Trans Tuscany















Trans Tuscany
The mecca of Italian cycling, Tuscany is the ultimate destination for the keen cyclist
The quintessential Italy, Tuscany is famous for hilltop towns, Chianti, cypress trees, great food and the ultimate in Italian style. But it’s also home to some of the most spectacular cycling in Europe.
Featured Climbs
Monte Amiata, Castello di Brolio, Poggio di Sugame, Volterra
Overview
Details
Next Departure
October 6th 2024
From
USD $4,795
Duration
8 days / 7 nights
Non-Rider Friendly
No
Rental Bike
From USD $550
Ride Program
Total Distance
Total Elevation
Daily Av. Distance
Daily Av. Elevation
Overview
Tuscany is the perfect destination for a classic Thomson trip — stunningly beautiful rides, great climbs, wonderful hotels, and arguably the best food, wine and coffee in Europe.
Your journey starts in the medieval town of San Gimignano with it’s impressive 14 towers, each a symbol of past wealth. From San Gimignano you’ll ride to the hilltop town of Volterra and into the world-famous Chianti region. Chianti is home to the legendary Eroica bike race and you’ll get the opportunity to test your gravel riding skills on the official strade bianche climb to Castello di Brolio. From Chianti you’ll head south over the Crete Senesi to the medieval town of Pienza and a ride to Montalcino, home of the famous Brunello di Montalcino wine. The trip concludes with the climb to Southern Tuscany’s highest peak, Monte Amiata.
Join us in Tuscany for an unforgettable experience and some of the best bike riding Europe has to offer!
Susan & Craig Moerer, USA — 2022
Linda Taylor, UK — 2022
Tom Barberi, USA — 2022

Itinerary
Day | Description | Distance | Elevation | Hotel | |
---|---|---|---|---|---|
01 | Benvenuti in Toscana | Hotel Villa San Paolo | |||
02 | Volterra | Hotel Villa San Paolo | |||
03 | Into Chianti | Hotel CDH Radda | |||
04 | The Chianti Hills | Hotel CDH Radda | |||
05 | Through the Crete Senesi to Pienza | Hotel Il Chiostro di Pienza | |||
06 | Montalcino | Hotel Il Chiostro di Pienza | |||
07 | The Queen Stage: Monte Amiata | Hotel Il Chiostro di Pienza | |||
08 | Arrivederci! | ||||
Daily Averages |
Itinerary Detail
Day 1
Distance
Elevation
Benvenuti in Toscana
Your trip starts at Florence Airport where our staff will meet you before the transfer to your hotel in the medieval town of San Gimignano.
After lunch, orientation meeting and bike build-up, you’ll head out for your first ride through the rolling Vernaccia vineyards that surround San Gimignano.

Day 2
Distance
Elevation
Volterra
The magnificent, walled mountaintop town of Volterra is the main highlight of today’s ride.
To get to Volterra you’ll head into some rugged terrain in the beautifully remote region of Tuscany between Castagno and Villamagna. At the 40km (25 miles) mark you’ll see the medieval walls of Volterra perched high on the hill above you, signalling the start of the steep 5km (3 miles) climb from the valley floor to the town gates. Ride through the town gate into the medieval town and stop at one of the magnificent plazas for a coffee or a gelato (or both!).
From Volterra enjoy the sweeping descents, then a wonderful ride through the Castelvecchio Natural Reserve back to the hotel in San Gimignano.

Day 3
Distance
Elevation
Into Chianti
From the famous white wine Vernaccia vineyards around San Gimignano today’s ride takes you into the famous red wine vineyards of Chianti.
Leaving your hotel in San Gimignano, you’ll head east through the Val d’Elsa and Val di Pesa. The bridge over the Pesa river in Bargino marks the start of the long climb to the world-famous Chianti region. The climb tops out in Castellina in Chianti and from there the road rolls through the typical Tuscan oak forests before reaching your hotel in Radda in Chianti.

Day 4
Day 5
Day 6
Day 7
Day 8
Map & Profile
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
No major climbs today |
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
Volterra from Prato d’Era |
7.7% | 2 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
Castellina in Chianti from Tavernelle |
2.8% | 2 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
Sugame from Greve in Chianti |
4.8% | 3 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
|||||
Badia a Montemuro from Dudda |
5.2% | 2 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
|||||
Badia a Coltibuono from Cavriglia |
5.1% | 2 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
Castello di Brolio from SP408 Junction |
4.3% | 3 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
Montalcino from Via Cassia |
4.5% | 3 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
|||||
Poggio Rosa from Amiata |
5.2% | 2 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
|||||
Pienza from Prugnano |
5.6% | 3 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
Monte Amiata from Castel del Piano |
7.3% | HC | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
|||||
Pienza from Prugnano |
5.6% | 3 | |||
Profile
Map
Gradient (%)
0
0-6
6-8
8-10
10-12
12-15
>15
|
Climb | Distance | Elevation | Av. Grade | Category | |
---|---|---|---|---|---|
No major climbs today |
Climbs
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Climbs

Dates & Prices
Date | Booking Status | Availability | Price / Per Person | Single Supplement | Non-rider Discount | ||
---|---|---|---|---|---|---|---|
2023 | |||||||
Book this tripClosed
|
Oct 17 - 24 |
Closed |
Places Available |
USD $4,495
|
USD $800 |
USD $840 |
Book this trip |
2024 | |||||||
Oct 6 - 13 |
Taking Bookings |
Places Available |
USD $4,795
|
USD $850 |
USD $900 |
Book this trip |
Waiting List
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Trip Hotels

Hotel Villa San Paolo

Hotel CDH Radda

Hotel Il Chiostro di Pienza
What's Included
What's Included | What's Not Included |
---|---|
Accommodations & Meals
Transportation
Cycling Support
Nutrition during the ride
|
|
What's Included |
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Accommodations & Meals
Transportation
Cycling Support
Nutrition during the ride
|
What's Not Included |
|

Pick-up/Drop-off Info
Arrival
Pickup Location | Time |
---|---|
Florence Airport |
9:00am |
OR |
|
Hotel Palazzo Castri 1874 |
9:00am |
Departure
Drop Off Location | Time |
---|---|
Florence Airport |
9:30am |
Rental Bikes

Felt FR Advanced
Read More
Frame
Felt FR Advanced
Groupset
2023 SRAM Force AXS 12-speed
Weight
7.7kg (size 53)
Wheels
Reynolds AR46 DB Custom
Chainrings
48x35
Cassette
10-33
Sizes
47, 51, 54, 56, 58, 61
USD $550
View Details
3T Exploro Boost e-bike
Read More
Frame
3T Exploro Ultra Boost Carbon
Groupset
Sram Rival AXS XPLR Electronic
Weight
12.8kg
Wheels
Rodi alloy 700c
Chainrings
40
Cassette
12-speed 10-44t
Sizes
XXS, 51, 54, 56, 58, 61
USD $750
View Details































Trans Tuscany
Let us introduce you to Tuscany and some of the most sensational riding in Europe.