For the cyclist that relishes a challenge, we have here our Challenging Cycling Holidays.
For some life behind bars is a reality, we know that addiction well here at Hooked on Cycling. Being active road cyclists ourselves, we have put together a selection of our most challenging tours. All of these tours will have Road Bikes available to hire and are designed to be ridden on road bikes.
Not sure if a particular tour suits your needs then Contact Us and we can help you plan your perfect Cycling Holiday.
Still want more of a challenge you may want to check out our Gran Fondo page for a couple of the most challenging Gran Fondo’s in Europe.
Duration: 5 Nights
Difficulty: Level 4/4+
Tour Type: Self Guided
Availability: Not Available In 2026
Starting Location: Geneva
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Daily from 4th April to 17th October.
Starting Location: Metz
Duration: 7 nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Daily 1st May to 15th October
Starting Location: Trani
Duration: 7 Nights
Difficulty: Level 2 (Some days 2-3)
Tour Type: Self Guided
Availability: Saturdays from 1st April to 10th October
Starting Location: Montecatini Terme
Duration: 7 Nights
Difficulty: Level 2-4
Tour Type: Guided
Availability: Daily March – 24th October.
Starting Location: Cesenatico
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Saturdays 1st March to 30th November (Starting on other days possible with a supplement).
Starting Location: Olbia
Duration: 7 Nights
Difficulty: Level 2-4
Tour Type: Guided
Availability: Daily from 1st April to 17th October.
Starting Location: Riccione
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Saturdays from February 1st to November 30th
Starting Location: Siracusa
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Daily April to 15th October
Starting Location: Bastia
Duration: 8 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Not Available In 2026
Starting Location: Avignon
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Daily on 1st March to 30th November.
Starting Location: Girona
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Sundays from March 29th to June 21st and September 6th to 18th October. (special dates available for groups or 6 or more).
Starting Location: Palma/Can Pastilla
Duration: 7 Nights
Difficulty: Level 3
Tour Type: Self Guided
Availability: Daily from 1st March – 15th November
Starting Location: Porec
Duration: 6 Nights
Difficulty: Level 3
Tour Type: Self Guided
Availability: Daily April 24th to October 18th
Starting Location: Garmisch Partenkirchen
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Daily April – September
Starting Location: Carlisle
Duration: 7 Nights
Difficulty: Level 3
Tour Type: Self Guided
Availability: Daily April 24th to October 11th.
Starting Location: Salzburg
Duration: 7 Nights
Difficulty: Level 3
Tour Type: Self Guided
Availability: Saturdays, Monday’s and Tuesday May 9th to September 22nd
Starting Location: Innsbruck
Duration: 6 Nights
Difficulty: Level 3
Tour Type: Self Guided
Availability: Daily April – October
Starting Location: Berwick upon Tweed
Duration: 7 Nights
Difficulty: Level 3
Tour Type: Self Guided
Availability: Daily April – October
Starting Location: Callander
Duration: 7 Nights
Difficulty: Level 3-4
Tour Type: Self Guided
Availability: Daily on 13th May to 27th September.
Starting Location: St Margrethen (Lake Constance)