Take on Ride to Monte Cassino, a fully supported 3 day cycling challenge that blends powerful military history with spectacular scenery. This is not "just" a fundraising cycle through the Italian countryside, but an opportunity to honour the bravery and sacrifice of those who served, with military historians to guide us on our journey.

1-5 October 2026

A route steeped in history

Cycle in the footsteps of the heroes of the Second World War as you make your way toward the historic Monte Cassino Abbey. Throughout the challenge, you’ll be joined by expert military historians who will share stories, context, and powerful insights at key points along the route.

We’re also committed to making this journey personally meaningful: if you have a family connection to Monte Cassino or the surrounding region, we would love to hear from you. We will do our best to shape the route to honour your family’s story and ensure their legacy is remembered.

Fully inclusive & fully supported

Your registration includes everything you need for a seamless and stress free experience:

• Accommodation for the full duration
• All meals from start to finish
• Airport and on route transfers
• Experienced ride leaders guiding the way
• Professional mechanics keeping your bike road ready
• Support vehicles with refreshments and encouragement
• Bike hire options for anyone not bringing their own

Be part of something extraordinary!

Join us for a 3 day cycling adventure that blends history, purpose, and breath-taking landscapes - sign up today and pedal in honour of those who served, and help fundraise for the Armed Forces community today.

Registration Fee: £150
Fundraising Target: £1,100

Itinerary 

Thursday 1 October - Arrival and welcome:

Touch down in Italy and meet your transfer at the airport. Depending on your arrival time, you’ll have the afternoon free to explore the vibrant streets of Naples, soak in its historic charm, or enjoy a coffee overlooking the bay. In the evening, we’ll come together for a welcome dinner and safety briefing, giving you the chance to meet your fellow riders and prepare for the adventure ahead.

Friday 2 October - Naples to Monte Cassino:

Your challenge begins! We set off from Naples and begin our inspiring journey towards Monte Cassino. Along the way, you’ll experience a mix of rolling countryside, historic landscapes, and powerful moments of reflection as we ride toward one of the most symbolic sites of the Second World War.

Saturday 3 October - Exploring Monte Cassino:

Today we take on a scenic loop ride around Monte Cassino, visiting key military locations that shaped the story of the area. With our expert military historians guiding the day, this is a chance to gain a deeper understanding of the events and sacrifices connected to this remarkable place.

Sunday 4th October - Return to Naples and Celebration:

We leave Monte Cassino and cycle back to Naples via a different and equally beautiful route, giving you new scenery and fresh challenges along the way. That evening, we’ll gather for a well earned celebration dinner, raising a glass to your achievement and the impact you’ll be making for our Armed Forces community.

Monday 5 October– Journey home:

After breakfast, you’ll begin your journey home—tired legs, full heart, and memories to last a lifetime.

A breakdown of the full route will be available shortly. 

Price includes:

• Shared accommodation each night
• Breakfast and evening meal
• Fully supported route with ride captains
• An experienced historian 
• A SSAFA cycling jersey 
• Medal, certificate and celebration upon completion!

Price does not include:

• Flights to Naples
• Single person room supplement
• Personal expenses
• Personal travel insurance
• Bicycle insurance

If you would like any more information, please email teamssafa@ssafa.org.uk or call 020 4566 7952.