Included: 7-day Tuscany self-guided bike tour Accommodation for 6 nights in 3 and 4-star hotels, guesthouses, and agriturismi (in shared twin or double ensuite rooms)* Breakfasts Local representative (with bike delivery and welcome meeting) Access to the navigation app for holiday information and navigation Luggage transfers Airport transfers On scheduled arrival day from Pisa Airport (PSA) On scheduled departure day to Pisa Airport (PSA) Add-ons: Bike rental — $355 for hybrid bike, $540 for e-bike Single supplement — $390 Hotel upgrade (based on double occupancy) — $320 Single supplement for the hotel upgrade — $470 Not included: Transportation to Italy Meals not listed in the itinerary Personal clothing and equipment Personal expenditure (souvenirs, bar bills, hotel facilities, etc.) Entrance fees to museums and other attractions enroute Local tourist tax — to be paid locally, approximately 2 euros per day Airport transfers on days other than the scheduled arrival/departure days Guide gratuities — optional Travel and medical insurance — optional *Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary (in case there is a detailed list).

How fit do I need to be?

Fitness and experience This Tuscany self-guided bike tour is suitable for those who perhaps have only recently gotten into cycling, and there’s an array of accessible, cycle-friendly paths and roads. Still, there will be some days and sections where you’ll have to tackle some ups and downs as well as the occasional steeper climb. This tour is ideal for those with a decent level of fitness, looking for some leisurely rides with occasional (though achievable!) challenges along the way. Generally, you’ll cover around 20 miles (32 km) every day. Terrain and roads Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, dotted with hilltop hamlets. Riding is mostly on quiet tarmac roads (95% – shared with traffic, can be busier in the summer months) and some well-beaten gravel roads (5% – mostly strade bianche), with days involving riding up to hilltop towns. You will find certain sections have some steeper, more challenging climbs. Day 4 riding up to the Chianti region will prove the most challenging following a roller coaster route. Hybrid bikes are recommended for this tour, but it’s possible to cycle the route on a road or gravel bike, bearing in mind there are some short gravel sections. An e-bike is also a great option if you wish to spend more time exploring towns and villages along the way. An e-bike would also help those in need of a little boost (particularly if riding in September when it can get quite hot) to cover some of the longer distances, and cheeky climbs mid-week. Just note that e-bikes are generally heavier than hybrid bikes, so worth considering when handling the bike. Bike rentals are possible upon checkout.

What do I need to bring?

Here’s a list of the equipment you need to bring: Bike — available to rent Helmet — available to rent Comfortable, season-appropriate riding or athletic clothing, preferably moisture wicking or synthetic material Padded shorts Peaked helmet Sneakers or sport shoes Breathable outside layer or jacket Sunglasses Plenty of water, water bottle or hydration bladder Daypack with snacks Biking gloves are optional but recommended Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.) Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

Indeed you can! If you don’t own a suitable bike or would prefer to avoid bringing your own to this Tuscany self-guided bike tour, you can rent one with your guides. Rental bikes will be provided with a pannier rack and 1 bag, a phone mount, a water bottle holder, a puncture repair kit, a spare inner tube, a bike lock and a bike pump. Hybrid bikes (typically Focus Univega Geo or equivalent) or e-bikes (typically Focus Univega Geo e-bikes or similar) are rented out for this tour. If you choose to bring your own e-bike, on any of departures, please contact us so we can discuss the bike specification and ensure it is suitable for the tour. Helmets can be provided locally on request. If you would like us to organise this please request a helmet at the time of booking.

What is a self-guided tour?

A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator, such as maps, guidebooks, audio guides, or digital apps. By going on this Tuscany self-guided bike tour, you’ll have lots of things arranged for you, making your cycling experience a lot less stressful and a lot more enjoyable: accommodation at 3 and 4-star hotels, guesthouses, and agriturismi all breakfasts airport transfers on arrival and departure app for information and navigation luggage transfers local representative for a welcome meeting After you get transferred to San Gimignano and once you’ve talked to a local representative, the self-guided tour starts! Keep in mind that your guides offer support along the way should you need anything.

Group sizes and age requirements

Group sizes and pricing For this Tuscany self-guided bike tour, the maximum group size is generally set to 14 participants. It takes a minimum of 2 people for this self-guided tour to operate. Please note that your chosen dates for the tour are not guaranteed until confirmed by the guide. If the guide is unable to secure your preferred dates/accommodation, you’ll get a full refund! Tuscany self-guided bike tours can be arranged for larger groups. Contact us to make arrangements. Min. age requirements If you are older than 18, you’re good to go. Children as young as 10 are able to go on trips with a legal guardian. They may be able to participate on a case-by-case basis. If your group has riders under the age of 18, contact us prior to booking to make arrangements.

Getting there and meeting location

To get to your Tuscany self-guided bike tour, first you’ll fly into Pisa Airport (PSA) . Transfer from the airport to the town of San Gimignano is included in the price of the tour. Please aim to arrive between 9 am and 4 pm, and depart between noon and 7 pm. Important note on dates & accommodations Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary. Also note that your chosen dates for the tour are not guaranteed until confirmed by the guide. Please don’t book any flights or accommodations before your trip is confirmed by your guide !

Safety measures and insurance

Medical and travel protection are mandatory on this adventure. To make your booking and traveling experience as carefree as possible , simply choose Redpoint—the official 57hours insurance partner ! Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered. Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!

TUSCANY | ITALY

Classic Tuscany Bike Tour: A Self-Guided Adventure

5.00

Cyclist in Tuscany on a sunny summer day

Group going along a quiet cycle path in Tuscany

Sunset view through the door of San Gimignano

Intro
Brochure
Reviews
Things to know

Duration

7 days

Season

March through October

Accommodation

3 or 4-star hotels, guesthouses, and agriturismi

Self-guided tour

Accommodation, breakfasts, app with navigation and information, luggage and airport transfers arranged for you

Sipping on a Negroni in a historic town center, under the Tuscan sun, refreshing yourself after a day’s ride through rolling hills and bucolic landscapes. This could be you soon, but it’s also just a tiny portion of what you’ll experience if you head on this week-long, self-guided bike tour through Tuscany. You’ll discover charming hilltop towns, taste the Chianti wine reminiscent of sour cherries, smell the fragrant olive and fruit trees, and hear the chirp of crickets on warm nights. Starting from the Town of Fine Towers, San Gimignano, you’ll pedal your way through quintessential Tuscan villages, vineyards, and cypress-lined paths, all the way to the remarkable Siena. This is cycling and exploring Italy at its finest.

Adventure highlights

Paradise for wine aficionados

Sample the finest wines of Chianti, Montepulciano, and Montalcino
Cycling how you like it

No need to rush or catch up with the group—explore this wonder of a region at your own pace
Absorbing the Tuscan atmosphere

Stay at Tuscan farms, visit Renaissance towns, and taste local Italian dishes

Highlighted reviews from other travellers

Lorna

All aspects of the cycling tour were excellent from the initial contact and followup emails back and forth in the months preceding our trip to the details provided at the very start of the trip in San Gimignano. Instructions were clear and the self guided maps and information provided were accurate and relatively easy to follow. Great bikes! Solid, easy to ride and well tuned. We were surprised somewhat to see that the tires provided were slicks instead of tires with some tread. We were a little concerned on the first day when it rained that the roads would be slippery but it wasn’t an issue. Overall, yes, good value for the money.

Pradeep

Tuscan scenery was awesome! Representatives were excellent. I needed some bike repair at the end of day 4 in Siena and it was done after a single text message with no hassle at all. No errors on the map and easy to follow!

Julie

Excellently described and true to the descriptions. A full and thorough briefing at the start of the trip and great directions (map and words) – we never got lost once. Excellent service during the booking process and on arrival, through to the taxi transfers to and from the airport. The ride from Casole D‘Elsa to Abbadia Isola (and for our changed itinerary) through to Monteriggiano was excellent – lovely road through some amazing countryside (though the whole week could be described this way) but we had a cappuccino stop at the restaurant recommended en route. Questions answered promptly and well and nothing was too much trouble. A really excellent trip – so well organised and made easy work (despite the hills & heat) of the beautiful Tuscan countryside. Thank you very much to all the team!

Show all reviews

Classic Tuscany Bike Tour: A Self-Guided Adventure

Adventure Brochure

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If you have questions or need help with planning a trip, schedule a call with one of our adventure experts.

Meet your guide

5.00

Saddle Skedaddle

Saddle Skedaddle was founded by a couple of MTB pros (Paul and Andrew) while trapped in a snowstorm during their year-long biking adventure in Chile. They believe travel should move you and that there’s no better way to see a place properly—its people, culture, and natural wonders—than by bike. Saddle Skedaddle currently runs tours in 36 destinations, offering adventure junkies incredible places to tour on two wheels.

5.00(4 reviews)

Lorna

Pradeep

Julie

Show all reviews

Lorna

Pradeep

Julie

Greg

Bikes were great – good quality and well set up. The route planning and maps worked fantastically and we didn’t get lost once. Superb arrangements and communication. Everything happened as you said it would and at the time it was arranged. The ride into Sienna was a favourite – as there were some fantastic views.

Things to know

Included:
- - 7-day Tuscany self-guided bike tour
  - Accommodation for 6 nights in 3 and 4-star hotels, guesthouses, and agriturismi (in shared twin or double ensuite rooms)*
  - Breakfasts
  - Local representative (with bike delivery and welcome meeting)
  - Access to the navigation app for holiday information and navigation
  - Luggage transfers
  - Airport transfers
    
    On scheduled arrival day from Pisa Airport (PSA)
    
    On scheduled departure day to Pisa Airport (PSA)
Add-ons:
- - Bike rental — $355 for hybrid bike, $540 for e-bike
  - Single supplement — $390
  - Hotel upgrade (based on double occupancy) — $320
  - Single supplement for the hotel upgrade — $470
Not included:
- - Transportation to Italy
  - Meals not listed in the itinerary
  - Personal clothing and equipment
  - Personal expenditure (souvenirs, bar bills, hotel facilities, etc.)
  - Entrance fees to museums and other attractions enroute
  - Local tourist tax — to be paid locally, approximately 2 euros per day
  - Airport transfers on days other than the scheduled arrival/departure days
  - Guide gratuities — optional
  - Travel and medical insurance — optional
*Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary (in case there is a detailed list).
Fitness and experience
This Tuscany self-guided bike tour is suitable for those who perhaps have only recently gotten into cycling, and there’s an array of accessible, cycle-friendly paths and roads. Still, there will be some days and sections where you’ll have to tackle some ups and downs as well as the occasional steeper climb. This tour is ideal for those with a decent level of fitness, looking for some leisurely rides with occasional (though achievable!) challenges along the way. Generally, you’ll cover around 20 miles (32 km) every day.

Terrain and roads
- - Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, dotted with hilltop hamlets. Riding is mostly on quiet tarmac roads (95% – shared with traffic, can be busier in the summer months) and some well-beaten gravel roads (5% – mostly strade bianche), with days involving riding up to hilltop towns. You will find certain sections have some steeper, more challenging climbs.
  - Day 4 riding up to the Chianti region will prove the most challenging following a roller coaster route.
  - Hybrid bikes are recommended for this tour, but it’s possible to cycle the route on a road or gravel bike, bearing in mind there are some short gravel sections.
  - An e-bike is also a great option if you wish to spend more time exploring towns and villages along the way. An e-bike would also help those in need of a little boost (particularly if riding in September when it can get quite hot) to cover some of the longer distances, and cheeky climbs mid-week. Just note that e-bikes are generally heavier than hybrid bikes, so worth considering when handling the bike.
  - Bike rentals are possible upon checkout.
Here’s a list of the equipment you need to bring:
- - Bike — available to rent
  - Helmet — available to rent
  - Comfortable, season-appropriate riding or athletic clothing, preferably moisture wicking or synthetic material
  - Padded shorts
  - Peaked helmet
  - Sneakers or sport shoes
  - Breathable outside layer or jacket
  - Sunglasses
  - Plenty of water, water bottle or hydration bladder
  - Daypack with snacks
  - Biking gloves are optional but recommended
  - Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
Indeed you can! If you don’t own a suitable bike or would prefer to avoid bringing your own to this Tuscany self-guided bike tour, you can rent one with your guides. Rental bikes will be provided with a pannier rack and 1 bag, a phone mount, a water bottle holder, a puncture repair kit, a spare inner tube, a bike lock and a bike pump.

Hybrid bikes (typically Focus Univega Geo or equivalent) or e-bikes (typically Focus Univega Geo e-bikes or similar) are rented out for this tour.

If you choose to bring your own e-bike, on any of departures, please contact us so we can discuss the bike specification and ensure it is suitable for the tour.

Helmets can be provided locally on request. If you would like us to organise this please request a helmet at the time of booking.
A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator, such as maps, guidebooks, audio guides, or digital apps.

By going on this Tuscany self-guided bike tour, you’ll have lots of things arranged for you, making your cycling experience a lot less stressful and a lot more enjoyable:
- - accommodation at 3 and 4-star hotels, guesthouses, and agriturismi
  - all breakfasts
  - airport transfers on arrival and departure
  - app for information and navigation
  - luggage transfers
  - local representative for a welcome meeting
After you get transferred to San Gimignano and once you’ve talked to a local representative, the self-guided tour starts! Keep in mind that your guides offer support along the way should you need anything.
Group sizes and pricing
- - For this Tuscany self-guided bike tour, the maximum group size is generally set to 14 participants.
  - It takes a minimum of 2 people for this self-guided tour to operate.
  - Please note that your chosen dates for the tour are not guaranteed until confirmed by the guide. If the guide is unable to secure your preferred dates/accommodation, you’ll get a full refund!
Tuscany self-guided bike tours can be arranged for larger groups. Contact us to make arrangements.

Min. age requirements
- - If you are older than 18, you’re good to go.
  - Children as young as 10 are able to go on trips with a legal guardian. They may be able to participate on a case-by-case basis.
If your group has riders under the age of 18, contact us prior to booking to make arrangements.
To get to your Tuscany self-guided bike tour, first you’ll fly into Pisa Airport (PSA). Transfer from the airport to the town of San Gimignano is included in the price of the tour. Please aim to arrive between 9 am and 4 pm, and depart between noon and 7 pm.

Important note on dates & accommodations

Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary.
Also note that your chosen dates for the tour are not guaranteed until confirmed by the guide. Please don’t book any flights or accommodations before your trip is confirmed by your guide!
Medical and travel protection are mandatory on this adventure. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!

Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!
A non-refundable $250 deposit to secure your place is due upon booking. The remaining amount is paid 2 months (60 days) prior to departure. Once the trip is confirmed by the guide, the cancellation policy stated below applies.
- - If the Client cancels the Booking anytime prior to sixty (60) calendar days in advance of the trip contemplated by the booking, the Client will forfeit the deposit.
  - For cancellations thirty (30) to sixty (60) calendar days in advance, Client is entitled to a refund in the amount of fifty percent (50%) of the trip price.
  - If you cancel your booking less than thirty (30) calendar days prior to the departure date, Client is not entitled to any refund.
If you need to cancel the trip, please contact us in writing. If you wish to transfer a booking to another person, please write to us at least seven (7) days before your trip. Administration charges may arise.