Tuscany's many rolling hills. Photo via Flickr:Giampoalo Macorig
Valdimontone di Siena, Siena, Tuscany, Italy. Photo via Flickr:Dimitry B.

Duomo in Florence, Tuscany, Italy. Photo by Patrick Hickey
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Tuscany - Florence, Siena, and the Chianti!

Italy Bike Tours

A glorious bike tour in Tuscany

This bicycle tour in Italy starts in Siena, with it’s amazing Piazza del Campo that has been declared a World Heritage Site. On it is the famous Palazzo Pubblico, a great art museum which is itself a marvel of architecture. The famous Palio horse races are also held in Siena. From Siena, the tour heads north to the beautiful village of Radda in Chianti. Situated on a hill covered with vineyards, Radda also produces the best olive oil in the region. Further along your bike in Tuscany, you’ll ride through the famous vineyards of the Chianti region to Greve and finish the day's bike in Florence. The capital of Tuscany, Florence is located on the banks of the Arno River in the very heart of Italy. Enjoy this very unique city when drinking your café latte on the Piazza della Signoria with the sculpture of David by Michelangelo in your sight.

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Skill Level

This Tuscany bike tour is classified as difficult. Though daily distances are not excessive, some climbs are very steep and continuous. The total vertical distance is 3,970m. Tour runs primarily on side roads. Entering and exiting the cities, you will encounter traffic, that at times can be heavy. Distances range from 25 to 28 miles per day.

Where You’ll Stay

Cozy and comfortable 2 star-3 star hotels, B&B’s, and agriturismos.

What’s Included

  • Hotel accommodations for 7 nights
  • Breakfast buffets
  • 21-speed hybrid bicycle
  • Luggage transfer
  • Route descriptions & maps
  • 7 day hotline service
  • Free parking (if arriving by car)

What’s Not Included

Extra Stay

Extra night in Florence, Siena, or Pisa possible.

TourBike
TypeSelf Guided
SkillDifficult
Length8 days
From685 Rates
Client Reviews

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Tour Dates

2016 Dates
Every Saturday from April 9 to October 8, 2016
*Special departure dates can be arranged for groups of at least 5.

Day-To-Day Itinerary

Tuscany - Florence, Siena, and the Chianti! Map

Varation 1: 

DAY 1: Arrival in Siena
DAY 2: Siena - Radda in Chianti, 28 mi. (45 km)
DAY 3: Radda in Chianti - Greve, 25 mi. (40 km)
DAY 4: Greve - Florence, 25 mi. (40 km)
DAY 5: Florence
DAY 6: Florence - Colle Val D'Elsa,  25 mi. (40 km) by train and then 16 mi. (25 km) by bike.
DAY 7: Colle Val D'Elsa - Siena, 25 mi. (40 km)
DAY 8: Siena

Variation 2:

DAY 5: Florence - Tavarnelle, 25 mi. (40 km)
DAY 6: Tavarnelle - Colle Val D'Elsa, 28 mi. (45 km)
DAY 7: Colle Val D'Elsa - Siena, 25 mi. (40 km)
DAY 8: Departure

*All distances are approximate.

Varation 1: 

DAY 1: Arrival in Siena
Arrival in Siena. Bikes can be picked up at a local bike shop.

DAY 2: Siena - Radda in Chianti, 28 mi. (45 km)
From Siena you will start your Tuscany bike tour by heading north towards the beautiful village of Radda in Chianti. This town is situated on a hill covered with woods and extensive vineyards forming the watershed between the Pesa and Arbia valleys. Formerly belonging to the Guidi family, it came under Florentine control in 1203. After being fortified in 1400 it was, from 1415 onwards, head of the League of Chianti, and it preserves the remains of its ancient walls.

DAY 3: Radda in Chianti - Greve, 25 mi. (40 km)
Today, you continue cycling through Italy over the Tuscan hills and breathtaking views will accompany you through the famous vineyards of the Chianti region. You will have the option once you reach Panzano to choose between the longer and shorter stages. If you chose the longer stage, your reward will be the challenges of the climbs with beautiful views and the small village of Sillano, famouse for its old parish, San Pietro whose recorded history dates back to before the year 884 when it is mentioned in the parchment of the Badia a Passignano. The shorter stage is all downhill into the enchanting down of Greve with its historic triangular main piazza, where a market has been running more or less continuously for centuries serving the nearby castle communities and hamlets. Greve is a town that invites you to stroll and experience as there are lovely, ancient alleyways that meander throughout the outskirts of the town. Observe the flowers and gardens, even on second story balconies, and the ever present laundry hanging from almost every window.

DAY 4: Greve - Florence, 25 mi. (40 km)
Today's you will bike Florence - the capital of Tuscany - located on the banks of the Arno River between the Adriatic and Tyrrhenian Seas, in the very heart of Italy. Your ride this day will have you climb the mountain tops where your view of Florence is usually bought with a price by your typcial tourist. You however, will merge with the Italians as you bike into the city, cross the street and are suddenly overjoyed to see the Ponte Vecchio on your left and the lovely Arno in front. Enjoy this very unique and artistic city when drinking your café latte on the Piazza della Signoria with the copy of the sculpture of David by Michelangelo in your sight. Renaissance villas, age old olive trees, romantic parishes and lonely cypresses make this opportunity worth an extra day in Florence.

DAY 5: Florence.
Florence is often considered the birthplace of the Italian Renaissance and was long ruled by the Medici family. Florence is also famous, of course, for it's magnificent art and architecture.  You have the entire day to spend in this city!

DAY 6: Florence - Colle Val D'Elsa,  25 mi. (40 km) by train and then 16 mi. (25 km) by bike.
You start your day with a short train transfer which will bring you to Certaldo and after ward  to your destination, Val d'Elsa. It is situated on the Via Francigena, a historic road leading to Rome from Canterbury, a major route which in the past was used by thousands of pilgrims on their way to Rome.

DAY 7: Colle Val D'Elsa - Siena, 25 mi. (40 km)
From the Val d'Elsa valley you cycle back to the beautiful town of Siena. Siena preserves its medieval character to a remarkable degree, and has been largely unspoiled by new buildings. Its beautiful Gothic buildings include the Cathedral and Palazzo Pubblico on the characteristic Piazza del Campo with its tower (La Mangia), as well as numerous churches.

DAY 8: Siena
This Italy bike tour will end after breakfast, or an extension is possible in this magnificent country. 

Variation 2:

DAY 5: Florence - Tavarnelle, 25 mi. (40 km)
 The village of Tavarnelle Val di Pesa has Roman origins; it is named after the ancient taverns offering accommodation and refreshment located alon the road which linked Florence to Siena and thence to Rome.

DAY 6: Tavarnelle - Colle Val D'Elsa, 28 mi. (45 km)
From Tavarnelle, you cycle to Colle di Val d'Elsa which lies in the heart of Tuscany, in a strategically favorable position near athe towns of Siena and Florence. It is situated ont eh via Francigena that connects Rome with the North. On the way you pass Certaldo whose upper portion has remained as it was in the middle ages. Further you you come across San Gimignano, which rises on a hill dominating the Elsa Valley with its towers. 

DAY 7: Colle Val D'Elsa - Siena, 25 mi. (40 km)
See above

DAY 8: Departure

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Customer Feedback

  • mary 9 months ago

    This is Mary from Tripsite and this was my very first Tripsite tour back in 2010, I believe. I was traveling alone and self guided so flexibility was required, not to mention that my first cycling day was the coldest on record for years! ( I was cycling in early April.) I did get turned around a few times as I learned to read the route descriptions and follow the maps but each Tuscan hilltop was a reward in and of itself. From this tour I learned that when cycling self guided do expect: 1. To get turned around at least once or twice 2. That the Italians will always tell you to go straight 3. That the ancient streets many times do not have their names clearly visible 4. That most of the towns are located on a hill. 5. That Tuscany is simply stunning! Highlight: seeing Florence from afar from a hilltop and then cycling down and into the ancient city itself. I also learned that some of the best experiences happen when you least expect it! I am giving this a four star because personally I felt the bike was very heavy (but thankfully geared low enough for the hills!)

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