Used Bike Guide: Harley Davidson Softail (1998-2003)

Harley Davidson Softail (1998-2003) £5500-£14,000

If you’re after a cruiser, then the Harley-Davidson Softail has got to be in the mix. The 2023 version will set you back close to £16,000, so you’d be much better looking back a few generations to try and bag yourself a bargain. That said, they hold their money extremely well, although with a bit of hunting you’ll likely be able to find a tidy example that’s not been messed about with for around £8000.  

It’s a lovely thing to look at, and with Harley’s old torque-rich 88B 1450cc engine, well-renowned build quality, a massive range of aftermarket accessories to choose from and strong residual values, you’ll be in safe hands with one of these.

This is the newest machine on this list by quite some distance. It’s a bike we’ve spent a bit of time on over the past couple of years,and it’s always impressed. It may not have the same gravitas as the big Beemer, but it more than makes up for it in other ways, offering truly outstanding handling, silky-smooth power delivery (from its Africa Twin-derived motor) and that legendary Honda build quality. It’s also ridiculously easy to get on with.

It’s competitively priced, too. When it first came out in 2021, you could snag yourself a brand-new one for less than 10 grand. It’s gone up a smidge now, but if you focus your search on the first-generation machine, you should be able to find a good example for around £8000. That’s appropriately good value. There’s also a DCT semi-automatic option available if you’re so inclined.

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