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May has owned many cars including a 2005 [[Saab 9-5#First generation (YS3E, 1997–2010)|Saab 9-5 Aero]], [[Bentley T-series|Bentley T2]], [[Rolls-Royce Phantom]], [[Triumph 2000]], [[Rover P6]], [[Alfa Romeo 164]], 1971 [[Rolls-Royce Corniche]], [[Triumph Vitesse]], [[Jaguar XJS]], 1992 [[Range Rover Classic]] Vogue, [[Fiat Panda#Second generation Mk3 (169; 2003)|Fiat Panda]], [[Nissan Sunny#B210 (1973–1977)|Datsun 120Y]], [[Vauxhall Cavalier#Mark I (1975–1981)|Vauxhall Cavalier Mk1]], a [[Ferrari 308 GTB/GTS|Ferrari 308 GTB]], a 2015 [[Toyota Mirai]], [[Ferrari F430]], [[Ferrari 458 Italia]], 1984 [[Porsche 930|Porsche 911]], 2005 [[Porsche Boxster/Cayman#Second generation: Boxster/Cayman (987.1) (2005–2008) & (987.2) (2009-2012)|Porsche Boxster S]] (which he claims is the first car he has ever purchased new).<ref>{{cite news|last=May |first=James |url=https://www.telegraph.co.uk/motoring/main.jhtml?xml=/motoring/2005/10/22/mrmay22.xml |archive-url=https://web.archive.org/web/20071012103741/http://www.telegraph.co.uk/motoring/main.jhtml?xml=/motoring/2005/10/22/mrmay22.xml |url-status=dead |archive-date=12 October 2007 |title=As seen on TV: Porsche breaks the spell of perfection |work=The Daily Telegraph |date=22 October 2005 |access-date=5 November 2009 | location=London}}</ref>
May currently owns a 2010 [[Porsche 997#Second
May obtained a [[Light aircraft pilot licence|light aircraft pilot's licence]] in October 2006, having trained at [[White Waltham Airfield]]. He has owned a [[Luscombe 8#Specifications: Model 8A (Silvaire)|Luscombe 8A Silvaire]], a [[Cessna 185 Skywagon|Cessna A185E Skywagon]],<ref>{{cite web |title=Incident Cessna A185E Skywagon - SE-FMX, 05 April 2014 |url=https://aviation-safety.net/wikibase/wiki.php?id=179976 |website=Aviation Safety Network - Flight Safety Foundation |access-date=14 August 2019}}</ref> and an [[American Champion Decathlon|American Champion 8KCAB Super Decathlon]] with registration G-OCOK, which serves as a reference to a common phrase attributed to him.<ref>{{cite web|url=http://www.airport-data.com/aircraft/G-OCOK.html |title=Aircraft G-OCOK, 1999 American Champion Aircraft 8KCAB C/N 825-99 |publisher=Airport-data.com |date=13 June 2008 |access-date=2 September 2013}}</ref>
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