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.

Overview

Details

Next Departure

October 6th 2024

From

USD $4,795

Duration

8 days / 7 nights

Non-Rider Friendly

No

Rental Bike

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!


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Trans Tuscany
The guides, the views, the food, the cycling… all spectacular!!! So professional. Booked as a 60th birthday present to myself and brought my 22 year ...

Philip & Anthony Fragassi, USA — 2022

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Trans Tuscany
This was a great trip. It restored my enthusiasm for cycling. The riding was challenging, but not impossible. Riding a section of L’Eroica was an ...

Linda Taylor, UK — 2022

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Trans Tuscany
Our first 'trans' trip. We really enjoyed the 'toned down' mileage and elevation gain of this trip. Still a challenge without being totally exhausting. It ...

Susan & Craig Moerer, USA — 2022

See more reviews
Cycling helmet, sunglasses and shoes illustration

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 View Itinerary View
Map View Map View
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02
03
04
05
06
07
08

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

Distance

Elevation


The Chianti Hills

A magnificent ride around the Chianti hills today.

The ride starts with a wonderful descent through the vast vineyards that surround Radda then continues with a series of short climbs and descents to Greve in Chianti. In Greve you’ll start the 6km (4 miles) climb to Sugame, the first of 3 climbs that come in quick succession. On the climbs, don’t forget to admire the Tuscan olive groves that share the scenery along with the typical vineyards and oak forests. The final climb tops out in Badia Coltibuono before the wonderfully scenic descent back to Radda.

Day 5

Distance

Elevation


Through the Crete Senesi to Pienza

Our destination today is the small hilltop town of Pienza in the Val d’Orcia. Pienza is a magnificent small medieval town with stunning views looking off to the south of Tuscany and the Monte Amiata mountains.

We’re in Eroica territory today so we thought we’d give you the opportunity to take on one of the first strada bianca sections of the famous race, the climb to the Castello di Brolio. From Brolio you’ll jump back onto asphalt and ride through the Crete Senesi to Asciano, with the quintessential Tuscan landscapes of rolling hills and lines of cypress trees leading to hilltop farms. In Asciano the landscape changes as we enter the vineyards of the Val d’Orica, and the small road becomes a complete roller-coaster of short, steep climbs and descents, all the way to our final destination in Pienza.

Day 6

Distance

Elevation


Montalcino

Today’s ride takes you on a magnificent loop into the hilly terrain to the south of Pienza.

Leaving the hotel you’ll head west towards the town of Montalcino, home of the world-famous Brunello di Montalcino wine. We’ll stop for a coffee in the town center – and maybe a wee sip of the famous red stuff…! From Montalcino, get your climbing legs on as the terrain gets decidedly lumpy from here. The 8km (5 miles) climb to Poggio Rosa is a taste of what’s on the agenda for tomorrow. From Poggio Rosa enjoy the descent through Castiglione and into the flat Orcia valley, before the final sting in the tail with the climb back to your hotel in the hilltop town of Pienza.

Day 7

Distance

Elevation


The Queen Stage: Monte Amiata

The Queen Stage of the trip with the major climb to Monte Amiata. With an elevation of 1,738m (5,700ft), Amiata is the highest peak in Southern Tuscany – and just too tempting not to include in our itinerary!

Enjoy the initial descent from Pienza – but remember that you’ll have to climb back up this descent at the end of the ride! The route heads south through Poggio Rosa to Castel del Piano where the serious climbing starts. The summit, with it’s fantastic café and gelato bar, lies 15km (9 miles) up the road at an average of over 7%, putting Amiata up there with some of the big climbs in the Alps. Forza!

Day 8

Distance

Elevation


Arrivederci!

Unfortunately, your trip across Tuscany has come to an end.

Our shuttle will drop you off at Florence Airport.

Map & Profile

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

Day 01
Day 02
Day 03
Day 04
Day 05
Day 06
Day 07

Climbs

Category Climb Day Difficulty Length Ele. Gain Av. Grade
2 Volterra (from Prato d’Era) 02 59 7.7%
2 Castellina in Chianti (from Tavernelle) 03 26 2.8%
3 Sugame (from Greve in Chianti) 04 34 4.8%
2 Badia a Montemuro (from Dudda) 04 46 5.2%
2 Badia a Coltibuono (from Cavriglia) 04 42 5.1%
3 Castello di Brolio (from SP408 Junction) 05 27 4.3%
3 Montalcino (from Via Cassia) 06 31 4.5%
2 Poggio Rosa (from Amiata) 06 41 5.2%
3 Pienza (from Prugnano) 06 31 5.6%
HC Monte Amiata (from Castel del Piano) 07 107 7.3%
3 Pienza (from Prugnano) 07 31 5.6%
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Dates & Prices Illustration

Dates & Prices



Date Booking Status Availability Price / Per Person Single Supplement Non-rider Discount
2024
Oct 6 - 13
Taking Bookings
Places Available
USD $4,795
USD $850
USD $900
Book this trip
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Waiting List


Sign up to the waiting list for this departure, to be notified if a space becomes available. Please fill out the information below:



    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 arrow
    • 8 days / 7 nights fully accompanied trip
    • All accommodations
    • All breakfasts
    • All dinners
    • Sit-down lunch on the 1st day
    • Picnic lunches during the rides
    • Transportation arrow
    • Pick up and drop off at Florence Airport
    • All transportation during the trip
    • All luggage & bike box transfers
    • Cycling Support arrow
    • 1 x Support Van & 1 x Ride Leader per 8 guests (approx.)
    • Experienced bike mechanic
    • Park Tools Toolkit
    • Daily ride gpx files provided
    • Nutrition during the ride arrow
    • Energy bars, gels and sports drink
    • Variety of snacks and local specialties for picnic lunches
    • Bottled water
    • Post-ride recovery food
    • Airfare
    • Travel and personal insurance
    • Additional hotel expenses i.e. phone charges, mini-bar, gratuities
    • Staff gratuities
    What's Included
      Accommodations & Meals arrow
    • 8 days / 7 nights fully accompanied trip
    • All accommodations
    • All breakfasts
    • All dinners
    • Sit-down lunch on the 1st day
    • Picnic lunches during the rides
    • Transportation arrow
    • Pick up and drop off at Florence Airport
    • All transportation during the trip
    • All luggage & bike box transfers
    • Cycling Support arrow
    • 1 x Support Van & 1 x Ride Leader per 8 guests (approx.)
    • Experienced bike mechanic
    • Park Tools Toolkit
    • Daily ride gpx files provided
    • Nutrition during the ride arrow
    • Energy bars, gels and sports drink
    • Variety of snacks and local specialties for picnic lunches
    • Bottled water
    • Post-ride recovery food
    What's Not Included
    • Airfare
    • Travel and personal insurance
    • Additional hotel expenses i.e. phone charges, mini-bar, gratuities
    • Staff gratuities

    Travel details - airport departures

    Pick-up/Drop-off Info

    Arrival

    Pickup Location Time

    Florence Airport

    9:00am

    OR

    Hotel Palazzo Castri 1874

    View website arrow

    9:00am

    Departure

    Drop Off Location Time

    Florence Airport

    9:30am


    Rental Bikes

    Specialized Aethos Expert

    Frame

    Aethos FACT 10r Carbon

    Groupset

    Di2 Shimano Ultegra

    Weight

    699g (size 56)

    Wheels

    Roval C38

    Chainrings

    52/36T

    Cassette

    11-36t (12-speed)

    Sizes

    49, 52, 54, 56, 58, 61

    USD $550

    View Details


    Trans Tuscany

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