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I test drove a Chesil almost 20 years ago. Wanted to see what a 1776 felt like in a lightweight shell as i was planning to rod my bug. From memory they were built very well, in terms of handling your talking basic bug chassis on 155 tyres. If it's for cruising then i'd go for the 356 with fuel injection on any size engine (1600 up). If he wants a bit of speed i wouldn't go lower than a well sorted 1776 but a 1914 would give you more power for the same cost. Also Chesil will do an IRS conversion for the rear for better handling.
It's been a while but back then they we're pretty friendly/helpful, i was just eighteen and they let me drive one along Chesil beach which is worth a journey there alone.
Anyone here have experience with 356 replica kit cars? Dad is looking to buy a chesil speedster.