Self Guided Walking Holidays & Cycling Holidays

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Sweeping Tuscan Roads & Montepulciano Vineyards


  • Cycle Tuscany’s classic hills of Chianti & Montepulciano
  • Visit the Ponte Vecchio Bridge of Florence
  • Ride historic stages of Giro d’Italia
  • Relax with a Chianti in Siena’s Piazza del Campo
  • Cycle the UNESCO Val d'Orica region

Take on our Tour of Tuscany cycling from Florence, through the world-class winelands of Chianti and Montepulciano.

Ride the rolling Chiantigiana to Radda in Chianti and Tuscany’s largest collection of wine, ‘Casa del Chianti’. Follow stages of Giro d’Italia to the towers of San Gimignano and the buzz of Siena’s Piazza del Campo (perfect for a post-ride vino rosso!). Ride the exquisite Val d’Orica and round off your tour with a glass of the reputed Vino di Nobile in medieval Montepulciano.

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 Chianti 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 be 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 region's largest vineyard. A rapid descent heads through
Castelnuovo dei Sabionni before a rolling route returns you 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 its 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 del Campo. The perfect spot for a post-ride beer!

Cycle: 58 km + (or 76 km)

Ascent/Descent: 850m/700m

Day 5 Siena & The Montagnola Region

Cycle the Montagnola Hills west of Siena. Take a spin to the fortified town of Sovicille. Roll through the hills of Poggio al Pero and through the villages of Maggiano and Lucerena. On the final descent to Siena take a rustic Toscana lunch in Carpineta. Back in Siena further explore the art-filled streets and the lure of entoneca’s packed with local pecorino cheese and salamis.

Cycle: 57 km +

Ascent/Descent: 1000 m +/-

Overnight: Siena

Day 6 Siena to Montepulciano

Ride to the world class wine region of Montepulciano. An easier spin on the legs today heads through lands rich in wine, olive and sunflower production. On arrival into Montepulciano the steeps streets of medieval Montepulciano offer countless and extensive views over the spectacular Val d’Orica and Val di Chaina.

Cycle: 60 km

Ascent/Descent: 700 m+ / 860m

Day 7 Montepulciano

Before being lured by the countless wine tasting experiences,
there are a choice of two rides today. A long but punchy route heads through
the sensational Val d’Orica region and via the hilltop town of Montalcino. Alternatively,
shortening the loop leaves ample time for a lazy afternoon lunch with a generous
glass (or two) of the revered Vino Nobile.

Cycle:  80km or 50km

Ascent/Descent: 1200m+/1160m- or 650m+/ 550m-

Day 8 Onward Travel

A simply arranged transfer from Montepulciano to Chiusi Train Station (20mins) will provide connections to Rome (1.5hrs), Florence (1.5hrs) and Pisa (3hrs). Alternatively, we would be happy to book extra nights in Tuscany if required.


Each Tuscan accommodation is different and full of character. Typical B&B's and hotels are listed
below, though on occasion we may have to book you an alternative accommodation especially during the busier periods of the year. We always book an
equal or better alternative hotel or bed and breakfast.


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 and Montepulciano, there is fine red wine in abundance.

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.




Casa dei Tintori - Florence

Casa dei Tintori - Florence

Casa dei Tintori is restored 13th century family guest house is only a few minutes walk of Florence’s major sights, cafes and bars.




Hotel le Vigne – Radda in Chianti

Nestled amongst the rolling vineyards, Hotel le Vigne is a short walk from Radda’s charming streets, cafes and bars. It’s rural setting with pool is perfect for any post 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.




Hotel lI Rondo - Montepulciano

A ten minute walk from the thriving streets of Montepulciano, Hotel Rondo is an 18th century property with relaxing gardens.


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.

July and August are the hottest months with little to no rainfall. The temperatures rise into the 30 degree celsius during the day. The months before and after the high season will be sunny but a little cooler, which could be preferable when cycling. Always make sure to stay hydrated, take plenty of water and wear sunscreen and a sunhat.

Navigation, Route Notes & Maps

The cycling in this region follows well surfaced roads through towns, villages and minor country routes. Make sure to always be mindful of other road users, especially on roads shared with traffic. 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 Montepulciano

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 Montepulciano

Montepulciano does not have an airport but is only a 20 minute drive from Chiusi Train Sation which has connections to the following cities. We can easily arrange a the short transfer to Chiusi train station if required.

Pisa, 3hrs journey time. Daily services, up to 1 per hour.

Florence, 1.5-2 hours journey time. Daily services, up to 1 per hour.

Rome, 1.5-2 hours journey time. Daily services up to 1 per hour.

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


  • 3 Nights B&B/Guesthouses & 4 nights 3* Hotel
  • 7 Breakfasts
  • Detailed route notes
  • Access to GPS tracks on the Macs Adventure smartphone app
  • 24/7 UK telephone support
  • Baggage Transfers


  • Travel to Siena / From Montepulciano
  • Bike hire
  • Lunches and dinners
  • Drinks and snacks
  • Personal equipment and expenditure
  • Travel insurance


  • Road bike hire
  • Extra nights (Florence or Montepulciano)
  • 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?

Graded moderate to challenging Tuscany is well known for rolling routes popular with pro's. Each day ride includes hill climbs between 5-8km with gradients of up to 12% in places. Punctuated by hill top towns famed for Tuscan wines and rustic regional dishes, soak up Italian life at the end of each day in the buzz of piazza or tranquil family run accommodation. 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.



I was impressed with all that Macs adventure had done for us. The personal touch on the phone when we first thought about the trip, the follow up if we sent further enquires concerning routes and the information pack that was sent to us prior to our departure. The choice of routes for the bike rides was excellent, most rides went through small pretty Tuscan villages and a lot of the routes offered some shade with treelined sections which was welcome due to the heat . It was 37degrees at times. I enjoyed all the cafe recommendations en route and the fact that each ride ended at a nice spot with a chance to relax with an ice cream or welcome drink before going to our accommodation. I have saved the best till last, Macs adventure came up trumps with all the accommodation. Each one was superb, well located and of a charmingly high standard.




Great mix of cycling and culture and very well organised


Lovely trip - cycling through the very pretty and varied Tuscany countryside and also staying in quality accommodation. The whole trip was very well organised by Macs Adventures and the cycle company were quickly responsive when we had some minor issues with a bike.

David A



Fantastic cycling, countryside and hotels


This holiday hit all the right buttons. Great comfortable bikes on well planned and strenuous routes but with welcoming accommodation at the end of the day. The route details were easy to follow and the Macsworld app enabled us to verify our position on the odd occasion we were uncertainof our position.




Tour of Tuscany: Florence to Montepulciano

5.0 3


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Macs Adventure - Head Office: Skypark 5, 45 Finnieston Street, Glasgow, G3 8JU, UK


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