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  • Tuscany cycling tours

Tuscany Cycling Holidays

Italy’s central regions of Tuscany and Umbria have some of the most stunning scenery for you to explore on your cycling holiday. The serene and beautiful rolling green hills, vineyards, olive groves and sun-baked stone villages make this one of our clients favourite Italian cycling destinations. Pedal along Tuscany’s Via Flaminia – once a Roman road over the Apennine mountains to Rome – visit the vineyards of Chianti and stop for a picnic by Lake Trasimeno. 

Cycle to charming medieval villages and hilltop towns in the countryside. San Quirico d’Orcia is a walled village in southern Tuscany with Etruscan origins, the 13th-century San Gimignano and Montepulciano are pretty towns made from sun-baked Tuscan stone on the hillside. E-bikes are available on Cycling for Softies tours to help you on the inclines, so you can save your energy for wine tastings and sightseeing.

The Tuscan and Umbrian cuisine does not disappoint, taste home-made parpadelle, pecorino cheese and fresh vegetables, paired with a glass of Chianti wine. Alon’t miss the Italian gelato for dessert, after a morning of cycling and sight-seeing you will have earnt it.

Insiders tips:

  • Visit the Etruscan hilltop town of Cortona
  • Cycle along the famed Via Flaminia
  • Experience Italian hospitality at an agriturismo
  • Glide up the beautiful hills on an e-bike
  • Learn how to make home-made pasta

Italian cuisine and wine

Tuscany and Umbria produce rich olive oil, which is doused on salads, vegetables and meats. After cycling the surrounding hills, dine on Florentine T-bone steak, Umbrian trout, wild boar, cured meats and dishes made with Norcia black truffles, accompanied with vegetables.

 

Produced in central Tuscany, medium-to-full-bodied red Chianti wine has been produced for over 2,000 years, since Etruscan times. Montepulciano is a rich, medium-bodied red wine that complements pork dishes and red meat. Brunello di Montalcino wine has notes of cherry and plum and pairs well with cold cuts.

Italian cuisine and wine - Textbox Image
Historical sights - Textbox Image

Historical sights

Pedal around the charming towns dotted through the Tuscan and Umbrian countryside that have a fascinating history. Assisi was the birthplace of Latin poet Propertius and St Francis, who founded the Franciscan religious order. Cortona is enclosed with stone walls atop a hill, offering sublime views of the countryside and Lake Trasimeno.

 

Take a break from cycling and visit the ancient castles and fortresses in the Niccone Valley, the Romanesque Abbey of Sant’antimo – formerly a Benedictine monastery – and medieval towns of Montone and Gubbio, which is on Mount Ingino and has views of the Apennine mountains.

  • Cycling Holidays in Tuscany

    E-Bike | Siena and San Gimignano

    Picture Tuscany in your imagination and chances are you are picturing the rolling hills, beautiful towns and spectacular colours that make this one of our most exciting new...

    From
    £1,185pp
    Ease
    Duration
    5 or 7 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
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  • Cycling Holidays in Tuscany

    E-Bike | The Day I Saw Siena | Guided

    Picture Tuscany in your imagination and chances are you are picturing the rolling hills, beautiful towns and spectacular colours that make this one of our best new itineraries...

    Ease
    Duration
    7 Nights
    Travel
    Flights and transfers available
    Enquire Now view details
  • Italian Cycling Holidays

    E-Bike | Exploring the River Tiber

    The Tiber valley runs from Mount Fumaiolo, on the Tuscan border with Emilia Romagna, through the Valtibertina and onwards through Umbria, to Rome and the Tirreno sea.

    Ease
    Duration
    7 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
    Enquire Now view details
  • Cycling Holiday in Tuscany

    E-Bike | Gubbio, Assisi & Umbria | Self Guided

    Pedal your way gently along quiet side roads and tracks and feast on wondrous Italian fayre and delicious Italian wines on your Tuscan E-bike self guided cycling holiday.

    • Self Guided E-bike tour
    • Guided route available
    • Dramatic scenery
    • Historic towns and chateaux
    • Suitable for vegetarians
    • Vineyards and wine tours
    From
    £955pp
    Ease
    Duration
    5 or 7 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
    Enquire Now view details
  • Cycling Holidays in Tuscany

    E-Bike | Tuscan Valleys | Self Guided

    A superb self guided E-bike adventure across a classic Tuscan landscape into the winelands. Starting high in the Tuscan hills, in the pretty town of Cortona, this tour takes you...

    • Self Guided E-bike tour
    • Helmets provided
    • Dramatic scenery
    • Historic towns and castles
    • Suitable for vegetarians
    • Vineyard and wine tours

    Offer available

    Reduced deposit of £150pp and no amendment fees. 2020 prices for 2021 departures. T&Cs apply.

    From
    £955pp
    Ease
    Duration
    5, 7 or 10 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
    Enquire Now view details
  • Cycling Holidays in Tuscany

    E-Bike | The Tuscan Experience | Guided Group

    This guided group e-bike tour takes you deep into the most enticing Chianti wine territory - your guide will reveal the region's secrets and recommend the very best local...

    • Expert local leader
    • Tasting Chianti wines
    • Abbey of Sant'antimo
    • Stunning Lake Trasimeno
    • Wine tasting sessions
    • The regions secrets
    From
    £2,145pp
    Ease
    Duration
    7 Nights
    Available
    May, September
    Travel
    Flights and transfers available
    Enquire Now view details
  • Walking & Cycling Base in Umbria

    Single Centre | Gianna's Agriturismo

    Gianna’s, as we affectionally know this guest house in the village of Lisciano Niccone, is a renovated olive oil mill and tobacco drying tower dating from 1750. Offering...

    • Self-guided E-bike tours
    • Self-guided walking routes
    • Stunning Umbrian scenery
    • Delicious dinners of traditional dishes

    Offer available

    Reduced deposit of £150pp and no amendment fees. 2020 prices for 2021 departures. T&Cs apply.

    From
    £455pp
    Ease
    Duration
    3, 5 or 7 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
    Enquire Now View Details
  • Cycling Holidays in Tuscany

    E-Bike | The Umbrian Experience | Guided Group

    Get off the beaten track and up close to Italy's local history and habitat on this food focused, fully guided, E-bike Safari through the wide open valleys of rural Umbria.

    • Guided Group tour
    • Helmets provided
    • Dramatic scenery
    • Historic towns
    • Suitable for vegetarians
    • Vineyards and wine tours
    From
    £1,995pp
    Ease
    Duration
    5 or 7 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
    Enquire Now view details
  • Cycling Holidays in Umbria

    E-Bike | Umbria & Lake Trasimeno | Self Guided

    There is no better way to enjoy the delights of the Tuscan and Umbrian countryside and the Italian lifestyle than by e-bike. This laid-lack tour takes you around the beautiful...

    • Delightful hotels with pools
    • Great local food
    • Quality E-bikes
    • Local support
    • Welcome briefing
    From
    £795pp
    Ease
    Duration
    5 or 7 Nights
    Available
    April, May, June, July, August, September, October
    Travel
    Flights and transfers available
    Enquire Now View Details
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