I have been to Lancerote. Loved it. Great roads, not a lot of cars. And nice scenery.
Edit: Surfing is great there as well
Outside of Lisbon - Sintra - is especially nice.
Look at http://weride.pt - they also have a road riding sister company. The area is full of nice places, small roads, MTB trails, mixed surfaces, and good food. It should be really cheap to get to from London and you basically just ride the metro to Rosso and the commuter train to Sintra from the airport (no need to rent a car or hire a cab).
Gran Canaria is a weird place. Lots of little micro-climates all over the island. I found the only boring bits were the undulating roads along the coast. The ‘Serenity’ and ‘Valley of the Tears’ climbs were both fantastic in my opinion with gorgeous scenery!
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That would be a staycation for me, as I’m from that part of the world. I certainly want better weather than the pros had this week!
Mallorca is getting a lot of attention. Does that mean it gets pretty crowded?
I hear Yorkshire has pleasant weather this time of year.
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I seriously doubt the islands are all that crowded this time of year, it’s the beginning of low(er) season from them and they have infrastructure to handle a lot of folks.
I’m doubling down on the Lisbon recommendation. Go to Lisbon/ Sintra/ Caiscais. Somewhere around there.
You can probably get a nicer bike in Prague. It’s not exactly cheap but if you can’t bring your own bike there are a few options: bikeclinic, Harfa Sport, Ski-Bike Radotin You can have SuperSix Evo HiMod for around 25 euros a day. Sites are in Czech so if you need any help drop me a message.
And some rides I would recommend: Sazava, Krivoklat, Krivoklat&Skryje. There’s more but I don’t want to bore you 
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Thanks so much for the tips! I will check out the shops, and the rides too hopefully. Those look like better bikes and prices than what I had seen before.
@Dostring - I was in Prague last week and have been several times with a bike. It’s beautiful, great terrain, great city. I did a ride really similar to your Krivoklat loop. That said, I think the weather might not be the greatest when compared to like Mallorca or the Iberian coast this time of year…
@jfluke - if you do go to Prague, there are also great restaurants all around. I stay in Karlin when I go and have never been disappointed with that neighborhood. Would highly recommend it, if you don’t mind riding in like 15-ish degree weather…
Yeah, I would definitely go to Mallorca instead but I live here so this weather will have to do. Got wet today but at least it was quite warm, probably last warm day. And you are right about my neighbourhood, Karlin is nice
I go pretty much every year with my wife for the Resite Conference, she goes and does her urbanist city thing and I enjoy the area. Next time I’m in town, I’m gonna hit you up for some rides. Really beautiful city and surrounding area - kind of sad everyone goes to see the clock and leave 
Thought about bring my mountain bike to hit Tocin hill in the south but wasn’t sure what it as like without a guide.
You’re making the right decision with Mallorca @tman1234. Gran Canaria, and its sister island Fuerteventura, have great riding but on Mallorca you’ll have more and better AirBNB and hotel options (many cycling friendly hotels) and, perhaps more importantly, amore and better restaurant options. There are a lot of variants to the 4 great suggestions listed by @pcp (not to mention a 130+ mile master loop of sorts) and these can easily include a pause at a cafe or restaurant for a coke, sweet, or lunch (fresh seafood, whatever).
As for crowds, it should be relatively light. Depending on when you go, there may be more cyclists (and families) than you might expect (so book your AirBNB or bike friendly hotel now), which will be because of the October break (mid-semester break for many schools), but overall, the roads will not be crowded with cyclists and yet you should see quite a number, which @o-rel can probably give you a better sense of.
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