Which would you do for a winter warmer with the family and hopefully a couple of days on a (rented) road bike for me?!

Not been to Gran Canaria but Madeira is lovely if you like walking. No beaches though which may be an issue.

gran canaria has good beaches and a very good bus system. good walks too, and popular with roadies
I went in february this year, we were just getting over the really cold spell, but they had just had their worst cold spell in many years.
still, the north was not so hot, but I got sunburnt in the south

Gran Canaria for sure. Madeira is nice but not as sunny and roads have lots of tunnels, which aren’t so pleasant for cycling.

Tarifa. Awesome nightlife and Morroco just across the road.

Gran Can has plenty of sandy beaches. You might even get more than you bargained for if you venture into the dunes….

Very good for road cycling with Free Motion offering road bikes in several locations.

Worked for FM for six months as a mtb guide on GC. Wouldn’t recommend it for biking, but would say for road riding it’s great.

The main centres of Playa etc are void of any cultural highlights. The capital makes for a nice day trip. Some nice villages up in the hills and a few good tapas places behind Playa…. Follow the locals.

We’re in GC at the moment. Never been to Madeira though.

GC is nice but it’s some of the toughest road biking I’ve ever done – it’s got a LOT of very long climbs, in fact it takes some doing to find routes that have less than a couple of thousand metres of climbing unless it’s up and down the coast in the south.

Most of the tourists go to the southern resorts, Maspalomas being the main one. Personally I can’t stand the place, it’s just standard tourist dump. We stay up in the north. 25 degrees here at the moment, warmer in the south and down by the coast.