Tuscany: Cycle Siena & Chianti

8 days
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4.7/5 Excellent
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Small Group Tour
The Tuscan landscape is one of the most evocative and romantic in Europe, with cypress tree-lined roads, olive groves, vineyards, ancient hilltop towns and, of course, classic Renaissance cities. Our group cycling tour is carefully planned to take in the best of Tuscany without feeling rushed: part of the joy of the Italian lifestyle is sitting and watching t...
$3,949
From$2,925
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Overview

Trip type
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

    • Explore the cultural cities of Siena and Florence
    • Enjoy Tuscan cuisine and wine
    • Visit some of the most beautiful hilltop towns in the region
    • Ride along the scenic country roads of classic Tuscany

What's this trip about?

    The Tuscan landscape is one of the most evocative and romantic in Europe, with cypress tree-lined roads, olive groves, vineyards, ancient hilltop towns and, of course, classic Renaissance cities. Our group cycling tour is carefully planned to take in the best of Tuscany without feeling rushed: part of the joy of the Italian lifestyle is sitting and watching the world go by with a glass of wine in your hand. We ride through historically diverse areas of Tuscany, such as the Chianti hills and beautiful countryside around Montepulciano. Riding north, we discover a wonderfully scenic region, home to some of Tuscany’s most beautiful towns and villages. We then enjoy the magnificent Piazza del Campo in Siena before biking past the towers of San Gimignano and on to our final destination in Florence. Following country roads wherever possible, we mix point-to-point and circular rides to make a perfect cycling tour of this region.Ride along the back roads of classic Tuscany­­

Details

Itinerary focusClassic Highlights
Group sizeSmall Group - max of 16 people
Age range16 years and up
Flights and transportAll internal ground transport included
Start CitySan Quirico D'Orcia or Pienza
End CityFlorence

Travel Themes

  • Cultural
  • Cycling & Biking

Destinations

Attractions

  • Florence
  • Siena
  • Tuscany

Activities

  • Culture
  • Cycling

Min Group Size

  • Min Group Size: 6

Max Group Size

  • Max Group Size: 16

Trip includes

    • All breakfasts
    • All accommodation
    • All transport and listed activities
    • Tour leader throughout
    • Local bike hire
    • Group arrival and departure transfers available

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Itinerary

Travel Map

Day 1 Start at your hotel in the Orcia Valley

We start in the Orcia Valley, staying in one the local hilltop towns, San Quirico D'Orcia or Pienza. There’ll be a welcome briefing at the hotel, where we gather as a group to go over the trip ahead.

Day 2 Circular ride through classic Tuscan countryside via the wine town of Montepulciano and thermal spa village of Bagno Vignoni

Today we enjoy a circular ride in the Orcia Valley. Taking in Pienza and San Quirico d'Orcia, we cycle to the beautifully situated wine centre of Montepulciano, best known for producing vino nobile. We then head towards the medieval village of Monticchiello and on to the well known thermal bath of Bagno Vignoni, before making our way back to the hotel.

Day 3 Ride through vineyards and the walled town of Murlo to Siena

A classic day's riding, showing Tuscany at its most picturesque. Following back roads, we head out of San Quirico with a first stop at Montalcino. We then descend on the road to Buonconvento and ride back up to Murlo, passing by Bibbiano. From here, we ascend the shor...

Day 4 Free day in Siena to explore or relax

Siena is one of the best-preserved medieval towns in Italy and home to the grand Piazza del Campo. There is plenty to see in Siena and its sights are best explored on foot as the town is compact but hilly. There are many museums and buildings of interest to visit, such as the impressive duomo (cathedral). Alternatively, you may choose to head out for an unguided ride.

Day 5 Ride via Gaiole and Radda to Castellina in Chianti

From Siena, we head directly into the heart of Chianti. Our picturesque route takes us via some lovely small villages and hamlets, plus spectacular vineyards and castles, such as Castello di Brolio. Here there is the option to taste some of the finest regional wines. ...

Day 6 Circular ride through the Chianti hills via towers of San Gimignano and Monteriggioni

From Castellina, we ride through rolling countryside before taking a scenic descent into the lower valley. From Poggibonsi, we head towards the distant towers of San Gimignano, nestled between hills and small hamlets. The Unesco-recognised town, famous for its towers,...

Day 7 Cycle to Florence via Panzano and Greve in Chianti

Our final ride passes through Panzano towards the market town of Greve in Chianti. This is considered one of the most scenic roads in Tuscany, which links Florence to Siena via the Chianti hills. On arrival in Greve in Chianti, we have time to admire the triangular pi...

Day 8 End Florence.

The trip comes to an end after breakfast. However, if you’d like a little longer to explore this magnificent city, please speak to your sales representative.

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Dates & Availability

Price From $2,925
Price per day$366
Last Updated: 5/22/2024

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

Check current availability, prices, specials & more.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

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Exodus Adventure Travels Reviews & Ratings

4.7/5  Excellent
Excellent
13,502
Great
3,265
Average
609
Disappointing
146
Terrible
190
A

Anonymous

Oct 2018

Lovely Hol

Second trip with Exodus. Lovely holiday cycling through Tuscany, finishing in Florence. Lots of clmb, but not too severe. Great weather, food & wine. Group we...

A

Anonymous

Oct 2018

Siena cycle trip review

organised and well supported cycle trip through beautiful tuscan countryside with visits to Florence and siena. Not one specific thing but generally enjoyed the cha...

A

Anonymous

Oct 2018

Cycling in Tuscany

Excellent and memorable cycling trip! This was my daughter's first cycling trip. She is athletic but not an experienced cyclist. She had a wonderful experience wit...

A

Anonymous

Oct 2018

Cycling Siena and Chianti

Great cycle routes, well planned stops, good climbs and descents. Reaching the tops of some of the more challenging hills Jon was a fabulous group leader, well org...

A

Anonymous

Oct 2018

Amazing adventure!

This was my first cycling tour and tour with Exodus. I had an amazing experience! The trip was well planned and I feel like it had the prefect balance of cycling, ...

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Sheila Bissell

Apr 2025

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Excellent service

Excellent service

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Apr 2025

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Roger

They were very helpful, polite and knowledgeable

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Gill Barber

Apr 2025

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Quick invoice receipt sent...prompt

Quick invoice receipt sent...prompt, good service

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Logistics

What's excluded

    • Travel insurance
    • Single accommodation (available on request)
    • Visas or vaccinations
    • Local taxes
    • E-bike hire

Accommodation

7 nights at 3 and 4 star hotels with en suite facilities 5 days cycling, average 58km/day 100% vehicle support (with limited seats) 85% tarmac, 15% easy gravel roads (most optional)
You will spend seven nights in family-run and comfortable three-star hotels. All accommodations have been carefully selected for their welcoming atmosphere and all rooms have en suite facilities. Some hotels have a swimming pool where we can relax after the long cycling days. Examples of hotels used are: Orcia Valley: Wellness Hotel Casanova or Relais Chiostro di Pienza Siena: Hotel Minerva Castellina in Chianti: Hotel Il Colombaio or Hotel Casafrassi Florence: Hotel Classic We can arrange single rooms throughout the trip (subject to availability). Please check with your sales representative for availability and prices. Please note that during peak travelling periods or in case of last minute bookings, alternative hotels may be assigned on an individual basis and that supplements may apply.
Cancellation policy

The cancellation policies of this trip when booked through Travelstride are determined by the stated policies of the tour operator - Exodus Adventure Travels.

If you or any other member of your party decides to cancel a confirmed booking you must notify Travelstride in writing. Your notice of cancellation will only take effect when it is received in writing by Travelstride and will be effective from the date on which we receive it.

Period before departure in which you notify us

From the date your Booking Confirmation is issued up to, and including, 90 days prior to the departure date specified on the Booking Confirmation.

  • 89 to 52 days (inclusive) prior to the departure date specified on the Booking Confirmation.
  • 51 to 31 days (inclusive) prior to the departure date specified on the Booking Confirmation.
  • 30 days or less prior to the departure date specified on the Booking Confirmation, or after the booking has started

Cancellation charge

Deposit can be transferred to a new booking which must be made within 3 months of the date the original booking was cancelled, and depart within 12 months of the new booking date. If a new booking is not made within this period then the deposit will be forfeited. Any remaining balance will be refunded excluding any non-refundable costs.

  • 50% of the total holiday cost. Any remaining balance will be refunded excluding any non-refundable costs.
  • 75% of the total holiday cost. Any remaining balance will be refunded excluding any non-refundable costs.
  • 100% of the total holiday cost.

For Polar holidays, the following cancellation charges will be made:

Cancellation period (before departure) - Cancellation Fee (per person)

Outside of 180 days - No fee if cancelled within 15 days of booking date. US $1,250 cancellation fee if cancelled 16 days or more of booking date.

179 to 120 days - Loss of deposit.

119 to 90 days prior to departure - 50% of the holiday cost.

89 to 60 days prior to departure - 75% of the holiday cost. 

59 to 0 days prior to departure - 100% of the holiday cost.

For more additional details, see the booking conditions of Exodus Adventure Travels at the following web address: https://www.exodustravels.com/us/about-exodus/exodus-booking-conditions

Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included
All breakfasts are included and are Continental in style, consisting of coffee or tea, cereals, cheese and cold meat, bread, pastries, yoghurt, jam and/or honey. Tuscan food is authentic and surprising – pizza and pasta are just the tip of the iceberg when it comes to the diverse cuisine on this trip. Starters may include antipasti of cured meats or a crostini di fegato made from toasted bread slices topped with chicken liver pâté . Soup options may include the classic bean dish of zuppa di fagioli or ribollita, a delicious, hearty vegetable and bread soup. For mains, you might try the truffle-infused pasta dish tagliatelle al tartufo or a mouth-watering T-bone steak delicacy known as bistecca alla Fiorentina. End your meal with cantucci biscuits dipped into a glass of the sweet dessert wine known as vin santo for a true taste of Tuscany. While Tuscan cuisine has a strong meat focus, vegetarians can be well catered for. Please inform us of any dietary requirements at the time of booking.
Age Requirements
16 years and up
Additional Information
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Trip ID
exodus-MWI

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