals
Breakfast
Included Activities
- Cycle towards Montechiello fortified village
- Cycle on Strade Bianche roads
- Pass through Pienza Renaissance town
- Cycle through Val d'Orcia landscape
- Wine tasting of Brunello wine in Montalcino
Landmarks
Montechiello
Pienza
Val d'Orcia
Montalcino
Day 5
Montalcino - Siena
Montalcino - Siena
Meals
Breakfast
Included Activities
- Cycle along Eroica routes through wheat fields
- Cycle across Campo square in Siena
Landmarks
Piazza del Campo
Palazzo Pubblico
Siena
Day 6
Siena - Radda in Chianti
Siena - Radda in Chianti
Meals
Breakfast
Included Activities
- Cycle on mountain road with vineyard views
- Stop in Vagliali stone village
- Cycle through vineyards and deciduous forests to Radda
- Enjoy typical pasta lunch in Radda
Optional Activities
- Alternative tour via Castellina through the heart of Chianti (approx. 30-70 km)
Landmarks
Vagliali
Radda in Chianti
Chianti
Castellina in Chianti
Day 7
Radda in Chianti - Florence
Radda in Chianti - Florence
Meals
Breakfast
Included Activities
- Cycle through vineyards and olive groves
- Pass through medieval villages
- Cycle through Greve in Chianti
- Descent to Ponte Vecchio in Florence
Landmarks
Greve in Chianti
Ponte Vecchio
Florence
Day 8
Florence
Florence
Meals
Breakfast
Landmarks
Florence

Landmarks
Florence

Landmarks
Arezzo
Val di Chiana
Cortona
Lake Trasimeno
Passignano sul Trasimeno

Landmarks
Castiglione del Lago
Lake Trasimeno
Montepulciano

Landmarks
Montechiello
Pienza
Val d'Orcia
Montalcino

Landmarks
Piazza del Campo
Palazzo Pubblico
Siena

Landmarks
Vagliali
Radda in Chianti
Chianti
Castellina in Chianti

Landmarks
Greve in Chianti
Ponte Vecchio
Florence

Landmarks
Florence

What's Included

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Accommodation
Meals
Additional Services
Transport

What's Not Included

Optional
Additional Services

Operated by

ASI Reisen

Rating: 4.1 (31 reviews)
Response time: within 1 day
Response rate: 96%
Cancellation policy: Learn more

Reviews from other tours by ASI Reisen

Tour Operator
4.1

M5.0•July 2026
A beautiful hike through the Dolomites. Accessible to anyone. The best part is the magnificent scenery; the worst...
Show more
Petra5.0•May 2026
Would book the trip again at any time.
Diana4.7•October 2026
You advertised this tour on your website as Sweden - Island Adventure near Stockholm 7 Days It was in fact a...
Show more

Dates & Prices

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Trip essentials

Good to know

Tour ID: 331322

The practical details for your trip across Italy: money, plugs and flexible ways to pay, all in one place.

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Pay in installments
Spread the cost in interest-free biweekly installments of $47.
Deposit only
Book now with just a 20% deposit. The remaining balance is due 65 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 20% deposit
Balance due
65 days before departure
Installments
Interest-free, every two weeks
Currency
USD
Booking fee
None
Book now with just a 20% deposit and pay the rest later. The remaining balance is due 65 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $47 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before December 24th, 2026 will need to be paid in full at checkout.
Accepted for ASI Reisen tours
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Maestro
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American Express
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.
Checking the cancellation terms for this tour…
Your money is protected. TourRadar is an authorized agent of ASI Reisen, 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.
Checking which travel protection options are available for you…
Best price guarantee
Found a lower price for the same tour elsewhere? We work directly with every tour operator, so we can match it.
How it works
Find a lower price
Spot the same tour cheaper on another site or agency.
Send us the quote
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If the quote qualifies, you book with us at that price.
Your quote needs
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Same number of travelers
Same inclusions and destinations
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What doesn’t count
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Every new booking also counts toward your , which unlocks extra savings.
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.
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From

US $

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select departure month

1 Adult2 Adults, 1 Child2 Children

Pay only 20% today. The rest is due 65 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

Picture Book Tuscany - Rolling Hills, picturesque Villages, Excellent Wines 8 Days

Explore our featured adventures

Itinerary

Included Activities

Included Activities

Included Activities

Included Activities

Included Activities

Optional Activities

Included Activities

Want to read it later?

What's Included

What's Not Included

Reviews from other tours by ASI Reisen

Dates & Prices

Want to read it later?

Why book with TourRadar?

Pay in installments

Deposit only

€ - Euro

Plug type L

Currency

Plugs & adapters

Visa

Payment information

Accepted for ASI Reisen tours

Cancellation Policy

Insurance

Best price guarantee

How it works

Your quote needs

What doesn’t count

Accessibility

People also viewed

Earn while you share

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