- Staying at Tuscan farms overlooking stunning countryside
- Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
- Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
- Trying delicious, regional dishes
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
Arrival into Pisa airport and transfer to San Gimignano (transfer approx. 1.5 hours). You will have the rest of the day to explore the local area and get prepared for your first day of cycling.
- Meals: Breakfast
- Ascent: 500 Metres Approx.
This morning your local representative will fit you to your rental bikes (if renting) and conduct your welcome meeting. Now is the perfect time to ask any questions you may have about the week ahead.
The fascinating town of San Gimignano is the town of towers and is one of the prettiest and best-preserved medieval settlements in the whole of Italy. San Gimignano is also known for its white wine, Vernaccia di San Gimignano, which is grown in the area. The old town is a UNESCO World Heritage Site. We recommend taking a walk through its narrow streets – a great opportunity to absorb the Tuscan atmosphere. Back on the bikes you will descend towards the plains of Colle Val d‘Elsa. You’ll ride past woodland and cultivated fields making your way towards the hill-top town of Casole d‘Elsa. The last few kilometres are challenging but the views from the top of the hill will certainly outweigh the effort. You’ll have some time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany. The accommodation is set just outside the walled centre, a short walk into town and where you can enjoy an evening drink. We recommend watching the sunset from the bastions overlooking the hills of Tuscany.
- Meals: Breakfast
- Ascent: 400 Metres Approx.
You’ll leave Casole d‘Elsa on a rolling road passing small stone villages scattered throughout the countryside. Sections of the route are part of the Via Francigena, the pilgrimage route from Canterbury to Rome. This ancient road will lead you straight to your accommodation, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. A short cycle away from your accommodation you’ll find Abbadia Isola.
The fields surrounding Abbadia Isola were once a large swamp or bog that accumulated rain water from Monte Maggio. ‘Isola’ refers to an island or the only solid piece of land on which the original ancient hamlet was built. The Abbey of St Salvatore was founded in the 11th century and was an important strategic crossroad on the Via Francigena between Florence, Fiesole, Siena and Volterra. Now the Abbey is surrounded by flat fields filled with sunflowers in summer, and it’s an easy-going and enjoyable cycle from your accommodation.
- Meals: Breakfast
- Ascent: 600 Metres Approx.
Today is the toughest stage of the week, with a roller coaster ride through the northwestern side of Siena and into the Chianti region. Don’t worry though, each new climb will be rewarded with a fantastic descent!
The first climb takes you to the Castle of Monteriggioni with its 13th-century architecture. The massive walls here are linked with Dante’s Divine Comedy and, at that time, served as a defensive stronghold of the town of Siena against rival Florence. A gentle stroll through the narrow streets is a must, as well as a cycle round the fortified walls. Back on the bikes, you’ll head towards Castellina in Chianti. You will soon realise you are cycling in wine territory as you pass acre after acre of vineyards. Castellina in Chianti is well worth exploring on foot; its importance is not only connected to wine, but also to the abundance of Etruscan sites found in this region.
Such rich archeological heritage justifies a visit to the territorial museum for Chianti Senese, its collection including findings not only from the township of Castellina in Chianti, but from Castelnuovo Berardenga, Gaiole in Chianti and Radda in Chianti as well. Leaving Castellina, another 11 Kms will take you to Radda in Chianti, a beautiful medieval town enclosed in large defensive walls.
- Meals: Breakfast
- Ascent: 500 Metres Approx.
Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent past vineyards towards Gaiole in Chianti, where you can take a slight detour to visit the town. The birthplace of Chianti Classico, Gaiole is celebrated in its own right.
In medieval times it was one of the three capitals of the Chianti League, along with Castellina and Radda. The hilltop town is set among oak and chestnut forests but also surveys vineyards and olive groves. As a former military stronghold, Gaiole is ringed by medieval castles and fortified abbeys. Today Gaiole is also known as the birthplace of the “Eroica” (1997) a vintage cycling event, that brings thousands of riders in the region cycling along the “strade bianche“. Gaiole is a perfect stop for a long lunch, before cycling back to Radda in Chianti.
- Meals: Breakfast
- Ascent: 550 Metres Approx.
Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent, the landscape changing from oak forests to cultivated fields as you make your way towards Siena.
This whole region is dotted with castles, once defensive systems but now privately owned by wine producers. Your route will then take you past Meleto, San Donato in Perano and Brolio Castle. You’ll follow a mixture of tarmac and “strade bianche” (gravel roads) as you get closer to Siena, with glimpses of bell towers and churches.
Entering Siena from the Porta Romana will lead you straight to the heart of the city, Piazza del Campo, where the famous Palio takes place. There will be time to wander through Siena in the late afternoon, with a visit to the Palio Square and the Duomo, before heading out to dinner for a mouthwatering Tuscan meal.
- Meals: Breakfast
Today you’ll say ciao to this beautiful part of Italy and we’ll transfer you back to Pisa airport for your outgoing flight. (Transfer approx. 1.5 hours.)
Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, dotted with hill-top hamlets. Riding is mostly on quiet tarmac roads (95% – shared with traffic, can be busier in the summer months) and some well-beaten gravel roads (5% – mostly strade bianche), with days involving riding up to hill-top towns.
You will find certain sections have some steeper more challenging climbs. Day 4 riding up to the Chianti region will prove the most challenging following a roller coaster route.
We recommend hybrid bikes for this tour, but it’s possible to cycle the route on a gravel, or road bike, bearing in mind there are some short gravel sections
Leisure Cycling Grade
Aspects of both our grade 2 and 3 holidays
Suitable for those looking for some cycle friendly routes
Features some modest climbs
Possibly sections of varying terrain (eg. forest tracks, gravel paths etc).
Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!
For more information about our grading system click here.
Is this suitable for you?
Holidays that are graded as a 2-3, will have aspects of both our grade 2 and 3 holidays. These tours are still suitable for those perhaps who have recently got into cycling, and offer an array of accessible, cycle friendly routes, cycle paths and quiet roads, however there will be some days / sections where you may have to tackle some ups and downs, the occasional steeper climb and perhaps some varying terrain (forest tracks, gravel paths etc). Suitable for those with a decent level of physical fitness, looking for some leisurely rides with occasional (achievable!) challenges along the way.
Dates & Prices
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2023 26 Mar – 30 Oct
Season 1 – £1195 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct
Season 2 – £1485 06 Apr – 14 Apr and 18 Jun – 03 Sep
Alternatively for a great value holiday choose one of our scheduled departures below.
A) Accommodation (shared twin / double en suite rooms) in small hotels / agriturismi / guesthouses
B) Meals as per the itinerary (B-Breakfast, L=Lunch, D=Dinner)
C) English-speaking local representative (with welcome meeting)
D) Access to the Skedaddle App for holiday information and navigation
E) Luggage transfers
F) Airport transfer on scheduled arrival day from Pisa airport (PSA)
G) Airport transfer on scheduled departure day to Pisa airport (PSA)
What's not Included
A) Bike rental (available if required)
B) Flights and charges for travelling with your bike (if applicable)
C) Single room (available if required)
D) Travel insurance
E) Meals not stated in the itinerary
F) Personal clothing and equipment
G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)
H) Entrance fees to museums and other attractions en route
I) Local tourist tax (to be paid locally – Approx. 2€ per day)
J) Airport transfers on days other than the scheduled arrival / departure days
News, Reviews & Stories
All aspects of the cycling tour were excellent from the initial contact and followup emails back and forth in the months preceding our trip to the details provided at the very start of the trip in San Gimignano. Instructions were clear and the self guided maps and information provided were accurate and relatively easy to follow. Great bikes! Solid, easy to ride and well tuned. We were surprised somewhat to see that the tires provided were slicks instead of tires with some tread. We were a little concerned on the first day when it rained that the roads would be slippery but it wasn’t an issue. Overall, yes, good value for the money.
Pradeep, SomersetHassle free holiday
Tuscan scenery was awesome! Representatives were excellent. I needed some bike repair at the end of day 4 in Siena and it was done after a single text message with no hassle at all. No errors on the map and easy to follow!
Julie, HertfordshireTrue to the descriptions!
Excellently described and true to the descriptions. A full and thorough briefing at the start of the trip and great directions (map and words) – we never got lost once. Excellent service during the booking process and on arrival, through to the taxi transfers to and from the airport.
The ride from Casole D‘Elsa to Abbadia Isola (and for our changed itinerary) through to Monteriggiano was excellent – lovely road through some amazing countryside (though the whole week could be described this way) but we had a cappuccino stop at the restaurant recommended en route.
Questions answered promptly and well and nothing was too much trouble. A really excellent trip – so well organised and made easy work (despite the hills & heat) of the beautiful Tuscan countryside. Thank you very much to all the team!
Greg, ShropshireFantastic views
Bikes were great – good quality and well set up. The route planning and maps worked fantastically and we didn’t get lost once. Superb arrangements and communication. Everything happened as you said it would and at the time it was arranged. The ride into Sienna was a favourite – as there were some fantastic views.
Fred, LancashireGreat accommodation..
Both of our tour guides were extremely knowledgeable and helpful. They were always available.
The standard of the accommodation was better than I have come to expect on ski holidays. It was my first cycling holiday, but it won’t be my last, and Skedaddle will definitely be top of my list!
Sara, West YorkshireBrilliant!
Really enjoyed every aspect of the holiday. Great scenery, wonderful food, brilliant guides!