Cycling Tuscany: Florence to Montepulciano
- Cycle Tuscany’s classic hills and winelands of Chianti & Montepulciano
- Explore the cultural cities of Siena and Florence
- Quintessential hilltop towns and villages amidst vineyards and farmland
- Fresh Tuscan organic produce —olive oil, pasta, cheeses & wines
- Hand-picked accommodations all in enchanting locations
Gallery
Itinerary
Day 1 Arrive FlorenceOn 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.
Casa dei Tintori is a restored 13th century family guest house is only a few minutes’ walk of Florence’s major sights, cafes and bars. Situated within 400 metres of Palazzo Vecchio and 700 metres of Ponte Vecchio, B&B La Casa dei Tintori has city and inner courtyard views, and is 500 metres from Piazza della Signoria. The property is 400 metres from Uffizi Gallery, and within 700 metres of the city centre.
Hotel David is situated at the start of Viale Michelangiolo, which leads to a panoramic hilltop view from the square of the same name. The hotel was a 19th century mansion converted into a hotel around 1950, and it has been run by the Cecioni family since then.
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.
Ascent/Descent: 850m/500m+
A beautifully renovated manor house dating from the 1700s, Relais Vignale is the perfect place to relax after a long day in the saddle. The hotel has a lounge with fireplace, garden, outdoor heated swimming pool, enoteca, and restaurant with panoramic terrace.
Nestled in the expanses of the vineyards of Chianti, Palazzo Leopoldo is set in an enchanting building originally built in the 1300’s. It retains its original structure both inside and out, where the modern furniture is complemented by antiques. Elegant and spacious bedrooms are furnished with original terracotta floor tiles and some with ceiling beams.
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.
Ascent/Descent: 1450m +/-
A beautifully renovated manor house dating from the 1700s, Relais Vignale is the perfect place to relax after a long day in the saddle. The hotel has a lounge with fireplace, garden, outdoor heated swimming pool, enoteca, and restaurant with panoramic terrace.
Nestled in the expanses of the vineyards of Chianti, Palazzo Leopoldo is set in an enchanting building originally built in the 1300’s. It retains its original structure both inside and out, where the modern furniture is complemented by antiques. Elegant and spacious bedrooms are furnished with original terracotta floor tiles and some with ceiling beams.
Leaving Radda, cycle sections of the Giro d’Italia stage 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 Camp. The perfect spot for a post-ride beer!
Cycle:Â 58 km + (or 76 km)
Ascent/Descent: 850m/700m
La Chicca B&B is run by the Garavini family. The accommodation is situated in an old villa in the San Prospero area, just outside of the historic Siena’s walls. Offering a garden and a terrace, La Chicca Siena is located in Siena, a 5 mins walk from the Piazza Campo and a 15-minute walk from the Cathedral.
Hotel Minerva is one of the most historic 3-star hotels in the city of Siena. The hotel is located within the ancient city walls of Siena, in the north of the city, just a few steps away from Piazza Campo: the heart of the historic city center, famous throughout the world as the City of the Palio.
Set in a 13th-century building, Hotel Alma Domus offers rooms in the historic centre of Siena, a 2-minute walk from Basilica Cateriniana San Domenico Church. Many of the rooms have balconies offering city views and they are all stylishly decorated.
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.
Ascent/Descent: 1000 m +/-
La Chicca B&B is run by the Garavini family. The accommodation is situated in an old villa in the San Prospero area, just outside of the historic Siena’s walls. Offering a garden and a terrace, La Chicca Siena is located in Siena, a 5 mins walk from the Piazza Campo and a 15-minute walk from the Cathedral.
Hotel Minerva is one of the most historic 3-star hotels in the city of Siena. The hotel is located within the ancient city walls of Siena, in the north of the city, just a few steps away from Piazza Campo: the heart of the historic city center, famous throughout the world as the City of the Palio.
Set in a 13th-century building, Hotel Alma Domus offers rooms in the historic centre of Siena, a 2-minute walk from Basilica Cateriniana San Domenico Church. Many of the rooms have balconies offering city views and they are all stylishly decorated.
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.
Ascent/Descent: 700 m+ / 860m
A ten minute walk from the thriving streets of Montepulciano, Hotel Rondo is an 18th century property with relaxing gardens.
Hotel San Biagio is set in Montepulciano in the heart of Tuscany. It features a heated swimming pool with whirlpool and a bar.
With a balcony, air-conditioned rooms come with a flat-screen TV, safe and private bathroom with free toiletries.
The San Biagio is a perfect base for trekking and cycling excursions in the Tuscan countryside. The on-site pool is open for May until November.
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-
A ten minute walk from the thriving streets of Montepulciano, Hotel Rondo is an 18th century property with relaxing gardens.
Hotel San Biagio is set in Montepulciano in the heart of Tuscany. It features a heated swimming pool with whirlpool and a bar.
With a balcony, air-conditioned rooms come with a flat-screen TV, safe and private bathroom with free toiletries.
The San Biagio is a perfect base for trekking and cycling excursions in the Tuscan countryside. The on-site pool is open for May until November.
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.
This trip has a carbon score of 10kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 10kg is equivalent to 18 lattes. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.
Other Information
Is it for me?This road cycling tour is graded moderate to challenging. Tuscany is well known for its rolling roads and is a firm favourite with the pro's. Each day ride includes hill climbs between 5-8km with gradients of up to 12% in places. At the end of each ride soak up Italian life in the buzz of a piazza with rustic regional dishes and a large glass of Chianti or Montepulciano!
Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!
Leisure Cycling | Leisure Cycling
Foodie, Wine
This cycling tour is graded moderate to strenuous. The grade is determined on the basis of the entire trip. Individual days may vary in terms of difficulty, i.e. some rides may be slightly more difficult or easier than the overall grade. The route is mainly on quiet country roads wherever possible but there will be busier stretches as you approach and exit towns. Â
This cycling tour is suitable for regular cyclists looking for a sense of achievement at the end of the day, who are comfortable with longer distances and hilly terrain with occasional steep ascents and descents. Each day ride includes hill climbs between 5-8km with gradients of up to 12% in places. Please note that the optional loop ride on Day 7 has a higher grade (strenuous), with challenging ascents and descents. Not only is the ride 90km, but the total elevation gain and loss for that day is 1434 metres ascent and 1434 metres descent. We do however offer a shorter 50km ride for this, whcih can be followed via our route notes - this shorter option is not yet available as a GPX track in our app.
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 alternative accommodation especially during the busier periods of the year. We always book an equal or better alternative hotel or bed and breakfast.
Meals
Included are 4 breakfasts, which usually consist of fresh pastries, breads, fruits, yogurts, cheeses, meats and granola. If you have special dietary requirements do let us know at the time of booking.
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.
Navigation is straightforward as you can use the Macs Adventure app which has maps, GPS tracks, and daily route info. Simply download the GPS tracks for offline use and follow the route on your phone with the assurance that navigation will be simple, and you can’t get lost.
The roads are also well signposted and are generally cycle-friendly. 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 conditions.
Should you require assistance, 24/7 telephone support will also be available throughout your trip
- 7 nights in B&B's, guesthouses and hotels
- All Breakfasts
- Baggage transfers
- Information pack and route notes
- Access to detailed maps and GPS tracks in the Macs Adventure smartphone navigation app
- 24/7 Emergency telephone support from our office
- Travel to Siena / from Montepulciano
- Standard bike hire
- E-Bike hire
- Lunches, dinners, drinks & snacks
- Personal equipment
- Travel insurance
- Additional nights along the route
- Standard bike hire
- E-bike hire
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.
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.Â
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.
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 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.
Your bags will be transferred between your accommodation as per your itinerary. We ask you to limit your luggage to one bag of up to 20kg per person.
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.
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.
E bikes are also available should you prefer a little pedal assist.
Your rental bike will be delivered to your hotel in Florence and can be set up with flat, Look or Shimano spd pedals.
If you’d like to rent 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 bikes.
If you would bring your own road bike please ensure it is thoroughly serviced and is an appropriate road bike for this trip.
It is strongly recommended that you secure adequate travel insurance.
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.
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.
Graded moderate to challenging Tuscany is well known for rolling routes popular with pros. 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!
We suggest you book as soon as your plans are finalised as this region is extremely popular especially May to June and September.
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