Tour of Tuscany

Scheduled

6 nights

Intermediate

320 km

5850 m

Tuscany

Summary

Welcome to the picturesque Chianti region, a perfect place to be introduced to Tuscany. Ride out to the quaint and charming villages of the region. In Greve, discover the architectural history and extrordinary Italian food & wines that make this region so unique. Gaiole offers a preview of what were the battles for local power that dominated these lands for over a hundred years. Pedal through the stunning vineyards and villages of Castelnuovo Berardenga as well as the UNESCO Siena hills. You’ll ride the “Crete Senesi” and a section of “Le Strade Bianche” passing through Asciano and San Giovanni D’Asso. This experience will allow you to fully immerse yourself in the beautiful Tuscan region of Italy.

The tour takes you to luxurious hotels across the Tuscan region. The first two nights are at the Realis Il Vignale in Radda in Chianti with a panoramic terrace overlooking the Chianti Hills. The Restaurant is an authentic example of culinary excellence, paired with their local wines. The next hotel, Certosa di Maggiano is loacted just outside of Siena. Enjoy wonderful hospitality and relax on the terrace overlooking the Chianti hills. Osteria dell Orcia is the final hotel for the tour in Bagno Vignoni it is situated in the UNESCO countryside, Val d’Orcia and is a 16th Century, historic building.

Dine out each evening at local restaurants and at your hotel on the more challenging ride days. The team will ensure you get to see and taste the best parts of the region. Each restuarant offers something different & our selection is designed to showcase the best food in the region. Lunches are served by your guide team in scenic locations along each route and feature healthy, fresh, seasonal produce designed to keep you riding all week.

DURATION

7 days / 6 nights

DISTANCE

320 km

HOTELS
★★★★★
REGION

Italy Cycling Tours

Terrain

Road

LEVEL

Intermediate

Average Distance X DAY

53 km

Average Time X DAY

2 h 40 min

PRICE PER PERSON FROM€ 3.699
Book now with a 30% DEPOSITfrom € 1110

TOUR highlights

White Gravel Roads

Wine tasting in Radda in Chianti

UNESCO site

Historical landmarks

Local cheese and wine

IS THIS TOUR FOR ME?

Intermediate

Rated 2 out of 4 our Intermediate tours are designed for sporty people who are looking to enjoy some more challenging rides. E-bikes are available on all of our tours.

ITINERARY

Day 1

Welcome to Tuscany

Welcome to the picturesque Chianti region. After checking in and meeting the team, head out on a short warm up ride to ensure everything is running smoothly for the week ahead. Enjoy a warm welcome evening meal tonight hosted by the hotel's excellent chef.

EAT

Light lunch upon arrival at the hotel, welcome evening meal at the hotel

SLEEP

Relais Il Vignale

CYCLE

Warm up ride 24 km, 460 m

Day 1

Village of Volpaia & Chianti Wine Tasting

Ride out to the quaint and charming village of Greve and discover the architetural history and extrordinary Italian food & wines that make this region so unique. as well enjoying a small tast of the Tuscan gravel roads. Have lunch in the village of Volpaia, a fortified village with hidden wine cellars. In the afternoon we'll shuttle to a local vinyeard to enjoy a touch of wine tasting. Dinner tonight is at one of our favoruite places in the village.

EAT

Breakfast, lunch en route, wine tasting in Chianti vineyard, evening meal in Radda

SLEEP

Relais Il Vignale

CYCLE

Village of Volpaia 50 km, 1,300 m

Day 1

Point to point ride to Siena

Today we pack up and start our joruney south towards Siena. Our ride passes by the stunning vineyards and villages to the stunning Certosa di Maggiano just outside of Siena.

EAT

Breakfast, lunch en route, evening meal at the hotel

SLEEP

Certosa di Maggiano

CYCLE

To Siena, 85 km, 900 m

Day 1

Crete Senesi & visit Siena

Today is a chance for a shorter ride, with time to explore Siena or relax at the hotel in the afternoon.

EAT

Breakfast, lunch en route, evening meal at the hotel

SLEEP

Certosa di Maggiano

CYCLE

Crete Senesi, 45 km, 780 m

Day 1

Le Strade Bianche to Bagno Vignoni

Our final point to point ride is to Bagno Vignoni. The UNESCO Siena hills and the countryside make this ride truely spectacular. You'll ride the "Crete Senesi" and a section of "Le Strade Bianche" passing through Asciano and San Giovanni D'Asso. Have lunch in San Quirico then bike to your final accommodation, the wonderful Osteria dell Orcia in Bagno Vignoni.

EAT

Breakfast, lunch en route, evening meal at the hotel

SLEEP

Osteria dell Orcia

CYCLE

Strade Bianche, 70 km, 1,000 m

Day 1

Pienza!

The final ride of the tour will take you to Pienza, a UNESCO site and very famous for the Pecorino cheese. Celebrate tonight with a farwell evening meal.

EAT

Breakfast, lunch en route, farewell evening meal in the village

SLEEP

Osteria dell Orcia

CYCLE

Loop ride to Pienza, 55 km, 890 m

Day 1

Departure day

Sadly, the tour has come to a close. Let us know your departure plans and we will organise any necessary transfers for you.

EAT

Breakfast

SLEEP

-

CYCLE

Departure day

THE TOUR
IN DETAIL

RIDE SUPPORT

Full Support

Enjoy full ride support from our professional guide team & support vehicle.

The ride support vehicle is stocked with natural ride nutrition, electrolytes and water, as well as a full set of tools to resolve any mechanicals. On selected days the support crew will serve a delicious picnic lunch in a scenic location en route. Enjoy local foods chosen to keep you feeling energized and healthy.

Eat Sleep Cycle guides are experienced riders from all walks of life united by a love of cycling who’ll help to keep the group safe, motivated and savouring the trip of a lifetime.

All guests will receive access to our digital Road Book and routes, giving everyone the flexibility to ride at their own pace.

HOTELS

Hotels shown are examples and are subject to change

BIKE HIRE

Not included
Bike hire is not included in the tour. Add bike rental to the trip from €40 per day

Basso Astra

The best all-rounder for long-distance comfort, the Basso Astra as a Campagnolo 12spd Wireless Groupset (48-32 || 10-29) and a Microtech RE38 Wheelset

Basso Diamante

The ulitmate Italian climbing bike from Basso. Equipped with Campagnolo 12spd Wireless Groupset (48-32 || 10-29) and Campagnolo WTO Wheelset

Premium Upgrade

THE GUIDES

Emanuela

Emanuela is Italian and after many years living in Barcelona relocated to Mallorca. She started triathlon 10 years ago and has made it her life! Alongside guiding Emanuela hosts guests from all over the world in her Airbnb.

Emanuela-Eat-Sleep-Cycle-Guide-Mallorca
Mario

During the past 10 years, Mario has lived in different countries, but now he's back home in Conegliano to ride every steep hill in the area! Despite his focus on road cycling, he's had some amazing moments with his beloved steel gravel bike! Mario has been a member of the ESC Team since 2019 and couldn't be happier! He looks forward to seeing you on the road soon!

Details

LOGISTICS AND TRANSPORTATION

HOW TO GET HERE

Travel to Florence

MEETING POINT

Florence Train Station

TIME

11:00 am

DEPARTURE

There is a 1 hour group transfer to Siena train station on the last day of the tour departing at 10:00 AM

WHAT THE TOUR INCLUDES

CYCLING

Full Support

ACCOMMODATION

4* luxury hotels

FOOD

Breakfast, lunch and 5 evening meals

TRANSFERS

Group transfers are incldued as described.

BIKE RENTAL

High end road bike rental is included in the tour.

EAT SLEEP CYCLE LOCATION

ESC Italy Cycling Tours

Italia! Pizza! Pasta! The Giro! Italy is a classic destination for cycling holidays, with a huge variety of landscapes to explore & a history steeped in cycling culture. Italy is best enjoyed from April through to June and in the Autumn months.

Italy cycling tours offer something special for every cyclist. Whether you’re looking for mountain ranges, excellent food or to ride around the lakes, our cycling holidays in Italy have you covered.

From the high mountains of the Alps and Dolomites in the North, to the Italian Lakes of Lombardia & Piemonte, to the rolling hills of Tuscany and Emilia Romagna, and off-shore to the islands of Siciliy & Sardinia, Italy promises to wow!

View our Italy YouTube video

Ready
to ride?

RESERVATION
& PAYMENT

If you have any questions about our tours, dates, or anything else, contact us here
/1
DEPOSIT

A 30% deposit will secure your place on the tour

/2
FINAL BALANCE

The final balance is due 90 days before the tour departs

Single Occupancy:  PLUS €899
Sunday

25 May 2025

Saturday

31 May 2025

€3.699Book now
Monday

16 June 2025

Sunday

22 June 2025

SOLD OUT
Monday

13 October 2025

Sunday

19 October 2025

€3.699Book now
Monday

27 October 2025

Sunday

2 November 2025

SOLD OUT
Start

Custom

Finish

Custom

€ Custom
MORE INFO

Any Questions?CONTACT US

FAQs

1

What happens if I need to cancel the trip?

We have a flexible cancelation policy – please take a look at our cancellation policy at the time of booking. If you have any doubts please reach out and we’re happy to help.

1

Is the tour the right level for me?

We rate our tours from Level 1 (Leisure) to Level 4 (Epic). Each tour contains a description of the level, expected daily ride time, distance and elevation. If you have any doubts we’re more that happy to speak to you on the phone and help to find you the perfect trip!

1

What about bikes? Can I hire one or should I bring my own?

We recommend that you hire a bike for your tour and will work with you after you book to help you to choose the best size and model for your ride style. If you prefer to bring your bike, it’s no problem. Please be aware that on some of our epic trips we charge a supplement to transport your bike box to our finishing location. If you have any doubts, please ask!

1

Is insurance included?

Insurance is not included in our tour packages. We highly recommend contracting travel insurance at the time of reservation with a company from where you are from.

Health insurance which covers you for illness or injury whilst cycling in your chosen destination is mandatory, we’ll ask you for details of your insurance providor before you travel.

cross