8 Days & 7 Nights

4.7

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

Tuscany is one of the most romantic regions in Europe, with cypress tree-lined roads, olive groves, vineyards, and ancient hilltop towns and cities. Take on our cycling tour of Tuscany, from Florence through to 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. Need some extra power for the Tuscan hills? Opt for an E-bike, allowing you more time for a dip in the pool once you arrive at your hotels.

From $2,780.00

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Itinerary

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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

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Casa Tintori | Bed and breakfast

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 | 3 Star | Hotel

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.

Day 2 Cycle to Radda in Chianti 35 miles / 55 km

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+

Overnight Radda in Chianti

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Relais Vignale | 4 Star | Hotel

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.

Palazzo Leopoldo | 4 Star | Hotel

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.

Day 3 Optional Chianti Winelands Loop Ride 35 miles / 55 km

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 +/-

Overnight Radda in Chianti

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Relais Vignale | 4 Star | Hotel

Palazzo Leopoldo | 4 Star | Hotel

Day 4 Cycle to Siena 48 miles / 76 km

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: 58 km + (or 76 km)

Ascent/Descent: 850m/700m

Overnight Siena

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

La Chicca B&B | Bed and breakfast

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 | 3 Star | Hotel

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.

Hotel Alma Domus | Hotel

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.

Day 5 Optional Siena loop ride in the Montagnola hills 36 miles / 57 km

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 +/-

Overnight Siena

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

La Chicca B&B | Bed and breakfast

Hotel Minerva | 3 Star | Hotel

Hotel Alma Domus | Hotel

Day 6 Siena to Montepulciano 38 miles / 60 km

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

Overnight Montepulciano

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Albergo il Rondo | Hotel

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

Albergo San Biagio | 3 Star

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.

Day 7 Optional Montepulciano loop ride 34.2 miles / 55.1 km

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-

Overnight Montepulciano

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Albergo il Rondo | Hotel

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

Albergo San Biagio | 3 Star

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.

Day 8 Onward Travel

THIS TRIP'S CARBON SCORE

This trip has a carbon score of 16kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 16kg is equivalent to 6 paperback books in the USA. 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.

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Other Information

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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!

Tour Type:

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 in Scotland, the world renown Tour Du Mont Blanc and Germany's Moselle Cycle Path, to name but a few!

Activity:

Leisure Cycling | Leisure Cycling

Ideal if you have an interest in:

Foodie, Wine

The minimum age for this tour is: 12 Years

Activity Level & Terrain

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.

Experience & Fitness

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 approximately 90km/55miles, but the total elevation gain and loss for that day is approximately 1400 metres / 4500 ft ascent & descent.

Accommodation & Meals Navigation What's Included

Included

7 nights in B&B's, guesthouses and hotels
All Breakfasts
Baggage transfers
Detailed trip info and mapped tracks for navigation, via the Macs App
24/7 Emergency telephone support from our office

Excluded

Travel to Siena / from Montepulciano
Bike hire
Lunches, dinners, drinks & snacks
Personal equipment
Travel insurance

Extras

Additional nights along the route
Bike hire

When to go Travel & Transfers Info & FAQ

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.

Equipment

The following bikes are available for hire:

Ebike: Hybrid ebike. Endeavour 1.B Move. Unisex gooseneck frame Alumium easy entry. Motor – Bosch performance line smart system 36V / 75 Nm. Battery – Bosch PowerPack Li-Ion 36 V – 545 Wh. Range up to 100km

Road Bike: Izalco Carbon SL frame and forks, Shimano Derailleurs and levers, Aluminium handlebar and stem.

Gravel & Road bikes are only recommended for experienced cyclists who understand the riding position and have the physical fitness needed for this style of biking.

Tandem bikes are not available on this tour.

Brand and model may vary depending on availability. Minimum age for ebike hire is 16yrs.

Please provide the following information on booking:

Your height for bike size

Bike Hire Inclusions:

Spare inner tube
Repair kit & pump
One lock
Battery charger (for ebikes only)

Helmets are not included and you must bring your own.

Many people choose to hire an e-bike, as the battery-powered assistance can be helpful when needed. Please note that e-bikes are heavier than standard bicycles. For more information on how ebikes work click here.

Travel Insurance

It is strongly recommended that you secure adequate travel insurance.