There was a moment, just ten minutes after I punctured my tyre on the England flag-painted mini-roundabout, shortly before a wave washed over the breakwater and forcibly removed my left AirPod, that I vowed never to sit on a bicycle again.

If you're accustomed to venturing out on a lengthy bike ride, then I'd wager that you have had a similar feeling. At its very best, hopping on the saddle and pedalling out of a morning, with a blue sky above and a self-powered adventure ahead of you, cycling is the greatest of all activities. At its very worst, it's horrible.

Sadly, it felt like one of the latter days. I'd whizzed down from London St Pancras to Ramsgate in Kent, encouraged by Trainline's recent push to get cyclists on the train. The ticket booking app now displays a bicycle icon next to services, allowing you to easily identify which accept cycles. This is more important than you might think, as many commuter services ban non-foldable bikes for several hours in the morning and evening.

Unfortunately for me, I'd booked myself on the worst day of the year. Weeks of curiously warm autumn weather disappeared overnight, to be replaced by a 'feels like' temperature of -2C, 25 mph winds helpfully coming right towards me from the North West, and loads of rain. After hiding in Salt coffee shop in Broadstairs for a couple of hours, I decided to properly get going.

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The path I was following was the Viking Trail, a flat, 25-mile circular around the Isle of Thanet, passing through Margate, Broadstairs, Ramsgate, Pegwell Bay, and Reculver. Handily, all the key towns are served by Southeastern rail services, so you can hop on or off with ease, and bail out if the going gets too tough.

Round the coast I went, head hunched down against the wind, sheets of drizzle bouncing off my helmet. As I approached Margate, I ignored my cycling proficiency training and put on some music. A quick blast of 150bpm donk powered me through the suburbs and into Margate proper.

While Broadstairs is a largely flag-free zone, Margate is not. On the way in, I'd cycled by several tatty Union Flags, seemingly half ripped off their lampposts by the wind. Just behind Dreamland, someone has packed their garden with England flags and little bird tables, and just outside that property is a mini-roundabout daubed with the familiar red cross.

I realise that you shouldn't go over roundabouts, regardless of their size, but such a flagrant politicization of our once-neutral street furniture rankled. Sadly for me (again), my comeuppance was instant. The pannier-laden back wheel skiddered off the top and quickly deflated.

My saviour came in the form of a puncture repair kit and a bus shelter.

Over the next couple of hours, I devised a grand theory of cycling. It is the Kent of the transport world. At its worst, Kent (and I hope I can write this as someone who's spent over half their life in the county) is a slightly unfriendly, flag-heavy place. Vans drive too close to cyclists; waves annoyingly surge over breakwaters, ruining your left earphone; and potholes cause you to swerve into the road. But at its best, it's unbeatable.

The variety of towns in a small area is enormous. Broadstairs, with its independent cinema and iconic ice cream parlour, sits next to Margate, home to Pete Doherty-defeatingly big fry-ups and sensational arcades. Margate, in turn, runs into Reculver, where two medieval towers dominate the skyline, hanging over the marshland below. The South East might get lumped together with "unfriendly London", but people are chatty here and not in too much of a hurry to stop.

Tyre pumped and AirPod drying in my bag, I came out of Margate and turned a corner, feeling the wind behind me for the first time. The rain had stopped and a patch of blue broke through the clouds. Enough for a pair of sailors' trousers. I decided I loved cycling again.

The Granite Way (Devon)

An 11-mile (18km) flat, traffic-free trail following the former railway between Okehampton and Lydford, featuring the historic Meldon and Lake Viaducts.

How To Get There: Start and finish at Okehampton station on the Dartmoor line in Devon, erved by Great Western Railway. You can reserve a bike on any service, but there are limited spaces, so booking ahead is essential.

Pennine Cycleway

A 327mile route traversing England's "backbone"-from Derbyshire through West Yorkshire to Northumberland. Known as one of Sustrans' greatest routes.

How To Get There: Start from Derby, which is served by East Midlands Railway. There is only guaranteed space for two regular bikes on a train, so booking in advance is essential.

Way of the Roses

A 170mile coasttocoast route across Lancashire and Yorkshire, weaving through Lancaster, York, the Yorkshire Dales, and the Wolds. Includes mixed road and disused railway paths - not to mention a whole load of history!

How To Get There: Morecambe station in Lancashire and Bridlington in Yorkshire are served by Northern rail, which has a first-come-first-served bike policy. However, some trains have no bike spaces, so it's essential to check your specific journey for the bike icon on the Trainline journey planner first.

Fallowfield Loop (Manchester)

Coming in at a slightly more manageable 5.4 miles, this route along a disused railway line travels from Chorlton-cum-Hardy to Fairfield. It's a classic urban railway path, ideal for families and new cyclists who need to build up their confidence away from road traffic.

How To Get There: Manchester Piccadilly is served by multiple rail operators - although there's no need to look up their bike allowances as the Trainline app will highlight any restrictions and whether a reservation is needed. From there, it's a 20 minute cycle from Manchester Piccadilly to join the route.