EROICA MONTALCINO

Self-Guided Cycling Holiday in Eroica Tuscany

by

Gusto Cycling - UK

Gusto Cycling is a bespoke cycling tour operator specializing in immersive cycling experiences across Tuscany. Founded by Marco, whose passion for cycling and deep roots in Tuscany inspired the creation of the company, Gusto Cycling offers tailored itineraries that showcase the region's rich culture, stunning landscapes, and culinary delights.
Trip duration

8 days, 7 nights, 6 days biking

Accommodation level

RURAL GLAM

Formula

Self guided

Trip style

E-bike ready, Gravel, Roadbike

Diffculty level

★ ★ / ★ ★ ★

Total distance & elevation

205 km / up to 3000 m D+

Price from

€ 1.600,00

from Siena to Montalcino 

Gusto Cycling Offers a wide range of Tuscany cycling options to suit all tastes. Tuscany has it all, History, Art, Culture, amazing gastronomy and great wine! plus the added bonus of an enjoyable cycle through its varied countryside and medieval places, which have hardly changed for over 600 years!

Embark on a self-guided cycling adventure through Southern Tuscany, a region celebrated for its rolling hills, medieval towns, and rich cultural heritage. This tour offers the flexibility to start on any day of the week, allowing you to tailor the experience to your schedule. With comprehensive support, including detailed route notes, GPS maps, and luggage transfers, you can focus on enjoying the ride and the breathtaking scenery.

Included

Package includes:

  • Flexible start date – choose any day of the year to begin your holiday with complete flexibility.
  • 7 nights' accommodation in a quality mix of personally selected hotels and agriturismos, on a bed and buffet breakfast basis.
  • 2 Hybrid Bikes delivered to your Siena accommodation, including helmets, water bottles, and puncture kit.
  • Bike collection from Montalcino at the end of your tour.
  • Luggage transfers included 4 times between accommodations.
  • Custom GPS routes for each day, downloadable to iPhone or Garmin, with suggested coffee stops, lunch spots, and points of interest along the way.
  • Local expertise – benefit from personal knowledge and insight of the area to ensure the best Tuscany cycling experience.
  • Daily contact to monitor your progress and provide support.

OPZIONI

Extra Services:

  • Bike upgrades – upgrade to carbon hybrid, electric hybrid, carbon racing, or gravel bikes.
  • Airport transfers – private transfer from Pisa or Florence Airport to Siena.
  • End of tour transfer – private transfer from Montalcino to Buonconvento train station for your onward journey.
  • Return transfers – from Montalcino to Pisa or Florence Airport, or to Buonconvento or Siena train station.
  • Additional nights – extra days pre or post-tour can be arranged upon request.

Not included

  • Flights or transportation to the starting point
  • Lunches and dinners
  • Bicycle rental (available upon request)
  • Travel insurance
  • Personal expenses
Dates and prices

Daily program

The complete program consists of 8 days, 7 nights, and 6 days of cycling.

  • Day 1: Arrival in Siena Arrive in the historic city of Siena, a UNESCO World Heritage site and one of the best-preserved medieval cities in Tuscany. Explore the famous Piazza del Campo, the stunning Duomo, and Santa Maria della Scala. Overnight in Siena.
  • Day 2: Siena to Radda in Chianti (44 km, 650m elevation) Begin your ride heading into the heart of Chianti, one of Italy's most famous wine regions. After just 4km from Siena, traffic becomes minimal. Visit Castellina in Chianti along the way before arriving at the medieval hilltop town of Radda in Chianti. Overnight in Radda in Chianti.
  • Day 3: Chianti Wine Tour (38 km, 658m elevation) A relaxing day exploring the Chianti wine estates. Visit three different wineries and the charming village of Gaiole in Chianti. Enjoy wine tastings and lunch among the vineyards. Return to Radda in Chianti for overnight.
  • Day 4: Radda to Crete Senesi (49-68 km, 708-993m elevation) Head south into the stunning Crete Senesi region, characterized by rolling clay hills and landscapes that change with the seasons – sunflowers in summer, wheat fields and red poppies in spring. Pass through Asciano with its panoramic views. Overnight in Serre di Rapolano area.
  • Day 5: Crete Senesi to Pienza (38 km, 831m elevation) Cycle through charming villages to reach Pienza, an exquisite Renaissance town in the heart of Val d'Orcia, a UNESCO World Heritage site. Famous for its pecorino cheese, enjoy tastings and stunning views of Monte Amiata. Overnight in Pienza.
  • Day 6: Pienza to Montepulciano and back (39 km, 758m elevation) Visit the imposing medieval hilltop town of Montepulciano, surrounded by vineyards and renowned for its Vino Nobile di Montepulciano wine. Enjoy coffee in the 14th-century Palazzo Comunale and wine tasting with stunning scenery. Return to Pienza for overnight.
  • Day 7: Pienza to Montalcino (30-43 km, 607-922m elevation) Cycle to Montalcino, one of the most evocative towns in the Val d'Orcia, home to the world-famous Brunello di Montalcino wine. Explore the beautiful medieval town and enjoy spectacular countryside views. Overnight in Montalcino.
  • Day 8: Departure Check out of the hotel. Private transfers can be arranged to Buonconvento train station (20 minutes) or Siena train station (1 hour) for your onward journey or airport connection.

Accommodation level

RURAL GLAM: Stay in a selection of charming 3-star hotels and agriturismos, offering authentic Tuscan hospitality and comfort.

Formula

 

Rider level

LEVEL 2 - 3: Suitable for intermediate to experienced cyclists comfortable with daily rides of 50-70 km over undulating terrain. For those seeking a more relaxed experience, electric bikes are available upon request.

Dates and prices

all year long
Self guided
from € 1600
THIS IS MINE!
Listed periods don't fit? Ask for your own custom tour
I WANT MY CUSTOM!
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What people say about us

Chianti landscape along Eroica route
Gravel, Eroica pure vintage style

INTIMATE EROICA, CYCLING SOLO IN THE MOST BEAUTIFUL PLACE IN THE WORLD!

I was alone, and cycling solo in those places is beautiful: you never get bored, just look up from the handlebars to realize that you are blessed and lucky to be there.

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