Self Guided Walking Holidays & Cycling Holidays

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Tuscany's vineyard cloaked landscapes


  • Ride the Chianti Classico wine routes of Tuscany
  • Ponte Vecchio Bridge & the Duomo of Florence
  • Cycle stages of the Giro d’Italia
  • Rustic Tuscan breads and local pomodori
  • Enjoy a Chianti in the buzz of Siena’s Piazzo del Campo

Ride from Florence to Siena through the heart of Tuscany’s Chianti postcard perfect wine region.

Steeped in road cycling heritage, ride stages of the Giro d’Italia through the café filled piazza’s of Strada and Greve in Chianti. Stay at the charming Radda in Chianti, home to Tuscany’s largest collection of wine at ‘Casa del Chianti Classico’. Cycle to the towers of San Gimignano with its world class gelato. Ride Cypress tree lined roads to Siena's Piazza del Campo, perfect for people watching and a post-ride dish of local parpadelle pasta.

Day 1 Arrive Florence

On arrival into Florence your centrally located accommodation is only a few minutes walk from the must sees of The Renaissance Gardens, Ponte Vecchio Bridge and the glorious Duomo. Depending on your arrival time you can have a bike fitting today, or alternatively assemble your own bike ready for a quick afternoon spin and stretch of the legs.

Overnight: Florence

Day 2 Cycle to Radda in Chianti

Ride into the heart of the Chianti wine region via the local and pro’s favourite route, the 'Via Chiantgiana'. Leaving Florence visit the museum of Tour de France and Italian cycling legend, Gino Bartali. Roll south through cafe filled piazza’s of Greve and Panzano in Chianti. Your last stop of the day is the charming, historic wine town of Radda in Chianti where you will spend the next 2 nights.

Cycle: 55 km

Ascent/Descent: 850m/500m+

Overnight: Radda in Chianti

Day 3 Chianti Winelands Loop Ride

Take in a loop ride through the Chianti wine lands. Tap out a steady rhythm on the climb to Giaole in Chianti, home to 12th century Brolio Castle, the regions largest vineyard. A rapid descent heads through Castelnuovo dei Sabionni before a rolling route returns to the pool and gardens of your hotel. Later, why not visit the Casa del Chianti Classico. This former 15th century convent houses the largest collection of Chianti labels ready for sampling under expert guidance.

Cycle: 55 km +

Ascent/Descent: 1450m +/-

Overnight: Radda in Chianti

Day 4 Cycle to Siena

Leaving Radda, cycle sections of the Giro d’Italia stages as you head west to the hilltop town of San Gimignano famed for it’s 14 towers (and the world’s best gelato shop!). On leaving San Gimignano, the route passes through the old town streets of  Monteriggioni and into the grandeur of Siena’s old town centre piece, the Piazza di Campo pefect for a post-ride beer!

Cycle: 58 km + (or 76 km)

Ascent/Descent: 850m/700m

Day 5 Onward Travel

With train links to Pisa (1hr45min), Florence (1-2 hours) and Rome (3hrs30min), onward travel from Siena is simple. However, you may prefer to further explore the art filled streets and Gothic architecture of Siena before your departure.


Each Tuscan accommodation is different and full of character. Typical hotels and B&B's are listed
below, though on occasion we may have to book you an alternative accommodation especially during the busier periods of the year. The price of your tour is based on a standard room at each of the listed accommodations.


Included are 4 breakfasts, which usually consists of fresh pastries, breads, fruits, yogurts, cheeses, meats and granola. If you have special dietary requirements do let us know at the time of

Lunches and dinners are not included. Never too far from a piazza, your route notes suggest a number of local places to dine
and of course, being in the heart of Chianti, there is fine red wine in abundace.

Single Rooms

If you're travelling with friends or family but prefer your own room, single rooms are subject to availability and a supplementary payment. This trip is not available to solo cyclists.




Hotel David - Florence

A 19th century mansion converted into a family run hotel is within easy reach of all the major sights of Florence. Sitting south of the River Arno also makes for an easy exit from Florence the following morning.




Relais Vignale – Radda in Chianti

In the heart of Radda in Chianti and only a few steps from the buzzing village centre, the peaceful grounds complete with pool is perfect for any post ride relaxation.




La Chicca - Siena

La Chicca - Siena

Owned by the Garavini family La Chicca is a 10 min walk from the Piazza Campo. The property has 6 bright, spacious, comfortable rooms along with a garden and private terrace.





This trip is available to start on any day from May to October and we suggest that you contact us as soon as
possible if you are considering a departure during the peak season of May-June and September.

Navigation, Route Notes & Maps

The cycling in this region follows well surfaced roads through towns, villages and minor country routes and is truly picture postcard Tuscany. Although the riding is not technical you must feel comfortable with rapid and sometimes narrow hairpin descents and be equipped to deal with a change in weather and road condition.

Although we can supply GPX tracks along with our tried and tested detailed routes notes and maps, the roads are well signposted and are generally cycle friendly.

Should you require assistance, 24/7 telephone support will also be available throughout your trip.

Rental Bikes

We recognise the importance of being at one with your bike, which is why we have  partnered with a preferred road bike supplier in Tuscany.

Focus Cayo 5.0 carbon bikes are available to hire in a number of sizes. All bikes come with a spare tube, pump, levers and a cycle computer.

Your hire bike will be delivered to your hotel in Florence and can be set up with flat, Look or Shimano spd pedals.

Focus Cayo Road Bike

If you’d like to hire a bike, please let us know your height and
frame size you currently ride, along with any other specific requests
you may have. We’re always happy to answer any questions regarding hire

If you would to bring your own road bike please ensure it is
thoroughly serviced and is an appropriate road bike for this trip.

General Information

All bike tours are unescorted. The distances listed are approximations of the recommended routes.
Please be prepared by packing all necessary items, for example, cycle clothing and personal medications etc.

Travel Insurance

It is a requirement of booking this tour
with Macs Bike that you have suitable Travel Insurance which covers you
for the activity, emergency evacuation and hospital care.

Getting to Florence / From Siena

To Florence

Florence Airport is served by a limited number of scheduled and low-cost airlines and is approximately a 20 minute bus or taxi journey to Florence Central Station. 

Alternatively Pisa Airport is just over a 60 minute train journey from Florence. From the airport a ten-minute connecting bus service will take you from the airport to Pisa Central station. From here hourly services run through to Florence.

Rome Fiumicino airport train station also connects with Florence via an approximate 2.5hr journey time.

Information on train journey times and booking, tickets can be accessed at  The Trainline Europe.

From Siena

Siena does not have an airport but is on a main train line and has a number of daily services to the following cities:

Pisa, 1hr 45min journey time. Daily services, up to 2 per hour.

Florence, 1-2 hours journey time. Daily services, up to 2 per hour.

Rome, 3.5 hours journey time. Daily services up to 5-6 per hour.

For more information on train times and tickets The Trainline Europe.


  • 2 Nights 4* hotel, 1 night 3* Hotel, 1 night boutique B&B
  • 4 Breakfasts
  • Detailed route notes with maps
  • 24/7 UK telephone support
  • Macs Adventure Navigation App
  • Baggage Transfers


  • Bike Hire
  • Lunches and Dinners
  • Arrival or Departure Transfers
  • Drinks and snacks
  • Personal equipment and expenditure
  • Travel insurance


  • Road Bike Hire
  • Extra Nights (Florence or Siena)
  • Arrival or Departure Transfers
  • Single Room Supplement

We are often asked the following questions and I hope that you will find the answers useful. Please don’t hesitate to contact us if you have any further queries.

How fit do I need to be?

This trip is graded moderate to challenging. Daily distances are up to 60km with up to 1000m+ of ascent. The rolling landscape of Tuscany is not to be underestimated! Each ride includes several climbs of 5-8km which are up to 12% gradient in places. After such climbs, descents must therefore treated with respect. The route is designed to enjoy the road cycling as much as the famous Tuscan foods and wine, so this trip isn’t just about the bike!

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as this region is extremely popular especially May to June and September.

Can I take my own bike?

Of course! We understand the relationship between rider and bike and know many cyclists would never consider riding another steed. If you are unsure, we are happy to discuss bike hire options with you.

When is the best time of year?

May is the month of Giro d’Italia so the nation is gripped by ‘bike fever’ depending on stage routings you may even get to see a stage of Giro.

May, June and September offer sunny, warm days and equally pleasant evenings. Sunflowers are in full bloom during May and June, whilst September is the grape harvest, so you will be sure to experience a local festival or two!

July and August temperatures may require earlier starts. Daytime temperatures are usually hit 30 degrees (+) with the evenings perfect for enjoying a glass of Chianti in the buzz of a piazza.


by PowerReviews
macs adventureRoad Cycling: Florence to Siena

(based on 2 reviews)

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(1 of 1 customers found this review helpful)


Florence to Siena

By 1deblackwell

from Seattle WA USA

About Me Avid Adventurer

Verified Buyer


  • Fun
  • Great Accommodations
  • Once in a Lifetime Experience
  • Well Organised


    Best Uses

    • Holiday

    Comments about macs adventure Road Cycling: Florence to Siena:

    The accommodations were amazing. The B&B food was perfect for a day of cycling. The 1:1 with the proprietors was exceptional.
    The bike drop off went smoothly and the bikes were great! I would suggest if your a woman to bring your own saddle for comfort. They brought helmets and a water bottle. I would suggest GPS or a handlebar map bag.

    (1 of 1 customers found this review helpful)


    One of our best holidays

    By DDF

    from Devon

    Verified Buyer


    • Great Accommodations
    • Great route
    • Stunning scenery and small atmospheric towns
    • Well Organised


      Best Uses

      • Holiday

      Comments about macs adventure Road Cycling: Florence to Siena:

      A really great 6 days away in Tuscany. Great accommodation and really stunning cycle routes, especially the loop ride in the beautiful Chianti region. Everything was v well organised and a minor glitch with the first night's accommodation was quickly sorted out without any fuss or bother

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